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5
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含四氢呋喃的隔山消酮类碳水化合物类似物的合成及抗肿瘤活性。

Synthesis and anti-tumor activity of carbohydrate analogues of the tetrahydrofuran containing acetogenins.

机构信息

Department of Chemistry, Hunter College, 695 Park Avenue, New York, NY 10065, USA.

出版信息

Bioorg Med Chem. 2013 Nov 1;21(21):6554-64. doi: 10.1016/j.bmc.2013.08.027. Epub 2013 Aug 29.

DOI:10.1016/j.bmc.2013.08.027
PMID:24045006
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3886712/
Abstract

The tetrahydrofuran (THF) containing annonaceous acetogenins (AAs) are attractive candidates for drug development because of their potent cytotoxicity against a wide range of tumors and their relatively simple and robust structures. Replacement of the THF segment with a sugar residue may deliver analogues with improved tumor selectivity and pharmacokinetics and are therefore attractive for drug development. As a first test to the feasibility of such structures, a set of such monosaccharide analogues was synthesized and assayed against four human tumor cell lines, cervical (HeLa), breast (MDA-MB231), T-cell leukemia (Jurkat) and prostate (PC-3). Certain analogues showed low micromolar activity that was comparable to a structurally similar, naturally occurring mono-THF acetogenin. A preliminary examination of the structure-activity profile of these carbohydrate analogues suggests that they have a similar mechanism of action as their THF congeners.

摘要

含有呋喃（THF）的番荔枝内酯（AAs）是药物开发的有吸引力的候选物，因为它们对广泛的肿瘤具有强大的细胞毒性，并且它们的结构相对简单和稳健。用糖残基取代 THF 片段可能会提供具有改善的肿瘤选择性和药代动力学的类似物，因此适合药物开发。作为对这种结构可行性的第一个测试，合成了一组这样的单糖类似物，并针对四种人类肿瘤细胞系（宫颈（HeLa），乳腺（MDA-MB231），T 细胞白血病（Jurkat）和前列腺（PC-3）进行了测定。某些类似物显示出低微摩尔的活性，与结构相似的天然单 THF 乙酰基生酮相当。对这些碳水化合物类似物的结构活性谱的初步检查表明，它们具有与 THF 同系物相似的作用机制。