Development of constrained tamoxifen mimics and their antiproliferative properties against breast cancer cells

Sivakumar Archana; Ramasatyaveni Geesala; Narasimha B. Rao; Suresh Satpati; Giridhar Puroshottam; Akhila Panasa; Anshuman Dixit; Amitava Das; Ajay Kumar Srivastava

doi:10.1016/j.bmcl.2014.11.077

Development of constrained tamoxifen mimics and their antiproliferative properties against breast cancer cells

Sivakumar Archana, Ramasatyaveni Geesala, Narasimha B. Rao, Suresh Satpati, Giridhar Puroshottam, Akhila Panasa, Anshuman Dixit, Amitava Das, Ajay Kumar Srivastava

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

Abstract

An efficient synthesis of a new series of tamoxifen mimics is described by employing iodine catalyzed ipsocyclization strategy followed by Suzuki coupling. A molecular docking studies of the synthesized compounds 11a-n and 12 in estrogen receptor (ER-α) showed that the scaffolds are fitting well in the groove, thereby suggesting them as promising antiproliferative agents for estrogen dependent breast cancer lines. All compounds were tested in vitro against breast cancer cell lines - ER positive, MCF-7; ER negative, MDA-MB-231; and control mammary epithelial cells, MEpiC. The biological results showed that most of the compounds are active against MCF-7 with IC₅₀ values less than 6.5 μM which corroborate the results of molecular docking studies.

Original language	English (US)
Pages (from-to)	680-684
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	25
Issue number	3
DOIs	https://doi.org/10.1016/j.bmcl.2014.11.077
State	Published - Feb 1 2015
Externally published	Yes

Keywords

Breast cancer
Ipsocyclization
Molecular docking
SERMs
Tamoxifen

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmcl.2014.11.077

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title = "Development of constrained tamoxifen mimics and their antiproliferative properties against breast cancer cells",

abstract = "An efficient synthesis of a new series of tamoxifen mimics is described by employing iodine catalyzed ipsocyclization strategy followed by Suzuki coupling. A molecular docking studies of the synthesized compounds 11a-n and 12 in estrogen receptor (ER-α) showed that the scaffolds are fitting well in the groove, thereby suggesting them as promising antiproliferative agents for estrogen dependent breast cancer lines. All compounds were tested in vitro against breast cancer cell lines - ER positive, MCF-7; ER negative, MDA-MB-231; and control mammary epithelial cells, MEpiC. The biological results showed that most of the compounds are active against MCF-7 with IC50 values less than 6.5 μM which corroborate the results of molecular docking studies.",

keywords = "Breast cancer, Ipsocyclization, Molecular docking, SERMs, Tamoxifen",

author = "Sivakumar Archana and Ramasatyaveni Geesala and Rao, {Narasimha B.} and Suresh Satpati and Giridhar Puroshottam and Akhila Panasa and Anshuman Dixit and Amitava Das and Srivastava, {Ajay Kumar}",

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doi = "10.1016/j.bmcl.2014.11.077",

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AU - Archana, Sivakumar

AU - Geesala, Ramasatyaveni

AU - Rao, Narasimha B.

AU - Satpati, Suresh

AU - Puroshottam, Giridhar

AU - Panasa, Akhila

AU - Dixit, Anshuman

AU - Das, Amitava

AU - Srivastava, Ajay Kumar

PY - 2015/2/1

Y1 - 2015/2/1

N2 - An efficient synthesis of a new series of tamoxifen mimics is described by employing iodine catalyzed ipsocyclization strategy followed by Suzuki coupling. A molecular docking studies of the synthesized compounds 11a-n and 12 in estrogen receptor (ER-α) showed that the scaffolds are fitting well in the groove, thereby suggesting them as promising antiproliferative agents for estrogen dependent breast cancer lines. All compounds were tested in vitro against breast cancer cell lines - ER positive, MCF-7; ER negative, MDA-MB-231; and control mammary epithelial cells, MEpiC. The biological results showed that most of the compounds are active against MCF-7 with IC50 values less than 6.5 μM which corroborate the results of molecular docking studies.

AB - An efficient synthesis of a new series of tamoxifen mimics is described by employing iodine catalyzed ipsocyclization strategy followed by Suzuki coupling. A molecular docking studies of the synthesized compounds 11a-n and 12 in estrogen receptor (ER-α) showed that the scaffolds are fitting well in the groove, thereby suggesting them as promising antiproliferative agents for estrogen dependent breast cancer lines. All compounds were tested in vitro against breast cancer cell lines - ER positive, MCF-7; ER negative, MDA-MB-231; and control mammary epithelial cells, MEpiC. The biological results showed that most of the compounds are active against MCF-7 with IC50 values less than 6.5 μM which corroborate the results of molecular docking studies.

KW - Breast cancer

KW - Ipsocyclization

KW - Molecular docking

KW - SERMs

KW - Tamoxifen

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Development of constrained tamoxifen mimics and their antiproliferative properties against breast cancer cells

Abstract

Keywords

ASJC Scopus subject areas

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