DE60222596T2 - Fettsäureverbindungen und deren herstellung und verwendungen - Google Patents
Fettsäureverbindungen und deren herstellung und verwendungen Download PDFInfo
- Publication number
- DE60222596T2 DE60222596T2 DE60222596T DE60222596T DE60222596T2 DE 60222596 T2 DE60222596 T2 DE 60222596T2 DE 60222596 T DE60222596 T DE 60222596T DE 60222596 T DE60222596 T DE 60222596T DE 60222596 T2 DE60222596 T2 DE 60222596T2
- Authority
- DE
- Germany
- Prior art keywords
- radical
- atom
- carbon atoms
- chain
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 18
- 239000000194 fatty acid Substances 0.000 title claims abstract description 18
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims description 69
- -1 Fatty Acid Compounds Chemical class 0.000 title abstract description 36
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 54
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims description 265
- 150000003254 radicals Chemical class 0.000 claims description 121
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 72
- 230000000694 effects Effects 0.000 claims description 67
- 125000004432 carbon atom Chemical group C* 0.000 claims description 64
- 229920006395 saturated elastomer Polymers 0.000 claims description 55
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 51
- 238000011282 treatment Methods 0.000 claims description 50
- 125000004434 sulfur atom Chemical group 0.000 claims description 45
- 239000000460 chlorine Substances 0.000 claims description 44
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 36
- 229910052711 selenium Inorganic materials 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 35
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 34
- 235000012000 cholesterol Nutrition 0.000 claims description 31
- 150000003626 triacylglycerols Chemical class 0.000 claims description 31
- 238000007254 oxidation reaction Methods 0.000 claims description 28
- 230000014509 gene expression Effects 0.000 claims description 21
- 102000023984 PPAR alpha Human genes 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 108091008725 peroxisome proliferator-activated receptors alpha Proteins 0.000 claims description 19
- 230000003647 oxidation Effects 0.000 claims description 18
- 150000004665 fatty acids Chemical class 0.000 claims description 15
- 239000002537 cosmetic Substances 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 12
- 230000002438 mitochondrial effect Effects 0.000 claims description 11
- 230000015572 biosynthetic process Effects 0.000 claims description 10
- 235000013305 food Nutrition 0.000 claims description 10
- 230000000858 peroxisomal effect Effects 0.000 claims description 10
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 9
- 102000004190 Enzymes Human genes 0.000 claims description 9
- 108090000790 Enzymes Proteins 0.000 claims description 9
- 206010012601 diabetes mellitus Diseases 0.000 claims description 9
- 206010020772 Hypertension Diseases 0.000 claims description 7
- 206010028980 Neoplasm Diseases 0.000 claims description 7
- 208000008589 Obesity Diseases 0.000 claims description 7
- 230000002440 hepatic effect Effects 0.000 claims description 7
- 230000001965 increasing effect Effects 0.000 claims description 7
- 235000020824 obesity Nutrition 0.000 claims description 7
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 6
- 208000037803 restenosis Diseases 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- 108010016731 PPAR gamma Proteins 0.000 claims description 5
- 102000000536 PPAR gamma Human genes 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 208000011580 syndromic disease Diseases 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 201000011510 cancer Diseases 0.000 claims description 4
- 230000012010 growth Effects 0.000 claims description 4
- 210000003470 mitochondria Anatomy 0.000 claims description 4
- 230000001590 oxidative effect Effects 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 230000009759 skin aging Effects 0.000 claims description 3
- 208000017520 skin disease Diseases 0.000 claims description 3
- 230000037303 wrinkles Effects 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 2
- 230000003213 activating effect Effects 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 230000001939 inductive effect Effects 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 210000001087 myotubule Anatomy 0.000 claims description 2
- 230000004936 stimulating effect Effects 0.000 claims description 2
- 210000004881 tumor cell Anatomy 0.000 claims description 2
- 230000004614 tumor growth Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 3
- 230000004075 alteration Effects 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 74
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 49
- 238000000034 method Methods 0.000 description 48
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 45
- 210000004027 cell Anatomy 0.000 description 40
- 241000700159 Rattus Species 0.000 description 36
- 241001465754 Metazoa Species 0.000 description 30
- 108090000623 proteins and genes Proteins 0.000 description 29
- 210000002381 plasma Anatomy 0.000 description 28
- 150000002148 esters Chemical class 0.000 description 27
- 238000011156 evaluation Methods 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 238000005259 measurement Methods 0.000 description 25
- 150000002632 lipids Chemical class 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 21
- 102000006587 Glutathione peroxidase Human genes 0.000 description 20
- 108700016172 Glutathione peroxidases Proteins 0.000 description 20
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 20
- 108020004414 DNA Proteins 0.000 description 19
- 239000000047 product Substances 0.000 description 19
- 239000002609 medium Substances 0.000 description 18
- 239000000523 sample Substances 0.000 description 18
- 239000011734 sodium Substances 0.000 description 18
- 238000012360 testing method Methods 0.000 description 18
- 239000012190 activator Substances 0.000 description 17
- 239000003153 chemical reaction reagent Substances 0.000 description 17
- LNZMEOLVTKHUAS-UHFFFAOYSA-N cyclohexane;dichloromethane Chemical compound ClCCl.C1CCCCC1 LNZMEOLVTKHUAS-UHFFFAOYSA-N 0.000 description 17
- 235000011187 glycerol Nutrition 0.000 description 17
- IPBCWPPBAWQYOO-UHFFFAOYSA-N 2-(tetradecylthio)acetic acid Chemical compound CCCCCCCCCCCCCCSCC(O)=O IPBCWPPBAWQYOO-UHFFFAOYSA-N 0.000 description 16
- 230000009467 reduction Effects 0.000 description 16
- 108010007622 LDL Lipoproteins Proteins 0.000 description 15
- 102000007330 LDL Lipoproteins Human genes 0.000 description 15
- 238000002474 experimental method Methods 0.000 description 15
- 210000002540 macrophage Anatomy 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 235000000346 sugar Nutrition 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- 238000011161 development Methods 0.000 description 13
- 230000018109 developmental process Effects 0.000 description 13
- 238000009826 distribution Methods 0.000 description 13
- 239000002244 precipitate Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 12
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 238000004587 chromatography analysis Methods 0.000 description 11
- 230000007423 decrease Effects 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- 239000000741 silica gel Substances 0.000 description 11
- 229910002027 silica gel Inorganic materials 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 108010018424 Carnitine O-palmitoyltransferase Proteins 0.000 description 10
- 102100027943 Carnitine O-palmitoyltransferase 1, liver isoform Human genes 0.000 description 10
- 101710120614 Carnitine O-palmitoyltransferase 1, liver isoform Proteins 0.000 description 10
- 101710108984 Carnitine O-palmitoyltransferase 1, muscle isoform Proteins 0.000 description 10
- 102000004877 Insulin Human genes 0.000 description 10
- 108090001061 Insulin Proteins 0.000 description 10
- 239000001963 growth medium Substances 0.000 description 10
- 229940125396 insulin Drugs 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- 230000008569 process Effects 0.000 description 10
- 102000004169 proteins and genes Human genes 0.000 description 10
- GFAZGHREJPXDMH-UHFFFAOYSA-N 1,3-dipalmitoylglycerol Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCC GFAZGHREJPXDMH-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000003480 eluent Substances 0.000 description 9
- 239000008103 glucose Substances 0.000 description 9
- 238000000338 in vitro Methods 0.000 description 9
- 210000004185 liver Anatomy 0.000 description 9
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 9
- 230000036470 plasma concentration Effects 0.000 description 9
- 238000003757 reverse transcription PCR Methods 0.000 description 9
- 210000002966 serum Anatomy 0.000 description 9
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 9
- 206010022489 Insulin Resistance Diseases 0.000 description 8
- 230000004913 activation Effects 0.000 description 8
- 230000003078 antioxidant effect Effects 0.000 description 8
- 230000008878 coupling Effects 0.000 description 8
- 238000010168 coupling process Methods 0.000 description 8
- 238000005859 coupling reaction Methods 0.000 description 8
- WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 8
- 229940088598 enzyme Drugs 0.000 description 8
- 230000003859 lipid peroxidation Effects 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 239000002953 phosphate buffered saline Substances 0.000 description 8
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 7
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 7
- 241000699670 Mus sp. Species 0.000 description 7
- 210000004369 blood Anatomy 0.000 description 7
- 239000008280 blood Substances 0.000 description 7
- 229940125753 fibrate Drugs 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 235000021588 free fatty acids Nutrition 0.000 description 7
- 210000003494 hepatocyte Anatomy 0.000 description 7
- 230000004060 metabolic process Effects 0.000 description 7
- 150000003904 phospholipids Chemical class 0.000 description 7
- 238000012453 sprague-dawley rat model Methods 0.000 description 7
- 201000001320 Atherosclerosis Diseases 0.000 description 6
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 6
- 102100024853 Carnitine O-palmitoyltransferase 2, mitochondrial Human genes 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 description 6
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 230000002526 effect on cardiovascular system Effects 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 230000009716 hepatic expression Effects 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 239000002502 liposome Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000001890 transfection Methods 0.000 description 6
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 5
- CFCXVKYVTRNBMB-UHFFFAOYSA-N 2-sulfooxyhexadecanoic acid Chemical compound CCCCCCCCCCCCCCC(C(O)=O)OS(O)(=O)=O CFCXVKYVTRNBMB-UHFFFAOYSA-N 0.000 description 5
- VQNHXIHDDSDHMK-UHFFFAOYSA-N 6-decylsulfanylhexanoic acid Chemical compound CCCCCCCCCCSCCCCCC(O)=O VQNHXIHDDSDHMK-UHFFFAOYSA-N 0.000 description 5
- 102100022900 Actin, cytoplasmic 1 Human genes 0.000 description 5
- 108010085238 Actins Proteins 0.000 description 5
- 206010002091 Anaesthesia Diseases 0.000 description 5
- 206010003210 Arteriosclerosis Diseases 0.000 description 5
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 5
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 5
- WSMYVTOQOOLQHP-UHFFFAOYSA-N Malondialdehyde Chemical compound O=CCC=O WSMYVTOQOOLQHP-UHFFFAOYSA-N 0.000 description 5
- 208000001145 Metabolic Syndrome Diseases 0.000 description 5
- CGNLCCVKSWNSDG-UHFFFAOYSA-N SYBR Green I Chemical compound CN(C)CCCN(CCC)C1=CC(C=C2N(C3=CC=CC=C3S2)C)=C2C=CC=CC2=[N+]1C1=CC=CC=C1 CGNLCCVKSWNSDG-UHFFFAOYSA-N 0.000 description 5
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 description 5
- 230000037005 anaesthesia Effects 0.000 description 5
- 239000003963 antioxidant agent Substances 0.000 description 5
- 208000011775 arteriosclerosis disease Diseases 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- 239000001768 carboxy methyl cellulose Substances 0.000 description 5
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 5
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 5
- 239000007822 coupling agent Substances 0.000 description 5
- 210000002615 epidermis Anatomy 0.000 description 5
- 239000012894 fetal calf serum Substances 0.000 description 5
- 210000002950 fibroblast Anatomy 0.000 description 5
- 108020004445 glyceraldehyde-3-phosphate dehydrogenase Proteins 0.000 description 5
- 238000001727 in vivo Methods 0.000 description 5
- 238000001802 infusion Methods 0.000 description 5
- 210000002510 keratinocyte Anatomy 0.000 description 5
- 108090000865 liver X receptors Proteins 0.000 description 5
- 229940118019 malondialdehyde Drugs 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 230000000144 pharmacologic effect Effects 0.000 description 5
- QHZLMUACJMDIAE-UHFFFAOYSA-N 1-monopalmitoylglycerol Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)CO QHZLMUACJMDIAE-UHFFFAOYSA-N 0.000 description 4
- JADYBWICRJWGBW-UHFFFAOYSA-N 2-hydroxy-3-(tetradecanoyloxy)propyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCC JADYBWICRJWGBW-UHFFFAOYSA-N 0.000 description 4
- HRDGPYWHDRZWEK-UHFFFAOYSA-N 4-dodecylsulfanylbutanoic acid Chemical compound CCCCCCCCCCCCSCCCC(O)=O HRDGPYWHDRZWEK-UHFFFAOYSA-N 0.000 description 4
- 102000007592 Apolipoproteins Human genes 0.000 description 4
- 108010071619 Apolipoproteins Proteins 0.000 description 4
- LUQGQZIVDLUXLE-UHFFFAOYSA-N CCCCCCCCCCCCCCCC(O)=[Se] Chemical compound CCCCCCCCCCCCCCCC(O)=[Se] LUQGQZIVDLUXLE-UHFFFAOYSA-N 0.000 description 4
- JWOWFSLPFNWGEM-UHFFFAOYSA-N Cl.Cl.NC(=N)C(C)CN=NCC(C)C(N)=N Chemical compound Cl.Cl.NC(=N)C(C)CN=NCC(C)C(N)=N JWOWFSLPFNWGEM-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 4
- 108010010234 HDL Lipoproteins Proteins 0.000 description 4
- 102000015779 HDL Lipoproteins Human genes 0.000 description 4
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 4
- 239000005089 Luciferase Substances 0.000 description 4
- 101000650578 Salmonella phage P22 Regulatory protein C3 Proteins 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 102000019197 Superoxide Dismutase Human genes 0.000 description 4
- 108010012715 Superoxide dismutase Proteins 0.000 description 4
- 101001040920 Triticum aestivum Alpha-amylase inhibitor 0.28 Proteins 0.000 description 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 239000006071 cream Substances 0.000 description 4
- 230000004069 differentiation Effects 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 235000019197 fats Nutrition 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 4
- 102000004311 liver X receptors Human genes 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- PHEDXBVPIONUQT-RGYGYFBISA-N phorbol 13-acetate 12-myristate Chemical compound C([C@]1(O)C(=O)C(C)=C[C@H]1[C@@]1(O)[C@H](C)[C@H]2OC(=O)CCCCCCCCCCCCC)C(CO)=C[C@H]1[C@H]1[C@]2(OC(C)=O)C1(C)C PHEDXBVPIONUQT-RGYGYFBISA-N 0.000 description 4
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 4
- 239000013612 plasmid Substances 0.000 description 4
- 239000003755 preservative agent Substances 0.000 description 4
- 210000003491 skin Anatomy 0.000 description 4
- 210000000329 smooth muscle myocyte Anatomy 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 238000004611 spectroscopical analysis Methods 0.000 description 4
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 description 4
- FMCAFXHLMUOIGG-JTJHWIPRSA-N (2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-JTJHWIPRSA-N 0.000 description 3
- UUVKKSNCZIXQRU-MAZCIEHSSA-N 1,3-bis[(9z,12z)-octadeca-9,12-dienoxy]propan-2-ol Chemical compound CCCCC\C=C/C\C=C/CCCCCCCCOCC(O)COCCCCCCCC\C=C/C\C=C/CCCCC UUVKKSNCZIXQRU-MAZCIEHSSA-N 0.000 description 3
- QHZLMUACJMDIAE-SFHVURJKSA-N 1-hexadecanoyl-sn-glycerol Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)CO QHZLMUACJMDIAE-SFHVURJKSA-N 0.000 description 3
- RVBUGGBMJDPOST-UHFFFAOYSA-N 2-thiobarbituric acid Chemical compound O=C1CC(=O)NC(=S)N1 RVBUGGBMJDPOST-UHFFFAOYSA-N 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- 206010060378 Hyperinsulinaemia Diseases 0.000 description 3
- 238000008214 LDL Cholesterol Methods 0.000 description 3
- 241000700157 Rattus norvegicus Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 229940123464 Thiazolidinedione Drugs 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 238000003149 assay kit Methods 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 3
- 239000004327 boric acid Substances 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 210000004351 coronary vessel Anatomy 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 230000007717 exclusion Effects 0.000 description 3
- 239000012634 fragment Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000003451 hyperinsulinaemic effect Effects 0.000 description 3
- 201000008980 hyperinsulinism Diseases 0.000 description 3
- 239000000411 inducer Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 210000001616 monocyte Anatomy 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- GVOISEJVFFIGQE-YCZSINBZSA-N n-[(1r,2s,5r)-5-[methyl(propan-2-yl)amino]-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 GVOISEJVFFIGQE-YCZSINBZSA-N 0.000 description 3
- LPKMPJUBYXOSMM-UHFFFAOYSA-N o-propyl hexadecanethioate Chemical compound CCCCCCCCCCCCCCCC(=S)OCCC LPKMPJUBYXOSMM-UHFFFAOYSA-N 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 description 3
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000011669 selenium Chemical group 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 3
- 239000013598 vector Substances 0.000 description 3
- 235000019786 weight gain Nutrition 0.000 description 3
- 230000004584 weight gain Effects 0.000 description 3
- 238000011680 zucker rat Methods 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- IKRGOMHPYPQNER-UHFFFAOYSA-N 1,2,3-trihydroxynonadecane-4-thione Chemical compound CCCCCCCCCCCCCCCC(=S)C(O)C(O)CO IKRGOMHPYPQNER-UHFFFAOYSA-N 0.000 description 2
- OVIBXFDXRSJJSX-CLFAGFIQSA-N 1,3-bis[(z)-octadec-9-enoxy]propan-2-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCOCC(O)COCCCCCCCC\C=C/CCCCCCCC OVIBXFDXRSJJSX-CLFAGFIQSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- FXEDIXLHKQINFP-UHFFFAOYSA-N 12-O-tetradecanoylphorbol-13-acetate Natural products CCCCCCCCCCCCCC(=O)OC1CC2(O)C(C=C(CO)CC3(O)C2C=C(C)C3=O)C4C(C)(C)C14OC(=O)C FXEDIXLHKQINFP-UHFFFAOYSA-N 0.000 description 2
- KJJPLEZQSCZCKE-UHFFFAOYSA-N 2-aminopropane-1,3-diol Chemical compound OCC(N)CO KJJPLEZQSCZCKE-UHFFFAOYSA-N 0.000 description 2
- YZQIZXDYMIEKKK-UHFFFAOYSA-N 2-tetradecylsulfonylacetic acid Chemical compound CCCCCCCCCCCCCCS(=O)(=O)CC(O)=O YZQIZXDYMIEKKK-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- HTGMODSTGYKJDG-UHFFFAOYSA-N 9-chloro-9-phenylxanthene Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C1(Cl)C1=CC=CC=C1 HTGMODSTGYKJDG-UHFFFAOYSA-N 0.000 description 2
- CVZUPKFPOSRRSK-UHFFFAOYSA-N 9-phenylxanthen-9-ol Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C1(O)C1=CC=CC=C1 CVZUPKFPOSRRSK-UHFFFAOYSA-N 0.000 description 2
- BWKDAAFSXYPQOS-UHFFFAOYSA-N Benzaldehyde glyceryl acetal Chemical compound O1CC(O)COC1C1=CC=CC=C1 BWKDAAFSXYPQOS-UHFFFAOYSA-N 0.000 description 2
- 206010010904 Convulsion Diseases 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 238000002965 ELISA Methods 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 108010024636 Glutathione Proteins 0.000 description 2
- 108010053070 Glutathione Disulfide Proteins 0.000 description 2
- 108010063907 Glutathione Reductase Proteins 0.000 description 2
- 102100036442 Glutathione reductase, mitochondrial Human genes 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 208000035150 Hypercholesterolemia Diseases 0.000 description 2
- 238000012404 In vitro experiment Methods 0.000 description 2
- 102000000589 Interleukin-1 Human genes 0.000 description 2
- 108010002352 Interleukin-1 Proteins 0.000 description 2
- 102000004125 Interleukin-1alpha Human genes 0.000 description 2
- 108010082786 Interleukin-1alpha Proteins 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 102000016267 Leptin Human genes 0.000 description 2
- 108010092277 Leptin Proteins 0.000 description 2
- 108060001084 Luciferase Proteins 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 108020005497 Nuclear hormone receptor Proteins 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- 229930182555 Penicillin Natural products 0.000 description 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
- 241000283984 Rodentia Species 0.000 description 2
- 231100000950 SkinEthic RHE Toxicity 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 102000040945 Transcription factor Human genes 0.000 description 2
- 108091023040 Transcription factor Proteins 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- PILZICIWJRGIPF-ZCXUNETKSA-N [2-hydroxy-3-[(z)-octadec-9-enoxy]propyl] hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)COCCCCCCCC\C=C/CCCCCCCC PILZICIWJRGIPF-ZCXUNETKSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 229940053200 antiepileptics fatty acid derivative Drugs 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 235000014633 carbohydrates Nutrition 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 230000004663 cell proliferation Effects 0.000 description 2
- 230000001413 cellular effect Effects 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 238000007887 coronary angioplasty Methods 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 238000010511 deprotection reaction Methods 0.000 description 2
- 210000004207 dermis Anatomy 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 235000005911 diet Nutrition 0.000 description 2
- 230000037213 diet Effects 0.000 description 2
- 229940008099 dimethicone Drugs 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 2
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 2
- 231100000673 dose–response relationship Toxicity 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 235000020673 eicosapentaenoic acid Nutrition 0.000 description 2
- 229960005135 eicosapentaenoic acid Drugs 0.000 description 2
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000006911 enzymatic reaction Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000013604 expression vector Substances 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 229940093181 glucose injection Drugs 0.000 description 2
- 238000007446 glucose tolerance test Methods 0.000 description 2
- 229960003180 glutathione Drugs 0.000 description 2
- YPZRWBKMTBYPTK-BJDJZHNGSA-N glutathione disulfide Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@H](C(=O)NCC(O)=O)CSSC[C@@H](C(=O)NCC(O)=O)NC(=O)CC[C@H](N)C(O)=O YPZRWBKMTBYPTK-BJDJZHNGSA-N 0.000 description 2
- 208000006454 hepatitis Diseases 0.000 description 2
- 231100000283 hepatitis Toxicity 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- NRYBAZVQPHGZNS-ZSOCWYAHSA-N leptin Chemical compound O=C([C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CC(C)C)CCSC)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CS)C(O)=O NRYBAZVQPHGZNS-ZSOCWYAHSA-N 0.000 description 2
- 229940039781 leptin Drugs 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 235000015263 low fat diet Nutrition 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 2
- MTDZYWDQRFUNMZ-UHFFFAOYSA-N n-(1,3-dihydroxypropyl)hexadecanethioamide Chemical compound CCCCCCCCCCCCCCCC(=S)NC(O)CCO MTDZYWDQRFUNMZ-UHFFFAOYSA-N 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- 102000006255 nuclear receptors Human genes 0.000 description 2
- 108020004017 nuclear receptors Proteins 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- YPZRWBKMTBYPTK-UHFFFAOYSA-N oxidized gamma-L-glutamyl-L-cysteinylglycine Natural products OC(=O)C(N)CCC(=O)NC(C(=O)NCC(O)=O)CSSCC(C(=O)NCC(O)=O)NC(=O)CCC(N)C(O)=O YPZRWBKMTBYPTK-UHFFFAOYSA-N 0.000 description 2
- 229940049954 penicillin Drugs 0.000 description 2
- 229960001412 pentobarbital Drugs 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 210000002824 peroxisome Anatomy 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 230000004983 pleiotropic effect Effects 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 229920001515 polyalkylene glycol Polymers 0.000 description 2
- 230000002335 preservative effect Effects 0.000 description 2
- 230000035755 proliferation Effects 0.000 description 2
- BEKZXQKGTDVSKX-UHFFFAOYSA-N propyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCCC BEKZXQKGTDVSKX-UHFFFAOYSA-N 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 238000002731 protein assay Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical compound CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 description 2
- 238000005063 solubilization Methods 0.000 description 2
- 230000007928 solubilization Effects 0.000 description 2
- 238000002798 spectrophotometry method Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 2
- 235000000891 standard diet Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 230000035882 stress Effects 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 2
- 150000001467 thiazolidinediones Chemical class 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 description 2
- JQZIKLPHXXBMCA-UHFFFAOYSA-N triphenylmethanethiol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(S)C1=CC=CC=C1 JQZIKLPHXXBMCA-UHFFFAOYSA-N 0.000 description 2
- GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 2
- 229960001641 troglitazone Drugs 0.000 description 2
- GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 2
- DVSZKTAMJJTWFG-SKCDLICFSA-N (2e,4e,6e,8e,10e,12e)-docosa-2,4,6,8,10,12-hexaenoic acid Chemical compound CCCCCCCCC\C=C\C=C\C=C\C=C\C=C\C=C\C(O)=O DVSZKTAMJJTWFG-SKCDLICFSA-N 0.000 description 1
- DRCWOKJLSQUJPZ-DZGCQCFKSA-N (4ar,9as)-n-ethyl-1,4,9,9a-tetrahydrofluoren-4a-amine Chemical compound C1C2=CC=CC=C2[C@]2(NCC)[C@H]1CC=CC2 DRCWOKJLSQUJPZ-DZGCQCFKSA-N 0.000 description 1
- KVJHGPAAOUGYJX-UHFFFAOYSA-N 1,1,3,3-tetraethoxypropane Chemical compound CCOC(OCC)CC(OCC)OCC KVJHGPAAOUGYJX-UHFFFAOYSA-N 0.000 description 1
- OCBCKLNPFLODGO-UHFFFAOYSA-N 1,3-dioctadecoxypropan-2-ol Chemical compound CCCCCCCCCCCCCCCCCCOCC(O)COCCCCCCCCCCCCCCCCCC OCBCKLNPFLODGO-UHFFFAOYSA-N 0.000 description 1
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QYOXLKAKUAASNA-UHFFFAOYSA-N 1-bromodocosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCBr QYOXLKAKUAASNA-UHFFFAOYSA-N 0.000 description 1
- KOFZTCSTGIWCQG-UHFFFAOYSA-N 1-bromotetradecane Chemical compound CCCCCCCCCCCCCCBr KOFZTCSTGIWCQG-UHFFFAOYSA-N 0.000 description 1
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
- QLVGHFBUSGYCCG-UHFFFAOYSA-N 2-amino-n-(1-cyano-2-phenylethyl)acetamide Chemical compound NCC(=O)NC(C#N)CC1=CC=CC=C1 QLVGHFBUSGYCCG-UHFFFAOYSA-N 0.000 description 1
- ODTKANQYEKJAIH-UHFFFAOYSA-N 2-aminooxypropane-1,3-diol Chemical class NOC(CO)CO ODTKANQYEKJAIH-UHFFFAOYSA-N 0.000 description 1
- CCKCNPPGFPKBTQ-UHFFFAOYSA-N 3,4,5-trihydroxy-3-tetradecylsulfonylpentan-2-one Chemical compound C(CCCCCCCCCCCCC)S(=O)(=O)C(O)(C(O)CO)C(C)=O CCKCNPPGFPKBTQ-UHFFFAOYSA-N 0.000 description 1
- HVYWMOMLDIMFJA-UHFFFAOYSA-N 3-cholesterol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 HVYWMOMLDIMFJA-UHFFFAOYSA-N 0.000 description 1
- VBVUIWHYKCBYQY-UHFFFAOYSA-N 3-octadec-9-enylsulfanylpropanoic acid Chemical compound CCCCCCCCC=CCCCCCCCCSCCC(O)=O VBVUIWHYKCBYQY-UHFFFAOYSA-N 0.000 description 1
- GRHQDJDRGZFIPO-UHFFFAOYSA-N 4-bromobutanoic acid Chemical compound OC(=O)CCCBr GRHQDJDRGZFIPO-UHFFFAOYSA-N 0.000 description 1
- GZJLLYHBALOKEX-UHFFFAOYSA-N 6-Ketone, O18-Me-Ussuriedine Natural products CC=CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O GZJLLYHBALOKEX-UHFFFAOYSA-N 0.000 description 1
- WTNQHOJPBCMJLI-UHFFFAOYSA-N 6-decoxysulfonyloxyhexanoic acid Chemical compound CCCCCCCCCCOS(=O)(=O)OCCCCCC(O)=O WTNQHOJPBCMJLI-UHFFFAOYSA-N 0.000 description 1
- SEVGYHRSXUDVBJ-UHFFFAOYSA-N 6-decylsulfonylhexanoic acid Chemical compound CCCCCCCCCCS(=O)(=O)CCCCCC(O)=O SEVGYHRSXUDVBJ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 101150092476 ABCA1 gene Proteins 0.000 description 1
- 208000004998 Abdominal Pain Diseases 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 235000006491 Acacia senegal Nutrition 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 241001136792 Alle Species 0.000 description 1
- 102000005666 Apolipoprotein A-I Human genes 0.000 description 1
- 108010059886 Apolipoprotein A-I Proteins 0.000 description 1
- 108010056301 Apolipoprotein C-III Proteins 0.000 description 1
- 102000030169 Apolipoprotein C-III Human genes 0.000 description 1
- 208000037260 Atherosclerotic Plaque Diseases 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- 0 CC*OCC(CO*)N* Chemical compound CC*OCC(CO*)N* 0.000 description 1
- OXEKMOOZIOGZRB-UHFFFAOYSA-N CCCC(CCCCCCCC)SC(C(C(C)SC(CCC)CCCCCCCC)(SC(CCC)CCCCCCCC)C(O)C(O)CO)=O Chemical compound CCCC(CCCCCCCC)SC(C(C(C)SC(CCC)CCCCCCCC)(SC(CCC)CCCCCCCC)C(O)C(O)CO)=O OXEKMOOZIOGZRB-UHFFFAOYSA-N 0.000 description 1
- YXWXBKSFQZCKBZ-UHFFFAOYSA-N CCCCCC(CCCC)SC(C(C(CCC)SC(CCCCC)CCCC)(SC(CCCCC)CCCC)C(O)C(O)CO)=O Chemical compound CCCCCC(CCCC)SC(C(C(CCC)SC(CCCCC)CCCC)(SC(CCCCC)CCCC)C(O)C(O)CO)=O YXWXBKSFQZCKBZ-UHFFFAOYSA-N 0.000 description 1
- 108010078791 Carrier Proteins Proteins 0.000 description 1
- 206010008631 Cholera Diseases 0.000 description 1
- 108010004103 Chylomicrons Proteins 0.000 description 1
- 208000002881 Colic Diseases 0.000 description 1
- 102000029816 Collagenase Human genes 0.000 description 1
- 108060005980 Collagenase Proteins 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 102100024785 Fibroblast growth factor 2 Human genes 0.000 description 1
- 108090000379 Fibroblast growth factor 2 Proteins 0.000 description 1
- 208000002705 Glucose Intolerance Diseases 0.000 description 1
- 206010018429 Glucose tolerance impaired Diseases 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 239000012981 Hank's balanced salt solution Substances 0.000 description 1
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 101001008429 Homo sapiens Nucleobindin-2 Proteins 0.000 description 1
- 101000741797 Homo sapiens Peroxisome proliferator-activated receptor delta Proteins 0.000 description 1
- 101001074035 Homo sapiens Zinc finger protein GLI2 Proteins 0.000 description 1
- 102000004286 Hydroxymethylglutaryl CoA Reductases Human genes 0.000 description 1
- 108090000895 Hydroxymethylglutaryl CoA Reductases Proteins 0.000 description 1
- 229930182816 L-glutamine Natural products 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- 229910010084 LiAlH4 Inorganic materials 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 102000004895 Lipoproteins Human genes 0.000 description 1
- 108090001030 Lipoproteins Proteins 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 108090000301 Membrane transport proteins Proteins 0.000 description 1
- 102000003939 Membrane transport proteins Human genes 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 208000021642 Muscular disease Diseases 0.000 description 1
- 201000009623 Myopathy Diseases 0.000 description 1
- 102100022691 NACHT, LRR and PYD domains-containing protein 3 Human genes 0.000 description 1
- XJLXINKUBYWONI-NNYOXOHSSA-N NADP zwitterion Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-NNYOXOHSSA-N 0.000 description 1
- 102100027441 Nucleobindin-2 Human genes 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 102000003992 Peroxidases Human genes 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- 239000012979 RPMI medium Substances 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- 101001022386 Rattus norvegicus Leptin Proteins 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 229920002684 Sepharose Polymers 0.000 description 1
- 206010040914 Skin reaction Diseases 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 108090001109 Thermolysin Proteins 0.000 description 1
- 108090000190 Thrombin Proteins 0.000 description 1
- GLNADSQYFUSGOU-GPTZEZBUSA-J Trypan blue Chemical compound [Na+].[Na+].[Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(/N=N/C3=CC=C(C=C3C)C=3C=C(C(=CC=3)\N=N\C=3C(=CC4=CC(=CC(N)=C4C=3O)S([O-])(=O)=O)S([O-])(=O)=O)C)=C(O)C2=C1N GLNADSQYFUSGOU-GPTZEZBUSA-J 0.000 description 1
- 108090000631 Trypsin Proteins 0.000 description 1
- 102000004142 Trypsin Human genes 0.000 description 1
- 102100035558 Zinc finger protein GLI2 Human genes 0.000 description 1
- FMGMZXFNINREEZ-UHFFFAOYSA-N [2-oxo-3,4,5-tri(tetradecoxy)pentyl] hydrogen sulfate Chemical compound CCCCCCCCCCCCCCOCC(OCCCCCCCCCCCCCC)C(OCCCCCCCCCCCCCC)C(=O)COS(O)(=O)=O FMGMZXFNINREEZ-UHFFFAOYSA-N 0.000 description 1
- HMNZFMSWFCAGGW-XPWSMXQVSA-N [3-[hydroxy(2-hydroxyethoxy)phosphoryl]oxy-2-[(e)-octadec-9-enoyl]oxypropyl] (e)-octadec-9-enoate Chemical compound CCCCCCCC\C=C\CCCCCCCC(=O)OCC(COP(O)(=O)OCCO)OC(=O)CCCCCCC\C=C\CCCCCCCC HMNZFMSWFCAGGW-XPWSMXQVSA-N 0.000 description 1
- 210000000683 abdominal cavity Anatomy 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 108010022164 acetyl-LDL Proteins 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 210000000577 adipose tissue Anatomy 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 230000002225 anti-radical effect Effects 0.000 description 1
- 230000001153 anti-wrinkle effect Effects 0.000 description 1
- 210000000709 aorta Anatomy 0.000 description 1
- 208000037849 arterial hypertension Diseases 0.000 description 1
- 230000036523 atherogenesis Effects 0.000 description 1
- 230000003143 atherosclerotic effect Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 210000000941 bile Anatomy 0.000 description 1
- 239000003613 bile acid Substances 0.000 description 1
- 229940098773 bovine serum albumin Drugs 0.000 description 1
- 229960001631 carbomer Drugs 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 238000010367 cloning Methods 0.000 description 1
- 229960002424 collagenase Drugs 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- 229940125796 compound 3d Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- VTXVGVNLYGSIAR-UHFFFAOYSA-N decane-1-thiol Chemical compound CCCCCCCCCCS VTXVGVNLYGSIAR-UHFFFAOYSA-N 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000003831 deregulation Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 229960003957 dexamethasone Drugs 0.000 description 1
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 235000020669 docosahexaenoic acid Nutrition 0.000 description 1
- KAUVQQXNCKESLC-UHFFFAOYSA-N docosahexaenoic acid (DHA) Natural products COC(=O)C(C)NOCC1=CC=CC=C1 KAUVQQXNCKESLC-UHFFFAOYSA-N 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- 210000000981 epithelium Anatomy 0.000 description 1
- XIMFCGSNSKXPBO-UHFFFAOYSA-N ethyl 2-bromobutanoate Chemical compound CCOC(=O)C(Br)CC XIMFCGSNSKXPBO-UHFFFAOYSA-N 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 235000020977 fat-enriched diet Nutrition 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000001506 fluorescence spectroscopy Methods 0.000 description 1
- 210000000497 foam cell Anatomy 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- IZHVBANLECCAGF-UHFFFAOYSA-N glyceryl distearate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 description 1
- ZJYYHGLJYGJLLN-UHFFFAOYSA-N guanidinium thiocyanate Chemical compound SC#N.NC(N)=N ZJYYHGLJYGJLLN-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 229960002897 heparin Drugs 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 230000013632 homeostatic process Effects 0.000 description 1
- 229960000890 hydrocortisone Drugs 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
- 229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
- 201000001421 hyperglycemia Diseases 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 208000006575 hypertriglyceridemia Diseases 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 230000001976 improved effect Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 229940090044 injection Drugs 0.000 description 1
- 230000006362 insulin response pathway Effects 0.000 description 1
- 238000001361 intraarterial administration Methods 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 238000012886 linear function Methods 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 230000037356 lipid metabolism Effects 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 210000000191 macrophage derived foam cell Anatomy 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 208000030159 metabolic disease Diseases 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 239000003226 mitogen Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002759 monoacylglycerols Chemical class 0.000 description 1
- 210000005087 mononuclear cell Anatomy 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 230000003387 muscular Effects 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229940100460 peg-100 stearate Drugs 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 108040007629 peroxidase activity proteins Proteins 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 150000007965 phenolic acids Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 210000003240 portal vein Anatomy 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 238000007420 radioactive assay Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 210000003786 sclera Anatomy 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000035483 skin reaction Effects 0.000 description 1
- 231100000430 skin reaction Toxicity 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 1
- 229940032094 squalane Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000002103 transcriptional effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- 230000010415 tropism Effects 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 238000005199 ultracentrifugation Methods 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 210000004509 vascular smooth muscle cell Anatomy 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/20—Esters of monothiocarboxylic acids
- C07C327/28—Esters of monothiocarboxylic acids having sulfur atoms of esterified thiocarboxyl groups bound to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Child & Adolescent Psychology (AREA)
- Vascular Medicine (AREA)
- Dermatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0110645 | 2001-08-09 | ||
| FR0110645A FR2828487B1 (fr) | 2001-08-09 | 2001-08-09 | Nouveaux composes derives d'acides gras, preparation et utilisations |
| PCT/FR2002/002831 WO2003014073A1 (fr) | 2001-08-09 | 2002-08-08 | Composes derives d'acides gras preparation et utilisations |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60222596D1 DE60222596D1 (de) | 2007-10-31 |
| DE60222596T2 true DE60222596T2 (de) | 2008-07-24 |
Family
ID=8866413
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60222596T Expired - Fee Related DE60222596T2 (de) | 2001-08-09 | 2002-08-08 | Fettsäureverbindungen und deren herstellung und verwendungen |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US7375135B2 (enExample) |
| EP (1) | EP1673338B1 (enExample) |
| JP (1) | JP2004537595A (enExample) |
| AT (1) | ATE373638T1 (enExample) |
| AU (1) | AU2002342968B2 (enExample) |
| CA (1) | CA2456288A1 (enExample) |
| CY (1) | CY1107806T1 (enExample) |
| DE (1) | DE60222596T2 (enExample) |
| DK (1) | DK1673338T3 (enExample) |
| ES (1) | ES2292824T3 (enExample) |
| FR (1) | FR2828487B1 (enExample) |
| PT (1) | PT1673338E (enExample) |
| WO (1) | WO2003014073A1 (enExample) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NO328803B1 (no) | 2000-03-03 | 2010-05-18 | Thia Medica | Nye fettsyreanaloger |
| FR2828487B1 (fr) | 2001-08-09 | 2005-05-27 | Genfit S A | Nouveaux composes derives d'acides gras, preparation et utilisations |
| AU2003278602C1 (en) | 2002-06-20 | 2010-08-12 | Pronova Biopharma Norge As | Sulfur-containing phospholipid derivatives |
| FR2850650B1 (fr) * | 2003-01-31 | 2005-03-25 | Genfit S A | Utilisation therapeutique d'acylglycerols et de leurs analogues azotes et sulfures |
| FR2850869B1 (fr) * | 2003-02-12 | 2005-03-25 | Genfit S A | Utilisations d'aminopropanediols acyles et de leurs analogues azotes et sulfures |
| FR2850870B1 (fr) * | 2003-02-12 | 2006-07-28 | Genfit S A | Utilisation therapeutique de glycerols acyles et de leurs analogues azotes et sulfures |
| FR2853834B1 (fr) * | 2003-04-17 | 2008-08-15 | Vincience | Composition cosmetique ou pharmaceutique comprenant l'association d'au moins un diacyglycerol et d'au moins un alcool gras |
| FR2858216B1 (fr) * | 2003-07-31 | 2008-04-04 | Oreal | Composition contenant un 2-thioacetamide, son utilisation pour stimuler la pousse des fibres keratiniques et/ou freiner leur chute |
| RU2261705C1 (ru) * | 2004-01-29 | 2005-10-10 | Медведев Илья Николаевич | Способ лечения тромбоцитопатии при метаболическом синдроме |
| JP2008506773A (ja) * | 2004-07-19 | 2008-03-06 | ティア メディカ アクスイェ セルスカプ | タンパク質材料と非酸化性脂肪酸体を含む組成物 |
| RU2394598C2 (ru) * | 2004-07-19 | 2010-07-20 | Тиа Медика Ас | Композиция, содержащая белковый материал и соединения, содержащие неокисляющиеся структурные элементы жирных кислот |
| DE102006019907A1 (de) * | 2006-04-28 | 2007-10-31 | Müller-Enoch, Dieter, Prof. Dr. | Verwendung von substituierten Glycerinderivaten zur Herstellung einer pharmazeutischen Zubereitung |
| DE102007051338A1 (de) * | 2007-10-26 | 2009-04-30 | Müller-Enoch, Dieter, Prof. Dr. | Verwendung von substituierten Glycerinderivaten zur Herstellung einer pharmazeutischen Zubereitung zur Behandlung und zur Vorbeugung von Dyslipidämien |
| WO2009061208A1 (en) | 2007-11-09 | 2009-05-14 | Pronova Biopharma Norge As | Lipid compounds for use in cosmetic products, as food supplement or as a medicament |
| EP2147910A1 (en) | 2008-07-15 | 2010-01-27 | Pronova BioPharma Norge AS | Novel lipid compounds |
| KR101783817B1 (ko) | 2009-05-08 | 2017-10-23 | 프로노바 바이오파마 너지 에이에스 | 심혈관 질병, 대사 질병, 및 염증성 질환 분야관련 질병의 치료를 위한 다중 불포화 지방산 |
| WO2010149170A1 (en) * | 2009-06-24 | 2010-12-29 | Københavns Universitet | Treatment of insulin resistance and obesity by stimulating glp-1 release |
| SG10201509127YA (en) | 2010-11-05 | 2015-12-30 | Pronova Biopharma Norge As | Methods of treatment using lipid compounds |
| US11351139B2 (en) | 2013-02-28 | 2022-06-07 | Basf As | Composition comprising a lipid compound, a triglyceride, and a surfactant, and methods of using the same |
| WO2014140934A2 (en) | 2013-03-11 | 2014-09-18 | Life Science Nutrition As | Natural lipids containing non-oxidizable fatty acids |
| AU2014228387B2 (en) | 2013-03-11 | 2016-09-01 | Sciadonics, Inc. | Lipid compositions containing bioactive fatty acids |
| US9744542B2 (en) | 2013-07-29 | 2017-08-29 | Apeel Technology, Inc. | Agricultural skin grafting |
| AU2016256552B2 (en) | 2015-04-28 | 2021-04-01 | Pronova Biopharma Norge As | Use of structurally enhanced fatty acids containing sulphur for preventing and/or treating non-alcoholic steatohepatitis |
| JP7157531B2 (ja) | 2015-05-20 | 2022-10-20 | アピール テクノロジー，インコーポレイテッド | 植物抽出物組成物およびその調製方法 |
| EP4793326A2 (en) | 2015-09-16 | 2026-08-19 | Apeel Technology, Inc. | Method for forming a protective coating by applying fatty acid glyceride compounds to a surface |
| FR3044556B1 (fr) | 2015-12-08 | 2019-10-18 | Pierre Fabre Dermo-Cosmetique | Utilisation de diglyceride 1,3 dans une composition topique pour lutter contre la fragilisation de la barriere cutanee |
| EP3386303B1 (en) | 2015-12-10 | 2020-03-11 | Apeel Technology, Inc. | Process for depolymerising cutin |
| TWI731928B (zh) | 2016-01-26 | 2021-07-01 | 美商ａＰＥＥＬ科技公司 | 製備及保存經消毒產品之方法 |
| WO2018094269A1 (en) | 2016-11-17 | 2018-05-24 | Apeel Technology, Inc. | Compositions formed from plant extracts and methods of preparation thereof |
| AU2018354090B2 (en) | 2017-10-23 | 2024-10-24 | Epitracker, Inc. | Fatty acid analogs and their use in the treatment of conditions related to metabolic syndrome |
| IL308604B2 (en) | 2017-12-06 | 2025-08-01 | Basf As | Fatty acid derivatives for treating non-alcoholic steatohepatitis |
| AU2019271067B2 (en) * | 2018-05-16 | 2023-08-03 | Epitracker, Inc. | Compositions and methods for diagnosis and treatment of conditions related to aging |
| EP3796976A4 (en) | 2018-05-23 | 2022-03-30 | Epitracker, Inc. | COMPOSITIONS AND METHODS FOR THE DIAGNOSIS AND TREATMENT OF CONDITIONS RELATED TO LONGEVITY AND QUALITY OF AGING |
| US12245605B2 (en) | 2018-09-05 | 2025-03-11 | Apeel Technology, Inc. | Compounds and formulations for protective coatings |
| EP3908374A4 (en) | 2019-01-09 | 2022-12-28 | Epitracker, Inc. | COMPOSITIONS AND METHODS FOR DIAGNOSIS AND TREATMENT OF NEURODEGENERATIVE DISEASES |
| JP7404382B2 (ja) | 2019-03-04 | 2023-12-25 | エピトラッカー インコーポレイテッド | 脂肪酸アナログ、ならびに認知機能障害、行動症状および慢性疼痛の処置におけるそれらの使用 |
| EP4114181A1 (en) | 2020-03-04 | 2023-01-11 | Apeel Technology, Inc. | Coated agricultural products and corresponding methods |
| IL302360B2 (en) | 2020-10-30 | 2025-01-01 | Apeel Tech Inc | Preparations and methods of their preparation |
| US12408680B2 (en) | 2021-09-08 | 2025-09-09 | Apeel Technology, Inc. | Compounds and formulations for protective coatings |
| JP2024539823A (ja) | 2021-11-03 | 2024-10-31 | エピトラッカー インコーポレイテッド | 老化の質および寿命に関係する状態の治療のためのペンタデカノイルカルニチン |
| US12133863B1 (en) * | 2023-06-07 | 2024-11-05 | King Saud University | Green synthesis of silver nanoparticles encapsulated in a nanostructured lipid carrier |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2010154A (en) * | 1933-06-27 | 1935-08-06 | Herbert S Kreighbaum | Ether acid ester of polyhydric alcohols |
| GB1271179A (en) * | 1969-06-11 | 1972-04-19 | Mitsubishi Petrochemical Co | Polyolefin resin composition |
| JPS5738616B2 (enExample) * | 1974-06-19 | 1982-08-17 | ||
| US4134770A (en) * | 1976-09-22 | 1979-01-16 | Mitsubishi Paper Mills, Ltd. | Gelatin-containing photographic layer incorporated with hardener |
| IL59407A (en) * | 1979-03-06 | 1983-12-30 | Sanofi Sa | Di-n-propylacetic acid diesters of glycerol,their preparation and pharmaceutical compositions containing them |
| JPS5782573A (en) * | 1980-11-05 | 1982-05-24 | Matsumoto Yushi Seiyaku Kk | Smoothening treatment agent for thermoplastic synthetic fiber |
| GB8813012D0 (en) | 1988-06-02 | 1988-07-06 | Norsk Hydro As | Non-b-oxidizable fatty acid analogues to reduce concentration of cholesterol & triglycerides in blood of mammals |
| WO1991003542A1 (fr) * | 1989-09-11 | 1991-03-21 | Kao Corporation | Composition de blanchiment |
| NO952796D0 (no) | 1995-07-14 | 1995-07-14 | Rolf Berge | Fettsyre analoger med ikkeoksyderbart B-sete, fremstilling og anvendelse i krapeutiske preparater |
| US5885595A (en) * | 1996-05-13 | 1999-03-23 | Elizabeth Arden Co., Division Of Conopco, Inc. | Cosmetic composition with a retinol fatty acid ester |
| AU9036998A (en) | 1997-08-29 | 1999-03-16 | Johns Hopkins University, The | Antimicrobial compounds |
| JP2000169443A (ja) | 1998-10-02 | 2000-06-20 | Sankyo Co Ltd | ジチオ―ル誘導体 |
| US6117904A (en) * | 1999-09-03 | 2000-09-12 | Murphy; Donald M. | Treatment of pruritus |
| FR2828487B1 (fr) | 2001-08-09 | 2005-05-27 | Genfit S A | Nouveaux composes derives d'acides gras, preparation et utilisations |
| AU2003278602C1 (en) | 2002-06-20 | 2010-08-12 | Pronova Biopharma Norge As | Sulfur-containing phospholipid derivatives |
| FR2850650B1 (fr) | 2003-01-31 | 2005-03-25 | Genfit S A | Utilisation therapeutique d'acylglycerols et de leurs analogues azotes et sulfures |
| FR2850969B1 (fr) | 2003-02-12 | 2005-03-25 | Genfit S A | Aminopropanediols acyles et analogues et leurs utilisations therapeutiques |
| FR2850869B1 (fr) | 2003-02-12 | 2005-03-25 | Genfit S A | Utilisations d'aminopropanediols acyles et de leurs analogues azotes et sulfures |
| FR2850870B1 (fr) | 2003-02-12 | 2006-07-28 | Genfit S A | Utilisation therapeutique de glycerols acyles et de leurs analogues azotes et sulfures |
-
2001
- 2001-08-09 FR FR0110645A patent/FR2828487B1/fr not_active Expired - Fee Related
-
2002
- 2002-08-08 WO PCT/FR2002/002831 patent/WO2003014073A1/fr not_active Ceased
- 2002-08-08 DE DE60222596T patent/DE60222596T2/de not_active Expired - Fee Related
- 2002-08-08 US US10/484,350 patent/US7375135B2/en not_active Expired - Fee Related
- 2002-08-08 AU AU2002342968A patent/AU2002342968B2/en not_active Ceased
- 2002-08-08 PT PT02779622T patent/PT1673338E/pt unknown
- 2002-08-08 ES ES02779622T patent/ES2292824T3/es not_active Expired - Lifetime
- 2002-08-08 JP JP2003519023A patent/JP2004537595A/ja active Pending
- 2002-08-08 EP EP02779622A patent/EP1673338B1/fr not_active Expired - Lifetime
- 2002-08-08 AT AT02779622T patent/ATE373638T1/de not_active IP Right Cessation
- 2002-08-08 CA CA002456288A patent/CA2456288A1/fr not_active Abandoned
- 2002-08-08 DK DK02779622T patent/DK1673338T3/da active
-
2007
- 2007-11-16 CY CY20071101482T patent/CY1107806T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US7375135B2 (en) | 2008-05-20 |
| CY1107806T1 (el) | 2013-06-19 |
| EP1673338A1 (fr) | 2006-06-28 |
| ATE373638T1 (de) | 2007-10-15 |
| CA2456288A1 (fr) | 2003-02-20 |
| WO2003014073A1 (fr) | 2003-02-20 |
| ES2292824T3 (es) | 2008-03-16 |
| EP1673338B1 (fr) | 2007-09-19 |
| DE60222596D1 (de) | 2007-10-31 |
| DK1673338T3 (da) | 2008-01-14 |
| AU2002342968B2 (en) | 2008-05-15 |
| US20040192908A1 (en) | 2004-09-30 |
| PT1673338E (pt) | 2007-12-12 |
| FR2828487A1 (fr) | 2003-02-14 |
| FR2828487B1 (fr) | 2005-05-27 |
| JP2004537595A (ja) | 2004-12-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP1673338B1 (fr) | Composes derives d'acides gras preparation et utilisations | |
| DE69528291T2 (de) | Nicht-beta oxidierbare fettsäureanaloge,deren verwendung als therapeutisch wirksame medikamente sowie deren herstellung | |
| US5508275A (en) | Lipid-selective antioxidants and their preparation and use | |
| DE68910386T2 (de) | Nicht-beta-oxidierbare Fettsäure-Analoge, die die Blutkonzentration von Cholesterin und Triglyceriden bei Säugetieren senken. | |
| DE60314420T2 (de) | Zusammensetzung auf grundlage substituierter 1,3-diphenylprop-2-en-1-on-derivaten, deren herstellung und verwendungen | |
| DE69829966T2 (de) | Ein monoether von probucol und methoden zur hemmung der vcam-1 expression | |
| DE69910560T2 (de) | Wasserlöslische prodrugs von 2,6-diisopropylphenol-analoga | |
| US5874468A (en) | Brain targeted low molecular weight hydrophobic antioxidant compounds | |
| DE60020873T2 (de) | Nervonsäurederivate,ihre herstellung und anwendung | |
| KR20020072296A (ko) | 특이 구조를 가진 일 군의 항암 화합물 및 그 제조방법 | |
| EP1701938A1 (fr) | Composes derives de 1,3-diphenylprop-2-en-1-one, preparation et utilisations | |
| US20060035977A1 (en) | Uses of acylated aminopropanediols and sulphur and nitrogen analogues of same f | |
| US7799830B2 (en) | Cinnamic acid dimers, their preparation and the use thereof for treating neurodegenerative disease | |
| EP0737476A2 (en) | A pharmaceutical preparation containing a 3-(2H)-furanone derivative for prevention and/or treatment of cataracts | |
| EP1587508A1 (fr) | Utilisation therapeutique d 'acylglycerols et de leurs analogues azotes et sulfures |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |