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Quinocidin, a Cytotoxic Antibiotic with an Unusual 3,4-Dihydroquinolizinium Ring and Michael Acceptor Reactivity toward Thiols
http://hdl.handle.net/2237/00027907
http://hdl.handle.net/2237/000279070b28903f-0cf7-456e-bb18-41ef7de8d570
名前 / ファイル | ライセンス | アクション |
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Item type | 学術雑誌論文 / Journal Article(1) | |||||
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公開日 | 2018-04-16 | |||||
タイトル | ||||||
タイトル | Quinocidin, a Cytotoxic Antibiotic with an Unusual 3,4-Dihydroquinolizinium Ring and Michael Acceptor Reactivity toward Thiols | |||||
言語 | en | |||||
著者 |
Nakagawa, Yu
× Nakagawa, Yu× Sawaki, Yuki× Kimura, Takahiro× Tomura, Tomohiko× Igarashi, Yasuhiro× Ojika, Makoto |
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アクセス権 | ||||||
アクセス権 | open access | |||||
アクセス権URI | http://purl.org/coar/access_right/c_abf2 | |||||
権利 | ||||||
言語 | en | |||||
権利情報 | "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." | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | drug discovery | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | Michael addition | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | natural products | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | nitrogen heterocycles | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | structure elucidation | |||||
抄録 | ||||||
内容記述 | 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. | |||||
言語 | en | |||||
内容記述タイプ | Abstract | |||||
内容記述 | ||||||
内容記述 | ファイル公開:2018-12-19 | |||||
言語 | ja | |||||
内容記述タイプ | Other | |||||
出版者 | ||||||
言語 | en | |||||
出版者 | Wiley | |||||
言語 | ||||||
言語 | eng | |||||
資源タイプ | ||||||
資源タイプresource | http://purl.org/coar/resource_type/c_6501 | |||||
タイプ | journal article | |||||
出版タイプ | ||||||
出版タイプ | AM | |||||
出版タイプResource | http://purl.org/coar/version/c_ab4af688f83e57aa | |||||
DOI | ||||||
関連タイプ | isVersionOf | |||||
識別子タイプ | DOI | |||||
関連識別子 | https://doi.org/10.1002/chem.201704729 | |||||
ISSN | ||||||
収録物識別子タイプ | PISSN | |||||
収録物識別子 | 09476539 | |||||
書誌情報 |
en : Chemistry - A European Journal 巻 23, 号 71, p. 17894-17897, 発行日 2017-12-19 |
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著者版フラグ | ||||||
値 | author |