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对杀稻瘟菌素的重新研究表明，戊-2,4-二烯-1-醇残基赋予了皮摩尔级别的效力和8构型。

Reinvestigation of Mycothiazole Reveals the Penta-2,4-dien-1-ol Residue Imparts Picomolar Potency and 8 Configuration.

作者信息

Johnson Tyler A, Morris Joseph D, Coppage David A, Cook Colon V, Persi Lauren N, Ogarrio Marcos A, Garcia Taylor C, McIntosh Nicole L, McCauley Erin P, Media Joseph, Maheshwari Mani, Valeriote Frederick A, Shaw Jiajiu, Crews Phillip

机构信息

Department of Natural Sciences & Mathematics, Dominican University of California, San Rafael, California 94901, United States.

Department of Chemistry & Biochemistry, University of California, Santa Cruz, Santa Cruz, California 95064, United States.

出版信息

ACS Med Chem Lett. 2020 Jan 2;11(2):108-113. doi: 10.1021/acsmedchemlett.9b00302. eCollection 2020 Feb 13.

DOI:10.1021/acsmedchemlett.9b00302
PMID:32071675
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7025380/
Abstract

Reinvestigation of mycothiazole () revealed picomolar potency (IC = 0.00016, 0.00027, 0.00035 μM) against pancreatic, (PANC-1), liver (HepG2), and colon (HCT-116) tumor cell lines. Reevaluation of provided [α] data indicating Vanuatu specimens of contain the 8 enantiomer of and not the 8 configuration previously reported. Semisynthesis provided 8--acetylmycothiazole (), 8-oxomycothiazole (), mycothiazole nitrosobenzene derivatives (MND1, MND2: , ), and MND3 () with IC = 0.00129, >1.0, >1.0, >1.0, >1.0 μM, respectively, against PANC-1 cell lines. These results highlight the significance of the penta-2,4-dien-1-ol residue as a key structural feature of required for its cytotoxicty against tumor cell lines.

摘要

对杀真菌噻唑（）的重新研究显示，其对胰腺（PANC - 1）、肝脏（HepG2）和结肠（HCT - 116）肿瘤细胞系具有皮摩尔级别的效力（IC = 0.00016、0.00027、0.00035 μM）。对的重新评估提供了[α]数据，表明瓦努阿图的标本含有杀真菌噻唑的8 - 对映体，而非先前报道的8 - 构型。半合成提供了8 - - 乙酰杀真菌噻唑（）、8 - 氧代杀真菌噻唑（）、杀真菌噻唑亚硝基苯衍生物（MND1、MND2：，）和MND3（），它们对PANC - 1细胞系的IC分别为0.00129、>1.0、>1.0、>1.0、>1.0 μM。这些结果突出了2,4 - 戊二烯 - 1 - 醇残基作为杀真菌噻唑对肿瘤细胞系具有细胞毒性所需的关键结构特征的重要性。