CA2240183A1 - Composes de bases de schiff contenant du cobalt - Google Patents
Composes de bases de schiff contenant du cobalt Download PDFInfo
- Publication number
- CA2240183A1 CA2240183A1 CA002240183A CA2240183A CA2240183A1 CA 2240183 A1 CA2240183 A1 CA 2240183A1 CA 002240183 A CA002240183 A CA 002240183A CA 2240183 A CA2240183 A CA 2240183A CA 2240183 A1 CA2240183 A1 CA 2240183A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- alcohol
- amine
- cobalt
- compound
- 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.)
- Abandoned
Links
- 229910017052 cobalt Inorganic materials 0.000 title abstract description 38
- 239000010941 cobalt Substances 0.000 title abstract description 38
- -1 Cobalt schiff base compounds Chemical class 0.000 title description 24
- 239000002262 Schiff base Substances 0.000 title description 2
- 150000001869 cobalt compounds Chemical class 0.000 claims abstract description 111
- 150000001875 compounds Chemical class 0.000 claims abstract description 70
- 102000004190 Enzymes Human genes 0.000 claims abstract description 66
- 108090000790 Enzymes Proteins 0.000 claims abstract description 66
- 108090000765 processed proteins & peptides Proteins 0.000 claims abstract description 64
- 230000008685 targeting Effects 0.000 claims abstract description 53
- 150000007523 nucleic acids Chemical class 0.000 claims abstract description 41
- 108020004707 nucleic acids Proteins 0.000 claims abstract description 40
- 102000039446 nucleic acids Human genes 0.000 claims abstract description 40
- 102000004196 processed proteins & peptides Human genes 0.000 claims abstract description 40
- 229920001184 polypeptide Polymers 0.000 claims abstract description 34
- 101710185494 Zinc finger protein Proteins 0.000 claims abstract description 16
- 102100023597 Zinc finger protein 816 Human genes 0.000 claims abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 108090000623 proteins and genes Proteins 0.000 claims description 91
- 102000004169 proteins and genes Human genes 0.000 claims description 90
- 239000003446 ligand Substances 0.000 claims description 73
- 125000000217 alkyl group Chemical group 0.000 claims description 41
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 claims description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 30
- 150000001412 amines Chemical class 0.000 claims description 24
- 150000007524 organic acids Chemical class 0.000 claims description 23
- 125000005233 alkylalcohol group Chemical group 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 22
- 230000002209 hydrophobic effect Effects 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 230000002401 inhibitory effect Effects 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 19
- 150000003973 alkyl amines Chemical class 0.000 claims 16
- 229940088598 enzyme Drugs 0.000 abstract description 64
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract description 38
- 108090000190 Thrombin Proteins 0.000 abstract description 27
- 229960004072 thrombin Drugs 0.000 abstract description 27
- 125000004429 atom Chemical group 0.000 abstract description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 5
- 125000004430 oxygen atom Chemical group O* 0.000 abstract description 2
- 235000018102 proteins Nutrition 0.000 description 72
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 52
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 239000003112 inhibitor Substances 0.000 description 41
- 239000000243 solution Substances 0.000 description 39
- 235000013495 cobalt Nutrition 0.000 description 37
- 102000003846 Carbonic anhydrases Human genes 0.000 description 35
- 108090000209 Carbonic anhydrases Proteins 0.000 description 35
- 230000027455 binding Effects 0.000 description 34
- 235000014304 histidine Nutrition 0.000 description 33
- 230000005764 inhibitory process Effects 0.000 description 30
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 28
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 23
- 125000003729 nucleotide group Chemical group 0.000 description 20
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 18
- 230000000694 effects Effects 0.000 description 18
- 239000002773 nucleotide Substances 0.000 description 17
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 17
- 150000001413 amino acids Chemical class 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- 239000007983 Tris buffer Substances 0.000 description 15
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 15
- 125000003277 amino group Chemical group 0.000 description 15
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 15
- 229910052725 zinc Inorganic materials 0.000 description 15
- 239000011701 zinc Substances 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 239000002585 base Substances 0.000 description 14
- 125000000487 histidyl group Chemical group [H]N([H])C(C(=O)O*)C([H])([H])C1=C([H])N([H])C([H])=N1 0.000 description 14
- 239000000758 substrate Substances 0.000 description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- 239000000523 sample Substances 0.000 description 13
- 125000000524 functional group Chemical group 0.000 description 12
- 235000001014 amino acid Nutrition 0.000 description 11
- 229940024606 amino acid Drugs 0.000 description 11
- 239000000872 buffer Substances 0.000 description 11
- 239000000460 chlorine Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 229940088597 hormone Drugs 0.000 description 10
- 239000005556 hormone Substances 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 230000004071 biological effect Effects 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000005859 coupling reaction Methods 0.000 description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
- 238000011534 incubation Methods 0.000 description 9
- 230000003993 interaction Effects 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000004475 Arginine Substances 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- 108010054964 H-hexahydrotyrosyl-alanyl-arginine-4-nitroanilide Proteins 0.000 description 8
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 8
- 235000009697 arginine Nutrition 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 8
- 150000004700 cobalt complex Chemical class 0.000 description 8
- 230000008878 coupling Effects 0.000 description 8
- 238000010168 coupling process Methods 0.000 description 8
- 230000003247 decreasing effect Effects 0.000 description 8
- 230000007062 hydrolysis Effects 0.000 description 8
- 238000006460 hydrolysis reaction Methods 0.000 description 8
- 125000005647 linker group Chemical group 0.000 description 8
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 7
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical class CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 150000001720 carbohydrates Chemical class 0.000 description 7
- 235000014633 carbohydrates Nutrition 0.000 description 7
- 235000018417 cysteine Nutrition 0.000 description 7
- 230000002255 enzymatic effect Effects 0.000 description 7
- 230000003647 oxidation Effects 0.000 description 7
- 238000007254 oxidation reaction Methods 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 230000009467 reduction Effects 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 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 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 239000007995 HEPES buffer Substances 0.000 description 6
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 6
- 108091005804 Peptidases Proteins 0.000 description 6
- 239000004365 Protease Substances 0.000 description 6
- 108090001109 Thermolysin Proteins 0.000 description 6
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 6
- 238000003556 assay Methods 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 6
- 230000002779 inactivation Effects 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 108091034117 Oligonucleotide Proteins 0.000 description 5
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 5
- 238000002835 absorbance Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 150000002411 histidines Chemical class 0.000 description 5
- 150000002632 lipids Chemical class 0.000 description 5
- 230000007246 mechanism Effects 0.000 description 5
- 102000044158 nucleic acid binding protein Human genes 0.000 description 5
- 108700020942 nucleic acid binding protein Proteins 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- WYEPBHZLDUPIOD-UHFFFAOYSA-N 4,6-dioxoheptanoic acid Chemical compound CC(=O)CC(=O)CCC(O)=O WYEPBHZLDUPIOD-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 4
- 206010010904 Convulsion Diseases 0.000 description 4
- 108091023040 Transcription factor Proteins 0.000 description 4
- 102000040945 Transcription factor Human genes 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 125000003282 alkyl amino group Chemical group 0.000 description 4
- 125000000539 amino acid group Chemical group 0.000 description 4
- 238000013459 approach Methods 0.000 description 4
- 239000001110 calcium chloride Substances 0.000 description 4
- 235000011148 calcium chloride Nutrition 0.000 description 4
- 229910001628 calcium chloride Inorganic materials 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 238000002523 gelfiltration Methods 0.000 description 4
- 125000002883 imidazolyl group Chemical group 0.000 description 4
- 235000006109 methionine Nutrition 0.000 description 4
- GWUSZQUVEVMBPI-UHFFFAOYSA-N nimetazepam Chemical compound N=1CC(=O)N(C)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1 GWUSZQUVEVMBPI-UHFFFAOYSA-N 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 102000005962 receptors Human genes 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 description 4
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 3
- 239000005695 Ammonium acetate Substances 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000283690 Bos taurus Species 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 3
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 3
- 102000010750 Metalloproteins Human genes 0.000 description 3
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
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- 108010022999 Serine Proteases Proteins 0.000 description 3
- 102000012479 Serine Proteases Human genes 0.000 description 3
- 235000019257 ammonium acetate Nutrition 0.000 description 3
- 229940043376 ammonium acetate Drugs 0.000 description 3
- 230000000845 anti-microbial effect Effects 0.000 description 3
- 230000000840 anti-viral effect Effects 0.000 description 3
- 229940006133 antiglaucoma drug and miotics carbonic anhydrase inhibitors Drugs 0.000 description 3
- 239000004599 antimicrobial Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000003489 carbonate dehydratase inhibitor Substances 0.000 description 3
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- 239000003795 chemical substances by application Substances 0.000 description 3
- 150000001868 cobalt Chemical group 0.000 description 3
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- DMSZORWOGDLWGN-UHFFFAOYSA-N ctk1a3526 Chemical compound NP(N)(N)=O DMSZORWOGDLWGN-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- NAGJZTKCGNOGPW-UHFFFAOYSA-K dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [O-]P([O-])([S-])=S NAGJZTKCGNOGPW-UHFFFAOYSA-K 0.000 description 3
- 239000002532 enzyme inhibitor Substances 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 229910021645 metal ion Inorganic materials 0.000 description 3
- 229930182817 methionine Natural products 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000000816 peptidomimetic Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000002441 reversible effect Effects 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 3
- UHPQFNXOFFPHJW-UHFFFAOYSA-N (4-methylphenyl)-phenylmethanamine Chemical compound C1=CC(C)=CC=C1C(N)C1=CC=CC=C1 UHPQFNXOFFPHJW-UHFFFAOYSA-N 0.000 description 2
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- 150000003254 radicals Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 230000007363 regulatory process Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000001177 retroviral effect Effects 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 239000013037 reversible inhibitor Substances 0.000 description 1
- 239000002336 ribonucleotide Substances 0.000 description 1
- 125000002652 ribonucleotide group Chemical group 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- SQVRNKJHWKZAKO-OQPLDHBCSA-N sialic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)OC1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-OQPLDHBCSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229940037128 systemic glucocorticoids Drugs 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 229960003604 testosterone Drugs 0.000 description 1
- 229940126585 therapeutic drug Drugs 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 229930192474 thiophene Chemical group 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 125000000430 tryptophan group Chemical group [H]N([H])C(C(=O)O*)C([H])([H])C1=C([H])N([H])C2=C([H])C([H])=C([H])C([H])=C12 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 229960003726 vasopressin Drugs 0.000 description 1
- FEPMHVLSLDOMQC-UHFFFAOYSA-N virginiamycin-S1 Natural products CC1OC(=O)C(C=2C=CC=CC=2)NC(=O)C2CC(=O)CCN2C(=O)C(CC=2C=CC=CC=2)N(C)C(=O)C2CCCN2C(=O)C(CC)NC(=O)C1NC(=O)C1=NC=CC=C1O FEPMHVLSLDOMQC-UHFFFAOYSA-N 0.000 description 1
- 239000011534 wash buffer Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000012608 weak cation exchange resin Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/06—Cobalt compounds
- C07F15/065—Cobalt compounds without a metal-carbon linkage
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Engineering & Computer Science (AREA)
- Virology (AREA)
- Peptides Or Proteins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Detergent Compositions (AREA)
Abstract
L'invention se rapporte à des composés de cobalt dans lesquels le cobalt divalent ou trivalent est complexé avec des bases de Schiff tétradentées solubles dans l'eau. Les bases de Schiff tétradentées contiennent de préférence deux atomes d'azote et deux atomes d'oxygène jouant le rôle d'atomes de coordination. Ces composés peuvent contenir des fractions de ciblage de polypeptides ou d'acide nucléique et peuvent être utilisés pour inhiber des enzymes telles que la thrombine et des protéines à doigts de zinc.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/570,761 US6008190A (en) | 1994-12-15 | 1995-12-12 | Cobalt Schiff base compounds |
US08/570,761 | 1995-12-12 |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2240183A1 true CA2240183A1 (fr) | 1997-06-19 |
Family
ID=24280957
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002240183A Abandoned CA2240183A1 (fr) | 1995-12-12 | 1996-12-12 | Composes de bases de schiff contenant du cobalt |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP1021176A4 (fr) |
JP (1) | JP2001503376A (fr) |
AU (1) | AU720841B2 (fr) |
CA (1) | CA2240183A1 (fr) |
IL (1) | IL124844A0 (fr) |
WO (1) | WO1997021431A1 (fr) |
Families Citing this family (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6008190A (en) * | 1994-12-15 | 1999-12-28 | California Institute Of Technology | Cobalt Schiff base compounds |
US6713045B1 (en) | 1995-06-02 | 2004-03-30 | Research Corporation Technologies, Inc. | Targeted magnetic resonance imaging agents for the detection of physiological processes |
US6770261B2 (en) | 1995-06-02 | 2004-08-03 | Research Corporation Technologies | Magnetic resonance imaging agents for the detection of physiological agents |
US5900228A (en) | 1996-07-31 | 1999-05-04 | California Institute Of Technology | Bifunctional detection agents having a polymer covalently linked to an MRI agent and an optical dye |
US6713046B1 (en) | 1997-10-27 | 2004-03-30 | Research Corporation Technologies | Magnetic resonance imaging agents for the delivery of therapeutic agents |
JP2001521011A (ja) * | 1997-10-27 | 2001-11-06 | カリフォルニア・インスティテュート・オブ・テクノロジー | 治療成分送達のための磁気共鳴イメージング剤 |
AU752812B2 (en) * | 1997-11-17 | 2002-10-03 | Research Corporation Technologies, Inc. | Magnetic resonance imaging agents for the detection of physiological agents |
AUPQ180499A0 (en) | 1999-07-23 | 1999-08-19 | Biomolecular Research Institute Limited | Beta-amyloid peptide inhibitors |
US6673333B1 (en) | 2000-05-04 | 2004-01-06 | Research Corporation Technologies, Inc. | Functional MRI agents for cancer imaging |
AU2001276956A1 (en) | 2000-07-17 | 2002-01-30 | California Institute Of Technology | Macrocyclic mri contrast agents |
WO2002028441A2 (fr) | 2000-10-04 | 2002-04-11 | California Institute Of Technology | Agents d'imagerie par resonance magnetique pour la detection et l'etiquetage in vivo de depots amyloides |
US7118916B2 (en) * | 2002-10-21 | 2006-10-10 | Lifescan, Inc. | Method of reducing analysis time of endpoint-type reaction profiles |
US8951400B2 (en) | 2007-10-17 | 2015-02-10 | Ohmx Corporation | Chemistry used in biosensors |
EP2210268A4 (fr) | 2007-10-17 | 2012-02-15 | Ohmx Corp | Chimie novatrice utilisée dans des biocapteurs |
WO2011146143A2 (fr) | 2010-05-21 | 2011-11-24 | Ohmx Corporation | Détection du cancer par dosage de l'activité enzymatique du psa |
EP2773650A1 (fr) | 2011-11-04 | 2014-09-10 | Ohmx Corporation | Nouvelle chimie utilisée dans des biocapteurs |
EP3047274A2 (fr) | 2013-09-20 | 2016-07-27 | Ohmx Corporation | Activité enzymatique du psa : nouveau biomarqueur pour évaluer l'agressivité du cancer de la prostate |
CN103936618B (zh) * | 2014-04-16 | 2016-04-20 | 济南大学 | 手性四齿氮锌配合物及其制备方法和应用 |
JP7184282B2 (ja) * | 2018-12-13 | 2022-12-06 | 株式会社Ihi | 金属アセン錯体を含む薬剤送達システム |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4451270A (en) * | 1982-06-30 | 1984-05-29 | Bend Research, Inc. | Absorption process for producing oxygen and nitrogen and solution therefor |
US4514522A (en) * | 1984-07-27 | 1985-04-30 | University Patents, Inc. | Oxygen sorbent |
US5106841A (en) * | 1986-05-13 | 1992-04-21 | Chai-Tech Corporation | Antiviral compositions and method for their use |
US4866053A (en) * | 1986-05-13 | 1989-09-12 | Chai-Tech Corporation | Method of treating a burn employing a metallo-organic cobalt compound |
US5756491A (en) * | 1986-05-13 | 1998-05-26 | Chai-Tech Corporation | Antiviral cobalt-organic compounds |
US5142076A (en) * | 1986-05-13 | 1992-08-25 | Chai-Tech Corporation | Metallo-organic salt compounds and pharmaceutical uses thereof |
US4948506A (en) * | 1986-07-07 | 1990-08-14 | Bend Research, Inc. | Physicochemically functional ultrathin films by interfacial polymerization |
US4735634A (en) * | 1986-08-28 | 1988-04-05 | Air Products And Chemicals, Inc. | Pillared cobalt complexes for oxygen separation |
AU5871494A (en) * | 1992-12-15 | 1994-07-04 | Redox Pharmaceutical Corporation | Antiviral compositions and method for their use |
US6008190A (en) * | 1994-12-15 | 1999-12-28 | California Institute Of Technology | Cobalt Schiff base compounds |
-
1996
- 1996-12-12 EP EP96944811A patent/EP1021176A4/fr not_active Withdrawn
- 1996-12-12 AU AU13336/97A patent/AU720841B2/en not_active Ceased
- 1996-12-12 WO PCT/US1996/019900 patent/WO1997021431A1/fr not_active Application Discontinuation
- 1996-12-12 IL IL12484496A patent/IL124844A0/xx unknown
- 1996-12-12 CA CA002240183A patent/CA2240183A1/fr not_active Abandoned
- 1996-12-12 JP JP52223997A patent/JP2001503376A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
AU1333697A (en) | 1997-07-03 |
WO1997021431A1 (fr) | 1997-06-19 |
IL124844A0 (en) | 1999-01-26 |
EP1021176A1 (fr) | 2000-07-26 |
EP1021176A4 (fr) | 2001-04-11 |
JP2001503376A (ja) | 2001-03-13 |
AU720841B2 (en) | 2000-06-15 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
FZDE | Discontinued |