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シスアコニチン酸の酸性解離性結合を含んだポリビニルアルコールードキソルビシン結合体の合成とそのアイソマーによるドキソルビシン遊離への依存性(発表論文抄録(2008))
https://fukuyama-u.repo.nii.ac.jp/records/8572
https://fukuyama-u.repo.nii.ac.jp/records/85727fe28ac1-9501-46a5-99c1-26ce91c0aca9
名前 / ファイル | ライセンス | アクション |
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シスアコニチン酸の酸性解離性結合を含んだポリビニルアルコールードキソルビシン結合体の合成とそのアイソマーによるドキソルビシン遊離への依存性 (102.3 kB)
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Copyright (c) 2009 by Fukuyama University
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Item type | 紀要論文 / Departmental Bulletin Paper(1) | |||||
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公開日 | 2017-01-26 | |||||
タイトル | ||||||
タイトル | シスアコニチン酸の酸性解離性結合を含んだポリビニルアルコールードキソルビシン結合体の合成とそのアイソマーによるドキソルビシン遊離への依存性(発表論文抄録(2008)) | |||||
タイトル | ||||||
言語 | en | |||||
タイトル | Synthesis of poly(vinyl alcohol)-doxorubicin conjugates containing cis-aconityl acid-cleavable bond and its isomer dependent doxorubicin release. | |||||
言語 | ||||||
言語 | eng | |||||
キーワード | ||||||
言語 | en | |||||
主題Scheme | Other | |||||
主題 | Animals | |||||
キーワード | ||||||
言語 | en | |||||
主題Scheme | Other | |||||
主題 | Antineoplastic Agents | |||||
キーワード | ||||||
言語 | en | |||||
主題Scheme | Other | |||||
主題 | Doxorubicin | |||||
キーワード | ||||||
言語 | en | |||||
主題Scheme | Other | |||||
主題 | Humans | |||||
キーワード | ||||||
言語 | en | |||||
主題Scheme | Other | |||||
主題 | Hydrogen-Ion Concentration | |||||
キーワード | ||||||
言語 | en | |||||
主題Scheme | Other | |||||
主題 | Mice | |||||
キーワード | ||||||
言語 | en | |||||
主題Scheme | Other | |||||
主題 | Polyvinyl Alcohol | |||||
資源タイプ | ||||||
資源タイプ識別子 | http://purl.org/coar/resource_type/c_6501 | |||||
資源タイプ | departmental bulletin paper | |||||
著者 |
柿木, 充史
× 柿木, 充史× 金尾, 義治× 池田, 有香× 田中, 哲郎× 藤田, 佳平衛 |
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抄録 | ||||||
内容記述タイプ | Abstract | |||||
内容記述 | 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 (1)H- and (13)C-NMR experiments. The yields of cis-ADOX and trans-ADOX were 36.3 and 44.8%, respectively. The free gamma-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 [(3)H]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. | |||||
内容記述 | ||||||
内容記述タイプ | Other | |||||
内容記述 | 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 (1)H- and (13)C-NMR experiments. The yields of cis-ADOX and trans-ADOX were 36.3 and 44.8%, respectively. The free gamma-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 [(3)H]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. | |||||
書誌情報 |
福山大学薬学部研究年報 en : Annual report of the Faculty of Pharmacy & Pharmaceutical Sciences, Fukuyama University 号 27, p. 40-41, 発行日 2009-12-25 |
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出版者 | ||||||
出版者 | 福山大学薬学部 | |||||
ISSN | ||||||
収録物識別子タイプ | ISSN | |||||
収録物識別子 | 0288-724X | |||||
書誌レコードID | ||||||
収録物識別子タイプ | NCID | |||||
収録物識別子 | AN10064550 |