{"created":"2023-05-15T16:43:52.168657+00:00","id":19374,"links":{},"metadata":{"_buckets":{"deposit":"251d43c2-25c2-4913-8bd0-e13b7e788a38"},"_deposit":{"created_by":2,"id":"19374","owners":[2],"pid":{"revision_id":0,"type":"depid","value":"19374"},"status":"published"},"_oai":{"id":"oai:nagasaki-u.repo.nii.ac.jp:00019374","sets":["73:74"]},"author_link":["80688","80686","80687","80689","80685"],"item_2_biblio_info_6":{"attribute_name":"書誌情報","attribute_value_mlt":[{"bibliographicIssueDates":{"bibliographicIssueDate":"2008-01","bibliographicIssueDateType":"Issued"},"bibliographicIssueNumber":"1","bibliographicPageEnd":"110","bibliographicPageStart":"103","bibliographicVolumeNumber":"31","bibliographic_titles":[{"bibliographic_title":"Biological and Pharmaceutical Bulletin"}]}]},"item_2_description_4":{"attribute_name":"抄録","attribute_value_mlt":[{"subitem_description":"Aconityl-doxorubicin (ADOX) was synthesized by the modified method of Shen and Ryser. Two isomers of cis-ADOX (cis-configuration) and trans-ADOX (trans-configuration) were generated in the reaction of DOX and cis-aconitic anhydride. These products were separated completely by using HPLC and analyzed by TOF-MS spectroscopy and 1H- and 13C-NMR experiments. The yields of cis-ADOX and trans-ADOX were 36.3 and 44.8%, respectively. The free g -carboxylic group of ADOX molecule was coupled to poly(vinyl alcohol) (PVA) via ethylenediamine spacer, resulting the macromolecular conjugates of PVA.cis-ADOX and PVA.trans-ADOX, respectively.The DOX content of the conjugates estimated by the hydrolysis method detected the aglycone of DOX which can be estimated as the PVA-bound DOX selectively was 4.4 w/w% which was similar to 4.6 w/w% by the ordinary UV method. Both PVA.cis-ADOX and PVA.trans-ADOX were very stable at neutral pH, but the release of DOX was increased markedly under acidic conditions. Half-life of the release of DOX from PVA.cis-ADOX at pH 5.0 was 3 h which was 4.7-fold shorter than that from PVA.trans-ADOX (14 h). The cytotoxicities of PVA.cis- ADOX and PVA.trans-ADOX were evaluated by using J774.1 cells employing a [3H]uridine incorporation assay as a measure of RNA synthesis. A significant difference in antitumor activity between PVA.cis-ADOX and PVA.trans-ADOX was observed where the former was much active than the later. It was suggested that the conjugate enters the cells and reaches the lysosomal/endosomal compartment, and that the aconityl spacer releases DOX from the conjugate in the acidic compartment of lysosomes/endosomes due to the participation of a free carboxylic group.","subitem_description_type":"Abstract"}]},"item_2_description_63":{"attribute_name":"引用","attribute_value_mlt":[{"subitem_description":"Biological and Pharmaceutical Bulletin, 31(1), pp.103-110; 2008","subitem_description_type":"Other"}]},"item_2_publisher_33":{"attribute_name":"出版者","attribute_value_mlt":[{"subitem_publisher":"The Pharmaceutical Society of Japan"}]},"item_2_relation_11":{"attribute_name":"PubMed番号","attribute_value_mlt":[{"subitem_relation_type":"isIdenticalTo","subitem_relation_type_id":{"subitem_relation_type_id_text":"18175951","subitem_relation_type_select":"PMID"}}]},"item_2_relation_12":{"attribute_name":"DOI","attribute_value_mlt":[{"subitem_relation_type":"isIdenticalTo","subitem_relation_type_id":{"subitem_relation_type_id_text":"10.1248/bpb.31.103","subitem_relation_type_select":"DOI"}}]},"item_2_rights_13":{"attribute_name":"権利","attribute_value_mlt":[{"subitem_rights":"(c) 2008 The Pharmaceutical Society of Japan"}]},"item_2_source_id_10":{"attribute_name":"書誌レコードID","attribute_value_mlt":[{"subitem_source_identifier":"AA10885497","subitem_source_identifier_type":"NCID"}]},"item_2_source_id_7":{"attribute_name":"ISSN","attribute_value_mlt":[{"subitem_source_identifier":"09186158","subitem_source_identifier_type":"ISSN"}]},"item_2_source_id_8":{"attribute_name":"EISSN","attribute_value_mlt":[{"subitem_source_identifier":"13475215","subitem_source_identifier_type":"ISSN"}]},"item_2_version_type_16":{"attribute_name":"著者版フラグ","attribute_value_mlt":[{"subitem_version_resource":"http://purl.org/coar/version/c_970fb48d4fbd8a85","subitem_version_type":"VoR"}]},"item_creator":{"attribute_name":"著者","attribute_type":"creator","attribute_value_mlt":[{"creatorNames":[{"creatorName":"Kakinoki, Atsufumi"}],"nameIdentifiers":[{}]},{"creatorNames":[{"creatorName":"Kaneo, Yoshiharu"}],"nameIdentifiers":[{}]},{"creatorNames":[{"creatorName":"Ikeda, Yuka"}],"nameIdentifiers":[{}]},{"creatorNames":[{"creatorName":"Tanaka, Tetsuro"}],"nameIdentifiers":[{}]},{"creatorNames":[{"creatorName":"Fujita, Kahee"}],"nameIdentifiers":[{}]}]},"item_files":{"attribute_name":"ファイル情報","attribute_type":"file","attribute_value_mlt":[{"accessrole":"open_date","date":[{"dateType":"Available","dateValue":"2020-12-23"}],"displaytype":"detail","filename":"BPB31_103.pdf","filesize":[{"value":"405.4 kB"}],"format":"application/pdf","licensetype":"license_note","mimetype":"application/pdf","url":{"label":"BPB31_103.pdf","url":"https://nagasaki-u.repo.nii.ac.jp/record/19374/files/BPB31_103.pdf"},"version_id":"5f32a073-a2b2-4ca8-a5dd-4c5b96122294"}]},"item_keyword":{"attribute_name":"キーワード","attribute_value_mlt":[{"subitem_subject":"poly(vinyl alcohol)","subitem_subject_scheme":"Other"},{"subitem_subject":"doxorubicin","subitem_subject_scheme":"Other"},{"subitem_subject":"acid-sensitive spacer","subitem_subject_scheme":"Other"},{"subitem_subject":"macromolecular prodrug","subitem_subject_scheme":"Other"},{"subitem_subject":"cytotoxicity","subitem_subject_scheme":"Other"},{"subitem_subject":"cellular uptake","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":"Synthesis of poly(vinyl alcohol)-doxorubicin conjugates containing cis-aconityl acid-cleavable bond and its isomer dependent doxorubicin release","item_titles":{"attribute_name":"タイトル","attribute_value_mlt":[{"subitem_title":"Synthesis of poly(vinyl alcohol)-doxorubicin conjugates containing cis-aconityl acid-cleavable bond and its isomer dependent doxorubicin release"}]},"item_type_id":"2","owner":"2","path":["74"],"pubdate":{"attribute_name":"公開日","attribute_value":"2008-07-14"},"publish_date":"2008-07-14","publish_status":"0","recid":"19374","relation_version_is_last":true,"title":["Synthesis of poly(vinyl alcohol)-doxorubicin conjugates containing cis-aconityl acid-cleavable bond and its isomer dependent doxorubicin release"],"weko_creator_id":"2","weko_shared_id":2},"updated":"2023-05-15T19:17:30.201535+00:00"}