233756-97-3Relevant academic research and scientific papers
Molecular docking of bisphenol A and its nitrated and chlorinated metabolites onto human estrogen-related receptor-gamma
Babu, Sainath,Kasibotla, Agasthya V.,Uppu, Rao M.,Vellore, Nadeem A.,Dwayne, Harlan J.,Stubblefield, Michael A.
, p. 215 - 220,6 (2012)
A xenoestrogen and known endocrine disruptor, bisphenol A (BPA) binds the human estrogen-related receptor-gamma (ERRγ) with high affinity (Kd≈5.5nM). It is likely that BPA undergoes oxidative biotransformation by hypochlorite/hypochlorous acid (-OCl/HOCl) and peroxynitrite (PN) and the products formed in these reactions may serve as secondary estrogens and contribute to the toxicodynamics of BPA. Therefore, in the present study we have examined the formation of chlorinated and nitrated BPA in reactions of BPA with -OCl/HOCl and PN(+CO2) performed around the neutral pH. We have identified four major products in these reactions and they include 3-chloro-BPA (CBPA), 3,3'-dichloro-BPA (DCBPA), 3-nitro-BPA (NBPA) and 3,3'-dinitro-BPA (DNBPA). Towards understanding the toxicodynamics and estrogenic activity of BPA in biological systems, we have performed molecular docking of BPA, CBPA, DCBPA, DNBPA and NBPA onto the ERRγ using AutoDock 4.2 software and compared the binding energies with those of estradiol, the natural ligand. Based on the genetic algorithm, the three best conformations were selected and averaged for each ligand and a detailed analysis of molecular interactions based on free energies of binding (kcal/mol) was computed. The results indicate the following rank order of binding to ERRγ: BPA (-8.78±0.06)>CBPA (-8.53±0.41)>NBPA (-7.36±0.74)>DCBPA (-5.24±0.17)>DNBPA (-4.95±0.78)>estradiol (-4.94±1.04). The docking studies revealed that the OH group of one of the phenyl rings forms a hydrogen bond with Glu275/Arg316, while the OH group of other phenyl ring was bound to Asp346. These results suggest that both BPA and its putative chlorinated and nitrated metabolites have strong binding affinity compared to estradiol.
Melamine-(H2SO4)3 and PVP-(H 2SO4)n as solid acids: Synthesis and application in the first mono- and di-nitration of bisphenol A and other phenols
Chehardoli, Gholamabbas,Zolfigol, Mohammad Ali,Azimi, Seyedeh Bahareh,Alizadeh, Ebadollah
experimental part, p. 827 - 830 (2012/02/14)
Melamine and poly vinylpyrrolidone (PVP) reacted with neat sulfuric acid readily to form two new organic solid acids namely melamine-(H 2SO4)3 and PVP-(H2SO 4)n. These solid acids were used for the first nitration of bisphenol A as well as other phenols in the presence of NH4NO 3. Mono- and di-nitro bisphenol A have been characterized with IR and 1H NMR techniques.
