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Bioorg Med Chem Lett. 2016 Aug 1;26(15):3464-7. doi: 10.1016/j.bmcl.2016.06.043. Epub 2016 Jun 16.

Structural modification of luteolin from Flos Chrysanthemi leads to increased tumor cell growth inhibitory activity.

Author information

1
School of Pharmacy, Second Military Medical University, Shanghai 200433, China.
2
Changhai Hospital, Second Military Medical University, Shanghai 200433, China.
3
School of Pharmacy, Second Military Medical University, Shanghai 200433, China; Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing, Jiangsu 210009, China.
4
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China.
5
School of Pharmacy, Second Military Medical University, Shanghai 200433, China. Electronic address: zhouyoujun@smmu.edu.cn.
6
School of Pharmacy, Second Military Medical University, Shanghai 200433, China. Electronic address: zhuju@smmu.edu.cn.
7
School of Pharmacy, Second Military Medical University, Shanghai 200433, China. Electronic address: canhuizheng@smmu.edu.cn.

Abstract

The luteolin from Flos Chrysanthemi was found to directly bind to the Bcl-2 protein and inhibit the tumor cell growth in our previous study. However, it has been shown to possess wide and week biological activities. In this study, a series of derivatives of luteolin were designed and synthesized, and their tumor cell growth inhibitory activities were evaluated against human leukemia cell line HL-60. The results showed that compounds 1B-2, 2A-3, and 2B-5, with hydrophobic substituted benzyl groups introduced to B ring and hydrogen or methyl introduced to 7-OH group of luteolin, exhibited the strongest inhibitory activity with the IC50 lower than 10μM, which were significantly more potent than luteolin. The studies presented here offer a good example for modifications of flavones to improve their tumor cell growth inhibitory activities.

KEYWORDS:

Anti-tumor; Bcl-2 protein; Flos Chrysanthemi; Luteolin; Structural modification

PMID:
27353532
DOI:
10.1016/j.bmcl.2016.06.043
[Indexed for MEDLINE]

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