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  1. B300 農学部/生命農学研究科
  2. B300a 雑誌掲載論文
  3. 学術雑誌

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/2237/00027907
0b28903f-0cf7-456e-bb18-41ef7de8d570
名前 / ファイル ライセンス アクション
Manuscript_Nakagawa.pdf Manuscript_Nakagawa (330.1 kB)
Item type 学術雑誌論文 / Journal Article(1)
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

WEKO 76094

en Nakagawa, Yu

Search repository
Sawaki, Yuki

× Sawaki, Yuki

WEKO 76095

en Sawaki, Yuki

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Kimura, Takahiro

× Kimura, Takahiro

WEKO 76096

en Kimura, Takahiro

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Tomura, Tomohiko

× Tomura, Tomohiko

WEKO 76097

en Tomura, Tomohiko

Search repository
Igarashi, Yasuhiro

× Igarashi, Yasuhiro

WEKO 76098

en Igarashi, Yasuhiro

Search repository
Ojika, Makoto

× Ojika, Makoto

WEKO 76099

en Ojika, Makoto

Search repository
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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