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Synthesis of poly(vinyl alcohol)-doxorubicin conjugates containing cis-aconityl acid-cleavable bond and its isomer dependent doxorubicin release
http://hdl.handle.net/10069/18705
http://hdl.handle.net/10069/18705a9246a7e-104f-46aa-81aa-7063a07cb617
名前 / ファイル | ライセンス | アクション |
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BPB31_103.pdf (405.4 kB)
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Item type | 学術雑誌論文 / Journal Article(1) | |||||
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公開日 | 2008-07-14 | |||||
タイトル | ||||||
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 | ||||||
主題Scheme | Other | |||||
主題 | poly(vinyl alcohol) | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | doxorubicin | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | acid-sensitive spacer | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | macromolecular prodrug | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | cytotoxicity | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | cellular uptake | |||||
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 | journal article | |||||
著者 |
Kakinoki, Atsufumi
× Kakinoki, Atsufumi× Kaneo, Yoshiharu× Ikeda, Yuka× Tanaka, Tetsuro× Fujita, Kahee |
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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 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. | |||||
書誌情報 |
Biological and Pharmaceutical Bulletin 巻 31, 号 1, p. 103-110, 発行日 2008-01 |
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出版者 | ||||||
出版者 | The Pharmaceutical Society of Japan | |||||
ISSN | ||||||
収録物識別子タイプ | ISSN | |||||
収録物識別子 | 09186158 | |||||
EISSN | ||||||
収録物識別子タイプ | ISSN | |||||
収録物識別子 | 13475215 | |||||
書誌レコードID | ||||||
収録物識別子タイプ | NCID | |||||
収録物識別子 | AA10885497 | |||||
PubMed番号 | ||||||
関連タイプ | isIdenticalTo | |||||
識別子タイプ | PMID | |||||
関連識別子 | 18175951 | |||||
DOI | ||||||
関連タイプ | isIdenticalTo | |||||
識別子タイプ | DOI | |||||
関連識別子 | 10.1248/bpb.31.103 | |||||
権利 | ||||||
権利情報 | (c) 2008 The Pharmaceutical Society of Japan | |||||
著者版フラグ | ||||||
出版タイプ | VoR | |||||
出版タイプResource | http://purl.org/coar/version/c_970fb48d4fbd8a85 | |||||
引用 | ||||||
内容記述タイプ | Other | |||||
内容記述 | Biological and Pharmaceutical Bulletin, 31(1), pp.103-110; 2008 |