17 Xenobiotic Metabolism by Cytochrome P450 …
363
31. Ji L, Schueuermann G (2013) Model and mechanism: N-hydroxylation of primary aromatic
amines by cytochrome P450. Angew Chem Int Edit 52(2):744–748
32. Li CS, Zhang LX, Zhang C, Hirao H, Wu W, Shaik S (2007) Which oxidant is really responsible
for sulfur oxidation by cytochrome P450? Angew Chem Int Edit 46(43):8168–8170
33. Porro CS, Sutcliffe MJ, de Visser SP (2009) Quantum mechanics/molecular mechanics studies
on the sulfoxidation of dimethyl sulfide by Compound I and Compound 0 of cytochrome P450:
which is the better oxidant? J Phys Chem A 113(43):11635–11642
34. Bathelt CM, Mulholland AJ, Harvey JN (2008) QM/MM modeling of benzene hydroxylation
in human cytochrome P450 2C9. J Phys Chem A 112(50):13149–13156
35. Hackett JC, Sanan TT, Hadad CM (2007) Oxidative dehalogenation of perhalogenated benzenes
by cytochrome P450 Compound I. Biochemistry 46(20):5924–5940
36. Shaik S, Milko P, Schyman P, Usharani D, Chen H (2011) Trends in aromatic oxidation reactions
catalyzed by cytochrome P450 enzymes: a valence bond modeling. J Chem Theory Comput
7(2):327–339
37. Asaka M, Fujii H (2016) Participation of electron transfer process in rate-limiting step of
aromatic hydroxylation reactions by compound I models of heme enzymes. J Am Chem Soc
138(26):8048–8051
38. Zhai C, Peng SN, Yang LM, Wang QQ (2014) Evaluation of BDE-47 hydroxylation metabolic
pathways based on a strong electron-withdrawing pentafluorobenzoyl derivatization gas chromatography/electron capture negative ionization quadrupole mass spectrometry. Environ Sci
Technol 48(14):8117–8126
39. Luisa Feo M, Gross MS, McGarrigle BP, Eljarrat E, Barcelo D, Aga DS, Olson JR (2013)
Biotransformation of BDE-47 to potentially toxic metabolites is predominantly mediated by
human CYP2B6. Environ Health Persp 121(4):440–446
40. Wang XB, Wang Y, Chen JW, Ma YQ, Zhou J, Fu ZQ (2012) Computational toxicological
investigation on the mechanism and pathways of xenobiotics metabolized by cytochrome P450:
a case of BDE-47. Environ Sci Technol 46(9):5126–5133
41. Wang XB, Chen JW, Wang Y, Xie HB, Fu ZQ (2015) Transformation pathways of MeO-PBDEs
catalyzed by active center of P450 enzymes: a DFT investigation employing 6-MeO-BDE-47
as a case. Chemosphere 120:631–636
42. Fu ZQ, Wang Y, Chen JW, Wang ZY, Wang XB (2016) How PBDEs are transformed into
dihydroxylated and dioxin metabolites catalyzed by the active center of cytochrome P450s: a
DFT study. Environ Sci Technol 50(15):8155–8163
43. Lupton SJ, McGarrigle BP, Olson JR, Wood TD, Aga DS (2009) Human liver microsomemediated metabolism of brominated diphenyl ethers 47, 99, and 153 and identification of their
major metabolites. Chem Res Toxicol 22(11):1802–1809
44. Lai YQ, Cai ZW (2012) In vitro metabolism of hydroxylated polybrominated diphenyl ethers
and their inhibitory effects on 17β-estradiol metabolism in rat liver microsomes. Environ Sci
Pollut R 19(8):3219–3227
45. Erratico CA, Szeitz A, Bandiera SM (2013) Biotransformation of 2,2 ,4,4 -tetrabromodiphenyl
ether (BDE-47) by human liver microsomes: Identification of cytochrome P450 2B6 as the
major enzyme involved. Chem Res Toxicol 26(5):721–731
46. Agarwal V, Moore BS (2014) Enzymatic synthesis of polybrominated dioxins from the marine
environment. ACS Chem Biol 9(9):1980–1984
47. Altarawneh M, Dlugogorski BZ (2013) A mechanistic and kinetic study on the formation of
PBDD/Fs from PBDEs. Environ Sci Technol 47(10):5118–5127
48. Cao HJ, He MX, Han DD, Li J, Li MY, Wang WX, Yao SD (2013) OH-initiated oxidation mechanisms and kinetics of 2,4,4 -tribrominated diphenyl ether. Environ Sci Technol
47(15):8238–8247
49. Erickson PR, Grandbois M, Arnold WA, McNeill K (2012) Photochemical formation of brominated dioxins and other products of concern from hydroxylated polybrominated diphenyl ethers
(HO-PBDEs). Environ Sci Technol 46(15):8174–8180
50. Fu ZQ, Wang Y, Wang ZY, Xie HB, Chen JW (2015) Transformation pathways of isomeric
perfluorooctanesulfonate precursors catalyzed by the active species of P450 enzymes: in silicoinvestigation. Chem Res Toxicol 28(3):482–489
363
31. Ji L, Schueuermann G (2013) Model and mechanism: N-hydroxylation of primary aromatic
amines by cytochrome P450. Angew Chem Int Edit 52(2):744–748
32. Li CS, Zhang LX, Zhang C, Hirao H, Wu W, Shaik S (2007) Which oxidant is really responsible
for sulfur oxidation by cytochrome P450? Angew Chem Int Edit 46(43):8168–8170
33. Porro CS, Sutcliffe MJ, de Visser SP (2009) Quantum mechanics/molecular mechanics studies
on the sulfoxidation of dimethyl sulfide by Compound I and Compound 0 of cytochrome P450:
which is the better oxidant? J Phys Chem A 113(43):11635–11642
34. Bathelt CM, Mulholland AJ, Harvey JN (2008) QM/MM modeling of benzene hydroxylation
in human cytochrome P450 2C9. J Phys Chem A 112(50):13149–13156
35. Hackett JC, Sanan TT, Hadad CM (2007) Oxidative dehalogenation of perhalogenated benzenes
by cytochrome P450 Compound I. Biochemistry 46(20):5924–5940
36. Shaik S, Milko P, Schyman P, Usharani D, Chen H (2011) Trends in aromatic oxidation reactions
catalyzed by cytochrome P450 enzymes: a valence bond modeling. J Chem Theory Comput
7(2):327–339
37. Asaka M, Fujii H (2016) Participation of electron transfer process in rate-limiting step of
aromatic hydroxylation reactions by compound I models of heme enzymes. J Am Chem Soc
138(26):8048–8051
38. Zhai C, Peng SN, Yang LM, Wang QQ (2014) Evaluation of BDE-47 hydroxylation metabolic
pathways based on a strong electron-withdrawing pentafluorobenzoyl derivatization gas chromatography/electron capture negative ionization quadrupole mass spectrometry. Environ Sci
Technol 48(14):8117–8126
39. Luisa Feo M, Gross MS, McGarrigle BP, Eljarrat E, Barcelo D, Aga DS, Olson JR (2013)
Biotransformation of BDE-47 to potentially toxic metabolites is predominantly mediated by
human CYP2B6. Environ Health Persp 121(4):440–446
40. Wang XB, Wang Y, Chen JW, Ma YQ, Zhou J, Fu ZQ (2012) Computational toxicological
investigation on the mechanism and pathways of xenobiotics metabolized by cytochrome P450:
a case of BDE-47. Environ Sci Technol 46(9):5126–5133
41. Wang XB, Chen JW, Wang Y, Xie HB, Fu ZQ (2015) Transformation pathways of MeO-PBDEs
catalyzed by active center of P450 enzymes: a DFT investigation employing 6-MeO-BDE-47
as a case. Chemosphere 120:631–636
42. Fu ZQ, Wang Y, Chen JW, Wang ZY, Wang XB (2016) How PBDEs are transformed into
dihydroxylated and dioxin metabolites catalyzed by the active center of cytochrome P450s: a
DFT study. Environ Sci Technol 50(15):8155–8163
43. Lupton SJ, McGarrigle BP, Olson JR, Wood TD, Aga DS (2009) Human liver microsomemediated metabolism of brominated diphenyl ethers 47, 99, and 153 and identification of their
major metabolites. Chem Res Toxicol 22(11):1802–1809
44. Lai YQ, Cai ZW (2012) In vitro metabolism of hydroxylated polybrominated diphenyl ethers
and their inhibitory effects on 17β-estradiol metabolism in rat liver microsomes. Environ Sci
Pollut R 19(8):3219–3227
45. Erratico CA, Szeitz A, Bandiera SM (2013) Biotransformation of 2,2 ,4,4 -tetrabromodiphenyl
ether (BDE-47) by human liver microsomes: Identification of cytochrome P450 2B6 as the
major enzyme involved. Chem Res Toxicol 26(5):721–731
46. Agarwal V, Moore BS (2014) Enzymatic synthesis of polybrominated dioxins from the marine
environment. ACS Chem Biol 9(9):1980–1984
47. Altarawneh M, Dlugogorski BZ (2013) A mechanistic and kinetic study on the formation of
PBDD/Fs from PBDEs. Environ Sci Technol 47(10):5118–5127
48. Cao HJ, He MX, Han DD, Li J, Li MY, Wang WX, Yao SD (2013) OH-initiated oxidation mechanisms and kinetics of 2,4,4 -tribrominated diphenyl ether. Environ Sci Technol
47(15):8238–8247
49. Erickson PR, Grandbois M, Arnold WA, McNeill K (2012) Photochemical formation of brominated dioxins and other products of concern from hydroxylated polybrominated diphenyl ethers
(HO-PBDEs). Environ Sci Technol 46(15):8174–8180
50. Fu ZQ, Wang Y, Wang ZY, Xie HB, Chen JW (2015) Transformation pathways of isomeric
perfluorooctanesulfonate precursors catalyzed by the active species of P450 enzymes: in silicoinvestigation. Chem Res Toxicol 28(3):482–489