BE556196A

BE556196A -

Info

Publication number: BE556196A
Authority: BE; Belgium
Prior art keywords: antibiotic; echinomycin; called; streptomyces; water
Prior art date

Application number

Other languages

English (en)

French (fr)

Publication of BE556196A publication Critical patent/BE556196A/fr

Links

230000003115 biocidal Effects 0.000 claims description 42
239000000243 solution Substances 0.000 claims description 40
108010009858 Echinomycin Proteins 0.000 claims description 29
AUJXLBOHYWTPFV-CVLRASHMSA-N N-[(1R,4R,7R,11S,14R,17R,20R,24S)-2,4,12,15,17,25-hexamethyl-29-methylsulfanyl-3,6,10,13,16,19,23,26-octaoxo-11,24-di(propan-2-yl)-7-(quinoxaline-2-carbonylamino)-9,22-dioxa-28-thia-2,5,12,15,18,25-hexazabicyclo[12.12.3]nonacosan-20-yl]quinoxaline-2-carbo Chemical compound C([C@H](C(=O)N[C@H](C)C(=O)N1C)NC(=O)C=2N=C3C=CC=CC3=NC=2)OC(=O)[C@H](C(C)C)N(C)C(=O)[C@H]2N(C)C(=O)[C@@H](C)NC(=O)[C@H](NC(=O)C=3N=C4C=CC=CC4=NC=3)COC(=O)[C@H](C(C)C)N(C)C(=O)[C@@H]1CSC2SC AUJXLBOHYWTPFV-CVLRASHMSA-N 0.000 claims description 29
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
239000000047 product Substances 0.000 claims description 15
235000015097 nutrients Nutrition 0.000 claims description 13
239000000126 substance Substances 0.000 claims description 13
OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
241000958242 Streptomyces echinatus Species 0.000 claims description 10
239000003960 organic solvent Substances 0.000 claims description 10
238000003776 cleavage reaction Methods 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 7
230000000694 effects Effects 0.000 claims description 7
239000000825 pharmaceutical preparation Substances 0.000 claims description 7
241000187747 Streptomyces Species 0.000 claims description 6
238000000605 extraction Methods 0.000 claims description 6
238000006460 hydrolysis reaction Methods 0.000 claims description 6
239000011780 sodium chloride Substances 0.000 claims description 6
238000009826 distribution Methods 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 5
238000004587 chromatography analysis Methods 0.000 claims description 4
230000001747 exhibiting Effects 0.000 claims description 4
239000000706 filtrate Substances 0.000 claims description 4
238000000034 method Methods 0.000 claims description 4
230000003647 oxidation Effects 0.000 claims description 4
238000007254 oxidation reaction Methods 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
239000007864 aqueous solution Substances 0.000 claims description 3
239000000843 powder Substances 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
238000000638 solvent extraction Methods 0.000 claims description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N al2o3 Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
150000001720 carbohydrates Chemical class 0.000 claims description 2
235000014633 carbohydrates Nutrition 0.000 claims description 2
239000006071 cream Substances 0.000 claims description 2
239000008298 dragée Substances 0.000 claims description 2
239000000839 emulsion Substances 0.000 claims description 2
150000002830 nitrogen compounds Chemical class 0.000 claims description 2
239000002674 ointment Substances 0.000 claims description 2
239000000829 suppository Substances 0.000 claims description 2
239000000725 suspension Substances 0.000 claims description 2
230000000699 topical Effects 0.000 claims description 2
YBZRLMLGUBIIDN-UHFFFAOYSA-N Spicamycin Chemical compound O1C(C(O)CO)C(NC(=O)CNC(=O)CCCCCCCCCCCCC(C)C)C(O)C(O)C1NC1=NC=NC2=C1NC=N2 YBZRLMLGUBIIDN-UHFFFAOYSA-N 0.000 claims 1
230000003301 hydrolyzing Effects 0.000 claims 1
230000001737 promoting Effects 0.000 claims 1
UCKMPCXJQFINFW-UHFFFAOYSA-N sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 1
229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 38
CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
239000000203 mixture Substances 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
239000000284 extract Substances 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000008103 glucose Substances 0.000 description 8
WQZGKKKJIJFFOK-GASJEMHNSA-N D-Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 7
229910052799 carbon Inorganic materials 0.000 description 7
239000002609 media Substances 0.000 description 7
WQZGKKKJIJFFOK-VFUOTHLCSA-N β-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 7
229920001817 Agar Polymers 0.000 description 6
LRHPLDYGYMQRHN-UHFFFAOYSA-N Butanol Natural products CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
239000008272 agar Substances 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
239000000727 fraction Substances 0.000 description 6
238000002844 melting Methods 0.000 description 6
239000000049 pigment Substances 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
238000000862 absorption spectrum Methods 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
239000008399 tap water Substances 0.000 description 5
235000020679 tap water Nutrition 0.000 description 5
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 4
VWDWKYIASSYTQR-UHFFFAOYSA-N Sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 4
241000194017 Streptococcus Species 0.000 description 4
235000004279 alanine Nutrition 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M buffer Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
238000004821 distillation Methods 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
230000003287 optical Effects 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
230000001954 sterilising Effects 0.000 description 4
229960003563 Calcium Carbonate Drugs 0.000 description 3
MTCFGRXMJLQNBG-UWTATZPHSA-N D-serine Chemical compound OC[C@@H](N)C(O)=O MTCFGRXMJLQNBG-UWTATZPHSA-N 0.000 description 3
108010010803 Gelatin Proteins 0.000 description 3
235000010469 Glycine max Nutrition 0.000 description 3
GUBGYTABKSRVRQ-UUNJERMWSA-N Lactose Natural products O([C@@H]1[C@H](O)[C@H](O)[C@H](O)O[C@@H]1CO)[C@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@H](CO)O1 GUBGYTABKSRVRQ-UUNJERMWSA-N 0.000 description 3
FBPFZTCFMRRESA-KVTDHHQDSA-N Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 3
FEMOMIGRRWSMCU-UHFFFAOYSA-N Ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
241001494960 Streptomyces griseoflavus Species 0.000 description 3
241000209149 Zea Species 0.000 description 3
235000002017 Zea mays subsp mays Nutrition 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
238000005903 acid hydrolysis reaction Methods 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
239000003242 anti bacterial agent Substances 0.000 description 3
230000000844 anti-bacterial Effects 0.000 description 3
-1 butyl alcohols Chemical class 0.000 description 3
229910000019 calcium carbonate Inorganic materials 0.000 description 3
235000005822 corn Nutrition 0.000 description 3
235000005824 corn Nutrition 0.000 description 3
239000008273 gelatin Substances 0.000 description 3
229920000159 gelatin Polymers 0.000 description 3
235000019322 gelatine Nutrition 0.000 description 3
235000011852 gelatine desserts Nutrition 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
239000008101 lactose Substances 0.000 description 3
GUBGYTABKSRVRQ-XLOQQCSPSA-N lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 3
238000000746 purification Methods 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
210000004215 spores Anatomy 0.000 description 3
239000008107 starch Substances 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
238000004659 sterilization and disinfection Methods 0.000 description 3
238000005406 washing Methods 0.000 description 3
LLVUHQYJZJUDAM-ZETCQYMHSA-N (2S)-2-azaniumyl-3-(2,4-dinitrophenyl)propanoate Chemical compound OC(=O)[C@@H](N)CC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O LLVUHQYJZJUDAM-ZETCQYMHSA-N 0.000 description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N (3β)-Cholest-5-en-3-ol 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 description 2
229940064005 Antibiotic throat preparations Drugs 0.000 description 2
229940083879 Antibiotics FOR TREATMENT OF HEMORRHOIDS AND ANAL FISSURES FOR TOPICAL USE Drugs 0.000 description 2
229940042052 Antibiotics for systemic use Drugs 0.000 description 2
229940042786 Antitubercular Antibiotics Drugs 0.000 description 2
210000003711 Chorioallantoic Membrane Anatomy 0.000 description 2
GZCGUPFRVQAUEE-KCDKBNATSA-N D-(+)-Galactose Natural products OC[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-KCDKBNATSA-N 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N D-sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
BJHIKXHVCXFQLS-UYFOZJQFSA-N Fructose Natural products OC[C@@H](O)[C@@H](O)[C@H](O)C(=O)CO BJHIKXHVCXFQLS-UYFOZJQFSA-N 0.000 description 2
240000007842 Glycine max Species 0.000 description 2
229940093922 Gynecological Antibiotics Drugs 0.000 description 2
GUBGYTABKSRVRQ-YOLKTULGSA-N Maltose Natural products O([C@@H]1[C@H](O)[C@@H](O)[C@H](O)O[C@H]1CO)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 GUBGYTABKSRVRQ-YOLKTULGSA-N 0.000 description 2
FFRBMBIXVSCUFS-UHFFFAOYSA-N Martius yellow Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 2
239000001888 Peptone Substances 0.000 description 2
108010080698 Peptones Proteins 0.000 description 2
XSCHRSMBECNVNS-UHFFFAOYSA-N Quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
241000958221 Streptomyces flaveolus Species 0.000 description 2
CZMRCDWAGMRECN-GDQSFJPYSA-N Sucrose Natural products O([C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O1)[C@@]1(CO)[C@H](O)[C@@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-GDQSFJPYSA-N 0.000 description 2
229940024982 Topical Antifungal Antibiotics Drugs 0.000 description 2
241000224526 Trichomonas Species 0.000 description 2
239000003929 acidic solution Substances 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
235000001014 amino acid Nutrition 0.000 description 2
150000001413 amino acids Chemical class 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
239000007853 buffer solution Substances 0.000 description 2
150000001721 carbon Chemical class 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
230000000875 corresponding Effects 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
235000013312 flour Nutrition 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
229940079866 intestinal antibiotics Drugs 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 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
235000013372 meat Nutrition 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
229940005935 ophthalmologic Antibiotics Drugs 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
235000019319 peptone Nutrition 0.000 description 2
239000004317 sodium nitrate Substances 0.000 description 2
235000010344 sodium nitrate Nutrition 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
230000001131 transforming Effects 0.000 description 2
239000001052 yellow pigment Substances 0.000 description 2
SBQZBOCQYMVLTC-SSDOTTSWSA-N (2R)-2-(2,4-dinitroanilino)-3-hydroxypropanoic acid Chemical compound OC[C@H](C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O SBQZBOCQYMVLTC-SSDOTTSWSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
LOTKRQAVGJMPNV-UHFFFAOYSA-N 1-Fluoro-2,4-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C([N+]([O-])=O)=C1 LOTKRQAVGJMPNV-UHFFFAOYSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical class CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
CATSNJVOTSVZJV-UHFFFAOYSA-N 2-Heptanone Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 1
XNLICIUVMPYHGG-UHFFFAOYSA-N 2-Pentanone Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K 2qpq Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
241000186361 Actinobacteria <class> Species 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
PGMYKACGEOXYJE-UHFFFAOYSA-N Amyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
229960001230 Asparagine Drugs 0.000 description 1
241000193830 Bacillus <bacterium> Species 0.000 description 1
QFFVPLLCYGOFPU-UHFFFAOYSA-N Barium chromate Chemical compound [Ba+2].[O-][Cr]([O-])(=O)=O QFFVPLLCYGOFPU-UHFFFAOYSA-N 0.000 description 1
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
241000589968 Borrelia Species 0.000 description 1
108091003117 Bovine Serum Albumin Proteins 0.000 description 1
229940016114 Calcium Malate Drugs 0.000 description 1
OLOZVPHKXALCRI-UHFFFAOYSA-L Calcium malate Chemical compound [Ca+2].[O-]C(=O)C(O)CC([O-])=O OLOZVPHKXALCRI-UHFFFAOYSA-L 0.000 description 1
241000222120 Candida <Saccharomycetales> Species 0.000 description 1
CZTQZXZIADLWOZ-CRAIPNDOSA-N Cephaloridine Chemical compound O=C([C@@H](NC(=O)CC=1SC=CC=1)[C@H]1SC2)N1C(C(=O)[O-])=C2C[N+]1=CC=CC=C1 CZTQZXZIADLWOZ-CRAIPNDOSA-N 0.000 description 1
HAWPXGHAZFHHAD-UHFFFAOYSA-N Chlormethine Chemical compound ClCCN(C)CCCl HAWPXGHAZFHHAD-UHFFFAOYSA-N 0.000 description 1
241000186216 Corynebacterium Species 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
241000699800 Cricetinae Species 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
240000002860 Daucus carota Species 0.000 description 1
235000002243 Daucus carota subsp sativus Nutrition 0.000 description 1
210000002969 Egg Yolk Anatomy 0.000 description 1
241000224431 Entamoeba Species 0.000 description 1
210000003754 Fetus Anatomy 0.000 description 1
241000233866 Fungi Species 0.000 description 1
241000287828 Gallus gallus Species 0.000 description 1
CDAISMWEOUEBRE-GPIVLXJGSA-N Inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 1
229940029339 Inulin Drugs 0.000 description 1
JYJIGFIDKWBXDU-MNNPPOADSA-N Inulin Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)OC[C@]1(OC[C@]2(OC[C@]3(OC[C@]4(OC[C@]5(OC[C@]6(OC[C@]7(OC[C@]8(OC[C@]9(OC[C@]%10(OC[C@]%11(OC[C@]%12(OC[C@]%13(OC[C@]%14(OC[C@]%15(OC[C@]%16(OC[C@]%17(OC[C@]%18(OC[C@]%19(OC[C@]%20(OC[C@]%21(OC[C@]%22(OC[C@]%23(OC[C@]%24(OC[C@]%25(OC[C@]%26(OC[C@]%27(OC[C@]%28(OC[C@]%29(OC[C@]%30(OC[C@]%31(OC[C@]%32(OC[C@]%33(OC[C@]%34(OC[C@]%35(OC[C@]%36(O[C@@H]%37[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O%37)O)[C@H]([C@H](O)[C@@H](CO)O%36)O)[C@H]([C@H](O)[C@@H](CO)O%35)O)[C@H]([C@H](O)[C@@H](CO)O%34)O)[C@H]([C@H](O)[C@@H](CO)O%33)O)[C@H]([C@H](O)[C@@H](CO)O%32)O)[C@H]([C@H](O)[C@@H](CO)O%31)O)[C@H]([C@H](O)[C@@H](CO)O%30)O)[C@H]([C@H](O)[C@@H](CO)O%29)O)[C@H]([C@H](O)[C@@H](CO)O%28)O)[C@H]([C@H](O)[C@@H](CO)O%27)O)[C@H]([C@H](O)[C@@H](CO)O%26)O)[C@H]([C@H](O)[C@@H](CO)O%25)O)[C@H]([C@H](O)[C@@H](CO)O%24)O)[C@H]([C@H](O)[C@@H](CO)O%23)O)[C@H]([C@H](O)[C@@H](CO)O%22)O)[C@H]([C@H](O)[C@@H](CO)O%21)O)[C@H]([C@H](O)[C@@H](CO)O%20)O)[C@H]([C@H](O)[C@@H](CO)O%19)O)[C@H]([C@H](O)[C@@H](CO)O%18)O)[C@H]([C@H](O)[C@@H](CO)O%17)O)[C@H]([C@H](O)[C@@H](CO)O%16)O)[C@H]([C@H](O)[C@@H](CO)O%15)O)[C@H]([C@H](O)[C@@H](CO)O%14)O)[C@H]([C@H](O)[C@@H](CO)O%13)O)[C@H]([C@H](O)[C@@H](CO)O%12)O)[C@H]([C@H](O)[C@@H](CO)O%11)O)[C@H]([C@H](O)[C@@H](CO)O%10)O)[C@H]([C@H](O)[C@@H](CO)O9)O)[C@H]([C@H](O)[C@@H](CO)O8)O)[C@H]([C@H](O)[C@@H](CO)O7)O)[C@H]([C@H](O)[C@@H](CO)O6)O)[C@H]([C@H](O)[C@@H](CO)O5)O)[C@H]([C@H](O)[C@@H](CO)O4)O)[C@H]([C@H](O)[C@@H](CO)O3)O)[C@H]([C@H](O)[C@@H](CO)O2)O)[C@@H](O)[C@H](O)[C@@H](CO)O1 JYJIGFIDKWBXDU-MNNPPOADSA-N 0.000 description 1
229920001202 Inulin Polymers 0.000 description 1
SRBFZHDQGSBBOR-HWQSCIPKSA-N L-arabinose Chemical compound O[C@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-HWQSCIPKSA-N 0.000 description 1
DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 1
229960004961 Mechlorethamine Drugs 0.000 description 1
210000004379 Membranes Anatomy 0.000 description 1
SBQZBOCQYMVLTC-ZETCQYMHSA-N N-(2,4-dinitrophenyl)-L-serine Chemical compound OC[C@@H](C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O SBQZBOCQYMVLTC-ZETCQYMHSA-N 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
229940066779 Peptones Drugs 0.000 description 1
240000005158 Phaseolus vulgaris Species 0.000 description 1
235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
108010009736 Protein Hydrolysates Proteins 0.000 description 1
MUPFEKGTMRGPLJ-ZQSKZDJDSA-N Raffinose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 description 1
MUPFEKGTMRGPLJ-RMMQSMQOSA-N Raffinose Natural products O(C[C@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O[C@@]2(CO)[C@H](O)[C@@H](O)[C@@H](CO)O2)O1)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 MUPFEKGTMRGPLJ-RMMQSMQOSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
PNNNRSAQSRJVSB-BXKVDMCESA-N Rhamnose Chemical compound C[C@H](O)[C@H](O)[C@@H](O)[C@@H](O)C=O PNNNRSAQSRJVSB-BXKVDMCESA-N 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
NGFMICBWJRZIBI-UJPOAAIJSA-N Salicin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=CC=C1CO NGFMICBWJRZIBI-UJPOAAIJSA-N 0.000 description 1
NGFMICBWJRZIBI-JZRPKSSGSA-N Salicin Natural products O([C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](CO)O1)c1c(CO)cccc1 NGFMICBWJRZIBI-JZRPKSSGSA-N 0.000 description 1
210000002966 Serum Anatomy 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N Silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
229940074404 Sodium succinate Drugs 0.000 description 1
240000001016 Solanum tuberosum Species 0.000 description 1
235000002595 Solanum tuberosum Nutrition 0.000 description 1
241001655322 Streptomycetales Species 0.000 description 1
240000008529 Triticum aestivum Species 0.000 description 1
241000607598 Vibrio Species 0.000 description 1
241000700605 Viruses Species 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
UGAPHEBNTGUMBB-UHFFFAOYSA-N acetic acid;ethyl acetate Chemical compound CC(O)=O.CCOC(C)=O UGAPHEBNTGUMBB-UHFFFAOYSA-N 0.000 description 1
238000007792 addition Methods 0.000 description 1
239000002156 adsorbate Substances 0.000 description 1
230000001476 alcoholic Effects 0.000 description 1
PYMYPHUHKUWMLA-WISUUJSJSA-N aldehydo-L-xylose Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WISUUJSJSA-N 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
230000003569 amebicidal Effects 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
229940072049 amyl acetate Drugs 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000002152 aqueous-organic solution Substances 0.000 description 1
235000009582 asparagine Nutrition 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
150000003938 benzyl alcohols Chemical class 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000001362 calcium malate Substances 0.000 description 1
235000013962 calcium malate Nutrition 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
235000013339 cereals Nutrition 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
239000002036 chloroform fraction Substances 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
238000005345 coagulation Methods 0.000 description 1
230000015271 coagulation Effects 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000005712 crystallization Effects 0.000 description 1
230000001419 dependent Effects 0.000 description 1
YXHKONLOYHBTNS-UHFFFAOYSA-N diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
201000009910 diseases by infectious agent Diseases 0.000 description 1
ZDQYSKICYIVCPN-UHFFFAOYSA-L disodium butanedioate Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 1
239000003814 drug Substances 0.000 description 1
235000013345 egg yolk Nutrition 0.000 description 1
235000013601 eggs Nutrition 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
230000001605 fetal Effects 0.000 description 1
PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
239000001056 green pigment Substances 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxyl anion Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
PWHULOQIROXLJO-UHFFFAOYSA-N manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
239000011572 manganese Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
239000012528 membrane Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
QDHHCQZDFGDHMP-UHFFFAOYSA-N monochloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 1
230000035772 mutation Effects 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N n-methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
239000006916 nutrient agar Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
125000004043 oxo group Chemical group O=* 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
238000004816 paper chromatography Methods 0.000 description 1
238000004810 partition chromatography Methods 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
239000000546 pharmaceutic aid Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
239000011148 porous material Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
230000002335 preservative Effects 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
235000018102 proteins Nutrition 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
UPUZGXILYFKSGE-UHFFFAOYSA-N quinoxaline-2-carboxylic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CN=C21 UPUZGXILYFKSGE-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229940120668 salicin Drugs 0.000 description 1
238000000926 separation method Methods 0.000 description 1
150000003354 serine derivatives Chemical class 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
235000020275 sunflower milk Nutrition 0.000 description 1
230000002522 swelling 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
239000003760 tallow Substances 0.000 description 1
230000002588 toxic Effects 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
108010046845 tryptones Proteins 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
235000021307 wheat Nutrition 0.000 description 1
235000005765 wild carrot Nutrition 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1