2. Academic Validation
  3. Bismuth nitrate-induced novel nitration of estradiol: an entry to new anticancer agents

Bismuth nitrate-induced novel nitration of estradiol: an entry to new anticancer agents

  • Eur J Med Chem. 2014 Jul 23:82:574-83. doi: 10.1016/j.ejmech.2014.06.010.
Debasish Bandyopadhyay 1,  Gildardo Rivera 2,  Jorge L Sanchez 3,  Jesse Rivera 4,  Jose C Granados 5,  Adrian M Guerrero 3,  Fang-Mei Chang 5,  Robert K Dearth 4,  John D Short 6,  Bimal K Banik 7
Affiliations

Affiliations

  • 1 Department of Chemistry, The University of Texas-Pan American, 1201 West University Drive, Edinburg, TX 78539, USA. Electronic address: banyopad@utpa.edu.
  • 2 Centro de Biotecnologia Genomica, Instituto Politecnico Nacional, Blvd. del Maestro, s/n, esq. Elias Piña, Col. Narciso Mendoza, 88710 Reynosa, Mexico.
  • 3 Department of Chemistry, The University of Texas-Pan American, 1201 West University Drive, Edinburg, TX 78539, USA; University of Texas Health Science Center at San Antonio, Regional Academic Health Center, Medical Research Division, 1214 West Schunior Street, Edinburg, TX 78541, USA.
  • 4 Department of Biology, The University of Texas-Pan American, 1201 West University Drive, Edinburg, TX 78539, USA.
  • 5 University of Texas Health Science Center at San Antonio, Regional Academic Health Center, Medical Research Division, 1214 West Schunior Street, Edinburg, TX 78541, USA.
  • 6 University of Texas Health Science Center at San Antonio, Regional Academic Health Center, Medical Research Division, 1214 West Schunior Street, Edinburg, TX 78541, USA; Department of Pharmacology, University of Texas Health Science Center at San Antonio, 7703 Floyd Curl Drive, San Antonio, TX 78229, USA. Electronic address: shortj@uthscsa.edu.
  • 7 Department of Chemistry, The University of Texas-Pan American, 1201 West University Drive, Edinburg, TX 78539, USA.
PMID: 24946145 DOI: 10.1016/j.ejmech.2014.06.010
Abstract

Direct nitration of estradiol was carried out using metal nitrates on solid surfaces under mild condition, and a combination of bismuth nitrate pentahydrate impregnated KSF clay was found to be the best reagent to synthesize 2- and 4-nitroestradiol effectively. Furthermore, various basic side chains were introduced, through O-linker at C-3, to these nitroestradiols. The ability of these derivatives to cause cytotoxicity in Estrogen Receptor (ER)-positive and ER-negative breast Cancer cell lines, as well as Cancer cell lines of Other origins, was examined. Qualitative structure activity relationship (SAR) has also been studied. We found that a basic side chain containing either a piperidine or morpholine ring, when conjugated to 2-nitroestradiol, was particularly effective at causing cytotoxicity in each of the Cancer cell lines examined. Surprisingly, this effective cytotoxicity was even seen in ER-negative breast Cancer cells.

Keywords

Anticancer; Apoptosis; Bismuth nitrate; Estradiol; Estrogen receptor; Nitration; Solid-support.

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