DNA Alkylation by leinamycin can be triggered by cyanide and phosphines
Previous work has shown that alkylation of DNA by the antitumor agent leinamycin ( 1) is potentiated by reaction of the antibiotic with thiols. Here, it is shown that other soft nucleophiles such as cyanide and phosphines can also trigger DNA alkylation by leinamycin. Overall, the results suggest th...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2001-06, Vol.11 (12), p.1511-1515 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Zang, Hong Breydo, Leonid Mitra, Kaushik Dannaldson, Jeffrey Gates, Kent S. |
| description | Previous work has shown that alkylation of DNA by the antitumor agent leinamycin (
1) is potentiated by reaction of the antibiotic with thiols. Here, it is shown that other soft nucleophiles such as cyanide and phosphines can also trigger DNA alkylation by leinamycin. Overall, the results suggest that reactions of cyanide and phosphines with leinamycin produce the oxathiolanone intermediate (
2), which is known to undergo rearrangement to the DNA-alkylating episulfonium ion
4.
Previous work has shown that alkylation of DNA by the antitumor agent leinamycin (
1) is potentiated by reaction of the antibiotic with thiols. Here it is shown that other soft nucleophiles such as cyanide and phosphines can also trigger DNA alkylation by leinamycin. |
| doi_str_mv | 10.1016/S0960-894X(01)00196-2 |
| format | Article |
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1) is potentiated by reaction of the antibiotic with thiols. Here, it is shown that other soft nucleophiles such as cyanide and phosphines can also trigger DNA alkylation by leinamycin. Overall, the results suggest that reactions of cyanide and phosphines with leinamycin produce the oxathiolanone intermediate (
2), which is known to undergo rearrangement to the DNA-alkylating episulfonium ion
4.
Previous work has shown that alkylation of DNA by the antitumor agent leinamycin (
1) is potentiated by reaction of the antibiotic with thiols. Here it is shown that other soft nucleophiles such as cyanide and phosphines can also trigger DNA alkylation by leinamycin.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/S0960-894X(01)00196-2</identifier><identifier>PMID: 11412971</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Alkylation - drug effects ; Antibiotics, Antineoplastic - metabolism ; Antineoplastic agents ; Biological and medical sciences ; Cyanides - pharmacology ; DNA - chemistry ; DNA - metabolism ; DNA Damage - drug effects ; Electrophoresis, Polyacrylamide Gel ; General aspects ; Lactams ; Macrolides ; Medical sciences ; Oligonucleotides - chemistry ; Oligonucleotides - metabolism ; Pharmacology. Drug treatments ; Phosphines - pharmacology ; Plasmids - chemistry ; Plasmids - metabolism ; Thiazoles ; Thiones</subject><ispartof>Bioorganic & medicinal chemistry letters, 2001-06, Vol.11 (12), p.1511-1515</ispartof><rights>2001 Elsevier Science Ltd</rights><rights>2001 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c390t-886f669e33bd699b9234664804778d8cc1a315aafe9fa729aa3da891fd84c6ec3</citedby><cites>FETCH-LOGICAL-c390t-886f669e33bd699b9234664804778d8cc1a315aafe9fa729aa3da891fd84c6ec3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/S0960-894X(01)00196-2$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3549,27923,27924,45994</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=1025056$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11412971$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zang, Hong</creatorcontrib><creatorcontrib>Breydo, Leonid</creatorcontrib><creatorcontrib>Mitra, Kaushik</creatorcontrib><creatorcontrib>Dannaldson, Jeffrey</creatorcontrib><creatorcontrib>Gates, Kent S.</creatorcontrib><title>DNA Alkylation by leinamycin can be triggered by cyanide and phosphines</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>Previous work has shown that alkylation of DNA by the antitumor agent leinamycin (
1) is potentiated by reaction of the antibiotic with thiols. Here, it is shown that other soft nucleophiles such as cyanide and phosphines can also trigger DNA alkylation by leinamycin. Overall, the results suggest that reactions of cyanide and phosphines with leinamycin produce the oxathiolanone intermediate (
2), which is known to undergo rearrangement to the DNA-alkylating episulfonium ion
4.
Previous work has shown that alkylation of DNA by the antitumor agent leinamycin (
1) is potentiated by reaction of the antibiotic with thiols. Here it is shown that other soft nucleophiles such as cyanide and phosphines can also trigger DNA alkylation by leinamycin.</description><subject>Alkylation - drug effects</subject><subject>Antibiotics, Antineoplastic - metabolism</subject><subject>Antineoplastic agents</subject><subject>Biological and medical sciences</subject><subject>Cyanides - pharmacology</subject><subject>DNA - chemistry</subject><subject>DNA - metabolism</subject><subject>DNA Damage - drug effects</subject><subject>Electrophoresis, Polyacrylamide Gel</subject><subject>General aspects</subject><subject>Lactams</subject><subject>Macrolides</subject><subject>Medical sciences</subject><subject>Oligonucleotides - chemistry</subject><subject>Oligonucleotides - metabolism</subject><subject>Pharmacology. Drug treatments</subject><subject>Phosphines - pharmacology</subject><subject>Plasmids - chemistry</subject><subject>Plasmids - metabolism</subject><subject>Thiazoles</subject><subject>Thiones</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2001</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkE1LxDAQhoMoun78BKUHET1UkyZNm5MsfsOiBxW8hdlkqtFuuiZdof_e7gfqzdPAzPPODA8h-4yeMsrk2SNVkqalEi_HlJ1QypRMszUyYEKKlAuar5PBD7JFtmN87yFBhdgkW4wJlqmCDcjN5f0wGdYfXQ2ta3wy7pIanYdJZ5xPDPQdTNrgXl8xoJ2PTQfeWUzA22T61sTpm_MYd8lGBXXEvVXdIc_XV08Xt-no4ebuYjhKDVe0TctSVlIq5HxspVJjlXEhpSipKIrSlsYw4CwHqFBVUGQKgFsoFatsKYxEw3fI0XLvNDSfM4ytnrhosK7BYzOLuqAqk0XOezBfgiY0MQas9DS4CYROM6rnBvXCoJ7r0ZTphUGd9bmD1YHZeIL2N7VS1gOHKwCigboK4I2Lf7ZnOc1lj50vMextfDkMOhqH3qB1AU2rbeP--eQbabyMlg</recordid><startdate>20010618</startdate><enddate>20010618</enddate><creator>Zang, Hong</creator><creator>Breydo, Leonid</creator><creator>Mitra, Kaushik</creator><creator>Dannaldson, Jeffrey</creator><creator>Gates, Kent S.</creator><general>Elsevier Ltd</general><general>Elsevier</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>7X8</scope></search><sort><creationdate>20010618</creationdate><title>DNA Alkylation by leinamycin can be triggered by cyanide and phosphines</title><author>Zang, Hong ; Breydo, Leonid ; Mitra, Kaushik ; Dannaldson, Jeffrey ; Gates, Kent S.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c390t-886f669e33bd699b9234664804778d8cc1a315aafe9fa729aa3da891fd84c6ec3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2001</creationdate><topic>Alkylation - drug effects</topic><topic>Antibiotics, Antineoplastic - metabolism</topic><topic>Antineoplastic agents</topic><topic>Biological and medical sciences</topic><topic>Cyanides - pharmacology</topic><topic>DNA - chemistry</topic><topic>DNA - metabolism</topic><topic>DNA Damage - drug effects</topic><topic>Electrophoresis, Polyacrylamide Gel</topic><topic>General aspects</topic><topic>Lactams</topic><topic>Macrolides</topic><topic>Medical sciences</topic><topic>Oligonucleotides - chemistry</topic><topic>Oligonucleotides - metabolism</topic><topic>Pharmacology. Drug treatments</topic><topic>Phosphines - pharmacology</topic><topic>Plasmids - chemistry</topic><topic>Plasmids - metabolism</topic><topic>Thiazoles</topic><topic>Thiones</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zang, Hong</creatorcontrib><creatorcontrib>Breydo, Leonid</creatorcontrib><creatorcontrib>Mitra, Kaushik</creatorcontrib><creatorcontrib>Dannaldson, Jeffrey</creatorcontrib><creatorcontrib>Gates, Kent S.</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>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zang, Hong</au><au>Breydo, Leonid</au><au>Mitra, Kaushik</au><au>Dannaldson, Jeffrey</au><au>Gates, Kent S.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>DNA Alkylation by leinamycin can be triggered by cyanide and phosphines</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2001-06-18</date><risdate>2001</risdate><volume>11</volume><issue>12</issue><spage>1511</spage><epage>1515</epage><pages>1511-1515</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>Previous work has shown that alkylation of DNA by the antitumor agent leinamycin (
1) is potentiated by reaction of the antibiotic with thiols. Here, it is shown that other soft nucleophiles such as cyanide and phosphines can also trigger DNA alkylation by leinamycin. Overall, the results suggest that reactions of cyanide and phosphines with leinamycin produce the oxathiolanone intermediate (
2), which is known to undergo rearrangement to the DNA-alkylating episulfonium ion
4.
Previous work has shown that alkylation of DNA by the antitumor agent leinamycin (
1) is potentiated by reaction of the antibiotic with thiols. Here it is shown that other soft nucleophiles such as cyanide and phosphines can also trigger DNA alkylation by leinamycin.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>11412971</pmid><doi>10.1016/S0960-894X(01)00196-2</doi><tpages>5</tpages></addata></record> |
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| subjects | Alkylation - drug effects Antibiotics, Antineoplastic - metabolism Antineoplastic agents Biological and medical sciences Cyanides - pharmacology DNA - chemistry DNA - metabolism DNA Damage - drug effects Electrophoresis, Polyacrylamide Gel General aspects Lactams Macrolides Medical sciences Oligonucleotides - chemistry Oligonucleotides - metabolism Pharmacology. Drug treatments Phosphines - pharmacology Plasmids - chemistry Plasmids - metabolism Thiazoles Thiones |
| title | DNA Alkylation by leinamycin can be triggered by cyanide and phosphines |
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