2-Amino-3,4,5-Trimethoxybenzophenones as Potent Tubulin Polymerization Inhibitors

Hsun-Yueh Chuang; Jang-Yang Chang; Mei-Jung Lai; Ching-Chuan Kuo; Hsueh Yun Lee; Hsing-Pang Hsieh; Ying-Jen Chen; Li-Tzong Chen; Wen-Yu Pan; Jing Ping Liou

doi:10.1002/cmdc.201000479

2-Amino-3,4,5-Trimethoxybenzophenones as Potent Tubulin Polymerization Inhibitors

Hsun-Yueh Chuang, Jang-Yang Chang, Mei-Jung Lai, Ching-Chuan Kuo, Hsueh Yun Lee, Hsing-Pang Hsieh, Ying-Jen Chen, Li-Tzong Chen, Wen-Yu Pan, Jing Ping Liou

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

13 Citations (Scopus)

Abstract

A series of novel 2-amino-3,4,5-trimethoxybenzophenone analogues exhibited excellent activity as tubulin polymerization inhibitors by targeting the colchicine binding site of microtubules. The lead compound 17 exhibited an IC₅₀ value of 1.6μM, similar to that of combretastatin A-4 (IC₅₀=1.9μM). It also displayed remarkable anti-proliferative activity, with IC₅₀ values ranging from 7-16nM against a variety of human cancer cell lines and one MDR(+) cancer cell line. SAR information indicated that the introduction of an amino group at the C2 position of benzophenone ringA and the C3' position of benzophenone ringB play important roles in maximizing activity.

Original language	English
Pages (from-to)	450-456
Number of pages	7
Journal	ChemMedChem
Volume	6
Issue number	3
DOIs	https://doi.org/10.1002/cmdc.201000479
Publication status	Published - Mar 7 2011

Keywords

Antimitotic agents
Benzophenones
Inhibitors
Polymerization
Tubulin

ASJC Scopus subject areas

Pharmacology, Toxicology and Pharmaceutics(all)
Organic Chemistry
Molecular Medicine

UN SDGs

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

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10.1002/cmdc.201000479

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title = "2-Amino-3,4,5-Trimethoxybenzophenones as Potent Tubulin Polymerization Inhibitors",

abstract = "A series of novel 2-amino-3,4,5-trimethoxybenzophenone analogues exhibited excellent activity as tubulin polymerization inhibitors by targeting the colchicine binding site of microtubules. The lead compound 17 exhibited an IC50 value of 1.6μM, similar to that of combretastatin A-4 (IC50=1.9μM). It also displayed remarkable anti-proliferative activity, with IC50 values ranging from 7-16nM against a variety of human cancer cell lines and one MDR(+) cancer cell line. SAR information indicated that the introduction of an amino group at the C2 position of benzophenone ringA and the C3' position of benzophenone ringB play important roles in maximizing activity.",

keywords = "Antimitotic agents, Benzophenones, Inhibitors, Polymerization, Tubulin",

author = "Hsun-Yueh Chuang and Jang-Yang Chang and Mei-Jung Lai and Ching-Chuan Kuo and Lee, {Hsueh Yun} and Hsing-Pang Hsieh and Ying-Jen Chen and Li-Tzong Chen and Wen-Yu Pan and Liou, {Jing Ping}",

year = "2011",

month = mar,

day = "7",

doi = "10.1002/cmdc.201000479",

language = "English",

volume = "6",

pages = "450--456",

journal = "Farmaco",

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publisher = "John Wiley and Sons Ltd",

number = "3",

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TY - JOUR

T1 - 2-Amino-3,4,5-Trimethoxybenzophenones as Potent Tubulin Polymerization Inhibitors

AU - Chuang, Hsun-Yueh

AU - Chang, Jang-Yang

AU - Lai, Mei-Jung

AU - Kuo, Ching-Chuan

AU - Lee, Hsueh Yun

AU - Hsieh, Hsing-Pang

AU - Chen, Ying-Jen

AU - Chen, Li-Tzong

AU - Pan, Wen-Yu

AU - Liou, Jing Ping

PY - 2011/3/7

Y1 - 2011/3/7

N2 - A series of novel 2-amino-3,4,5-trimethoxybenzophenone analogues exhibited excellent activity as tubulin polymerization inhibitors by targeting the colchicine binding site of microtubules. The lead compound 17 exhibited an IC50 value of 1.6μM, similar to that of combretastatin A-4 (IC50=1.9μM). It also displayed remarkable anti-proliferative activity, with IC50 values ranging from 7-16nM against a variety of human cancer cell lines and one MDR(+) cancer cell line. SAR information indicated that the introduction of an amino group at the C2 position of benzophenone ringA and the C3' position of benzophenone ringB play important roles in maximizing activity.

AB - A series of novel 2-amino-3,4,5-trimethoxybenzophenone analogues exhibited excellent activity as tubulin polymerization inhibitors by targeting the colchicine binding site of microtubules. The lead compound 17 exhibited an IC50 value of 1.6μM, similar to that of combretastatin A-4 (IC50=1.9μM). It also displayed remarkable anti-proliferative activity, with IC50 values ranging from 7-16nM against a variety of human cancer cell lines and one MDR(+) cancer cell line. SAR information indicated that the introduction of an amino group at the C2 position of benzophenone ringA and the C3' position of benzophenone ringB play important roles in maximizing activity.

KW - Antimitotic agents

KW - Benzophenones

KW - Inhibitors

KW - Polymerization

KW - Tubulin

UR - http://www.scopus.com/inward/record.url?scp=79952087207&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=79952087207&partnerID=8YFLogxK

U2 - 10.1002/cmdc.201000479

DO - 10.1002/cmdc.201000479

M3 - Article

C2 - 21360819

AN - SCOPUS:79952087207

SN - 1860-7179

VL - 6

SP - 450

EP - 456

JO - Farmaco

JF - Farmaco

IS - 3

ER -

2-Amino-3,4,5-Trimethoxybenzophenones as Potent Tubulin Polymerization Inhibitors

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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