Allosteric phenomena in cytochrome P450-catalyzed monooxygenations

European Journal of Biochemistry

Volumn 268, Issue 18, 2001, Pages 4817-4832

  Hlavica, Peter ^a   Lewis, David F V ^b  

^a UNIVERSITY OF MUNICH   (Germany)

^b UNIVERSITY OF SURREY   (United Kingdom)

Author keywords

Allosteric activation; Conformer equilibria; Cytochrome P450; Dioxygen association; Electron transfer; Kinetic models; Substrate binding

Indexed keywords

CARBON MONOXIDE; CYTOCHROME B5; CYTOCHROME P450; CYTOCHROME P450 REDUCTASE; HEME; IRON; ISOENZYME; ISOPROTEIN; LIGAND; LIPID; OXYGEN; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; UNSPECIFIC MONOOXYGENASE;

ALLOSTERISM; CATALYSIS; DIATOM; DRUG METABOLISM; ELECTRON TRANSPORT; ENZYME ACTIVATION; ENZYME ACTIVITY; ENZYME METABOLISM; IN VIVO STUDY; KINETICS; LIGAND BINDING; MICHAELIS MENTEN KINETICS; OXIDATION REDUCTION REACTION; OXYGENATION; PRIORITY JOURNAL; PROTEIN BINDING; PROTEIN LIPID INTERACTION; PROTEIN PROTEIN INTERACTION; PROTEIN STRUCTURE; REVIEW;

BACILLARIOPHYTA;

EID: 0034800477     PISSN: 00142956     EISSN: None     Source Type: Journal    
DOI: 10.1046/j.1432-1327.2001.02412.x     Document Type: Review

References (184)

1. P450 superfamily: Update on new sequences, gene mapping, accession numbers and nomenclature
2. Cytochrome P450. Multiplicity of isoforms, substrates, and catalytic and regulatory mechanisms
3. Twenty-five years of P450 research. Mechanistic insights into oxygenase catalysis
4. Role of hemoprotein P-450 in fatty acid 4-hydroxylation in a soluble enzyme system from liver microsomes
5. 5
6. Structure of a cytochrome P450-redox partner electron-transfer complex
7. Heme proteins in prostaglandin biosynthesis
8. Cytochrome P450 55A1 (P450dNIR) acts as a nitric oxide reductase employing NADH as the direct electron donor
9. On the nature of allosteric transitions: A plausible model
10. Transients and cooperativity. A slow transition model for relating transients and cooperative kinetics of enzymes
11. Regulatory behaviour of monomeric enzymes. 1. The mnemonical enzyme concept
12. Biphasic kinetic behaviour of rat cytochrome P450 1A1-dependent monooxygenation in recombinant yeast microsomes
13. Evaluation of atypical cytochrome P450 kinetics with two-substrate models: Evidence that multiple substrates can simultaneously bind to cytochrome P450 active sites
14. Sigmoidal kinetic model for two cooperative substrate-binding sites in a cytochrome P450 3A4 active site: An example of the metabolism of diazepam and its derivatives
15. Triazolam substrate inhibition: Evidence of competition for heme-bound reactive oxygen within the CYP3A4 active site
16. Cooperativity in oxidations catalyzed by cytochrome P450 3A4
17. Analysis of four residues within substrate recognition site 4 of human cytochrome P450 3A4: Role of steroid hydroxylase activity and α-naphthoflavone stimulation
18. Specificity of the activation and inhibition by flavonoids of benzo[α]pyrene hydroxylation by cytochrome P-450 isozymes from rabbit liver microsomes
19. Interactions of cytochrome P-450, NADPH-cytochrome P-450 reductase, phospholipid, and substrate in the reconstituted liver microsomal enzyme system
20. 5 from rabbit liver
21. Evidence for lipid involvement in the high-affinity interaction between cimetidine and rat liver cytochrome P-450
22. Substrates of human hepatic cytochrome P450 3A4
23. The human CYP3A subfamily: Practical considerations
24. Nature of cytochrome P450 involved in the 2-/4-hydroxylations of estradiol in human liver microsomes
25. Identification of three key residues in substrate recognition site 5 of human cytochrome P450 3A4 by casette and site-directed mutagenesis
26. Analysis of human cytochrome P450 3A4 cooperativity: Construction and characterization of a site-directed mutant that displays hyperbolic steroid hydroxylation kinetics
27. Dual role of human cytochrome P450 3A4 residue Phe-304 in substrate specificity and cooperativity
28. Elucidation of distinct ligand binding sites for cytochrome P450 3A4
29. 5 in yeast
30. In vitro assessment of human cytochrome P450
31. Sigmoidal kinetics of CYP3A substrates: An approach for scaling dextromethorphan metabolism in hepatic microsomes and isolated hepatocytes to predict in vivo clearance in rat
32. Kinetic characterization and identification of the enzymes responsible for the hepatic biotransformation of adinazolam and N-desmethyladinazolam in man
33. 1 by bacterial recombinant human cytochrome P450 enzymes
34. Allosteric regulation of the 16β-hydroxylation of progesterone as catalyzed by rabbit liver microsomal cytochrome P-450 3b
35. Constitutive forms of rabbit-liver microsomal cytochrome P-450: Enzymatic diversity, polymorphism and allosteric regulation
36. Two catalytically distinct subforms of cytochrome P-450 3b as obtained from inbred rabbits
37. Catalytic properties of purified forms of rabbit liver microsomal cytochrome P-450 in reconstituted phospholipid vesicles
38. eryF the ability to oxidize alternative substrates
39. Heterogeneity in rabbit liver cytochrome P450LM2 observed by cation exchange HPLC: Partial biochemical characterization of the two major LM2 subfractions
40. Functional and structural polymorphism of rabbit microsomal cytochrome P-450 form 3b
41. Enzyme kinetic and inhibition analyses of cytochrome P450XVII, a protein with a bifunctional catalytic site. Quantification of effective substrate concentrations at the active site and their significance for intrinsic control of the hydroxylase/lyase reaction sequence
42. Flavonols and flavones in food plants
43. Alanine-scanning mutagenesis of a putative substrate recognition site in human cytochrome P450 3A4: Role of residues 210 and 211 in flavonoid activation and substrate specificity
44. Modulation of rabbit and human hepatic cytochrome P-450-catalyzed steroid hydroxylations by α-naphthoflavone
45. Positive effectors of the binding of an active site-directed amino steroid to rabbit cytochrome P-450 3c
46. Activation of CYP3A4: Evidence for the simultaneous binding of two substrates in a cytochrome P450 active site
47. Inhibition of cytochrome P-450 activity in rat liver microsomes by naturally occurring flavonoid, quercetin
48. Effect of flavonoids on cytochrome P450-dependent acetaminophen metabolism in rats and human liver microsomes
49. Human cytochrome P-450 3A4: In vitro drug-drug interaction patterns are substrate-dependent
50. Molecular modelling of CYP3A4 from an alignment with CYP102: Identification of key interactions between putative active site residues and CYP3A-specific chemicals
51. eryF exhibiting homotropic cooperativity
52. Molecular modeling of cytochrome P450 3A4
53. Drug-drug interactions: Effect of quinidine on nifedipine binding to human cytochrome P450 3A4
54. Differential mechanism of cytochrome P450 inhibition and activation by α-naphthoflavone
55. 2+
56. Alternative allosteric effects exerted by end products upon a two-substrate enzyme in Rhodomicrobium vannielii
57. Studies on the mechanism of activation of microsomal benzo[α]pyrene hydroxylation by flavonoids
58. Influence of N,N-dimethylaniline on the association of phenobarbital-induced cytochrome P-450 and NADPH-cytochrome c (P-450) reductase in a reconstituted rabbit liver microsomal enzyme system
59. 5 and cytochrome P450 reductase
60. Identification of key residues in rabbit liver microsomal cytochrome P450 2B4: Importance in interactions with NADPH-cytochrome P450 reductase
61. 2-terminal hydrophobic sequence has a role in the functional association of NADPH-cytochrome P450 reductase
62. Analysis of interactions among purified components of the liver microsomal cytochrome P-450-containing monooxygenase system by second derivative spectroscopy
63. A fluorescence study of the interactions of benzo[α]pyrene, cytochrome P450c and NADPH-cytochrome P450 reductase
64. 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine as a substrate of cytochrome P450 2D6: Allosteric effects of NADPH-cytochrome P450 reductase
65. 5 binding site and comparisons with CYP2B1 and CYP2B4
66. 5 in the cytochrome P-450-dependent oxygenase system
67. 5 and cytochrome P450 reductase
68. 2
69. 5
70. 5
71. 5 effects vary with substrate
72. scc. Cholesterol and adrenodoxin interactions at equilibrium and during turnover
73. Cytochrome P-450 organization and membrane interactions
74. Comparative study of two highly purified forms of liver microsomal cytochrome P-450: Circular dichroism and other properties
75. Conformational change and activation of cytochrome P450 2B1 induced by salt and phospholipid
76. Liver microsomal membranes: Reconstitution of the hydroxylation system containing cytochrome P-450
77. Rapid conformational changes of cytochrome P450: Effect of dimyristoyl lecithin
78. Conformational change of cytochrome P-450 1A2 induced by phospholipids and detergents
79. Conformational change of cytochrome P-450 indicated by the measurement of fluorescence-energy transfer
80. Conformation between the substrate-binding site and heme of cytochrome P450 studied by excitation energy transfer
81. The effect of dilauroyl-L-3-phosphatidylcholine on the interaction between cytochrome P-450 1A1 and benzo[α]pyrene
82. Regulation of allosteric membrane-bound enzymes through changes in membrane lipid composition
83. Studies on the stimulation of cytochrome P-450-dependent monooxygenase activity by dilauroylphosphatidylcholine
84. Interaction of liver microsomal cytochrome P-450 and NADPH-cytochrome P-450 reductase in the presence and absence of lipid
85. Cytochrome P-450 facilitates phospha-tidylcholine flip-flop in proteoliposomes
86. scc: Role of the membrane in control of activity and spin state of the cytochrome
87. scc: Cardiolipin as an effector of activity in mitochondrial cytochrome P-450
88. scc-phospholipid interactions. Evidence for a cardiolipin binding site and thermodynamics of enzyme interactions with cardiolipin, cholesterol and adrenodoxin
89. Spectral studies of drug interaction with hepatic microsomal cytochrome
90. Effect of substrate on the spin state of cytochrome P-450 in hepatic microsomes
91. Coupling of spin, substrate, and redox equilibria in cytochrome P-450
92. CO binding kinetics of human cytochrome P450 3A4. Specific interaction of substrates with kinetically distinguishable conformers
93. Observation of structural variation and spin state conversion of cytochrome P450 CYP2B4 on binding of sterically different substrates
94. Circular dichroism studies on the binding of type I substrates and reverse type I compounds to rabbit liver microsomal cytochrome P-450
95. scc from bovine adrenocortical mitochondria
96. cam spin equilibrium
97. High-pressure investigations of cytochrome P-450 spin and substrate binding equilibria
98. cam and P450 2B4
99. Primary structures of multiple forms of cytochrome P-450 isozyme 2 derived from rabbit pulmonary and hepatic cDNAs
100. Rabbit liver cytochrome P-450 2B5: High-level expression of the full-length protein in Escherichia coli, purification, and catalytic activity
101. Chemical modification of cytochrome P-450LM2 with N-acetylimidazole. Evidence for the functional involvement of tyrosyl residues
102. cam
103. Steady-state and picosecond-time-resolved fluorescence studies on the recombinant heme domain of Bacillus megaterium cytochrome P-450
104. Kinetics of cytochrome P-450 reduction: Evidence for faster reduction of the high-spin ferric state
105. Correlations between spin equilibrium shift, reduction rate, and N-demethylation activity in liver microsomal cytochrome P-450 and a series of benzphetamine analogues as substrates
106. Reduction kinetics of purified rat liver cytochrome P450. Evidence for a sequential reaction mechanism dependent on the hemoprotein spin state
107. Spin state control of cytochrome P-450 reduction and catalytic activity in a reconstituted P-450LM2 system as induced by a series of benzphetamine analogues
108. Differences in the spectral interactions between NADPH-cytochrome P-450 reductase and a series of cytochrome P-450 enzymes
109. Cytochrome P-450LM2 reduction. Substrate effects on the rate of reductase-LM2 association
110. Relationship between the rate of reductase-cytochrome P450 complex formation and the rate of first electron transfer
111. Betamethasone-mediated activation of biphenyl 2-hydroxylation in rat liver microsomes
112. Cytochrome P-450 rotamers control mixed-function oxygenation in reconstituted membranes. Rotational diffusion studied by delayed fluorescence depolarization
113. Amino acid residue 250 has a functional role in the assembly of rabbit liver microsomal cytochrome P450 2B4
114. Molecular modelling of mammalian CYP2B isoforms and their interaction with substrates, inhibitors and redox partners
115. Construction of a 3D model of cytochrome P450 2B4
116. The molecular basis of electron transfer in redox enzyme systems
117. Modification of cytochrome P-450 with fluorescein isothiocyanate
118. Influence of mutation of the amino-terminal signal anchor sequence of cytochrome P450 2B4 on the enzyme structure and electron transfer processes
119. Interactions of cytochrome P450 2B4 with NADPH-cytochrome P450 reductase studied by fluorescent probe
120. 5 in microsomes
121. scc. Mutually facilitated binding of cholesterol and adrenodoxin
122. scc and adrenodoxin - Analysis in the median UV-region by second derivative spectroscopy
123. A thermodynamic model of regulation: Modulation of redox equilibria in camphor monooxygenase
124. Control of heme protein redox potential and reduction rate: Linear free energy relation between potential and ferric spin state equilibrium
125. Spin state control of the hepatic cytochrome P450 redox potential
126. Oxidation-reduction properties of rat liver cytochromes P-450 and NADPH-cytochrome P-450 reductase related to catalysis in reconstituted systems
127. Positive increase of redox potential of the extramitochondrial NADP(H) system by mixed function oxidations in hemoglobin-free perfused rat liver
128. Purified liver microsomal cytochrome P-450. Electron-accepting properties and oxidation-reduction potential
129. Beef adrenal cortical cytochrome P-450 which catalyzes the conversion of cholesterol to pregnenolone. Oxidation-reduction potentials of the free, steroid-complexed, and adrenodoxin-complexed P-450
130. The contribution of electrostatic factors to the oxidation-reduction potentials of c-type cytochromes
131. Interaction of NADP(H) with oxidized and reduced P450 reductase during catalysis. Studies with nucleotide analogues
132. Regulation mechanisms of the activity of the hepatic endoplasmic cytochrome P450
133. Effect of a zwitterionic detergent on the state of aggregation and catalytic activity of cytochrome P-450LM2 and NADPH-cytochrome P-450 reductase
134. High-pressure-induced transitions in microsomal cytochrome P450 2B4 in solution. Evidence for conformational inhomogeneity in the oligomers
135. Stabilization of P450 2B4 by its association with P450 1A2 revealed by high-pressure spectroscopy
136. Interactions among P450 enzymes when combined in reconstituted systems: Formation of a 2B4-1A2 complex with a high affinity for NADPH-cytochrome P450 reductase
137. 5 interactions
138. scc in zone specificity of aldosterone biosynthesis in bovine adrenal
139. Roles of divalent metal ions in oxidations catalyzed by recombinant cytochrome P450 3A4 and replacement of NADPH-cytochrome P450 reductase with other flavoproteins, ferredoxin, and oxygen surrogates
140. 5 in the oxidation of testosterone and nifedipine by recombinant cytochrome P450 3A4 and by human liver microsomes
141. 5 in stimulation of catalytic activities of cytochrome P450 3A4
142. Interactions between redox partners in various cytochrome P450 systems: Functional and structural aspects
143. Identification of unique amino acids that modulate CYP4A7 activity
144. 5 augments the 17,20-lyase activity of human P450c17 without direct electron transfer
145. Some properties of mitochondrial adrenodoxin associated with its nonconventional electron donor function toward rabbit liver microsomal cytochrome P450 2B4
146. Conformational studies of NADPH-cytochrome P-450 reductase by circular dichroism. Interaction with phospholipids
147. Hydrodynamic characterization of highly purified and functionally active liver microsomal cytochrome P-450
148. 5
149. 5 to phospholipid vesicles and biological membranes. Effect of orientation on intermembrane transfer and digestion by carboxypeptidase Y
150. 5 tail
151. 5
152. 5 affects interaction with cytochrome P-450 2B4
153. 5 upon productive complex formation within a monomeric reconstituted system
154. 5 in the interaction with cytochrome P-450LM2
155. 5 on electron flow from NADPH-cytochrome c (P-450) reductase to cytochrome P450
156. Cytochrome P-450 spin state and leakiness of the monooxygenase pathway
157. Die sauerstoffabhängigkeit der hydroxylierung von acetanilid zu 4-acetamino-phenol durch kaninchenlebermikrosomen
158. Hepatic mixed function amine oxidase. An allosteric system
159. Interaction of oxygen and aromatic amines with hepatic microsomal mixed-function oxidase
160. Studies on the mechanism of hepatic microsomal N-oxide formation, I. Effect of carbon monoxide on the N-oxidation of N,N-dimethylaniline
161. The isolation and comparison of multiple forms of CYP2B from untreated and phenobarbital-treated rabbit liver microsomes
162. scc. Effect of cholesterol and intermediates on its stability and optical characteristics
163. scc. Effect of cholesterol, intermediates, and phosphatidylcholine vesicles
164. Spectral intermediates in the reaction of oxygen with purified liver microsomal cytochrome P-450
165. CAM: Oxygenated complexes stabilized at low temperature
166. Substrate analogue induced changes of the CO-stretching mode in the cytochrome P450cam-carbon monoxide complex
167. Studies on the reactivity of the oxyferro intermediate of highly purified microsomal P-450
168. cam
169. 5-enriched rabbit liver microsomal fractions
170. 5 rules uncoupling mechanisms
171. 5
172. dS: Effects of mutations at putative distal sites in the presence of polycyclic hydrocarbons
173. scc
174. Kinetics of CO binding to cytochromes P450 in the endoplasmic reticulum
175. Interaction of polycyclic aromatic hydrocarbons and flavones with cytochromes P450 in the endoplasmic reticulum: Effect on CO binding kinetics
176. Cytochrome P450 conformation and substrate interactions as probed by CO binding kinetics
177. Kinetics and mechanism of CO binding to cytochromes P-450LM2 and P-450LM4
178. An infrared spectroscopic study of CO bonding to ferrous cytochrome P-450
179. Metyrapone interaction with hepatic microsomal cytochrome P-450 from rats treated with phenobarbital
180. cam
181. In vitro-in vivo scaling of CYP kinetic data not consistent with the classical Michaelis-Menten model
182. Human cytochrome P450 3A (CYP3A) mediated midazolam metabolism: The effect of assay conditions and regioselective stimulation by α-naphthoflavone, terfenadine and testosterone
183. In vitro and in vivo activation of oxidative drug metabolism by flavonoids