Synthesis and anticancer activity of novel 9,13-disubstituted berberine derivatives

Zhi Cheng Wang; Jing Wang; Huang Chen; Jie Tang; Ai Wu Bian; Ting Liu; Li Fang Yu; Zhengfang Yi; Fan Yang

doi:10.1016/j.bmcl.2019.126821

Synthesis and anticancer activity of novel 9,13-disubstituted berberine derivatives

Zhi Cheng Wang, Jing Wang, Huang Chen, Jie Tang, Ai Wu Bian, Ting Liu, Li Fang Yu, Zhengfang Yi, Fan Yang

East China Normal University

Research output: Contribution to journal › Article › peer-review

27 Scopus citations

Abstract

Novel berberine derivatives with disubstituents on positions C9 and C13 were synthesized and evaluated for antiproliferative activities against human prostate cancer cell lines (PC3 and DU145), breast cancer cell line (MDA-MB-231) and human colon cancer cell lines (HT29 and HCT116). All compounds showed significantly enhanced antiproliferative activities compared with berberine. Notably, compound 18e exhibited the strongest cytotoxicity against PC3 cells with an IC₅₀ value of 0.19 μM, and the highest selectivity index (SI^PC3 > 20). Further studies showed that 18e could arrest the cell cycle at G1 phase, and significantly inhibit tumor cell colony forming and migration even at low concentrations. Interestingly, 18e could significantly induce cytoplasmic vacuolation, suggesting a different mode of action from berberine.

Original language	English
Article number	126821
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	30
Issue number	2
DOIs	https://doi.org/10.1016/j.bmcl.2019.126821
State	Published - 15 Jan 2020

Keywords

Anticancer activity
Berberine derivatives
Cell migration
Colony forming
Lipophilic group

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.bmcl.2019.126821

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title = "Synthesis and anticancer activity of novel 9,13-disubstituted berberine derivatives",

abstract = "Novel berberine derivatives with disubstituents on positions C9 and C13 were synthesized and evaluated for antiproliferative activities against human prostate cancer cell lines (PC3 and DU145), breast cancer cell line (MDA-MB-231) and human colon cancer cell lines (HT29 and HCT116). All compounds showed significantly enhanced antiproliferative activities compared with berberine. Notably, compound 18e exhibited the strongest cytotoxicity against PC3 cells with an IC50 value of 0.19 μM, and the highest selectivity index (SIPC3 > 20). Further studies showed that 18e could arrest the cell cycle at G1 phase, and significantly inhibit tumor cell colony forming and migration even at low concentrations. Interestingly, 18e could significantly induce cytoplasmic vacuolation, suggesting a different mode of action from berberine.",

keywords = "Anticancer activity, Berberine derivatives, Cell migration, Colony forming, Lipophilic group",

author = "Wang, \{Zhi Cheng\} and Jing Wang and Huang Chen and Jie Tang and Bian, \{Ai Wu\} and Ting Liu and Yu, \{Li Fang\} and Zhengfang Yi and Fan Yang",

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year = "2020",

month = jan,

day = "15",

doi = "10.1016/j.bmcl.2019.126821",

language = "英语",

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journal = "Bioorganic and Medicinal Chemistry Letters",

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TY - JOUR

T1 - Synthesis and anticancer activity of novel 9,13-disubstituted berberine derivatives

AU - Wang, Zhi Cheng

AU - Wang, Jing

AU - Chen, Huang

AU - Tang, Jie

AU - Bian, Ai Wu

AU - Liu, Ting

AU - Yu, Li Fang

AU - Yi, Zhengfang

AU - Yang, Fan

PY - 2020/1/15

Y1 - 2020/1/15

N2 - Novel berberine derivatives with disubstituents on positions C9 and C13 were synthesized and evaluated for antiproliferative activities against human prostate cancer cell lines (PC3 and DU145), breast cancer cell line (MDA-MB-231) and human colon cancer cell lines (HT29 and HCT116). All compounds showed significantly enhanced antiproliferative activities compared with berberine. Notably, compound 18e exhibited the strongest cytotoxicity against PC3 cells with an IC50 value of 0.19 μM, and the highest selectivity index (SIPC3 > 20). Further studies showed that 18e could arrest the cell cycle at G1 phase, and significantly inhibit tumor cell colony forming and migration even at low concentrations. Interestingly, 18e could significantly induce cytoplasmic vacuolation, suggesting a different mode of action from berberine.

AB - Novel berberine derivatives with disubstituents on positions C9 and C13 were synthesized and evaluated for antiproliferative activities against human prostate cancer cell lines (PC3 and DU145), breast cancer cell line (MDA-MB-231) and human colon cancer cell lines (HT29 and HCT116). All compounds showed significantly enhanced antiproliferative activities compared with berberine. Notably, compound 18e exhibited the strongest cytotoxicity against PC3 cells with an IC50 value of 0.19 μM, and the highest selectivity index (SIPC3 > 20). Further studies showed that 18e could arrest the cell cycle at G1 phase, and significantly inhibit tumor cell colony forming and migration even at low concentrations. Interestingly, 18e could significantly induce cytoplasmic vacuolation, suggesting a different mode of action from berberine.

KW - Anticancer activity

KW - Berberine derivatives

KW - Cell migration

KW - Colony forming

KW - Lipophilic group

UR - https://www.scopus.com/pages/publications/85076577817

U2 - 10.1016/j.bmcl.2019.126821

DO - 10.1016/j.bmcl.2019.126821

M3 - 文章

C2 - 31812467

AN - SCOPUS:85076577817

SN - 0960-894X

VL - 30

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 2

M1 - 126821

ER -

Synthesis and anticancer activity of novel 9,13-disubstituted berberine derivatives

Abstract

Keywords

UN SDGs

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