Comparison of the sequence selectivity of the DNA-alkylating pluramycin antitumour antibiotics DC92-B and hedamycin
The sequence selectivity of DNA alkylation by the recently isolated pluramycin antitumour antibiotic DC92-B has been investigated using two methods: a piperidine-induced strand-breaking procedure and a Taq DNA polymerase/linear amplification method. These techniques reveal that guanines are the most...
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| Veröffentlicht in: | Chemico-biological interactions 1995-03, Vol.95 (1), p.17-28 |
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| creator | Prakash, A.S. Moore, Anthony G. Murray, Vincent Matias, Christina McFadyen, W.David Wickham, Geoffrey |
| description | The sequence selectivity of DNA alkylation by the recently isolated pluramycin antitumour antibiotic DC92-B has been investigated using two methods: a piperidine-induced strand-breaking procedure and a
Taq DNA polymerase/linear amplification method. These techniques reveal that guanines are the most reactive sites for alkylation and that the level of adduct formation at these sites is clearly sequence dependent. The highest levels of alkylation occurred at isolated guanines located in 5′-C
GT sequences and also at the 5′-G in some 5′-CGG sequences. Isolated guanines in 5′-T
GT sequences were also quite reactive. We have also re-examined, in parallel, the sequence selectivity of binding of the structurally-related compound hedamycin: the first known example of a bis(epoxide)-containing, DNA-alkylating pluramycin. Our studies included a more extensive sequence analysis of hedamycin binding than that previously reported and we are able, therefore, to define more precisely the sequence preference. Despite significant differences in the stereochemistry and substitution of their bis(epoxide) sidechains, hedamycin and DC92-B exhibited very similar sequence selectivities in our assays. |
| doi_str_mv | 10.1016/0009-2797(94)03341-2 |
| format | Article |
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Taq DNA polymerase/linear amplification method. These techniques reveal that guanines are the most reactive sites for alkylation and that the level of adduct formation at these sites is clearly sequence dependent. The highest levels of alkylation occurred at isolated guanines located in 5′-C
GT sequences and also at the 5′-G in some 5′-CGG sequences. Isolated guanines in 5′-T
GT sequences were also quite reactive. We have also re-examined, in parallel, the sequence selectivity of binding of the structurally-related compound hedamycin: the first known example of a bis(epoxide)-containing, DNA-alkylating pluramycin. Our studies included a more extensive sequence analysis of hedamycin binding than that previously reported and we are able, therefore, to define more precisely the sequence preference. Despite significant differences in the stereochemistry and substitution of their bis(epoxide) sidechains, hedamycin and DC92-B exhibited very similar sequence selectivities in our assays.</description><identifier>ISSN: 0009-2797</identifier><identifier>EISSN: 1872-7786</identifier><identifier>DOI: 10.1016/0009-2797(94)03341-2</identifier><identifier>PMID: 7697748</identifier><identifier>CODEN: CBINA8</identifier><language>eng</language><publisher>Shannon: Elsevier Ireland Ltd</publisher><subject>Alkylation ; Animals ; Anthraquinones - metabolism ; Anthraquinones - pharmacology ; Antibiotics, Antineoplastic - metabolism ; Antibiotics, Antineoplastic - pharmacology ; Antineoplastic agents ; Antitumour ; Base Sequence ; Binding Sites ; Biological and medical sciences ; Cattle ; Chemotherapy ; DC92-B ; Deoxyribonuclease BamHI - metabolism ; Deoxyribonuclease EcoRI - metabolism ; DNA - drug effects ; DNA - metabolism ; DNA alkylation ; DNA-Directed DNA Polymerase - metabolism ; Hedamycin ; Medical sciences ; Molecular Sequence Data ; Nucleic Acid Synthesis Inhibitors ; Pharmacology. Drug treatments ; Pluramycins ; Sequence selectivity ; Spectrophotometry ; Taq Polymerase</subject><ispartof>Chemico-biological interactions, 1995-03, Vol.95 (1), p.17-28</ispartof><rights>1995</rights><rights>1995 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c332t-447545aad7d9a61faef5fb129bc6f0e818cf22f88456ed9e6e6c0b1db9d8568d3</citedby><cites>FETCH-LOGICAL-c332t-447545aad7d9a61faef5fb129bc6f0e818cf22f88456ed9e6e6c0b1db9d8568d3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/0009279794033412$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=3457046$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/7697748$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Prakash, A.S.</creatorcontrib><creatorcontrib>Moore, Anthony G.</creatorcontrib><creatorcontrib>Murray, Vincent</creatorcontrib><creatorcontrib>Matias, Christina</creatorcontrib><creatorcontrib>McFadyen, W.David</creatorcontrib><creatorcontrib>Wickham, Geoffrey</creatorcontrib><title>Comparison of the sequence selectivity of the DNA-alkylating pluramycin antitumour antibiotics DC92-B and hedamycin</title><title>Chemico-biological interactions</title><addtitle>Chem Biol Interact</addtitle><description>The sequence selectivity of DNA alkylation by the recently isolated pluramycin antitumour antibiotic DC92-B has been investigated using two methods: a piperidine-induced strand-breaking procedure and a
Taq DNA polymerase/linear amplification method. These techniques reveal that guanines are the most reactive sites for alkylation and that the level of adduct formation at these sites is clearly sequence dependent. The highest levels of alkylation occurred at isolated guanines located in 5′-C
GT sequences and also at the 5′-G in some 5′-CGG sequences. Isolated guanines in 5′-T
GT sequences were also quite reactive. We have also re-examined, in parallel, the sequence selectivity of binding of the structurally-related compound hedamycin: the first known example of a bis(epoxide)-containing, DNA-alkylating pluramycin. Our studies included a more extensive sequence analysis of hedamycin binding than that previously reported and we are able, therefore, to define more precisely the sequence preference. Despite significant differences in the stereochemistry and substitution of their bis(epoxide) sidechains, hedamycin and DC92-B exhibited very similar sequence selectivities in our assays.</description><subject>Alkylation</subject><subject>Animals</subject><subject>Anthraquinones - metabolism</subject><subject>Anthraquinones - pharmacology</subject><subject>Antibiotics, Antineoplastic - metabolism</subject><subject>Antibiotics, Antineoplastic - pharmacology</subject><subject>Antineoplastic agents</subject><subject>Antitumour</subject><subject>Base Sequence</subject><subject>Binding Sites</subject><subject>Biological and medical sciences</subject><subject>Cattle</subject><subject>Chemotherapy</subject><subject>DC92-B</subject><subject>Deoxyribonuclease BamHI - metabolism</subject><subject>Deoxyribonuclease EcoRI - metabolism</subject><subject>DNA - drug effects</subject><subject>DNA - metabolism</subject><subject>DNA alkylation</subject><subject>DNA-Directed DNA Polymerase - metabolism</subject><subject>Hedamycin</subject><subject>Medical sciences</subject><subject>Molecular Sequence Data</subject><subject>Nucleic Acid Synthesis Inhibitors</subject><subject>Pharmacology. Drug treatments</subject><subject>Pluramycins</subject><subject>Sequence selectivity</subject><subject>Spectrophotometry</subject><subject>Taq Polymerase</subject><issn>0009-2797</issn><issn>1872-7786</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1995</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkU9v1DAQxS0EKtvCNyhSDgi1h4DtOP5zQSrbFpAquLRny7HHrSGJF9uptN--SXfZI5w89vvNaPweQqcEfySY8E8YY1VTocSZYue4aRip6Qu0IlLQWgjJX6LVAXmNjnP-NV8xZfgIHQmuhGByhfI6DhuTQo5jFX1VHqDK8GeC0S5FD7aEx1C2f7XLHxe16X9ve1PCeF9t-imZYWvDWJmxhDINcUrPZRdiCTZXl2tF6y_zk6sewO3YN-iVN32Gt_vzBN1dX92uv9U3P79-X1_c1LZpaKkZEy1rjXHCKcOJN-Bb3xGqOss9Bkmk9ZR6KVnLwSngwC3uiOuUky2XrjlBH3ZzNynOX8pFDyFb6HszQpyyFoIoIpX8L0i4krxt6QyyHWhTzDmB15sUBpO2mmC9hKIXx_XiuFZMP4eil7Z3-_lTN4A7NO1TmPX3e91ka3qfzGhDPmANawVmfMY-7zCYTXsMkHS2YUnKhTQHpV0M_97jCcPqqbc</recordid><startdate>19950330</startdate><enddate>19950330</enddate><creator>Prakash, A.S.</creator><creator>Moore, Anthony G.</creator><creator>Murray, Vincent</creator><creator>Matias, Christina</creator><creator>McFadyen, W.David</creator><creator>Wickham, Geoffrey</creator><general>Elsevier Ireland Ltd</general><general>Elsevier Science</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>7TM</scope><scope>7U7</scope><scope>C1K</scope><scope>7X8</scope></search><sort><creationdate>19950330</creationdate><title>Comparison of the sequence selectivity of the DNA-alkylating pluramycin antitumour antibiotics DC92-B and hedamycin</title><author>Prakash, A.S. ; Moore, Anthony G. ; Murray, Vincent ; Matias, Christina ; McFadyen, W.David ; Wickham, Geoffrey</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c332t-447545aad7d9a61faef5fb129bc6f0e818cf22f88456ed9e6e6c0b1db9d8568d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1995</creationdate><topic>Alkylation</topic><topic>Animals</topic><topic>Anthraquinones - metabolism</topic><topic>Anthraquinones - pharmacology</topic><topic>Antibiotics, Antineoplastic - metabolism</topic><topic>Antibiotics, Antineoplastic - pharmacology</topic><topic>Antineoplastic agents</topic><topic>Antitumour</topic><topic>Base Sequence</topic><topic>Binding Sites</topic><topic>Biological and medical sciences</topic><topic>Cattle</topic><topic>Chemotherapy</topic><topic>DC92-B</topic><topic>Deoxyribonuclease BamHI - metabolism</topic><topic>Deoxyribonuclease EcoRI - metabolism</topic><topic>DNA - drug effects</topic><topic>DNA - metabolism</topic><topic>DNA alkylation</topic><topic>DNA-Directed DNA Polymerase - metabolism</topic><topic>Hedamycin</topic><topic>Medical sciences</topic><topic>Molecular Sequence Data</topic><topic>Nucleic Acid Synthesis Inhibitors</topic><topic>Pharmacology. Drug treatments</topic><topic>Pluramycins</topic><topic>Sequence selectivity</topic><topic>Spectrophotometry</topic><topic>Taq Polymerase</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Prakash, A.S.</creatorcontrib><creatorcontrib>Moore, Anthony G.</creatorcontrib><creatorcontrib>Murray, Vincent</creatorcontrib><creatorcontrib>Matias, Christina</creatorcontrib><creatorcontrib>McFadyen, W.David</creatorcontrib><creatorcontrib>Wickham, Geoffrey</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>Nucleic Acids Abstracts</collection><collection>Toxicology Abstracts</collection><collection>Environmental Sciences and Pollution Management</collection><collection>MEDLINE - Academic</collection><jtitle>Chemico-biological interactions</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Prakash, A.S.</au><au>Moore, Anthony G.</au><au>Murray, Vincent</au><au>Matias, Christina</au><au>McFadyen, W.David</au><au>Wickham, Geoffrey</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Comparison of the sequence selectivity of the DNA-alkylating pluramycin antitumour antibiotics DC92-B and hedamycin</atitle><jtitle>Chemico-biological interactions</jtitle><addtitle>Chem Biol Interact</addtitle><date>1995-03-30</date><risdate>1995</risdate><volume>95</volume><issue>1</issue><spage>17</spage><epage>28</epage><pages>17-28</pages><issn>0009-2797</issn><eissn>1872-7786</eissn><coden>CBINA8</coden><abstract>The sequence selectivity of DNA alkylation by the recently isolated pluramycin antitumour antibiotic DC92-B has been investigated using two methods: a piperidine-induced strand-breaking procedure and a
Taq DNA polymerase/linear amplification method. These techniques reveal that guanines are the most reactive sites for alkylation and that the level of adduct formation at these sites is clearly sequence dependent. The highest levels of alkylation occurred at isolated guanines located in 5′-C
GT sequences and also at the 5′-G in some 5′-CGG sequences. Isolated guanines in 5′-T
GT sequences were also quite reactive. We have also re-examined, in parallel, the sequence selectivity of binding of the structurally-related compound hedamycin: the first known example of a bis(epoxide)-containing, DNA-alkylating pluramycin. Our studies included a more extensive sequence analysis of hedamycin binding than that previously reported and we are able, therefore, to define more precisely the sequence preference. Despite significant differences in the stereochemistry and substitution of their bis(epoxide) sidechains, hedamycin and DC92-B exhibited very similar sequence selectivities in our assays.</abstract><cop>Shannon</cop><pub>Elsevier Ireland Ltd</pub><pmid>7697748</pmid><doi>10.1016/0009-2797(94)03341-2</doi><tpages>12</tpages></addata></record> |
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| ispartof | Chemico-biological interactions, 1995-03, Vol.95 (1), p.17-28 |
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| subjects | Alkylation Animals Anthraquinones - metabolism Anthraquinones - pharmacology Antibiotics, Antineoplastic - metabolism Antibiotics, Antineoplastic - pharmacology Antineoplastic agents Antitumour Base Sequence Binding Sites Biological and medical sciences Cattle Chemotherapy DC92-B Deoxyribonuclease BamHI - metabolism Deoxyribonuclease EcoRI - metabolism DNA - drug effects DNA - metabolism DNA alkylation DNA-Directed DNA Polymerase - metabolism Hedamycin Medical sciences Molecular Sequence Data Nucleic Acid Synthesis Inhibitors Pharmacology. Drug treatments Pluramycins Sequence selectivity Spectrophotometry Taq Polymerase |
| title | Comparison of the sequence selectivity of the DNA-alkylating pluramycin antitumour antibiotics DC92-B and hedamycin |
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