CA1241282A - Bbm-1675, a new antitumor antibiotic complex - Google Patents
Bbm-1675, a new antitumor antibiotic complexInfo
- Publication number
- CA1241282A CA1241282A CA000453762A CA453762A CA1241282A CA 1241282 A CA1241282 A CA 1241282A CA 000453762 A CA000453762 A CA 000453762A CA 453762 A CA453762 A CA 453762A CA 1241282 A CA1241282 A CA 1241282A
- Authority
- CA
- Canada
- Prior art keywords
- bbm
- exhibits
- ch3oh
- methanol
- strain
- 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
Links
- 239000003972 antineoplastic antibiotic Substances 0.000 title claims description 18
- 241000201778 Actinomadura verrucosospora Species 0.000 claims abstract description 37
- 230000003115 biocidal effect Effects 0.000 claims abstract description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 225
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 80
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 44
- 239000002609 medium Substances 0.000 claims description 38
- 239000000741 silica gel Substances 0.000 claims description 37
- 229910002027 silica gel Inorganic materials 0.000 claims description 37
- 238000004809 thin layer chromatography Methods 0.000 claims description 37
- 239000002904 solvent Substances 0.000 claims description 35
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 30
- 208000032839 leukemia Diseases 0.000 claims description 30
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- 238000001228 spectrum Methods 0.000 claims description 23
- 238000012360 testing method Methods 0.000 claims description 23
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 22
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 21
- 241000699670 Mus sp. Species 0.000 claims description 18
- 238000004519 manufacturing process Methods 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 241000894006 Bacteria Species 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 235000015097 nutrients Nutrition 0.000 claims description 17
- 101150041968 CDC13 gene Proteins 0.000 claims description 16
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 239000001963 growth medium Substances 0.000 claims description 15
- 230000002401 inhibitory effect Effects 0.000 claims description 15
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 14
- 238000000862 absorption spectrum Methods 0.000 claims description 13
- 230000001320 lysogenic effect Effects 0.000 claims description 12
- 238000010521 absorption reaction Methods 0.000 claims description 11
- 230000002441 reversible effect Effects 0.000 claims description 11
- 230000003287 optical effect Effects 0.000 claims description 10
- 208000001382 Experimental Melanoma Diseases 0.000 claims description 9
- 230000008859 change Effects 0.000 claims description 9
- 241000233866 Fungi Species 0.000 claims description 8
- 239000003153 chemical reaction reagent Substances 0.000 claims description 8
- 244000005700 microbiome Species 0.000 claims description 8
- 230000014759 maintenance of location Effects 0.000 claims description 7
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims description 6
- 208000006552 Lewis Lung Carcinoma Diseases 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 239000013078 crystal Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 18
- GRONZTPUWOOUFQ-UHFFFAOYSA-M sodium;methanol;hydroxide Chemical compound [OH-].[Na+].OC GRONZTPUWOOUFQ-UHFFFAOYSA-M 0.000 claims 7
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims 6
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 claims 6
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 claims 6
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims 6
- 238000002844 melting Methods 0.000 claims 6
- 230000008018 melting Effects 0.000 claims 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- 239000001301 oxygen Substances 0.000 claims 4
- 238000004949 mass spectrometry Methods 0.000 claims 2
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 claims 1
- 238000000855 fermentation Methods 0.000 abstract description 27
- 230000004151 fermentation Effects 0.000 abstract description 27
- 230000000259 anti-tumor effect Effects 0.000 abstract description 19
- 230000000845 anti-microbial effect Effects 0.000 abstract description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 66
- 150000001875 compounds Chemical class 0.000 description 50
- 230000000694 effects Effects 0.000 description 31
- 239000007787 solid Substances 0.000 description 17
- 238000011282 treatment Methods 0.000 description 17
- 206010028980 Neoplasm Diseases 0.000 description 16
- 239000000126 substance Substances 0.000 description 16
- 239000000523 sample Substances 0.000 description 15
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 14
- 230000000975 bioactive effect Effects 0.000 description 14
- 241000187362 Actinomadura Species 0.000 description 12
- 210000004027 cell Anatomy 0.000 description 11
- 239000002002 slurry Substances 0.000 description 11
- 229920002472 Starch Polymers 0.000 description 10
- 235000018936 Vitellaria paradoxa Nutrition 0.000 description 10
- 238000007792 addition Methods 0.000 description 10
- 239000008107 starch Substances 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- ZYVSOIYQKUDENJ-UHFFFAOYSA-N [6-[[6-[4-[4-(5-acetyloxy-4-hydroxy-4,6-dimethyloxan-2-yl)oxy-5-hydroxy-6-methyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]oxy-7-(3,4-dihydroxy-1-methoxy-2-oxopentyl)-4,10-dihydroxy-3-methyl-5-oxo-7,8-dihydro-6h-anthracen-2-yl]oxy]-4-(4-hydroxy-5-methoxy-6 Chemical compound CC=1C(O)=C2C(O)=C3C(=O)C(OC4OC(C)C(O)C(OC5OC(C)C(O)C(OC6OC(C)C(OC(C)=O)C(C)(O)C6)C5)C4)C(C(OC)C(=O)C(O)C(C)O)CC3=CC2=CC=1OC(OC(C)C1OC(C)=O)CC1OC1CC(O)C(OC)C(C)O1 ZYVSOIYQKUDENJ-UHFFFAOYSA-N 0.000 description 9
- 239000003242 anti bacterial agent Substances 0.000 description 9
- 229940088710 antibiotic agent Drugs 0.000 description 9
- 210000002421 cell wall Anatomy 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 8
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 8
- 150000002500 ions Chemical group 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- -1 L(~)-arabinose Chemical compound 0.000 description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 7
- 229940041514 candida albicans extract Drugs 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 235000019698 starch Nutrition 0.000 description 7
- 235000000346 sugar Nutrition 0.000 description 7
- 239000012138 yeast extract Substances 0.000 description 7
- 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 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 6
- 241000699666 Mus <mouse, genus> Species 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 239000002054 inoculum Substances 0.000 description 6
- 239000000401 methanolic extract Substances 0.000 description 6
- 239000008188 pellet Substances 0.000 description 6
- 239000003643 water by type Substances 0.000 description 6
- HYPYXGZDOYTYDR-HAJWAVTHSA-N 2-methyl-3-[(2e,6e,10e,14e)-3,7,11,15,19-pentamethylicosa-2,6,10,14,18-pentaenyl]naphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(C/C=C(C)/CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)=C(C)C(=O)C2=C1 HYPYXGZDOYTYDR-HAJWAVTHSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- 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 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 239000007943 implant Substances 0.000 description 5
- 230000000813 microbial effect Effects 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 241000894007 species Species 0.000 description 5
- 235000019143 vitamin K2 Nutrition 0.000 description 5
- 239000011728 vitamin K2 Substances 0.000 description 5
- 229940041603 vitamin k 3 Drugs 0.000 description 5
- UQZSVIGPZAULMV-DKWTVANSSA-N (2s)-2,4-diamino-4-oxobutanoic acid;propane-1,2,3-triol Chemical compound OCC(O)CO.OC(=O)[C@@H](N)CC(N)=O UQZSVIGPZAULMV-DKWTVANSSA-N 0.000 description 4
- 241000186361 Actinobacteria <class> Species 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 241000124429 Phlox Species 0.000 description 4
- 239000004743 Polypropylene Substances 0.000 description 4
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 4
- 229920005654 Sephadex Polymers 0.000 description 4
- 239000012507 Sephadex™ Substances 0.000 description 4
- 241000191940 Staphylococcus Species 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000012634 fragment Substances 0.000 description 4
- 238000011534 incubation Methods 0.000 description 4
- 230000006698 induction Effects 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- 238000002955 isolation Methods 0.000 description 4
- 235000012054 meals Nutrition 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 229920001155 polypropylene Polymers 0.000 description 4
- 239000004576 sand Substances 0.000 description 4
- 230000003595 spectral effect Effects 0.000 description 4
- 230000001954 sterilising effect Effects 0.000 description 4
- 238000004659 sterilization and disinfection Methods 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 230000004083 survival effect Effects 0.000 description 4
- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 description 3
- 235000009434 Actinidia chinensis Nutrition 0.000 description 3
- 244000298697 Actinidia deliciosa Species 0.000 description 3
- 235000009436 Actinidia deliciosa Nutrition 0.000 description 3
- 239000005695 Ammonium acetate Substances 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 3
- 235000019733 Fish meal Nutrition 0.000 description 3
- 239000007836 KH2PO4 Substances 0.000 description 3
- 229910002651 NO3 Inorganic materials 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 239000004809 Teflon Substances 0.000 description 3
- 229920006362 Teflon® Polymers 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 229940009456 adriamycin Drugs 0.000 description 3
- 229940024606 amino acid Drugs 0.000 description 3
- 235000019257 ammonium acetate Nutrition 0.000 description 3
- 229940043376 ammonium acetate Drugs 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000002021 butanolic extract Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000008120 corn starch Substances 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000004467 fishmeal Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000011491 glass wool Substances 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 230000001939 inductive effect Effects 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000002198 insoluble material Substances 0.000 description 3
- 235000010355 mannitol Nutrition 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- 235000013379 molasses Nutrition 0.000 description 3
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 3
- 235000019796 monopotassium phosphate Nutrition 0.000 description 3
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 3
- 239000013049 sediment Substances 0.000 description 3
- 238000011218 seed culture Methods 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 230000003068 static effect Effects 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 229940035024 thioglycerol Drugs 0.000 description 3
- WQZGKKKJIJFFOK-SVZMEOIVSA-N (+)-Galactose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-SVZMEOIVSA-N 0.000 description 2
- BBBFYZOJHSYQMW-LGDQNDJISA-N (2s)-2,4-diamino-4-oxobutanoic acid;(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal Chemical compound OC(=O)[C@@H](N)CC(N)=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O BBBFYZOJHSYQMW-LGDQNDJISA-N 0.000 description 2
- WTLKTXIHIHFSGU-UHFFFAOYSA-N 2-nitrosoguanidine Chemical compound NC(N)=NN=O WTLKTXIHIHFSGU-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 125000006519 CCH3 Chemical group 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 206010011732 Cyst Diseases 0.000 description 2
- RFSUNEUAIZKAJO-VRPWFDPXSA-N D-Fructose Natural products OC[C@H]1OC(O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-VRPWFDPXSA-N 0.000 description 2
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 description 2
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
- 241000192125 Firmicutes Species 0.000 description 2
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 description 2
- 208000028018 Lymphocytic leukaemia Diseases 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 241000014687 Maribacter flavus Species 0.000 description 2
- 102000016943 Muramidase Human genes 0.000 description 2
- 108010014251 Muramidase Proteins 0.000 description 2
- 108010062010 N-Acetylmuramoyl-L-alanine Amidase Proteins 0.000 description 2
- 241000282320 Panthera leo Species 0.000 description 2
- 240000007377 Petunia x hybrida Species 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N 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
- 241001441723 Takifugu Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 238000005273 aeration Methods 0.000 description 2
- PNNNRSAQSRJVSB-BXKVDMCESA-N aldehydo-L-rhamnose Chemical compound C[C@H](O)[C@H](O)[C@@H](O)[C@@H](O)C=O PNNNRSAQSRJVSB-BXKVDMCESA-N 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000004599 antimicrobial Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 2
- 238000004166 bioassay Methods 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 208000031513 cyst Diseases 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 2
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 2
- 235000019797 dipotassium phosphate Nutrition 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 208000018459 dissociative disease Diseases 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 208000003747 lymphoid leukemia Diseases 0.000 description 2
- 239000004325 lysozyme Substances 0.000 description 2
- 235000010335 lysozyme Nutrition 0.000 description 2
- 229960000274 lysozyme Drugs 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 201000001441 melanoma Diseases 0.000 description 2
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 235000013336 milk Nutrition 0.000 description 2
- 239000008267 milk Substances 0.000 description 2
- 210000004080 milk Anatomy 0.000 description 2
- 230000000877 morphologic effect Effects 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 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 2
- 239000005720 sucrose Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 241001446247 uncultured actinomycete Species 0.000 description 2
- 239000011800 void material Substances 0.000 description 2
- RMTFNDVZYPHUEF-JRTVQGFMSA-N (2r,3s,4s,5r)-2,4,5,6-tetrahydroxy-3-methoxyhexanal Chemical compound O=C[C@H](O)[C@@H](OC)[C@@H](O)[C@H](O)CO RMTFNDVZYPHUEF-JRTVQGFMSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- HORQAOAYAYGIBM-UHFFFAOYSA-N 2,4-dinitrophenylhydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O HORQAOAYAYGIBM-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- SHXWCVYOXRDMCX-UHFFFAOYSA-N 3,4-methylenedioxymethamphetamine Chemical compound CNC(C)CC1=CC=C2OCOC2=C1 SHXWCVYOXRDMCX-UHFFFAOYSA-N 0.000 description 1
- 229910000619 316 stainless steel Inorganic materials 0.000 description 1
- FDWRIIDFYSUTDP-UHFFFAOYSA-N 6-methyloxane-2,4,5-triol Chemical group CC1OC(O)CC(O)C1O FDWRIIDFYSUTDP-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 238000009631 Broth culture Methods 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000221204 Cryptococcus neoformans Species 0.000 description 1
- QWIZNVHXZXRPDR-KMHATNSDSA-N D(+)-Melezitose Chemical compound OC[C@H]1O[C@@](CO)(O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]1O QWIZNVHXZXRPDR-KMHATNSDSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 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
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
- QWIZNVHXZXRPDR-UHFFFAOYSA-N D-melezitose Natural products O1C(CO)C(O)C(O)C(O)C1OC1C(O)C(CO)OC1(CO)OC1OC(CO)C(O)C(O)C1O QWIZNVHXZXRPDR-UHFFFAOYSA-N 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- 241001050985 Disco Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000490229 Eucephalus Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241000110847 Kochia Species 0.000 description 1
- 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 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- RMTFNDVZYPHUEF-UHFFFAOYSA-N O3-methyl-D-galactose Natural products O=CC(O)C(OC)C(O)C(O)CO RMTFNDVZYPHUEF-UHFFFAOYSA-N 0.000 description 1
- MXETZQATVMJCFH-UHFFFAOYSA-N Olivomycin A Natural products COC(C1Cc2cc3cc(OC4CC(OC(=O)C)C(OC5CC(O)C(OC)C(C)O5)C(C)O4)cc(O)c3c(O)c2C(=O)C1OC6CC(OC7CC(OC8CC(C)(O)C(OC(=O)C(C)C)C(C)O8)C(O)C(C)O7)C(O)C(C)O6)C(=O)C(O)C(C)C MXETZQATVMJCFH-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 206010035664 Pneumonia Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000220317 Rosa Species 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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241000187747 Streptomyces Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229910052771 Terbium Inorganic materials 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 241001504505 Troglodytes troglodytes Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 238000012459 agar diffusion assay Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- NGFMICBWJRZIBI-UHFFFAOYSA-N alpha-salicin Natural products OC1C(O)C(O)C(CO)OC1OC1=CC=CC=C1CO NGFMICBWJRZIBI-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000012296 anti-solvent Substances 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000007640 basal medium Substances 0.000 description 1
- 150000007514 bases Chemical class 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
- DLRVVLDZNNYCBX-ZZFZYMBESA-N beta-melibiose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)O1 DLRVVLDZNNYCBX-ZZFZYMBESA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 230000025938 carbohydrate utilization Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- ZYVSOIYQKUDENJ-WKSBCEQHSA-N chromomycin A3 Chemical compound O([C@@H]1C[C@@H](O[C@H](C)[C@@H]1OC(C)=O)OC=1C=C2C=C3C[C@H]([C@@H](C(=O)C3=C(O)C2=C(O)C=1C)O[C@@H]1O[C@H](C)[C@@H](O)[C@H](O[C@@H]2O[C@H](C)[C@@H](O)[C@H](O[C@@H]3O[C@@H](C)[C@H](OC(C)=O)[C@@](C)(O)C3)C2)C1)[C@H](OC)C(=O)[C@@H](O)[C@@H](C)O)[C@@H]1C[C@@H](O)[C@@H](OC)[C@@H](C)O1 ZYVSOIYQKUDENJ-WKSBCEQHSA-N 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 230000000249 desinfective effect Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- PXEDJBXQKAGXNJ-QTNFYWBSSA-L disodium L-glutamate Chemical compound [Na+].[Na+].[O-]C(=O)[C@@H](N)CCC([O-])=O PXEDJBXQKAGXNJ-QTNFYWBSSA-L 0.000 description 1
- 239000000890 drug combination Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- FBPFZTCFMRRESA-GUCUJZIJSA-N galactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-GUCUJZIJSA-N 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229940069016 go-dry Drugs 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000003102 growth factor Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 231100000682 maximum tolerated dose Toxicity 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 230000000684 melanotic effect Effects 0.000 description 1
- DABXQFWXOSHIOQ-UHFFFAOYSA-N methyl 2-(2,2-dimethoxypropanoylamino)-4,5-dimethoxybenzoate Chemical compound COC(=O)C1=CC(OC)=C(OC)C=C1NC(=O)C(C)(OC)OC DABXQFWXOSHIOQ-UHFFFAOYSA-N 0.000 description 1
- QQFHCCQSCQBKBG-UHFFFAOYSA-N methyl 2-amino-4,5-dimethoxybenzoate Chemical compound COC(=O)C1=CC(OC)=C(OC)C=C1N QQFHCCQSCQBKBG-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 230000036562 nail growth Effects 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
- KELXKDDAALYTDI-BTVCFUMJSA-N nitric acid;(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal Chemical compound O[N+]([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O KELXKDDAALYTDI-BTVCFUMJSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000001477 organic nitrogen group Chemical group 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 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
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 239000012521 purified sample Substances 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 238000012552 review Methods 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
- 229940120668 salicin Drugs 0.000 description 1
- 230000002784 sclerotic effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 235000020183 skimmed milk Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001550 time effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- YWYZEGXAUVWDED-UHFFFAOYSA-N triammonium citrate Chemical compound [NH4+].[NH4+].[NH4+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O YWYZEGXAUVWDED-UHFFFAOYSA-N 0.000 description 1
- 210000005239 tubule Anatomy 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P1/00—Preparation of compounds or compositions, not provided for in groups C12P3/00 - C12P39/00, by using microorganisms or enzymes
- C12P1/02—Preparation of compounds or compositions, not provided for in groups C12P3/00 - C12P39/00, by using microorganisms or enzymes by using fungi
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/08—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to carbocyclic rings
-
- 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
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H11/00—Compounds containing saccharide radicals esterified by inorganic acids; Metal salts thereof
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P1/00—Preparation of compounds or compositions, not provided for in groups C12P3/00 - C12P39/00, by using microorganisms or enzymes
- C12P1/06—Preparation of compounds or compositions, not provided for in groups C12P3/00 - C12P39/00, by using microorganisms or enzymes by using actinomycetales
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Zoology (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Wood Science & Technology (AREA)
- Mycology (AREA)
- Public Health (AREA)
- General Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Microbiology (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Compounds Of Unknown Constitution (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US49523183A | 1983-05-16 | 1983-05-16 | |
| US495,231 | 1990-03-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1241282A true CA1241282A (en) | 1988-08-30 |
Family
ID=23967812
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000453762A Expired CA1241282A (en) | 1983-05-16 | 1984-05-08 | Bbm-1675, a new antitumor antibiotic complex |
Country Status (28)
| Country | Link |
|---|---|
| JP (2) | JPS59232094A (de) |
| KR (2) | KR840008817A (de) |
| AT (1) | AT393691B (de) |
| AU (1) | AU569294B2 (de) |
| BE (1) | BE899667A (de) |
| CA (1) | CA1241282A (de) |
| CY (1) | CY1465A (de) |
| DE (1) | DE3418023A1 (de) |
| DK (1) | DK163127C (de) |
| ES (1) | ES8700267A1 (de) |
| FI (1) | FI81114C (de) |
| FR (1) | FR2547594B1 (de) |
| GB (1) | GB2141425B (de) |
| GR (1) | GR81581B (de) |
| HK (1) | HK9889A (de) |
| HU (1) | HU193928B (de) |
| IE (1) | IE57444B1 (de) |
| IL (1) | IL71824A (de) |
| IT (1) | IT1175498B (de) |
| KE (1) | KE3846A (de) |
| LU (1) | LU85362A1 (de) |
| NL (1) | NL8401572A (de) |
| NZ (1) | NZ208013A (de) |
| PT (1) | PT78590A (de) |
| SE (1) | SE460364B (de) |
| SU (1) | SU1344249A3 (de) |
| YU (1) | YU43846B (de) |
| ZA (1) | ZA843591B (de) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GR78648B (de) * | 1982-07-26 | 1984-09-27 | Bristol Myers Co | |
| IL79519A0 (en) * | 1985-08-27 | 1986-10-31 | Bristol Myers Co | Bbm-1675c and d antitumor antibiotics |
| US4837206A (en) * | 1987-04-29 | 1989-06-06 | Bristol-Myers Company | Esperamicin derivatives |
| US4996305A (en) * | 1988-02-29 | 1991-02-26 | American Cyanamid Company | Process for producing the antibiotic and antitumor agents LL-E33288.epsilon.ε-Br |
| CA2027601A1 (en) * | 1989-11-06 | 1991-05-07 | Koko Sugawara | Antitumor antibiotic bu-3983t |
| CN115380211A (zh) * | 2021-03-17 | 2022-11-22 | 日本水产株式会社 | 精制的方法和经精制的产品 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4195079A (en) * | 1979-01-31 | 1980-03-25 | Pfizer Inc. | New polycyclic ether antibiotic |
| JPS56113791A (en) * | 1980-02-15 | 1981-09-07 | Kaken Pharmaceut Co Ltd | Novel antibiotic and its preparation |
| GR78648B (de) * | 1982-07-26 | 1984-09-27 | Bristol Myers Co | |
| US4539203A (en) * | 1984-11-13 | 1985-09-03 | Warner-Lambert Company | CL-1577D And CL-1577E antibiotic/antitumor compounds, their production and use |
-
1984
- 1984-05-01 NZ NZ208013A patent/NZ208013A/en unknown
- 1984-05-08 CA CA000453762A patent/CA1241282A/en not_active Expired
- 1984-05-08 AU AU27791/84A patent/AU569294B2/en not_active Ceased
- 1984-05-08 GR GR74646A patent/GR81581B/el unknown
- 1984-05-11 FI FI841906A patent/FI81114C/fi not_active IP Right Cessation
- 1984-05-11 ZA ZA843591A patent/ZA843591B/xx unknown
- 1984-05-14 ES ES532476A patent/ES8700267A1/es not_active Expired
- 1984-05-14 IL IL71824A patent/IL71824A/xx unknown
- 1984-05-15 BE BE0/212942A patent/BE899667A/fr not_active IP Right Cessation
- 1984-05-15 DE DE19843418023 patent/DE3418023A1/de active Granted
- 1984-05-15 SE SE8402619A patent/SE460364B/sv not_active IP Right Cessation
- 1984-05-15 GB GB08412368A patent/GB2141425B/en not_active Expired
- 1984-05-15 DK DK239784A patent/DK163127C/da not_active IP Right Cessation
- 1984-05-15 SU SU843744582A patent/SU1344249A3/ru active
- 1984-05-15 IT IT20928/84A patent/IT1175498B/it active
- 1984-05-15 LU LU85362A patent/LU85362A1/fr unknown
- 1984-05-15 IE IE1200/84A patent/IE57444B1/en not_active IP Right Cessation
- 1984-05-15 HU HU841877A patent/HU193928B/hu not_active IP Right Cessation
- 1984-05-15 FR FR8407477A patent/FR2547594B1/fr not_active Expired
- 1984-05-16 KR KR1019840002636A patent/KR840008817A/ko not_active Application Discontinuation
- 1984-05-16 YU YU849/84A patent/YU43846B/xx unknown
- 1984-05-16 PT PT78590A patent/PT78590A/pt not_active IP Right Cessation
- 1984-05-16 NL NL8401572A patent/NL8401572A/nl not_active Application Discontinuation
- 1984-05-16 AT AT0160984A patent/AT393691B/de not_active IP Right Cessation
- 1984-05-16 JP JP59096758A patent/JPS59232094A/ja active Granted
-
1988
- 1988-11-21 KE KE3846A patent/KE3846A/xx unknown
-
1989
- 1989-02-02 HK HK98/89A patent/HK9889A/xx unknown
- 1989-05-04 KR KR1019890006047A patent/KR920001366B1/ko not_active IP Right Cessation
- 1989-07-21 CY CY1465A patent/CY1465A/xx unknown
- 1989-08-24 JP JP1216009A patent/JPH02128693A/ja active Granted
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4675187A (en) | BBM-1675, a new antibiotic complex | |
| US4460765A (en) | Enzyme inhibitor produced by cultivation of streptomyces microorganisms | |
| US4518589A (en) | BBM-2478 Antibiotic complex | |
| US4524145A (en) | 4'-Deschlororebeccamycin pharmaceutical composition and method of use | |
| CA1241282A (en) | Bbm-1675, a new antitumor antibiotic complex | |
| CA1230568A (en) | Antitumor antibiotic compound | |
| EP0132118A2 (de) | Antibiotika, hergestellt durch Kibdelosporangium-Aridum-Shearer-Gen. NOV., SP. NOV. ATCC 39323 | |
| EP0274873A2 (de) | Antibiotikum-A10255-Komplex und Faktoren, Verfahren, Mikroorganismen für seine Herstellung | |
| US4916065A (en) | BU-3420T Antitumor antibiotic | |
| JPH0576350A (ja) | 抗腫瘍抗生物質産生菌 | |
| US4792522A (en) | Rigolettone antitumor complex | |
| Kamogashira et al. | A new glycopeptide antibiotic, OA-7653, produced by Streptomyces hygroscopicus subsp. hiwasaensis | |
| US4708872A (en) | Antitumor antibiotic complex | |
| US4956293A (en) | Nocardia sp. ATCC 53492, or an antibiotic A 42867 producing mutant or variant thereof | |
| US4868117A (en) | BBM-1675, a new antitumor antibiotic complex | |
| US4572895A (en) | Process for preparing an antibiotic complex by culturing actinomyces strain ATCC 39417 | |
| CA1235081A (en) | ANTITUMOR AGENTS LL-D49194 .alpha..SUB.1, LL-D49194 .beta., LL-D49194 .beta..SUB.2, LL-D49194 UPSILON, LL-D49194 DELTA, LL-D49194 EPSILON, LL-D49194 ZETA, AND LL-D49194 ETA | |
| US4461831A (en) | Antitumor agents albacarcins V and M | |
| US5021549A (en) | Physiologically active substances, probestin and prostatin and production thereof | |
| US4677071A (en) | Antibiotic agents from S. coeruleorubidus, rubidus | |
| US4482488A (en) | Antibiotic A53868 and process for production thereof | |
| CH663155A5 (en) | Antitumour antibiotics | |
| CA2001085A1 (en) | Coumamidine compounds |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |