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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

Relationship among structure, cytotoxicity, and Michael acceptor reactivity of quinocidin

http://hdl.handle.net/2237/00032335
e2195336-b428-468d-a6a3-c21568ecd0a4
名前 / ファイル ライセンス アクション
BMC_Nakagawa.pdf BMC_Nakagawa (709.0 kB)
Item type 学術雑誌論文 / Journal Article(1)
公開日 2020-06-10
タイトル
タイトル Relationship among structure, cytotoxicity, and Michael acceptor reactivity of quinocidin
著者 Nakagawa, Yu

× Nakagawa, Yu

WEKO 99538

Nakagawa, Yu

Search repository
Sawaki, Yuki

× Sawaki, Yuki

WEKO 99539

Sawaki, Yuki

Search repository
Miyanishi, Wataru

× Miyanishi, Wataru

WEKO 99540

Miyanishi, Wataru

Search repository
Shimomura, Sayako

× Shimomura, Sayako

WEKO 99541

Shimomura, Sayako

Search repository
Shibata, Takahiro

× Shibata, Takahiro

WEKO 99542

Shibata, Takahiro

Search repository
Ojika, Makoto

× Ojika, Makoto

WEKO 99543

Ojika, Makoto

Search repository
権利
権利情報 © 2020. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/
キーワード
主題Scheme Other
主題 Antibiotic
キーワード
主題Scheme Other
主題 Anticancer
キーワード
主題Scheme Other
主題 Heterocycle
キーワード
主題Scheme Other
主題 Michael addition
キーワード
主題Scheme Other
主題 Structure–activity relationship
抄録
内容記述 Quinocidin (QCD) is a cytotoxic antibiotic with an unusual 3,4-dihydroquinolizinium skeleton. We previously found that QCD captures thiols in neutral aqueous media via a Michael addition-type reaction. However, it remains unclear whether the Michael acceptor reactivity of QCD is responsible for its cytotoxicity. In this study, we synthesized thirteen analogs of QCD to examine the relationship among its structure, cytotoxicity, and reactivity toward thiols. Thiol-trapping experiments and cytotoxicity tests collectively suggested that the Michael acceptor function of QCD is independent of its cytotoxic activity, and that the pyridinium moiety with the hydrophobic side chain is a key structural factor for cytotoxicity. These findings further led us to demonstrate that incorporation of an amide group into the side chain of QCD significantly reduced its toxicity but hardly affected the Michael acceptor function. The present study lays the foundation for QCD-based drug design and highlights the potential of QCD as a unique electrophile for use in the development of covalent inhibitors and protein-labeling probes.
内容記述タイプ Abstract
内容記述
内容記述 ファイル公開:2022-02-15
内容記述タイプ Other
出版者
出版者 Elsevier
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
DOI
関連識別子
識別子タイプ DOI
関連識別子 https://doi.org/10.1016/j.bmc.2020.115308
ISSN(print)
収録物識別子タイプ ISSN
収録物識別子 0968-0896
書誌情報 Bioorganic & Medicinal Chemistry

巻 28, 号 4, p. 115308, 発行日 2020-02-15
著者版フラグ
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