JPH021157B2 - - Google Patents
Info
- Publication number
- JPH021157B2 JPH021157B2 JP56022277A JP2227781A JPH021157B2 JP H021157 B2 JPH021157 B2 JP H021157B2 JP 56022277 A JP56022277 A JP 56022277A JP 2227781 A JP2227781 A JP 2227781A JP H021157 B2 JPH021157 B2 JP H021157B2
- Authority
- JP
- Japan
- Prior art keywords
- anticancer
- anticancer substance
- organic solvent
- hydrophilic organic
- absorption
- 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 - Lifetime
Links
- 230000001093 anti-cancer Effects 0.000 claims description 46
- 239000000126 substance Substances 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 18
- 238000004519 manufacturing process Methods 0.000 claims description 17
- 238000011282 treatment Methods 0.000 claims description 15
- 241000894006 Bacteria Species 0.000 claims description 13
- 241000605909 Fusobacterium Species 0.000 claims description 12
- 108091005804 Peptidases Proteins 0.000 claims description 12
- 230000002255 enzymatic effect Effects 0.000 claims description 12
- 238000012258 culturing Methods 0.000 claims description 10
- 239000006228 supernatant Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 102000035195 Peptidases Human genes 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 7
- 241000605986 Fusobacterium nucleatum Species 0.000 claims description 5
- 239000002246 antineoplastic agent Substances 0.000 claims description 4
- 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 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 238000001556 precipitation Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims 14
- 238000010521 absorption reaction Methods 0.000 claims 13
- 238000006243 chemical reaction Methods 0.000 claims 12
- 239000002244 precipitate Substances 0.000 claims 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 4
- 239000004365 Protease Substances 0.000 claims 4
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims 4
- 238000011481 absorbance measurement Methods 0.000 claims 4
- 238000000862 absorption spectrum Methods 0.000 claims 4
- OQUKIQWCVTZJAF-UHFFFAOYSA-N phenol;sulfuric acid Chemical compound OS(O)(=O)=O.OC1=CC=CC=C1 OQUKIQWCVTZJAF-UHFFFAOYSA-N 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- MYKOKMFESWKQRX-UHFFFAOYSA-N 10h-anthracen-9-one;sulfuric acid Chemical compound OS(O)(=O)=O.C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 MYKOKMFESWKQRX-UHFFFAOYSA-N 0.000 claims 2
- 206010003445 Ascites Diseases 0.000 claims 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 claims 2
- 201000009030 Carcinoma Diseases 0.000 claims 2
- 241000699670 Mus sp. Species 0.000 claims 2
- 108010059712 Pronase Proteins 0.000 claims 2
- 108090000631 Trypsin Proteins 0.000 claims 2
- 102000004142 Trypsin Human genes 0.000 claims 2
- 239000007864 aqueous solution Substances 0.000 claims 2
- 229940098773 bovine serum albumin Drugs 0.000 claims 2
- 238000000921 elemental analysis Methods 0.000 claims 2
- 239000003480 eluent Substances 0.000 claims 2
- 239000008103 glucose Substances 0.000 claims 2
- RJTZUHVCZIGJMB-UHFFFAOYSA-N hydron;1h-indole;chloride Chemical compound Cl.C1=CC=C2NC=CC2=C1 RJTZUHVCZIGJMB-UHFFFAOYSA-N 0.000 claims 2
- 230000003308 immunostimulating effect Effects 0.000 claims 2
- 150000002500 ions Chemical class 0.000 claims 2
- 238000002844 melting Methods 0.000 claims 2
- 230000008018 melting Effects 0.000 claims 2
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 claims 2
- 239000008363 phosphate buffer Substances 0.000 claims 2
- 239000000843 powder Substances 0.000 claims 2
- 239000000243 solution Substances 0.000 claims 2
- 239000012588 trypsin Substances 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- 102000004190 Enzymes Human genes 0.000 claims 1
- 108090000790 Enzymes Proteins 0.000 claims 1
- ISFHAYSTHMVOJR-UHFFFAOYSA-N Phenindamine Chemical compound C1N(C)CCC(C2=CC=CC=C22)=C1C2C1=CC=CC=C1 ISFHAYSTHMVOJR-UHFFFAOYSA-N 0.000 claims 1
- 238000005194 fractionation Methods 0.000 claims 1
- 229960003534 phenindamine Drugs 0.000 claims 1
- 210000004027 cell Anatomy 0.000 description 5
- 230000001580 bacterial effect Effects 0.000 description 3
- 230000000694 effects Effects 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
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 230000005757 colony formation Effects 0.000 description 2
- 239000012531 culture fluid Substances 0.000 description 2
- 230000036737 immune function Effects 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 description 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 241000221198 Basidiomycota Species 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 102000016938 Catalase Human genes 0.000 description 1
- 108010053835 Catalase Proteins 0.000 description 1
- 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 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-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000003794 Gram staining Methods 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 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 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 description 1
- 108010046334 Urease Proteins 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- PYMYPHUHKUWMLA-VAYJURFESA-N aldehydo-L-arabinose Chemical compound OC[C@H](O)[C@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-VAYJURFESA-N 0.000 description 1
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000022534 cell killing Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 210000004748 cultured cell Anatomy 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 230000007236 host immunity Effects 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229940024999 proteolytic enzymes for treatment of wounds and ulcers Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 230000019086 sulfide ion homeostasis Effects 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 241001148471 unidentified anaerobic bacterium Species 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Peptides Or Proteins (AREA)
- Compounds Of Unknown Constitution (AREA)
Priority Applications (21)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56022277A JPS57139089A (en) | 1981-02-19 | 1981-02-19 | Carcinostatic substance tf-350, its preparation and carcinostatic agent containing the same |
| US06/347,871 US4477437A (en) | 1981-02-19 | 1982-02-11 | Substances having carcinostatic and immunostimulating activity |
| GB8204093A GB2093347B (en) | 1981-02-19 | 1982-02-12 | Immunostimulant material tf-2 from fusobacterium sp |
| DE19823205074 DE3205074A1 (de) | 1981-02-19 | 1982-02-12 | Neue carcinostatische und immunostimulierende substanzen, verfahren zur herstellung derselben und carcinostatische mittel mit einem gehalt derselben |
| DK069282A DK151640C (da) | 1981-02-19 | 1982-02-17 | Fremgangsmaade til fremstilling af forbindelser med carcinostatisk og immunostimulerende virkning |
| IT47817/82A IT1189224B (it) | 1981-02-19 | 1982-02-17 | Sostanze carcinostatiche ed immunostimolanti tf-2,procedimento per prepararle ed agente carcinostatico che le contiene |
| CH979/82A CH651052A5 (de) | 1981-02-19 | 1982-02-17 | Verfahren zur herstellung einer karzinostatischen substanz und karzinostatische substanz. |
| FI820527A FI69096C (fi) | 1981-02-19 | 1982-02-17 | Foerfarande foer framstaellning av en karcinostatisk och immunostimulerande tf-2-substans |
| CA000396425A CA1184864A (fr) | 1981-02-19 | 1982-02-17 | Substances ayant des proprietes carcinostatiques et immunostimulantes, procede de preparation et agent carinostatique les contenant |
| FR8202601A FR2499855B1 (fr) | 1981-02-19 | 1982-02-17 | Nouvelles substances a action carcinostatique et immuno-stimulante, procede pour les preparer a partir de bacteries du genre fusobacterium, et agent carcinostatique contenant de telles substances |
| DD82237480A DD202891A5 (de) | 1981-02-19 | 1982-02-17 | Neue carcinostatische und immunostimulierende substanzen,verfahren zu ihrer herstellung und carcinostatische mittel mit einem gehalt derselben |
| NZ199771A NZ199771A (en) | 1981-02-19 | 1982-02-18 | Carcinostatic and immunostimulating substances produced by fusobacterium nucleatum |
| NL8200640A NL8200640A (nl) | 1981-02-19 | 1982-02-18 | Nieuwe, carcinostatische stoffen, preparaten die ze bevatten, en werkwijze voor de bereiding daarvan. |
| NO820509A NO157426C (no) | 1981-02-19 | 1982-02-18 | Fremgangsmaate for fremstilling av terapeutisk aktive forbindelser ved dyrking av mikroorganismer. |
| PT74455A PT74455B (en) | 1981-02-19 | 1982-02-18 | Process for preparing novel substances having carcinostatic and immunostimulating activity and of a carcinostatic agent containing same |
| SE8201016A SE457000B (sv) | 1981-02-19 | 1982-02-18 | Foerfarande foer framstaellning av en carcinostatisk och immunostimulerande tf-2-substans, carcinostatisk tf-2-substans samt carcinostatiskt medel. |
| KR8200714A KR890002256B1 (ko) | 1981-02-19 | 1982-02-18 | 항암 물질 tf-2 제조 방법 |
| BE0/207355A BE892204A (fr) | 1981-02-19 | 1982-02-19 | Nouvelles substances a action carcinostatique et immunq-stimulante, procede pour les preparer a partir de bacteries du genre fusobacterium, et agent carcinostatique contenat de telles substances |
| AT0064682A AT381722B (de) | 1981-02-19 | 1982-02-19 | Verfahren zur herstellung einer neuen carcinostatischen substanz |
| US06/619,895 US4591558A (en) | 1981-02-19 | 1984-08-06 | Novel substances having antitumor and immunostimulating activity, process for preparing the same and antitumor agent containing the same |
| DK251186A DK165641C (da) | 1981-02-19 | 1986-05-29 | Fremgangsmaade til fremstilling af tf-220, tf-230 og tf-240 forbindelser og de tilsvarende proteinfrie forbindelser |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56022277A JPS57139089A (en) | 1981-02-19 | 1981-02-19 | Carcinostatic substance tf-350, its preparation and carcinostatic agent containing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57139089A JPS57139089A (en) | 1982-08-27 |
| JPH021157B2 true JPH021157B2 (fr) | 1990-01-10 |
Family
ID=12078259
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56022277A Granted JPS57139089A (en) | 1981-02-19 | 1981-02-19 | Carcinostatic substance tf-350, its preparation and carcinostatic agent containing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57139089A (fr) |
-
1981
- 1981-02-19 JP JP56022277A patent/JPS57139089A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57139089A (en) | 1982-08-27 |
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