BIOLOGICAL PROPERTIES OF STREPTONIGRIN DERIVATIVES: III. IN VITRO AND IN VIVO ANTIVIRAL AND ANTITUMOR ACTIVITIES
Antitumor antibiotic streptonigrin (STN-COOH) is a potent inhibitor of avian myeloblastosis virus (AMV) and human immunodeficiency virus reverse transcriptases. The carboxyl group at 2'-position of STN-COOH was modified to give esters, hydrazide, amides and amino acid derivatives for biological...
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| Veröffentlicht in: | Journal of antibiotics 1989/06/25, Vol.42(6), pp.968-976 |
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| container_title | Journal of antibiotics |
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| creator | TAKE, YUKINORI KUBO, TAB TAKEMORI, ERIKO INOUYE, YOSHIO NAKAMURA, SHOSHIRO NISHIMURA, TOSHIO SUZUKI, HIDEO YAMAGUCHI, HIDEYO |
| description | Antitumor antibiotic streptonigrin (STN-COOH) is a potent inhibitor of avian myeloblastosis virus (AMV) and human immunodeficiency virus reverse transcriptases. The carboxyl group at 2'-position of STN-COOH was modified to give esters, hydrazide, amides and amino acid derivatives for biological studies. Against AMV reverse transcriptase, the hydrazide, amides and amino acid derivatives showed inhibitory activity, which compared favorably to that of STN-COOH, with the ID50 values ranging 2-8 μg/ml. In contrast, the esters lacked this activity except for those having a dimethylamino group in the substituent. Splenomegaly caused by Friend leukemia virus infection was significantly inhibited by STN-COOH and STN-COO(CH2)3N(CH3)2, but not STN-CONH(CH2)3N(CH3)2. Doxorubicin-resistant murine lymphoblastoma L5178Y cells showed collateral sensitivity to both STN-COOH and STN-COO(CH2)3N(CH3)2 not only in vitro but also in vivo. |
| doi_str_mv | 10.7164/antibiotics.42.968 |
| format | Article |
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IN VITRO AND IN VIVO ANTIVIRAL AND ANTITUMOR ACTIVITIES</title><source>J-STAGE Free</source><source>MEDLINE</source><creator>TAKE, YUKINORI ; KUBO, TAB ; TAKEMORI, ERIKO ; INOUYE, YOSHIO ; NAKAMURA, SHOSHIRO ; NISHIMURA, TOSHIO ; SUZUKI, HIDEO ; YAMAGUCHI, HIDEYO</creator><creatorcontrib>TAKE, YUKINORI ; KUBO, TAB ; TAKEMORI, ERIKO ; INOUYE, YOSHIO ; NAKAMURA, SHOSHIRO ; NISHIMURA, TOSHIO ; SUZUKI, HIDEO ; YAMAGUCHI, HIDEYO</creatorcontrib><description>Antitumor antibiotic streptonigrin (STN-COOH) is a potent inhibitor of avian myeloblastosis virus (AMV) and human immunodeficiency virus reverse transcriptases. The carboxyl group at 2'-position of STN-COOH was modified to give esters, hydrazide, amides and amino acid derivatives for biological studies. Against AMV reverse transcriptase, the hydrazide, amides and amino acid derivatives showed inhibitory activity, which compared favorably to that of STN-COOH, with the ID50 values ranging 2-8 μg/ml. In contrast, the esters lacked this activity except for those having a dimethylamino group in the substituent. Splenomegaly caused by Friend leukemia virus infection was significantly inhibited by STN-COOH and STN-COO(CH2)3N(CH3)2, but not STN-CONH(CH2)3N(CH3)2. Doxorubicin-resistant murine lymphoblastoma L5178Y cells showed collateral sensitivity to both STN-COOH and STN-COO(CH2)3N(CH3)2 not only in vitro but also in vivo.</description><identifier>ISSN: 0021-8820</identifier><identifier>EISSN: 1881-1469</identifier><identifier>DOI: 10.7164/antibiotics.42.968</identifier><identifier>PMID: 2737955</identifier><identifier>CODEN: JANTAJ</identifier><language>eng</language><publisher>Tokyo: JAPAN ANTIBIOTICS RESEARCH ASSOCIATION</publisher><subject>AIDS/HIV ; Animals ; Antibiotics, Antineoplastic - pharmacology ; Antibiotics, Antineoplastic - therapeutic use ; Antineoplastic agents ; antitumor antibiotics ; antiviral agents ; Antiviral Agents - pharmacology ; Antiviral Agents - therapeutic use ; avian myeloblastosis virus ; Biological and medical sciences ; Chromatography, Gel ; Chromatography, Thin Layer ; Circular Dichroism ; Friend murine leukemia virus - drug effects ; General aspects ; human immunodeficiency virus ; Isomerism ; Leukemia, Experimental - drug therapy ; Lymphoma, Non-Hodgkin ; Male ; Medical sciences ; Mice ; Molecular Structure ; Pharmacology. Drug treatments ; streptonigrin ; Streptonigrin - analogs & derivatives ; Streptonigrin - pharmacology ; Tumor Cells, Cultured</subject><ispartof>The Journal of Antibiotics, 1989/06/25, Vol.42(6), pp.968-976</ispartof><rights>Japan Antibiotics Research Association</rights><rights>1990 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4518-c292fe1ee05f674321f006ba79455e5b49db560370d0aa6ef3661d480abd8f223</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,1877,4010,27900,27901,27902</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=6852106$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/2737955$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>TAKE, YUKINORI</creatorcontrib><creatorcontrib>KUBO, TAB</creatorcontrib><creatorcontrib>TAKEMORI, ERIKO</creatorcontrib><creatorcontrib>INOUYE, YOSHIO</creatorcontrib><creatorcontrib>NAKAMURA, SHOSHIRO</creatorcontrib><creatorcontrib>NISHIMURA, TOSHIO</creatorcontrib><creatorcontrib>SUZUKI, HIDEO</creatorcontrib><creatorcontrib>YAMAGUCHI, HIDEYO</creatorcontrib><title>BIOLOGICAL PROPERTIES OF STREPTONIGRIN DERIVATIVES: III. IN VITRO AND IN VIVO ANTIVIRAL AND ANTITUMOR ACTIVITIES</title><title>Journal of antibiotics</title><addtitle>J. Antibiot.</addtitle><description>Antitumor antibiotic streptonigrin (STN-COOH) is a potent inhibitor of avian myeloblastosis virus (AMV) and human immunodeficiency virus reverse transcriptases. The carboxyl group at 2'-position of STN-COOH was modified to give esters, hydrazide, amides and amino acid derivatives for biological studies. Against AMV reverse transcriptase, the hydrazide, amides and amino acid derivatives showed inhibitory activity, which compared favorably to that of STN-COOH, with the ID50 values ranging 2-8 μg/ml. In contrast, the esters lacked this activity except for those having a dimethylamino group in the substituent. Splenomegaly caused by Friend leukemia virus infection was significantly inhibited by STN-COOH and STN-COO(CH2)3N(CH3)2, but not STN-CONH(CH2)3N(CH3)2. Doxorubicin-resistant murine lymphoblastoma L5178Y cells showed collateral sensitivity to both STN-COOH and STN-COO(CH2)3N(CH3)2 not only in vitro but also in vivo.</description><subject>AIDS/HIV</subject><subject>Animals</subject><subject>Antibiotics, Antineoplastic - pharmacology</subject><subject>Antibiotics, Antineoplastic - therapeutic use</subject><subject>Antineoplastic agents</subject><subject>antitumor antibiotics</subject><subject>antiviral agents</subject><subject>Antiviral Agents - pharmacology</subject><subject>Antiviral Agents - therapeutic use</subject><subject>avian myeloblastosis virus</subject><subject>Biological and medical sciences</subject><subject>Chromatography, Gel</subject><subject>Chromatography, Thin Layer</subject><subject>Circular Dichroism</subject><subject>Friend murine leukemia virus - drug effects</subject><subject>General aspects</subject><subject>human immunodeficiency virus</subject><subject>Isomerism</subject><subject>Leukemia, Experimental - drug therapy</subject><subject>Lymphoma, Non-Hodgkin</subject><subject>Male</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Molecular Structure</subject><subject>Pharmacology. Drug treatments</subject><subject>streptonigrin</subject><subject>Streptonigrin - analogs & derivatives</subject><subject>Streptonigrin - pharmacology</subject><subject>Tumor Cells, Cultured</subject><issn>0021-8820</issn><issn>1881-1469</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1989</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkMFPgzAYxRujmXP6D5iYcDDemG1pSznOySZxGQvDXZsCRVkYTMoO_vd2AZfdvPRL837fe18eAPcIjl3EyLOs2iIp6rZI9Zjgscf4BRgizpGNCPMuwRBCjGzOMbwGN1pvIXRcx-UDMMBmepQOAX4JwkU4D6aThbWKwpUfxYG_tsKZtY4jfxWHy2AeBUvr1Y-CzSQONv76FlzlstTqrp8j8DHz4-mb3fvYKaGI2yn2cK6QUpDmzCUORjmELJGuRyhVNCFellBmLoIZlJKp3GEMZYRDmWQ8x9gZgafOd9_U3welW7ErdKrKUlaqPmjhepAg5vF_QUQdhhGnBsQdmDa11o3Kxb4pdrL5EQiKY6PirFFBsDCNmqWH3v2Q7FR2WukrNPpjr0udyjJvZJUW-oQxTjGCzGDvHbbVrfxUJ102JqxU58nIxB7TWfccf39U-iUboSrnF9Vdluo</recordid><startdate>1989</startdate><enddate>1989</enddate><creator>TAKE, YUKINORI</creator><creator>KUBO, TAB</creator><creator>TAKEMORI, ERIKO</creator><creator>INOUYE, YOSHIO</creator><creator>NAKAMURA, SHOSHIRO</creator><creator>NISHIMURA, TOSHIO</creator><creator>SUZUKI, HIDEO</creator><creator>YAMAGUCHI, HIDEYO</creator><general>JAPAN ANTIBIOTICS RESEARCH ASSOCIATION</general><general>Japan Antibiotics Research Association</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QL</scope><scope>7QO</scope><scope>7T7</scope><scope>7U9</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>H94</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>1989</creationdate><title>BIOLOGICAL PROPERTIES OF STREPTONIGRIN DERIVATIVES</title><author>TAKE, YUKINORI ; KUBO, TAB ; TAKEMORI, ERIKO ; INOUYE, YOSHIO ; NAKAMURA, SHOSHIRO ; NISHIMURA, TOSHIO ; SUZUKI, HIDEO ; YAMAGUCHI, HIDEYO</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4518-c292fe1ee05f674321f006ba79455e5b49db560370d0aa6ef3661d480abd8f223</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1989</creationdate><topic>AIDS/HIV</topic><topic>Animals</topic><topic>Antibiotics, Antineoplastic - pharmacology</topic><topic>Antibiotics, Antineoplastic - therapeutic use</topic><topic>Antineoplastic agents</topic><topic>antitumor antibiotics</topic><topic>antiviral agents</topic><topic>Antiviral Agents - pharmacology</topic><topic>Antiviral Agents - therapeutic use</topic><topic>avian myeloblastosis virus</topic><topic>Biological and medical sciences</topic><topic>Chromatography, Gel</topic><topic>Chromatography, Thin Layer</topic><topic>Circular Dichroism</topic><topic>Friend murine leukemia virus - drug effects</topic><topic>General aspects</topic><topic>human immunodeficiency virus</topic><topic>Isomerism</topic><topic>Leukemia, Experimental - drug therapy</topic><topic>Lymphoma, Non-Hodgkin</topic><topic>Male</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Molecular Structure</topic><topic>Pharmacology. Drug treatments</topic><topic>streptonigrin</topic><topic>Streptonigrin - analogs & derivatives</topic><topic>Streptonigrin - pharmacology</topic><topic>Tumor Cells, Cultured</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>TAKE, YUKINORI</creatorcontrib><creatorcontrib>KUBO, TAB</creatorcontrib><creatorcontrib>TAKEMORI, ERIKO</creatorcontrib><creatorcontrib>INOUYE, YOSHIO</creatorcontrib><creatorcontrib>NAKAMURA, SHOSHIRO</creatorcontrib><creatorcontrib>NISHIMURA, TOSHIO</creatorcontrib><creatorcontrib>SUZUKI, HIDEO</creatorcontrib><creatorcontrib>YAMAGUCHI, HIDEYO</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Virology and AIDS Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of antibiotics</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>TAKE, YUKINORI</au><au>KUBO, TAB</au><au>TAKEMORI, ERIKO</au><au>INOUYE, YOSHIO</au><au>NAKAMURA, SHOSHIRO</au><au>NISHIMURA, TOSHIO</au><au>SUZUKI, HIDEO</au><au>YAMAGUCHI, HIDEYO</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>BIOLOGICAL PROPERTIES OF STREPTONIGRIN DERIVATIVES: III. IN VITRO AND IN VIVO ANTIVIRAL AND ANTITUMOR ACTIVITIES</atitle><jtitle>Journal of antibiotics</jtitle><addtitle>J. Antibiot.</addtitle><date>1989</date><risdate>1989</risdate><volume>42</volume><issue>6</issue><spage>968</spage><epage>976</epage><pages>968-976</pages><issn>0021-8820</issn><eissn>1881-1469</eissn><coden>JANTAJ</coden><abstract>Antitumor antibiotic streptonigrin (STN-COOH) is a potent inhibitor of avian myeloblastosis virus (AMV) and human immunodeficiency virus reverse transcriptases. The carboxyl group at 2'-position of STN-COOH was modified to give esters, hydrazide, amides and amino acid derivatives for biological studies. Against AMV reverse transcriptase, the hydrazide, amides and amino acid derivatives showed inhibitory activity, which compared favorably to that of STN-COOH, with the ID50 values ranging 2-8 μg/ml. In contrast, the esters lacked this activity except for those having a dimethylamino group in the substituent. Splenomegaly caused by Friend leukemia virus infection was significantly inhibited by STN-COOH and STN-COO(CH2)3N(CH3)2, but not STN-CONH(CH2)3N(CH3)2. Doxorubicin-resistant murine lymphoblastoma L5178Y cells showed collateral sensitivity to both STN-COOH and STN-COO(CH2)3N(CH3)2 not only in vitro but also in vivo.</abstract><cop>Tokyo</cop><pub>JAPAN ANTIBIOTICS RESEARCH ASSOCIATION</pub><pmid>2737955</pmid><doi>10.7164/antibiotics.42.968</doi><tpages>9</tpages><oa>free_for_read</oa></addata></record> |
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| identifier | ISSN: 0021-8820 |
| ispartof | The Journal of Antibiotics, 1989/06/25, Vol.42(6), pp.968-976 |
| issn | 0021-8820 1881-1469 |
| language | eng |
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| source | J-STAGE Free; MEDLINE |
| subjects | AIDS/HIV Animals Antibiotics, Antineoplastic - pharmacology Antibiotics, Antineoplastic - therapeutic use Antineoplastic agents antitumor antibiotics antiviral agents Antiviral Agents - pharmacology Antiviral Agents - therapeutic use avian myeloblastosis virus Biological and medical sciences Chromatography, Gel Chromatography, Thin Layer Circular Dichroism Friend murine leukemia virus - drug effects General aspects human immunodeficiency virus Isomerism Leukemia, Experimental - drug therapy Lymphoma, Non-Hodgkin Male Medical sciences Mice Molecular Structure Pharmacology. Drug treatments streptonigrin Streptonigrin - analogs & derivatives Streptonigrin - pharmacology Tumor Cells, Cultured |
| title | BIOLOGICAL PROPERTIES OF STREPTONIGRIN DERIVATIVES: III. IN VITRO AND IN VIVO ANTIVIRAL AND ANTITUMOR ACTIVITIES |
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