{"@context":{"@vocab":"https://cir.nii.ac.jp/schema/1.0/","rdfs":"http://www.w3.org/2000/01/rdf-schema#","dc":"http://purl.org/dc/elements/1.1/","dcterms":"http://purl.org/dc/terms/","foaf":"http://xmlns.com/foaf/0.1/","prism":"http://prismstandard.org/namespaces/basic/2.0/","cinii":"http://ci.nii.ac.jp/ns/1.0/","datacite":"https://schema.datacite.org/meta/kernel-4/","ndl":"http://ndl.go.jp/dcndl/terms/","jpcoar":"https://github.com/JPCOAR/schema/blob/master/2.0/"},"@id":"https://cir.nii.ac.jp/crid/1390282679124367744.json","@type":"Article","productIdentifier":[{"identifier":{"@type":"DOI","@value":"10.7164/antibiotics.43.1286"}},{"identifier":{"@type":"NAID","@value":"130003501741"}}],"dc:title":[{"@language":"en","@value":"Evaluation of the electrophilicity of DNA-binding pyrrolo(2,1-c)(1,4)benzodiazepines by HPLC."}],"dc:language":"en","description":[{"type":"abstract","notation":[{"@language":"en","@value":"An HPLC assay is described that can be used to study the covalent bonding interaction of carbinolamine-containing pyrrolo[2, 1-c][1, 4]benzodiazepines with the model nucleophile thiophenol, in order to evaluate electrophilicity at the C-11-position. Preliminary experiments with anthramycin, tomaymycin and neothramycin show that their reaction with thiophenol follows second-order kinetics, but the ranking order of reactivity (neothramycin > tomaymycin > anthramycin), does not correlate with either <i>in vitro</i> cytotoxicity or <i>in vivo</i> antitumour activity. This suggests that other factors such as non-covalent DNA-interaction or drug transport play a more crucial role in biological activity than simple alkylating ability. This assay should, however, prove a useful tool in the study of structure-activity relationships for this series of compounds and provide \"C-11-electrophilicity\" parameters for use in Hansch analysis and related studies."}],"abstractLicenseFlag":"disallow"}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1410282679124367744","@type":"Researcher","personIdentifier":[{"@type":"NRID","@value":"9000253074130"}],"foaf:name":[{"@language":"en","@value":"MORRIS STEPHEN J."}],"jpcoar:affiliationName":[{"@language":"en","@value":"Division of Medicinal Chemistry, School of Pharmacy and Biomedical Sciences, Portsmouth Polytechnic"}]},{"@id":"https://cir.nii.ac.jp/crid/1410282679124367745","@type":"Researcher","personIdentifier":[{"@type":"NRID","@value":"9000253074131"}],"foaf:name":[{"@language":"en","@value":"THURSTON DAVID E."}],"jpcoar:affiliationName":[{"@language":"en","@value":"Division of Medicinal Chemistry, School of Pharmacy and Biomedical Sciences, Portsmouth Polytechnic"}]},{"@id":"https://cir.nii.ac.jp/crid/1410282679124367746","@type":"Researcher","personIdentifier":[{"@type":"NRID","@value":"9000253074132"}],"foaf:name":[{"@language":"en","@value":"NEVELL THOMAS G."}],"jpcoar:affiliationName":[{"@language":"en","@value":"Chemistry Department, Portsmouth Polytechnic"}]}],"publication":{"publicationIdentifier":[{"@type":"PISSN","@value":"00218820"},{"@type":"EISSN","@value":"18811469"}],"prism:publicationName":[{"@language":"en","@value":"The Journal of Antibiotics"},{"@language":"en","@value":"J. Antibiot."}],"dc:publisher":[{"@language":"en","@value":"JAPAN ANTIBIOTICS RESEARCH ASSOCIATION"},{"@language":"ja","@value":"公益財団法人 日本感染症医薬品協会"}],"prism:publicationDate":"1990","prism:volume":"43","prism:number":"10","prism:startingPage":"1286","prism:endingPage":"1292"},"reviewed":"false","availableAt":"1990","dataSourceIdentifier":[{"@type":"JALC","@value":"oai:japanlinkcenter.org:0007696280"},{"@type":"CROSSREF","@value":"10.7164/antibiotics.43.1286"},{"@type":"CIA","@value":"130003501741"}]}