References
- Atkins WM. 2006. Current views on the fundamental mechanisms of cytochrome P450 allosterism. Expert Opin Drug Metab Toxicol 2:573–9
- Backes WL, Cawley G, Eyer CS, et al. 1993. Aromatic hydrocarbon binding to cytochrome P450 and other enzyme binding sites: are hydrophobic compounds drawn into the active site or pushed from the aqueous phase? Arch Biochem and Biophys 304:27–37
- Barale R. 1991. The genetic toxicology of styrene and styrene oxide. Mutat Res 257:107–26
- Bond JA, Bolt HM. 1989. Review of the toxicology of styrene. Crit Rev Toxicol 19:227–49
- Boysen G, Scarlett CO, Temple B, et al. 2007. Identification of covalent modifications in P450 2E1 by 1,2-epoxy-3-butene in vitro. Chem Biol Interact 166:170–5
- Christakopoulos A, Bergmark E, Zorcec V, et al. 1993. Monitoring occupational exposure to styrene from hemoglobin adducts and metabolites in blood. Scand J Work Environ Health 19:255–63
- Collom SL, Jamakhandi AP, Tackett AJ, et al. 2007. CYP2E1 active site residues in substrate recognition sequence 5 identified by photoaffinity labeling and homology modeling. Arch Biochem Biophys 459:59–69
- Collom SL, Laddusaw RM, Burch AM, et al. 2008. CYP2E1 substrate inhibition: mechanistic interpretation through an effector site for monocyclic compounds. J Biol Chem 283:3487–96
- Crespi C, Francis E, Patten C. 2009. Optimizing donor number for consistent pooled human liver microsomes. Billerica (MA): BD Biosciences – Discovery Labware
- Denisov IG, Frank DJ, Sligar SG. 2009. Cooperative properties of cytochromes P450. Pharmacol Therapeut 124:151–67
- Guengerich F. 2002. Rate-limiting steps in cytochrome P450 catalysis. Biol Chem 383:1553–64
- Guengerich FP. 2007. Cytochrome P450 and chemical toxicology. Chem Res Toxicol 21:70–83
- Hargreaves MB, Jones BC, Smith DA, Gescher A. 1994. Inhibition of p-nitrophenol hydroxylase in rat liver microsomes by small aromatic and heterocyclic molecules. Drug Metab Dispos 22:806–10
- Harrelson JP, Atkins WM, Nelson SD. 2008. Multiple-ligand binding in CYP2A6: probing mechanisms of cytochrome P450 cooperativity by assessing substrate dynamics. Biochemistry 47:2978–88
- Hartman J, Boysen G, Miller GP. 2012. CYP2E1 metabolism of styrene involves allostery. Drug Metab Dispos 40:1976–83
- Isin EM, Sohl CD, Eoff RL, Guengerich FP. 2008. Cooperativity of cytochrome P450 1A2: interactions of 1,4-phenylene diisocyanide and 1-isopropoxy-4-nitrobenzene. Arch Biochem Biophys 473:69–75
- Kapelyukh Y, Paine MJ, Maréchal JD, et al. 2008. Multiple substrate binding by cytochrome P450 3A4: estimation of the number of bound substrate molecules. Drug Metab Dispos 36:2136–44
- Koop DR. 1986. Hydroxylation of p-nitrophenol by rabbit ethanol-inducible cytochrome P-450 isozyme 3a. Mol Pharmacol 29:399–404
- Kuzmic P. 1996. Program DYNAFIT for the analysis of enzyme kinetic data: application to HIV protease. Anal Biochem 237:260–73
- Li J, Wei D-Q, Wang J-F, Li Y-X. 2011. A negative cooperativity mechanism of human CYP2E1 inferred from molecular dynamics simulations and free energy calculations. J Chem Inf Model 51:3217–25
- Liu KH, Kim MJ, Jung WM, et al. 2005. Lansoprazole enantiomer activates human liver microsomal CYP2C9 catalytic activity in a stereospecific and substrate-specific manner. Drug Metab Dispos 33:209–13
- Miller GP. 2008. Advances in the Interpretation and Prediction of CYP2E1 Metabolism from a Biochemical Perspective. Exp Opin Drug Metab Toxicol 4:1053–64
- Miller GP, Guengerich FP. 2001. Binding and oxidation of alkyl 4-nitrophenyl ethers by rabbit cytochrome P450 1A2: evidence for two binding sites. Biochemistry 40:7262–72
- National Toxicology Program. 2008. Final report on carcinogens background document for styrene. Rep Carcinog Backgr Doc 8-5978:i--398
- Niwa T, Murayama N, Yamazaki H. 2008. Heterotropic cooperativity in oxidation mediated by cytochrome p450. Curr Drug Metab 9:453–62
- Porubsky PR, Meneely KM, Scott EE. 2008. Structures of human cytochrome P-450 2E1: insights into the binding of inhibitors and both small molecular weight and fatty acid substrates. J Biol Chem 283:33698–707
- Rappaport SM, Yeowell-O'Connell K, Bodell W, et al. 1996. An investigation of multiple biomarkers among workers exposed to styrene and styrene-7,8-oxide. Cancer Res 56:5410–16
- Řemínek R, Glatz Z. 2010. Study of atypical kinetic behaviour of cytochrome P450 2C9 isoform with diclofenac at low substrate concentrations by sweeping-MEKC combination. J Sep Sci 33:3201–6
- Roberts BJ, Song BJ, Soh Y, et al. 1995. Ethanol induces CYP2E1 by protein stabilization: role of ubiquitin conjugation in the rapid degradation of CYP2E1. J Biol Chem 270:29632–5
- Roberts AG, Yang J, Halpert JR, et al. 2011. The structural basis for homotropic and heterotropic cooperativity of midazolam metabolism by human cytochrome P450 3A4. Biochemistry 50:10804–18
- Song BJ, Veech RL, Park SS, et al. 1989. Induction of rat hepatic N-nitrosodimethylamine demethylase by acetone is due to protein stabilization. J Biol Chem 264:3568–72
- Spatzenegger M, Liu H, Wang Q, et al. 2003. Analysis of differential substrate selectivities of CYP2B6 and CYP2E1 by site-directed mutagenesis and molecular modeling. J Pharmacol Exp Ther 304:477–87
- Venkatakrishnan K, von Moltke LL, Greenblatt DJ. 1998. Human cytochrome P450 mediating phenacetin O-deethylation in vitro: validation of the high affinity component as an index of CYP1A2 activity. J Pharm Sci 87:1502–7
- Woods CM, Fernandez C, Kunze KL, Atkins WM. 2011. Allosteric activation of cytochrome P450 3A4 by α-naphthoflavone: branch point regulation revealed by isotope dilution analysis. Biochemistry 50:10041–51