Synthesis and biological evaluation of 1-arylsulfonyl-5-(N -hydroxyacrylamide)indoles as potent histone deacetylase inhibitors with antitumor activity in vivo

Mei Jung Lai; Han Li Huang; Shiow Lin Pan; Yi Min Liu; Chieh Yu Peng; Hsueh Yun Lee; Teng Kuang Yeh; Po Hsien Huang; Che Ming Teng; Ching Shih Chen; Hsun Yueh Chuang; Jing Ping Liou

doi:10.1021/jm300197a

Synthesis and biological evaluation of 1-arylsulfonyl-5-(N -hydroxyacrylamide)indoles as potent histone deacetylase inhibitors with antitumor activity in vivo

Mei Jung Lai
, Han Li Huang
, Shiow Lin Pan
, Yi Min Liu
, Chieh Yu Peng
, Hsueh Yun Lee
, Teng Kuang Yeh
, Po Hsien Huang
, Che Ming Teng
, Ching Shih Chen
, Hsun Yueh Chuang
, Jing Ping Liou

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

71 Citations (Scopus)

Abstract

A series of 1-arylsulfonyl-5-(N-hydroxyacrylamide)indoles has been identified as a new class of histone deacetylase inhibitors. Compounds 8, 11, 12, 13, and 14 demonstrated stronger antiproliferative activities than 1 (SAHA) with GI ₅₀ values ranging from 0.36 to 1.21 μM against Hep3B, MDA-MB-231, PC-3, and A549 human cancer cell lines. Lead compound 8 showed remarkable HDAC 1, 2, and 6 isoenzymes inhibitory activities with IC ₅₀ values of 12.3, 4.0, 1.0 nM, respectively, which are comparable to 1. In in vivo efficacy evaluation against lung A549 xenograft model, 8 displayed better antitumor activity than compound 1.

Original language	English
Pages (from-to)	3777-3791
Number of pages	15
Journal	Journal of Medicinal Chemistry
Volume	55
Issue number	8
DOIs	https://doi.org/10.1021/jm300197a
Publication status	Published - Apr 26 2012

UN SDGs

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

SDG 3 Good Health and Well-being

ASJC Scopus subject areas

Molecular Medicine
Drug Discovery

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10.1021/jm300197a

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Lai, M. J., Huang, H. L., Pan, S. L., Liu, Y. M., Peng, C. Y., Lee, H. Y., Yeh, T. K., Huang, P. H., Teng, C. M., Chen, C. S., Chuang, H. Y., & Liou, J. P. (2012). Synthesis and biological evaluation of 1-arylsulfonyl-5-(N -hydroxyacrylamide)indoles as potent histone deacetylase inhibitors with antitumor activity in vivo. Journal of Medicinal Chemistry, 55(8), 3777-3791. https://doi.org/10.1021/jm300197a

Lai, MJ, Huang, HL, Pan, SL , Liu, YM, Peng, CY, Lee, HY, Yeh, TK, Huang, PH, Teng, CM, Chen, CS, Chuang, HY & Liou, JP 2012, 'Synthesis and biological evaluation of 1-arylsulfonyl-5-(N -hydroxyacrylamide)indoles as potent histone deacetylase inhibitors with antitumor activity in vivo', Journal of Medicinal Chemistry, vol. 55, no. 8, pp. 3777-3791. https://doi.org/10.1021/jm300197a

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title = "Synthesis and biological evaluation of 1-arylsulfonyl-5-(N -hydroxyacrylamide)indoles as potent histone deacetylase inhibitors with antitumor activity in vivo",

abstract = "A series of 1-arylsulfonyl-5-(N-hydroxyacrylamide)indoles has been identified as a new class of histone deacetylase inhibitors. Compounds 8, 11, 12, 13, and 14 demonstrated stronger antiproliferative activities than 1 (SAHA) with GI 50 values ranging from 0.36 to 1.21 μM against Hep3B, MDA-MB-231, PC-3, and A549 human cancer cell lines. Lead compound 8 showed remarkable HDAC 1, 2, and 6 isoenzymes inhibitory activities with IC 50 values of 12.3, 4.0, 1.0 nM, respectively, which are comparable to 1. In in vivo efficacy evaluation against lung A549 xenograft model, 8 displayed better antitumor activity than compound 1.",

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doi = "10.1021/jm300197a",

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AU - Lai, Mei Jung

AU - Huang, Han Li

AU - Pan, Shiow Lin

AU - Liu, Yi Min

AU - Peng, Chieh Yu

AU - Lee, Hsueh Yun

AU - Yeh, Teng Kuang

AU - Huang, Po Hsien

AU - Teng, Che Ming

AU - Chen, Ching Shih

AU - Chuang, Hsun Yueh

AU - Liou, Jing Ping

PY - 2012/4/26

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AB - A series of 1-arylsulfonyl-5-(N-hydroxyacrylamide)indoles has been identified as a new class of histone deacetylase inhibitors. Compounds 8, 11, 12, 13, and 14 demonstrated stronger antiproliferative activities than 1 (SAHA) with GI 50 values ranging from 0.36 to 1.21 μM against Hep3B, MDA-MB-231, PC-3, and A549 human cancer cell lines. Lead compound 8 showed remarkable HDAC 1, 2, and 6 isoenzymes inhibitory activities with IC 50 values of 12.3, 4.0, 1.0 nM, respectively, which are comparable to 1. In in vivo efficacy evaluation against lung A549 xenograft model, 8 displayed better antitumor activity than compound 1.

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Synthesis and biological evaluation of 1-arylsulfonyl-5-(N -hydroxyacrylamide)indoles as potent histone deacetylase inhibitors with antitumor activity in vivo

Abstract

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