DNA degradation by the mixture of copper and catechol is caused by DNA-copper-hydroperoxo complexes, probably DNA-Cu(I)OOH
Free hydroxyl radicals (free ·OH), singlet oxygen (1O2), or ·OH produced by DNA‐copper‐hydroperoxo complexes are possible DNA‐damaging reactive oxygen species (ROS) in the reaction system containing copper, catechol, and DNA. para‐Chlorobenzoic acid (pCBA) degradation studies revealed that CuCl2 mix...
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creator | Schweigert, Nina Acero, Juan L. von Gunten, Urs Canonica, Silvio Zehnder, Alexander J.B. Eggen, Rik I.L. |
description | Free hydroxyl radicals (free ·OH), singlet oxygen (1O2), or ·OH produced by DNA‐copper‐hydroperoxo complexes are possible DNA‐damaging reactive oxygen species (ROS) in the reaction system containing copper, catechol, and DNA. para‐Chlorobenzoic acid (pCBA) degradation studies revealed that CuCl2 mixed with catechol produced free ·OH. In the presence of DNA, however, inhibition of the pCBA degradation suggested that another ROS is responsible for the DNA degradation. Of a series of ROS scavengers investigated, only KI, NaN3, and Na‐formate—all of the salts tested—strongly inhibited the DNA degradation, suggesting that the ionic strength rather than the reactivity of the individual scavengers could be responsible for the observed inhibition. The ionic strength effect was confirmed by increasing the concentration of phosphate buffer, which is a poor ·OH scavenger, and was interpreted as the result of destabilization of DNA‐copper‐hydroperoxo complexes. Piperidine‐labile site patterns in DNA degraded by copper and catechol showed that the mixture of Cu(II) and catechol degrades DNA via the intermediate formation of a DNA‐copper‐hydroperoxo complex. Replacement of guanine by 7‐deazaguanine did not retard the DNA degradation, suggesting that the DNA‐copper‐hydroperoxo complexes do not bind to the guanine N‐7 as proposed in the literature. Environ. Mol. Mutagen. 36:5–12, 2000. © 2000 Wiley‐Liss, Inc. |
doi_str_mv | 10.1002/1098-2280(2000)36:1<5::AID-EM2>3.0.CO;2-4 |
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In the presence of DNA, however, inhibition of the pCBA degradation suggested that another ROS is responsible for the DNA degradation. Of a series of ROS scavengers investigated, only KI, NaN3, and Na‐formate—all of the salts tested—strongly inhibited the DNA degradation, suggesting that the ionic strength rather than the reactivity of the individual scavengers could be responsible for the observed inhibition. The ionic strength effect was confirmed by increasing the concentration of phosphate buffer, which is a poor ·OH scavenger, and was interpreted as the result of destabilization of DNA‐copper‐hydroperoxo complexes. Piperidine‐labile site patterns in DNA degraded by copper and catechol showed that the mixture of Cu(II) and catechol degrades DNA via the intermediate formation of a DNA‐copper‐hydroperoxo complex. Replacement of guanine by 7‐deazaguanine did not retard the DNA degradation, suggesting that the DNA‐copper‐hydroperoxo complexes do not bind to the guanine N‐7 as proposed in the literature. Environ. Mol. Mutagen. 36:5–12, 2000. © 2000 Wiley‐Liss, Inc.</description><identifier>ISSN: 0893-6692</identifier><identifier>EISSN: 1098-2280</identifier><identifier>DOI: 10.1002/1098-2280(2000)36:1<5::AID-EM2>3.0.CO;2-4</identifier><identifier>PMID: 10918354</identifier><identifier>CODEN: EMMUEG</identifier><language>eng</language><publisher>New York: John Wiley & Sons, Inc</publisher><subject>Biological and medical sciences ; catechol ; Catechols - chemistry ; Catechols - pharmacology ; Chemical mutagenesis ; Copper - chemistry ; Copper - isolation & purification ; Copper - pharmacology ; DNA - chemistry ; DNA - drug effects ; DNA - metabolism ; DNA Damage - drug effects ; DNA degradation ; DNA-copper-hydroperoxo complex ; free hydroxyl radicals ; Free Radical Scavengers - chemistry ; Free Radical Scavengers - metabolism ; Guanine - analogs & derivatives ; Guanine - chemistry ; Guanine - metabolism ; Hydroxyl Radical ; Medical sciences ; Osmolar Concentration ; Piperidines - chemistry ; reactive oxygen species ; Reactive Oxygen Species - metabolism ; singlet oxygen ; Toxicology</subject><ispartof>Environmental and molecular mutagenesis, 2000, Vol.36 (1), p.5-12</ispartof><rights>Copyright © 2000 Wiley‐Liss, Inc.</rights><rights>2000 INIST-CNRS</rights><rights>Copyright 2000 Wiley-Liss, Inc.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c4722-ba0317a85ea084cc3723ef6e633aa0c21cf0b6b508b9db3e74f2620505116a2f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2F1098-2280%282000%2936%3A1%3C5%3A%3AAID-EM2%3E3.0.CO%3B2-4$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2F1098-2280%282000%2936%3A1%3C5%3A%3AAID-EM2%3E3.0.CO%3B2-4$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,4024,27923,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=1484265$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/10918354$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Schweigert, Nina</creatorcontrib><creatorcontrib>Acero, Juan L.</creatorcontrib><creatorcontrib>von Gunten, Urs</creatorcontrib><creatorcontrib>Canonica, Silvio</creatorcontrib><creatorcontrib>Zehnder, Alexander J.B.</creatorcontrib><creatorcontrib>Eggen, Rik I.L.</creatorcontrib><title>DNA degradation by the mixture of copper and catechol is caused by DNA-copper-hydroperoxo complexes, probably DNA-Cu(I)OOH</title><title>Environmental and molecular mutagenesis</title><addtitle>Environ. Mol. Mutagen</addtitle><description>Free hydroxyl radicals (free ·OH), singlet oxygen (1O2), or ·OH produced by DNA‐copper‐hydroperoxo complexes are possible DNA‐damaging reactive oxygen species (ROS) in the reaction system containing copper, catechol, and DNA. para‐Chlorobenzoic acid (pCBA) degradation studies revealed that CuCl2 mixed with catechol produced free ·OH. In the presence of DNA, however, inhibition of the pCBA degradation suggested that another ROS is responsible for the DNA degradation. Of a series of ROS scavengers investigated, only KI, NaN3, and Na‐formate—all of the salts tested—strongly inhibited the DNA degradation, suggesting that the ionic strength rather than the reactivity of the individual scavengers could be responsible for the observed inhibition. The ionic strength effect was confirmed by increasing the concentration of phosphate buffer, which is a poor ·OH scavenger, and was interpreted as the result of destabilization of DNA‐copper‐hydroperoxo complexes. Piperidine‐labile site patterns in DNA degraded by copper and catechol showed that the mixture of Cu(II) and catechol degrades DNA via the intermediate formation of a DNA‐copper‐hydroperoxo complex. Replacement of guanine by 7‐deazaguanine did not retard the DNA degradation, suggesting that the DNA‐copper‐hydroperoxo complexes do not bind to the guanine N‐7 as proposed in the literature. Environ. Mol. Mutagen. 36:5–12, 2000. © 2000 Wiley‐Liss, Inc.</description><subject>Biological and medical sciences</subject><subject>catechol</subject><subject>Catechols - chemistry</subject><subject>Catechols - pharmacology</subject><subject>Chemical mutagenesis</subject><subject>Copper - chemistry</subject><subject>Copper - isolation & purification</subject><subject>Copper - pharmacology</subject><subject>DNA - chemistry</subject><subject>DNA - drug effects</subject><subject>DNA - metabolism</subject><subject>DNA Damage - drug effects</subject><subject>DNA degradation</subject><subject>DNA-copper-hydroperoxo complex</subject><subject>free hydroxyl radicals</subject><subject>Free Radical Scavengers - chemistry</subject><subject>Free Radical Scavengers - metabolism</subject><subject>Guanine - analogs & derivatives</subject><subject>Guanine - chemistry</subject><subject>Guanine - metabolism</subject><subject>Hydroxyl Radical</subject><subject>Medical sciences</subject><subject>Osmolar Concentration</subject><subject>Piperidines - chemistry</subject><subject>reactive oxygen species</subject><subject>Reactive Oxygen Species - metabolism</subject><subject>singlet oxygen</subject><subject>Toxicology</subject><issn>0893-6692</issn><issn>1098-2280</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2000</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkdFu0zAUhiMEYmXwCigXCG0SKcd27CQFIVXp6Cq1yw1ol0eO49BA0gQ7ES1Pj6NUGxI3XPlY-vz51_k9jxCYEwD6nkASB5TGcEUB4JqJBfnIF4vlZhXc7OgnNod5mn2gQfjEmz2wT70ZxAkLhEjohffC2u8AhIQJfe5dOIjEjIcz7_fqbukX-puRheyr9uDnJ7_fa7-pjv1gtN-Wvmq7ThtfHgpfyV6rfVv7lXXzYHUx8k4RTFCwPxWmdUN7bN27pqv1Udt3fmfaXOb1hKbD1eY6y25fes9KWVv96nxeel8_33xJb4Nttt6ky22gwojSIJfASCRjriXEoVIsokyXQgvGpARFiSohFzmHOE-KnOkoLKmgwIETIiQt2aX3dvK6FD8HbXtsKqt0XcuDbgeLEaGc0Dh24GYClWmtNbrEzlSNNCckgGMROC4Xx-XiWAQygQQ5oisCXRHIEDDNkGLoXK_Pnw55o4u_TNPmHfDmDEirZF0aeVCVfeTCOKSCP2b6VdX69J-B_s0zXp0rmFyV7fXxwSXNDxQRizje360x3fL7dLXb4Zr9AZIsuEU</recordid><startdate>2000</startdate><enddate>2000</enddate><creator>Schweigert, Nina</creator><creator>Acero, Juan L.</creator><creator>von Gunten, Urs</creator><creator>Canonica, Silvio</creator><creator>Zehnder, Alexander J.B.</creator><creator>Eggen, Rik I.L.</creator><general>John Wiley & Sons, Inc</general><general>Wiley-Liss</general><scope>BSCLL</scope><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>2000</creationdate><title>DNA degradation by the mixture of copper and catechol is caused by DNA-copper-hydroperoxo complexes, probably DNA-Cu(I)OOH</title><author>Schweigert, Nina ; Acero, Juan L. ; von Gunten, Urs ; Canonica, Silvio ; Zehnder, Alexander J.B. ; Eggen, Rik I.L.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4722-ba0317a85ea084cc3723ef6e633aa0c21cf0b6b508b9db3e74f2620505116a2f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2000</creationdate><topic>Biological and medical sciences</topic><topic>catechol</topic><topic>Catechols - chemistry</topic><topic>Catechols - pharmacology</topic><topic>Chemical mutagenesis</topic><topic>Copper - chemistry</topic><topic>Copper - isolation & purification</topic><topic>Copper - pharmacology</topic><topic>DNA - chemistry</topic><topic>DNA - drug effects</topic><topic>DNA - metabolism</topic><topic>DNA Damage - drug effects</topic><topic>DNA degradation</topic><topic>DNA-copper-hydroperoxo complex</topic><topic>free hydroxyl radicals</topic><topic>Free Radical Scavengers - chemistry</topic><topic>Free Radical Scavengers - metabolism</topic><topic>Guanine - analogs & derivatives</topic><topic>Guanine - chemistry</topic><topic>Guanine - metabolism</topic><topic>Hydroxyl Radical</topic><topic>Medical sciences</topic><topic>Osmolar Concentration</topic><topic>Piperidines - chemistry</topic><topic>reactive oxygen species</topic><topic>Reactive Oxygen Species - metabolism</topic><topic>singlet oxygen</topic><topic>Toxicology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Schweigert, Nina</creatorcontrib><creatorcontrib>Acero, Juan L.</creatorcontrib><creatorcontrib>von Gunten, Urs</creatorcontrib><creatorcontrib>Canonica, Silvio</creatorcontrib><creatorcontrib>Zehnder, Alexander J.B.</creatorcontrib><creatorcontrib>Eggen, Rik I.L.</creatorcontrib><collection>Istex</collection><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>Environmental and molecular mutagenesis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Schweigert, Nina</au><au>Acero, Juan L.</au><au>von Gunten, Urs</au><au>Canonica, Silvio</au><au>Zehnder, Alexander J.B.</au><au>Eggen, Rik I.L.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>DNA degradation by the mixture of copper and catechol is caused by DNA-copper-hydroperoxo complexes, probably DNA-Cu(I)OOH</atitle><jtitle>Environmental and molecular mutagenesis</jtitle><addtitle>Environ. Mol. Mutagen</addtitle><date>2000</date><risdate>2000</risdate><volume>36</volume><issue>1</issue><spage>5</spage><epage>12</epage><pages>5-12</pages><issn>0893-6692</issn><eissn>1098-2280</eissn><coden>EMMUEG</coden><abstract>Free hydroxyl radicals (free ·OH), singlet oxygen (1O2), or ·OH produced by DNA‐copper‐hydroperoxo complexes are possible DNA‐damaging reactive oxygen species (ROS) in the reaction system containing copper, catechol, and DNA. para‐Chlorobenzoic acid (pCBA) degradation studies revealed that CuCl2 mixed with catechol produced free ·OH. In the presence of DNA, however, inhibition of the pCBA degradation suggested that another ROS is responsible for the DNA degradation. Of a series of ROS scavengers investigated, only KI, NaN3, and Na‐formate—all of the salts tested—strongly inhibited the DNA degradation, suggesting that the ionic strength rather than the reactivity of the individual scavengers could be responsible for the observed inhibition. The ionic strength effect was confirmed by increasing the concentration of phosphate buffer, which is a poor ·OH scavenger, and was interpreted as the result of destabilization of DNA‐copper‐hydroperoxo complexes. Piperidine‐labile site patterns in DNA degraded by copper and catechol showed that the mixture of Cu(II) and catechol degrades DNA via the intermediate formation of a DNA‐copper‐hydroperoxo complex. Replacement of guanine by 7‐deazaguanine did not retard the DNA degradation, suggesting that the DNA‐copper‐hydroperoxo complexes do not bind to the guanine N‐7 as proposed in the literature. Environ. Mol. Mutagen. 36:5–12, 2000. © 2000 Wiley‐Liss, Inc.</abstract><cop>New York</cop><pub>John Wiley & Sons, Inc</pub><pmid>10918354</pmid><doi>10.1002/1098-2280(2000)36:1<5::AID-EM2>3.0.CO;2-4</doi><tpages>8</tpages></addata></record> |
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subjects | Biological and medical sciences catechol Catechols - chemistry Catechols - pharmacology Chemical mutagenesis Copper - chemistry Copper - isolation & purification Copper - pharmacology DNA - chemistry DNA - drug effects DNA - metabolism DNA Damage - drug effects DNA degradation DNA-copper-hydroperoxo complex free hydroxyl radicals Free Radical Scavengers - chemistry Free Radical Scavengers - metabolism Guanine - analogs & derivatives Guanine - chemistry Guanine - metabolism Hydroxyl Radical Medical sciences Osmolar Concentration Piperidines - chemistry reactive oxygen species Reactive Oxygen Species - metabolism singlet oxygen Toxicology |
title | DNA degradation by the mixture of copper and catechol is caused by DNA-copper-hydroperoxo complexes, probably DNA-Cu(I)OOH |
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