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酮洛芬的碳硼烷类似物对人黑色素瘤和结肠癌细胞系具有细胞抑制活性。

Carboranyl Analogues of Ketoprofen with Cytostatic Activity against Human Melanoma and Colon Cancer Cell Lines.

作者信息

Buzharevski Antonio, Paskas Svetlana, Laube Markus, Lönnecke Peter, Neumann Wilma, Murganic Blagoje, Mijatovic Sanja, Maksimovic-Ivanic Danijela, Pietzsch Jens, Hey-Hawkins Evamarie

机构信息

Institut für Anorganische Chemie, Universität Leipzig, Johannisallee 29, D-04103 Leipzig, Germany.

Department of Immunology, Institute for Biological Research "Sinisa Stankovic", Belgrade University, Belgrade 11060, Serbia.

出版信息

ACS Omega. 2019 May 23;4(5):8824-8833. doi: 10.1021/acsomega.9b00412. eCollection 2019 May 31.

DOI:10.1021/acsomega.9b00412
PMID:31459970
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6648485/
Abstract

Ketoprofen is a widely used nonsteroidal anti-inflammatory drug (NSAID) that also exhibits cytotoxic activity against various cancers. This makes ketoprofen an attractive structural lead for the development of new NSAIDs and cytotoxic agents. Recently, the incorporation of carboranes as phenyl mimetics in structures of established drugs has emerged as an attractive strategy in drug design. Herein, we report the synthesis and evaluation of four novel carborane-containing derivatives of ketoprofen, two of which are prodrug esters with an nitric oxide-releasing moiety. One of these prodrug esters exhibited high cytostatic activity against melanoma and colon cancer cell lines. The most pronounced activity was found in cell lines that are sensitive to oxidative stress, which was apparently induced by the ketoprofen analogue.

摘要

酮洛芬是一种广泛使用的非甾体抗炎药（NSAID），它对多种癌症也具有细胞毒性活性。这使得酮洛芬成为开发新型NSAIDs和细胞毒性药物的一个有吸引力的结构先导。最近，将碳硼烷作为苯基模拟物引入已确立药物的结构中，已成为药物设计中一种有吸引力的策略。在此，我们报告了四种新型含碳硼烷的酮洛芬衍生物的合成与评价，其中两种是带有一氧化氮释放部分的前药酯。这些前药酯中的一种对黑色素瘤和结肠癌细胞系表现出高细胞生长抑制活性。在对氧化应激敏感的细胞系中发现了最显著的活性，这种氧化应激显然是由酮洛芬类似物诱导的。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/abc2/6648485/fe74ec8dd952/ao-2019-00412h_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/abc2/6648485/75f3a59e3cdf/ao-2019-00412h_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/abc2/6648485/802a2657549b/ao-2019-00412h_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/abc2/6648485/76929c6a6d1e/ao-2019-00412h_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/abc2/6648485/ff4834563e5c/ao-2019-00412h_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/abc2/6648485/b4df2b6923c0/ao-2019-00412h_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/abc2/6648485/f6d9475ef6e0/ao-2019-00412h_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/abc2/6648485/fe74ec8dd952/ao-2019-00412h_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/abc2/6648485/75f3a59e3cdf/ao-2019-00412h_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/abc2/6648485/802a2657549b/ao-2019-00412h_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/abc2/6648485/76929c6a6d1e/ao-2019-00412h_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/abc2/6648485/ff4834563e5c/ao-2019-00412h_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/abc2/6648485/b4df2b6923c0/ao-2019-00412h_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/abc2/6648485/f6d9475ef6e0/ao-2019-00412h_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/abc2/6648485/fe74ec8dd952/ao-2019-00412h_0005.jpg

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