TY - JOUR A1 - Scharkoi, O. A1 - Becker, Roland A1 - Esslinger, Susanne A1 - Weber, M. A1 - Nehls, Irene T1 - Predicting sites of cytochrome P450-mediated hydroxylation applied to CYP3A4 and hexabromocyclododecane T2 - Molecular simulation N2 - This article describes a simple and quick in silico method for the prediction of cytochrome P450 (CYP)-mediated hydroxylation of drug-like compounds. Testosterone and progesterone, two known substrates of CYP3A4, are used to test the method. Further, we apply the procedure to predict sites of hydroxylation of isomers of the flame retardant hexabromocyclododecane by CYP3A4. Within the method, the compound is rotated in the binding pocket of the cytochrome, so that each hydrogen under consideration is placed near the active centre. Afterwards, short molecular dynamics simulations are provided for each step of the rotation. All steps of the simulation are compared concerning the distances between the hydrogens and the active centre and the corresponding energies. The computational results correlate well with experimental results. PB - Gordon and Breach CY - New York, NY KW - Predicting sites of metabolism KW - Cytochrome P450 KW - Hydroxylation KW - Metabolism of HBCD PY - 2015 UR - https://opus4.kobv.de/opus4-bam/frontdoor/index/index/docId/30492 AN - OPUS4-30492 SN - 0892-7022 SN - 1029-0435 VL - 41 IS - 7 SP - 538 EP - 546 AD - Bundesanstalt fuer Materialforschung und -pruefung (BAM), Berlin, Germany