{"created":"2021-03-01T06:33:44.723450+00:00","id":25696,"links":{},"metadata":{"_buckets":{"deposit":"fd57c12e-ca30-4f36-8109-da3cfff18d5e"},"_deposit":{"id":"25696","owners":[],"pid":{"revision_id":0,"type":"depid","value":"25696"},"status":"published"},"_oai":{"id":"oai:nagoya.repo.nii.ac.jp:00025696","sets":["643:666:667"]},"author_link":["76094","76095","76096","76097","76098","76099"],"item_10_biblio_info_6":{"attribute_name":"書誌情報","attribute_value_mlt":[{"bibliographicIssueDates":{"bibliographicIssueDate":"2017-12-19","bibliographicIssueDateType":"Issued"},"bibliographicIssueNumber":"71","bibliographicPageEnd":"17897","bibliographicPageStart":"17894","bibliographicVolumeNumber":"23","bibliographic_titles":[{"bibliographic_title":"Chemistry - A European Journal","bibliographic_titleLang":"en"}]}]},"item_10_description_4":{"attribute_name":"抄録","attribute_value_mlt":[{"subitem_description":"Cytotoxicity‐guided fractionation of the culture broth of Actinomadura sp. TP‐A0019 led to the isolation of quinocidin (1), a cytotoxic antibiotic with an unusual 3,4‐dihydroquinolizinium ring. The structural assignment was made on the basis of high‐field NMR experiments and chemical synthesis. Comparison of the spectral properties of 1 with those of its synthetic counterparts revealed that 1 is a racemic mixture of two enantiomers, which showed similar cytotoxicity against HeLa‐S3 cells. Nucleophile‐trapping experiments demonstrated that 1 captured 2‐mercaptoethanol and N‐acetyl‐l‐cysteine by means of a Michael addition‐type reaction, but was inert toward 2‐aminoethanol and glycolic acid. Notably, the addition of 1 to thiols proceeded smoothly in neutral aqueous media at room temperature. In view of the thiol‐trapping ability and the unusual structure, 1 provides a unique scaffold for designing drug leads and protein‐labeling probes.","subitem_description_language":"en","subitem_description_type":"Abstract"}]},"item_10_description_5":{"attribute_name":"内容記述","attribute_value_mlt":[{"subitem_description":"ファイル公開：2018-12-19","subitem_description_language":"ja","subitem_description_type":"Other"}]},"item_10_publisher_32":{"attribute_name":"出版者","attribute_value_mlt":[{"subitem_publisher":"Wiley","subitem_publisher_language":"en"}]},"item_10_relation_11":{"attribute_name":"DOI","attribute_value_mlt":[{"subitem_relation_type":"isVersionOf","subitem_relation_type_id":{"subitem_relation_type_id_text":"https://doi.org/10.1002/chem.201704729","subitem_relation_type_select":"DOI"}}]},"item_10_rights_12":{"attribute_name":"権利","attribute_value_mlt":[{"subitem_rights":" \t\"This is the peer reviewed version of the following article: [Y. Nakagawa, Y. Sawaki, T. Kimura, T. Tomura, Y. Igarashi, M. Ojika, Chem. Eur. J. 2017, 23, 17894.], which has been published in final form at [http://doi.org/10.1002/chem.201704729]. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.\" ","subitem_rights_language":"en"}]},"item_10_select_15":{"attribute_name":"著者版フラグ","attribute_value_mlt":[{"subitem_select_item":"author"}]},"item_10_source_id_7":{"attribute_name":"ISSN","attribute_value_mlt":[{"subitem_source_identifier":"09476539","subitem_source_identifier_type":"PISSN"}]},"item_1615787544753":{"attribute_name":"出版タイプ","attribute_value_mlt":[{"subitem_version_resource":"http://purl.org/coar/version/c_ab4af688f83e57aa","subitem_version_type":"AM"}]},"item_access_right":{"attribute_name":"アクセス権","attribute_value_mlt":[{"subitem_access_right":"open access","subitem_access_right_uri":"http://purl.org/coar/access_right/c_abf2"}]},"item_creator":{"attribute_name":"著者","attribute_type":"creator","attribute_value_mlt":[{"creatorNames":[{"creatorName":"Nakagawa, Yu","creatorNameLang":"en"}],"nameIdentifiers":[{"nameIdentifier":"76094","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"Sawaki, Yuki","creatorNameLang":"en"}],"nameIdentifiers":[{"nameIdentifier":"76095","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"Kimura, Takahiro","creatorNameLang":"en"}],"nameIdentifiers":[{"nameIdentifier":"76096","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"Tomura, Tomohiko","creatorNameLang":"en"}],"nameIdentifiers":[{"nameIdentifier":"76097","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"Igarashi, Yasuhiro","creatorNameLang":"en"}],"nameIdentifiers":[{"nameIdentifier":"76098","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"Ojika, Makoto","creatorNameLang":"en"}],"nameIdentifiers":[{"nameIdentifier":"76099","nameIdentifierScheme":"WEKO"}]}]},"item_files":{"attribute_name":"ファイル情報","attribute_type":"file","attribute_value_mlt":[{"accessrole":"open_date","date":[{"dateType":"Available","dateValue":"2018-12-19"}],"displaytype":"detail","filename":"Manuscript_Nakagawa.pdf","filesize":[{"value":"330.1 kB"}],"format":"application/pdf","licensetype":"license_note","mimetype":"application/pdf","url":{"label":"Manuscript_Nakagawa","objectType":"fulltext","url":"https://nagoya.repo.nii.ac.jp/record/25696/files/Manuscript_Nakagawa.pdf"},"version_id":"22ddf184-35f4-4df7-b640-de2711ccb6e5"}]},"item_keyword":{"attribute_name":"キーワード","attribute_value_mlt":[{"subitem_subject":"drug discovery","subitem_subject_scheme":"Other"},{"subitem_subject":"Michael addition","subitem_subject_scheme":"Other"},{"subitem_subject":"natural products","subitem_subject_scheme":"Other"},{"subitem_subject":"nitrogen heterocycles","subitem_subject_scheme":"Other"},{"subitem_subject":"structure elucidation","subitem_subject_scheme":"Other"}]},"item_language":{"attribute_name":"言語","attribute_value_mlt":[{"subitem_language":"eng"}]},"item_resource_type":{"attribute_name":"資源タイプ","attribute_value_mlt":[{"resourcetype":"journal article","resourceuri":"http://purl.org/coar/resource_type/c_6501"}]},"item_title":"Quinocidin, a Cytotoxic Antibiotic with an Unusual 3,4-Dihydroquinolizinium Ring and Michael Acceptor Reactivity toward Thiols","item_titles":{"attribute_name":"タイトル","attribute_value_mlt":[{"subitem_title":"Quinocidin, a Cytotoxic Antibiotic with an Unusual 3,4-Dihydroquinolizinium Ring and Michael Acceptor Reactivity toward Thiols","subitem_title_language":"en"}]},"item_type_id":"10","owner":"1","path":["667"],"pubdate":{"attribute_name":"PubDate","attribute_value":"2018-04-16"},"publish_date":"2018-04-16","publish_status":"0","recid":"25696","relation_version_is_last":true,"title":["Quinocidin, a Cytotoxic Antibiotic with an Unusual 3,4-Dihydroquinolizinium Ring and Michael Acceptor Reactivity toward Thiols"],"weko_creator_id":"1","weko_shared_id":-1},"updated":"2023-01-16T04:54:44.477324+00:00"}