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本文引用的文献

1
Lavendamycin antitumor agents: structure-based design, synthesis, and NAD(P)H:quinone oxidoreductase 1 (NQO1) model validation with molecular docking and biological studies.薰衣草霉素抗肿瘤剂：基于结构的设计、合成以及通过分子对接和生物学研究对NAD(P)H：醌氧化还原酶1（NQO1）模型进行验证
J Med Chem. 2008 Jun 12;51(11):3104-15. doi: 10.1021/jm701066a. Epub 2008 May 6.
2
Synthesis and evaluation of antitumor activity of novel N-acyllavendamycin analogues and quinoline-5,8-diones.新型N-酰基薰衣草霉素类似物和喹啉-5,8-二酮的合成及其抗肿瘤活性评价
Bioorg Med Chem. 2007 Jan 1;15(1):495-510. doi: 10.1016/j.bmc.2006.09.039. Epub 2006 Oct 10.
3
Novel lavendamycin analogues as antitumor agents: synthesis, in vitro cytotoxicity, structure-metabolism, and computational molecular modeling studies with NAD(P)H:quinone oxidoreductase 1.新型薰衣草霉素类似物作为抗肿瘤药物：合成、体外细胞毒性、结构代谢以及与NAD(P)H：醌氧化还原酶1的计算分子模拟研究
J Med Chem. 2005 Dec 1;48(24):7733-49. doi: 10.1021/jm050758z.
4
DT-diaphorase: a target for new anticancer drugs.DT-黄递酶：新型抗癌药物的一个靶点。
Cancer Treat Rev. 2004 Aug;30(5):437-49. doi: 10.1016/j.ctrv.2004.01.002.
5
Role of nicotinamide quinone oxidoreductase 1 (NQO1) in protection against toxicity of electrophiles and reactive oxygen intermediates.烟酰胺醌氧化还原酶1（NQO1）在抵御亲电试剂和活性氧中间体毒性中的作用。
Methods Enzymol. 2004;382:355-64. doi: 10.1016/S0076-6879(04)82019-6.
6
Novel quinolinequinone antitumor agents: structure-metabolism studies with NAD(P)H:quinone oxidoreductase (NQO1).新型喹啉醌类抗肿瘤药物：与NAD(P)H：醌氧化还原酶（NQO1）的结构-代谢研究
Bioorg Med Chem. 2004 Apr 1;12(7):1667-87. doi: 10.1016/j.bmc.2004.01.021.
7
Novel lavendamycin analogues as potent HIV-reverse transcriptase inhibitors: synthesis and evaluation of anti-reverse transcriptase activity of amide and ester analogues of lavendamycin.新型薰衣草霉素类似物作为有效的HIV逆转录酶抑制剂：薰衣草霉素酰胺和酯类似物的合成及抗逆转录酶活性评估
J Med Chem. 2003 Dec 18;46(26):5773-80. doi: 10.1021/jm0304414.
8
Preliminary observations on the use of streptonigrin as an antitumor agent in human beings.关于链黑菌素作为一种抗肿瘤药物在人体中应用的初步观察。
Antibiot Chemother (Northfield). 1961 Mar;11:147-50.
9
Clinical observations on the effects of streptonigrin in patients with neoplastic disease.链黑菌素对肿瘤疾病患者疗效的临床观察
Antibiot Chemother (Northfield). 1961 Mar;11:178-83.
10
Characterization of the cytotoxic activities of novel analogues of the antitumor agent, lavendamycin.抗肿瘤药物薰衣草霉素新型类似物的细胞毒性活性表征
Mol Cancer Ther. 2003 Jun;2(6):517-26.

新型lavendamycin 抗肿瘤剂的合成、代谢及体外细胞毒性研究。

Synthesis, metabolism and in vitro cytotoxicity studies on novel lavendamycin antitumor agents.

机构信息

Chemistry Department, Ball State University, Muncie, IN 47306, USA.

出版信息

Bioorg Med Chem. 2010 Mar 1;18(5):1899-909. doi: 10.1016/j.bmc.2010.01.037. Epub 2010 Jan 25.

DOI:10.1016/j.bmc.2010.01.037
PMID:20149966
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2841014/
Abstract

A series of lavendamycin analogues with two, three or four substituents at the C-6, C-7 N, C-2', C-3' and C-11' positions were synthesized via short and efficient methods and evaluated as potential NAD(P)H:quinone oxidoreductase (NQO1)-directed antitumor agents. The compounds were prepared through Pictet-Spengler condensation of the desired 2-formylquinoline-5,8-diones with the required tryptophans followed by further needed transformations. Metabolism and toxicity studies demonstrated that the best substrates for NQO1 were also the most selectively toxic to NQO1-rich tumor cells compared to NQO1-deficient tumor cells.

摘要

通过短而高效的方法合成了一系列在 C-6、C-7 N、C-2'、C-3' 和 C-11' 位具有两个、三个或四个取代基的 lavendamycin 类似物，并将其评估为潜在的 NAD(P)H:醌氧化还原酶 (NQO1) 导向的抗肿瘤剂。这些化合物通过所需的 2-甲酰基喹啉-5,8-二酮与所需色氨酸的 Pictet-Spengler 缩合，然后进一步进行所需的转化来制备。代谢和毒性研究表明，与 NQO1 缺陷型肿瘤细胞相比，NQO1 最丰富的肿瘤细胞中，NQO1 的最佳底物也是最具选择性毒性的。