In vitro evidence for direct complexation of ADR-529/ICRF-187 [(+)-1,2-bis-(3,5-dioxo-piperazin-1-yl)propane] onto an existing ferric-anthracycline complex
ADR-529 protects against anthracycline cardiotoxicity, possibly by preventing free radical induction. We hypothesize that this occurs by ADR-529 forming a ternary anthracycline-iron-ADR-529 complex. This study used 200-MHz Fourier-transformed NMR to demonstrate the ability of ADR-529 to do this. Pea...
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| Veröffentlicht in: | Molecular pharmacology 1992-01, Vol.41 (1), p.8-17 |
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| container_title | Molecular pharmacology |
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| creator | SOBOL, M. M AMIET, R. G GREEN, M. D |
| description | ADR-529 protects against anthracycline cardiotoxicity, possibly by preventing free radical induction. We hypothesize that
this occurs by ADR-529 forming a ternary anthracycline-iron-ADR-529 complex. This study used 200-MHz Fourier-transformed NMR
to demonstrate the ability of ADR-529 to do this. Peak assignments were by proton-correlated spectroscopy and proton-carbon
heteronuclear-correlated spectroscopy. Ga3+ served as a probe for Fe3+, and D2O was the system solvent. Doxorubicin and epirubicin
were the studied drugs. Proton spectra of multiple combinations (including pure standards as controls) were obtained. Both
Ga3+ plus ADR-529 and Ga3+ plus doxorubicin showed evidence of complexation, as seen by appropriate peak shifts and changes
in the associated coupling constants. Ga3+ plus ADR-529 plus epirubicin showed complexation different from that of Ga3+ plus
ADR-529 or Ga3+ plus doxorubicin and consistent with the proposed structure. We conclude that ADR-529 would be able to form
a ternary complex with an existing anthracycline-Fe3+ complex in an isolated aqueous environment. |
| format | Article |
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this occurs by ADR-529 forming a ternary anthracycline-iron-ADR-529 complex. This study used 200-MHz Fourier-transformed NMR
to demonstrate the ability of ADR-529 to do this. Peak assignments were by proton-correlated spectroscopy and proton-carbon
heteronuclear-correlated spectroscopy. Ga3+ served as a probe for Fe3+, and D2O was the system solvent. Doxorubicin and epirubicin
were the studied drugs. Proton spectra of multiple combinations (including pure standards as controls) were obtained. Both
Ga3+ plus ADR-529 and Ga3+ plus doxorubicin showed evidence of complexation, as seen by appropriate peak shifts and changes
in the associated coupling constants. Ga3+ plus ADR-529 plus epirubicin showed complexation different from that of Ga3+ plus
ADR-529 or Ga3+ plus doxorubicin and consistent with the proposed structure. We conclude that ADR-529 would be able to form
a ternary complex with an existing anthracycline-Fe3+ complex in an isolated aqueous environment.</description><identifier>ISSN: 0026-895X</identifier><identifier>EISSN: 1521-0111</identifier><identifier>PMID: 1732725</identifier><identifier>CODEN: MOPMA3</identifier><language>eng</language><publisher>Bethesda, MD: American Society for Pharmacology and Experimental Therapeutics</publisher><subject>Antibiotics, Antineoplastic - chemistry ; Biological and medical sciences ; Computer Simulation ; Doxorubicin - chemistry ; Drug toxicity and drugs side effects treatment ; Ferric Compounds - chemistry ; Fourier Analysis ; Free Radicals ; Gallium - chemistry ; Magnetic Resonance Spectroscopy - methods ; Medical sciences ; Models, Chemical ; Molecular Conformation ; Pharmacology. Drug treatments ; Razoxane - chemistry ; Spectrum Analysis - methods ; Toxicity: cardiovascular system</subject><ispartof>Molecular pharmacology, 1992-01, Vol.41 (1), p.8-17</ispartof><rights>1992 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,4023</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=5098412$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/1732725$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>SOBOL, M. M</creatorcontrib><creatorcontrib>AMIET, R. G</creatorcontrib><creatorcontrib>GREEN, M. D</creatorcontrib><title>In vitro evidence for direct complexation of ADR-529/ICRF-187 [(+)-1,2-bis-(3,5-dioxo-piperazin-1-yl)propane] onto an existing ferric-anthracycline complex</title><title>Molecular pharmacology</title><addtitle>Mol Pharmacol</addtitle><description>ADR-529 protects against anthracycline cardiotoxicity, possibly by preventing free radical induction. We hypothesize that
this occurs by ADR-529 forming a ternary anthracycline-iron-ADR-529 complex. This study used 200-MHz Fourier-transformed NMR
to demonstrate the ability of ADR-529 to do this. Peak assignments were by proton-correlated spectroscopy and proton-carbon
heteronuclear-correlated spectroscopy. Ga3+ served as a probe for Fe3+, and D2O was the system solvent. Doxorubicin and epirubicin
were the studied drugs. Proton spectra of multiple combinations (including pure standards as controls) were obtained. Both
Ga3+ plus ADR-529 and Ga3+ plus doxorubicin showed evidence of complexation, as seen by appropriate peak shifts and changes
in the associated coupling constants. Ga3+ plus ADR-529 plus epirubicin showed complexation different from that of Ga3+ plus
ADR-529 or Ga3+ plus doxorubicin and consistent with the proposed structure. We conclude that ADR-529 would be able to form
a ternary complex with an existing anthracycline-Fe3+ complex in an isolated aqueous environment.</description><subject>Antibiotics, Antineoplastic - chemistry</subject><subject>Biological and medical sciences</subject><subject>Computer Simulation</subject><subject>Doxorubicin - chemistry</subject><subject>Drug toxicity and drugs side effects treatment</subject><subject>Ferric Compounds - chemistry</subject><subject>Fourier Analysis</subject><subject>Free Radicals</subject><subject>Gallium - chemistry</subject><subject>Magnetic Resonance Spectroscopy - methods</subject><subject>Medical sciences</subject><subject>Models, Chemical</subject><subject>Molecular Conformation</subject><subject>Pharmacology. Drug treatments</subject><subject>Razoxane - chemistry</subject><subject>Spectrum Analysis - methods</subject><subject>Toxicity: cardiovascular system</subject><issn>0026-895X</issn><issn>1521-0111</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1992</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo9kFFrFDEUhQdR6lr9CUJAkRYbTDKTSfJYVqsLBaH0QRAZ7mRudiIzyTSZrbv-Ff-so119ug_n45xzz6NixaXglHHOHxcrxkRNtZFfnhbPcv7OGK-kZifFCVelUEKuil-bQO79nCLBe99hsEhcTKTzCe1MbBynAfcw-xhIdOTy_Q2VwrzbrG-uKNeKfD17e075haCtz_SsvJC083Ef6eQnTPDTB8rpYTifUpwg4DcSwxwJBIJ7n2cftsRhSt5SCHOfwB7s4AP-i31ePHEwZHxxvKfF7dWH2_Unev3542Z9eU17rvRMoa1Bua5qAZanmKsr5qSpOg2lQsOxtGg6aIWRQrPWcSutqRRjwGpnmChPizcPtkvLux3muRl9tjgMS-O4y40SSqua_wFfHsFdO2LXTMmPkA7NccxFf33UIVsYXIJgff6PSWZ09dfm1QPW-23_Yxm6mXpII9g4xO2hqXjDG13-BuwpicE</recordid><startdate>19920101</startdate><enddate>19920101</enddate><creator>SOBOL, M. M</creator><creator>AMIET, R. G</creator><creator>GREEN, M. D</creator><general>American Society for Pharmacology and Experimental Therapeutics</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>19920101</creationdate><title>In vitro evidence for direct complexation of ADR-529/ICRF-187 [(+)-1,2-bis-(3,5-dioxo-piperazin-1-yl)propane] onto an existing ferric-anthracycline complex</title><author>SOBOL, M. M ; AMIET, R. G ; GREEN, M. D</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-h178t-ab6a7fd4baa3270f640f594d8a37e91e3ce9dab295280bf1c5c94700a06f9023</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1992</creationdate><topic>Antibiotics, Antineoplastic - chemistry</topic><topic>Biological and medical sciences</topic><topic>Computer Simulation</topic><topic>Doxorubicin - chemistry</topic><topic>Drug toxicity and drugs side effects treatment</topic><topic>Ferric Compounds - chemistry</topic><topic>Fourier Analysis</topic><topic>Free Radicals</topic><topic>Gallium - chemistry</topic><topic>Magnetic Resonance Spectroscopy - methods</topic><topic>Medical sciences</topic><topic>Models, Chemical</topic><topic>Molecular Conformation</topic><topic>Pharmacology. Drug treatments</topic><topic>Razoxane - chemistry</topic><topic>Spectrum Analysis - methods</topic><topic>Toxicity: cardiovascular system</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>SOBOL, M. M</creatorcontrib><creatorcontrib>AMIET, R. G</creatorcontrib><creatorcontrib>GREEN, M. D</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>MEDLINE - Academic</collection><jtitle>Molecular pharmacology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>SOBOL, M. M</au><au>AMIET, R. G</au><au>GREEN, M. D</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>In vitro evidence for direct complexation of ADR-529/ICRF-187 [(+)-1,2-bis-(3,5-dioxo-piperazin-1-yl)propane] onto an existing ferric-anthracycline complex</atitle><jtitle>Molecular pharmacology</jtitle><addtitle>Mol Pharmacol</addtitle><date>1992-01-01</date><risdate>1992</risdate><volume>41</volume><issue>1</issue><spage>8</spage><epage>17</epage><pages>8-17</pages><issn>0026-895X</issn><eissn>1521-0111</eissn><coden>MOPMA3</coden><abstract>ADR-529 protects against anthracycline cardiotoxicity, possibly by preventing free radical induction. We hypothesize that
this occurs by ADR-529 forming a ternary anthracycline-iron-ADR-529 complex. This study used 200-MHz Fourier-transformed NMR
to demonstrate the ability of ADR-529 to do this. Peak assignments were by proton-correlated spectroscopy and proton-carbon
heteronuclear-correlated spectroscopy. Ga3+ served as a probe for Fe3+, and D2O was the system solvent. Doxorubicin and epirubicin
were the studied drugs. Proton spectra of multiple combinations (including pure standards as controls) were obtained. Both
Ga3+ plus ADR-529 and Ga3+ plus doxorubicin showed evidence of complexation, as seen by appropriate peak shifts and changes
in the associated coupling constants. Ga3+ plus ADR-529 plus epirubicin showed complexation different from that of Ga3+ plus
ADR-529 or Ga3+ plus doxorubicin and consistent with the proposed structure. We conclude that ADR-529 would be able to form
a ternary complex with an existing anthracycline-Fe3+ complex in an isolated aqueous environment.</abstract><cop>Bethesda, MD</cop><pub>American Society for Pharmacology and Experimental Therapeutics</pub><pmid>1732725</pmid><tpages>10</tpages></addata></record> |
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| ispartof | Molecular pharmacology, 1992-01, Vol.41 (1), p.8-17 |
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| language | eng |
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| source | MEDLINE; EZB-FREE-00999 freely available EZB journals |
| subjects | Antibiotics, Antineoplastic - chemistry Biological and medical sciences Computer Simulation Doxorubicin - chemistry Drug toxicity and drugs side effects treatment Ferric Compounds - chemistry Fourier Analysis Free Radicals Gallium - chemistry Magnetic Resonance Spectroscopy - methods Medical sciences Models, Chemical Molecular Conformation Pharmacology. Drug treatments Razoxane - chemistry Spectrum Analysis - methods Toxicity: cardiovascular system |
| title | In vitro evidence for direct complexation of ADR-529/ICRF-187 [(+)-1,2-bis-(3,5-dioxo-piperazin-1-yl)propane] onto an existing ferric-anthracycline complex |
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