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dc.contributor.authorGuo, Chuanxinen
dc.contributor.authorAsamitsu, Sefanen
dc.contributor.authorKashiwazaki, Gengoen
dc.contributor.authorSato, Shinsukeen
dc.contributor.authorBando, Toshikazuen
dc.contributor.authorSugiyama, Hiroshien
dc.contributor.alternative柏﨑, 玄伍ja
dc.contributor.alternative佐藤, 慎祐ja
dc.contributor.alternative板東, 俊和ja
dc.contributor.alternative杉山, 弘ja
dc.date.accessioned2018-04-26T04:40:23Z-
dc.date.available2018-04-26T04:40:23Z-
dc.date.issued2017-01-17-
dc.identifier.issn1439-4227-
dc.identifier.urihttp://hdl.handle.net/2433/230874-
dc.description.abstractAlthough DNA interstrand crosslinking (ICL) agents are widely used as antitumor drugs, DNA sequence-specific ICL agents are quite rare. In this study, H-pin imidazole-pyrrole polyamide 1-(chloromethyl)-2, 3-dihydro-1H-benzo[e]indol-5-ol (seco-CBI) conjugates that produce sequence-specific DNA ICLs were designed and synthesized. Conjugates with H-pin polyamide and seco-CBI moieties were constructed to recognize a 7 bp DNA sequence, and their reactivity and selectivity in DNA alkylation were evaluated by using high-resolution denaturing gel electrophoresis and sequence-specific plasmid cleavage. One conjugate (6), which contained a chiral (S)-seco-CBI, exhibited greater sequence-specific ICL activity toward the target DNA sequence and was cytotoxic to a cancer cell line. Molecular modeling studies indicated that the greater activity of 6 resulted from the relative orientation of the cyclopropane group in the (S)-CBI unit.en
dc.format.mimetypeapplication/pdf-
dc.language.isoeng-
dc.publisherWiley-VCH Verlagen
dc.rightsThis is the accepted version of the following article: [Chuanxin Guo, Sefan Asamitsu, Gengo Kashiwazaki, Shinsuke Sato, Toshikazu Bando, Hiroshi Sugiyama. DNA Interstrand Crosslinks by H‐pin Polyamide (S)‐seco‐CBI Conjugates. ChemBioChem (2017), 18, 2, 166-170], which has been published in final form at https://doi.org/10.1002/cbic.201600425. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.en
dc.rightsThe full-text file will be made open to the public on 18 January 2018 in accordance with publisher's 'Terms and Conditions for Self-Archiving'.en
dc.rightsこの論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。ja
dc.rightsThis is not the published version. Please cite only the published version.en
dc.subjectDNA alkylationen
dc.subjectinterstrand crosslinksen
dc.subjectpolyamideen
dc.subjectseco-CBIen
dc.titleDNA Interstrand Crosslinks by H-pin Polyamide (S)-seco-CBI Conjugatesen
dc.typejournal article-
dc.type.niitypeJournal Article-
dc.identifier.jtitleChemBioChemen
dc.identifier.volume18-
dc.identifier.issue2-
dc.identifier.spage166-
dc.identifier.epage170-
dc.relation.doi10.1002/cbic.201600425-
dc.textversionauthor-
dc.addressDepartment of Chemistry, Graduate School of Science, Kyoto Universityen
dc.addressDepartment of Chemistry, Graduate School of Science, Kyoto Universityen
dc.addressDepartment of Chemistry, Graduate School of Science, Kyoto Universityen
dc.addressInstitute for Integrated Cell-Material Sciences (WPI-iCeMS), Kyoto Universityen
dc.addressDepartment of Chemistry, Graduate School of Science, Kyoto Universityen
dc.addressDepartment of Chemistry, Graduate School of Science, Kyoto University・Institute for Integrated Cell-Material Sciences (WPI-iCeMS), Kyoto Universityen
dc.identifier.pmid27862755-
dcterms.accessRightsopen access-
datacite.date.available2018-01-18-
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