Common and uncommon cytochrome P450 reactions related to metabolism and chemical toxicity

Chemical Research in Toxicology

Volumn 14, Issue 6, 2001, Pages 611-650

  Guengerich, F P ^a  

^a VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; ALDEHYDE; BASE; CYTOCHROME P450; ESTER; FATTY ACID; FERRIC OXIDE; HYDROPEROXIDE; IRON; OXYGEN; PHOSPHOLIPASE; PROSTAGLANDIN;

CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; DESICCATION; DETOXIFICATION; ENZYME ACTIVITY; ENZYME STRUCTURE; FATTY ACID DESATURATION; HUMAN; METABOLISM; NONHUMAN; OXIDATION; REDUCTION; REVIEW;

EID: 0034973773     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx0002583     Document Type: Review

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117. Effect of superoxide generation and dismutation on hydroxylation reactions catalyzed by liver microsomal cytochrome P-450
118. Aliphatic hydroxylation by highly purified liver microsomal cytochrome P-450: Evidence for a carbon radical intermediate
119. Hydroxylation and epoxidation catalyzed by iron-porphine complexes. Oxygen transfer from iodosylbenzene
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121. The catalytic mechanism of cytochrome P-450: Spin-trapping evidence for one-electron substrate oxidation
122. 4-Alkyl radical extrusion in the cytochrome P-450-catalyzed oxidation of 4-alkyl-1,4-dihydropyridines
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124. Mechanism-based inactivation of cytochrome P-450 by heteroatom-substituted cyclopropanes and formation of ring-opened products
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148. Evidence for specific base catalysis in N-dealkylation reactions catalyzed by cytochrome P450 and chloroperoxidase: Differences in rates of deprotonation of aminium radicals as an explanation for high kinetic hydrogen isotope effects observed with peroxidases
149. Control of the catalytic activity of prosthetic heme by the structure of hemoproteins
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168. Catalytic asymmetric epoxidations with chiral iron porphyrins
169. Mechanisms of hemincatalyzed epoxidations: Electron transfer from alkenes
170. Observations and comments on the mechanism of epoxidation of alkenes by manganese(III) porphyrins with hypochlorite
171. Intermediates in the epoxidation of alkenes by cytochrome P-450 models. 3. Mechanism of oxygen transfer from substituted oxochromium(V) porphyrins to olefinic substrates
172. Intermediates in the epoxidation of alkenes by cytochrome P-450 models. 2. Use of the trans-2,trans-3-diphenylcyclopropyl substituent in a search for radical intermediates
173. Intermediates in the epoxidation of alkenes by cytochrome P-450 models. 5. Epoxidation of alkenes catalyzed by a sterically hindered (meso-tetrakis(2,6-dibromophenyl)porphinato)iron(III) chloride
174. The rate-limiting step in the one-electron oxidation of an alkene by oxo[meso-tetrakis(2,-dibromophenyl)porphinato] chromium(V) is the formation of a charge-transfer complex
175. Model reactions related to cytochrome P-450. Effects of alkene structure on the rates of epoxide formation
176. Hydrogen-deuterium exchange during propylene epoxidation by cytochrome P-450
177. On the mechanism of olefin epoxidation by oxo-iron porphyrins. Direct observation of an intermediate
178. Alkene epoxidations catalyzed by iron(III), manganese(III), and chromium(III) porphyrins. Effects of metal and porphyrin substituents on selectivity and regiochemistry of epoxidation
179. Olefin epoxidation by manganese(IV) porphyrins: Evidence for two reaction pathways
180. Cis-trans isomerization of epoxides catalyzed by ruthenium(II) porphyrins
181. Epoxidation of olefins by cytochrome P-450 model compounds: Kinetics and stereochemistry of oxygen atom transfer and origin of shape selectivity
182. Mechanisms of cytochrome P-450 catalysis
183. Oxidation of 9-alkyl anthracenes by cytochrome P450 2B1, horseradish peroxidase, and iron tetraphenylporphin/iodosylbenzene systems. Anaerobic and aerobic mechanisms
184. Oxidation of trichloroethylene by liver microsomal cytochrome P-450: Evidence for chlorine migration in a transition state not involving trichloroethylene oxide
185. Oxidation of monosubstituted olefins by cytochrome P-450 and heme models: Evidence for the formation of aldehydes in addition to epoxides and allylic alcohols
186. Mechanism of oxidation of π bonds by cytochrome P-450: Electronic requirements of the transition state in the turnover of phenylacetylenes
187. Characterization of novel glutathione adducts of a nonnucleoside reverse transcriptase inhibitor, (S)-6-chloro-4-(cyclopropylethynyl) -4-(trifluoromethyl)-3,4-dihydro-2(1H)-quinazolinone (DPC 961), in rats. Possible formation of an oxirene metabolic intermediate from a disubstituted alkyne
188. Olefin oxidation by cytochrome P-450: Evidence for group migration in catalytic intermediates formed with vinylidene chloride and trans-1-phenyl-1-butene
189. Stereochemistry of cytochrome P-450-catalyzed epoxidation and prosthetic heme alkylation
190. Ab initio molecular orbital studies of structure and reactivity of transition metal-oxo compounds
191. Oxidation by molecular oxygen. I. Reactions of a possible model system for mixed-function oxidases
192. Quantum chemical studies of model cyctochrome P450 hydrocarbon oxidation mechanisms. II. Mechanisms and relative kinetics of oxene reactions with alkenes
193. Chemical models and mechanisms for oxygenases
194. Comments on the mechanism of the "Fenton-Like" reaction
195. Aliphatic hydroxylation via oxygen rebound: Oxygen transfer catalyzed by iron
196. Alkane activation and functionalization under mild conditions by a homogeneous manganese(III) porphyrin-iodosylbenzene oxidizing system
197. High-valent iron-porphyrin complexes related to peroxidase and cytochrome P-450
198. Hydroxylation and epoxidation reactions catalyzed by synthetic metalloporphyrinates. Models related to the active oxygen species of cytochrome P-450
199. Cytochrome P-450 as an oxene transferase
200. Iodosylbenzene derivatives as oxygen donors in cytochrome P-450 catalyzed steroid hydroxylations
201. Enzymatic monooxygenation of halogen atoms: Cytochrome P-450 catalyzed oxidation of iodobenzene by iodosobenzene
202. Biochemical mechanism of aromatization
203. Mechanistic studies on C-19 demethylation in oestrogen biocynthesis
204. Mechanism of the acyl-carbon cleavage and related reactions catalyzed by multifunctional P-450s: Studies on cytochrome P45017α
205. A peroxide model reaction for placental aromatase
206. Olefin formation in the oxidative deformylation of aldehydes by cytochrome P-450. Mechanistic implications for catalysis by oxygen derived peroxide
207. Catalysis by cytochrome P-450 of an oxidative reaction in xenobiotic aldehyde metabolism: Deformylation with olefin formation
208. Aromatization of a bicyclic steroid analog, 3-oxodecalin-4-ene-10-carbox-aldehyde, by liver microsomal cytochrome P450 2B4
209. Peroxo-iron and oxenoid-iron species as alternative oxygenating agents in cytochrome P450-catalyzed reactions: Switching by threonine-302 to alanine mutagenesis of cytochrome P450 2B4
210. Epoxidation of olefins by cytochrome P450: Evidence from sitespecific mutagenesis for hydroperoxo-iron as an electrophilic oxidant
211. Electronic and steric factors in regioselective hydroxylation catalyzed by purified cytochrome P-450
212. Timing of the radicai recombination step in cytochrome P-450 catalysis with ring-strained probes
213. Cytochrome P450-catalyzed hydroxylation of hydrocarbons: Kinetic deuterium isotope effects for the hydroxylation of an ultrafast radical clock
214. A nonsynchronous concerted mechanism for cytochrome P-450 catalyzed hydroxylation
215. Hypersenstive mechanistic probe studies of cytochrome P450-catalyzed hydroxylation reactions. Implications for the cationic pathway
216. Cytochrome P450 catalyzed hydroxylation of mechanistic probes that distinguish between radicals and cations. Evidence for cationic but not for radical intermediates
217. Adjusting the top end of the alkyl radical kinetic scale, laser flash photolysis calibrations of fast radical clocks and rate constants for reactions of benzeneselenol
218. An agostic alternative to the P-450 rebound mechanism
219. Multiple active oxidants in cytochrome P-450 model oxidations
220. A model for human cytochrome P450 2D6 based on homology modeling and NMR studies of substrate binding
221. Multiple mechanisms of cytochrome P450-catalyzed substrate hydroxylations
222. Mechanisms of hydroxylation by cytochrome P-450: Exchange of iron-oxygen intermediates with water
223. On the "rebound" mechanism of alkane hydroxylation by cytochrome P450: Electronic structure of the intermediate and the electron-transfer character in the rebound step
224. A model "rebound" mechanism of hydroxylation by cytochrome P450: Stepwise and effectively concerted pathways, and their reactivity patterns
225. Molecular cloning and expression of rat squalene epoxidase
226. 4a-hydroperoxyflavin N-oxidation of tertiary amines
227. Chemical mechanisms of cytochrome P-450 catalysis
228. Reactions and significance of cytochrome P-450 enzymes
229. Studies on the rate of reduction of hepatic microsomal cytochrome P-450 by reduced nicotinamide adenine dinucleotide phosphate: Effect of drug substrates
230. On the hydroxylation of cyclohexane in rat liver microsomes
231. Ratedetermining steps in phenacetin oxidations by human cytochrome P450 1A2 and selected mutants
232. 5 on steady-state kinetics
233. Oxidation of p-alkoxyacetanilides catalyzed by human cytochrome P450 1A2: Structure-activity relationships and simulation of rate constants of individual steps in catalysis
234. Camphor binding by Pseudomonas putida cytochrome P-450. Kinetics and thermodynamics of the reaction
235. Kinetics of elementary steps in the cytochrome P-450 reaction sequence. I. Substrate binding to cytochrome P-450 LM
236. Fluorescence quenching analysis of the association and dissociation of a diarylheterocycle to cyclooxygenase-1 and cyclooxygenase-2: Dynamic basis of cyclooxygenase-2 selectivity
237. Crystal structure of substrate-free Pseudomonas putida cytochrome P-450
238. cam complexed with its catalytic product, 5-exo-hydroxycamphor
239. Conformational dynamics in cytochrome P450-substrate interactions
240. The catalytic mechanism of cytochrome P-450 BM3 involves a 6 Å movement of the bound substrate on reduction
241. Relationship between the rate of reductase-cytochrome P450 complex formation and the rate of first electron transfer
242. Temperature dependence of cytochrome P-450 reduction: A model for NADPH-cytochrome P-450 reductase: Cytochrome P-450 interaction
243. 5 in cytochrome P-450 catalysis
244. Control of heme protein redox potential and reduction rate: Linear free energy relation between potential and ferric spin state equilibrium
245. Spin state control of the hepatic cytochrome P450 redox potential
246. 5
247. Thermodynamic properties of oxidation-reduction reactions of bacterial, microsomal, and mitochondrial cytochromes P-450: An entropy-enthalpy compensation effect
248. cam in the electron transfer from reduced putidaredoxin: Analyses with site-directed mutants
249. 5
250. 5 is modulated by its exposed heme edge
251. 5 interactions
252. 5 augments the 17,20-lyase activity of human P450c17 without direct electron transfer
253. Uncoupling of the cytochrome P-450cam monooxygenase reaction by a single mutation, threonine-252 to alanine or valine: A possible role of the hydroxy amino acid in oxygen activation
254. A conserved residue of cytochrome P-450 is involved in heme-oxygen stability and activation
255. eryF the ability to oxidize alternative substrates
256. Role of Glu318 and Thr319 in the catalytic function of cytochrome P450d (P4501A2): Effects of mutations on the methanol hydroxylation
257. 319 mutations of cytochrome P450 1A2 remarkably enhance homolytic O-O cleavage of alkyl hydroperoxides: An optical absorption spectral study
258. Epoxidation of olefins by cytochrome P450: Evidence from sitespecific mutagenesis by hydroperoxo-iron as an electrophilic oxidant
259. An incredibly fast apparent oxygen rebound rate constant for hydrocarbon hydroxylation by cytochrome P-450 enzymes
260. On the deprotonation of trialkylamine cation radicals by amines
261. Facile proton-transfer reactions of N,N-dimethylaniline cation radicals
262. Bond dissociation energies of the N-H bonds in anilines and in the corresponding radical anions. Equilibrium acidities of aniline radical cations
263. Understanding reactivity patterns of radical cations
264. Rate-limiting steps in cytochrome P450-catalyzed reactions: Studies on isotope effects in the O-deethylation of 7-ethoxycoumarin
265. Cytochrome P-450-catalyzed hydroxylation and carboxylic acid ester cleavage of Hantzsch pyridine esters
266. Oxygen activation by cytochrome P450
267. Radicals in enzymatic reactions
268. Deuterium isotope effects on toluene metabolism. Product release as a rate-limiting step in cytochrome P-450 catalysis
269. Selection and characterization of human cytochrome P450 1A2 mutants with altered catalytic properties
270. Reactions catalyzed by the cytochrome P-450 system
271. Biodehalogenation: Reactions of cytochrome P-450 with polyhalomethanes
272. Hydrocarbon formation in the reductive cleavage of hydroperoxides by cytochrome P-450
273. Microsomal reduction of gentian violet. Evidence for cytochrome P-450-catalyzed free radical formation
274. Reductive metabolism of the anticonvulsant agent zonisamide, a 1,2-benzisoxazole derivative
275. Formation of electrophilic chlorine from carbon tetrachloride-involvement of cytochrome P-450
276. Anaerobic release of fluoride from halothane. Relationship to the binding of halothane to hepatic cellular constitutents
277. Detection of cysteine conjugate metabolite adduct formation with specific mitochondrial proteins using antibodies raised against halothane metabolite adducts
278. Particular ability of cytochrome P-450 CYP3A to reduce glyceryl trinitrate in rat liver microsomes: Subsequent formation of nitric oxide
279. 2-insensitive NADH-benzamidoxime reductase
280. Oxidation-reduction potential of soluble and membrane-bound rabbit liver microsomal cytochrome P-450 LM2
281. 5 in the NADH-dependent hydroxylation of 3,4-benzpyrene by a reconstituted cytochrome P-448-containing system
282. Reductive cleavage of 4-dimethylaminoazobenzene by rat liver: Intracellular distribution of enzyme system and its requirement for triphosphopyridine nucleotide
283. The kinetics and mechanism of reduction of electron-transfer proteins and other compounds of biological interest by dithionite
284. The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature
285. Reductive metabolism and protein binding of chromium(VI) by P450 protein enzymes
286. Cytochrome P-450 55A1 (P-450dNIR) acts as nitric oxide reductase employing NADH as the direct electron donor
287. Proton delivery in NO reduction by fungal nitric-oxide reductase. Cryogenic crystallography, spectroscopy, and kinetics of ferric NO complexes of wild-type and mutant enzymes
288. Spectroscopic and kinetic studies on reaction of cytochrome P450nor with nitric oxide: Implication for its nitric oxide reduction mechanism
289. Changes in the metabolic profiles of R- and S-warfarin and R- and Sphenprocoumon as a probe to categorize the effect of inducing agents on microsomal hydroxylases
290. Comparison of different forros of liver, kidney, and lung microsomal cytochrome P-450 by immunological inhibition of regio-and stereoselective metabolism of warfarin
291. Vinyl carbamate as a promutagen and a more carcinogenic analogue of ethyl carbamate
292. Comparative carcinogenicities and mutagenicities of vinyl carbamate, ethyl carbamate, and ethyl N-hydroxycarbamate
293. 6-Ethenoadenosine formation, mutagenicity and murine tumor induction as indicators of the generation of an electrophilic epoxide metabolite of the closely related carcinogens ethyl carbamate (urethane) and vinyl carbamate
294. 4-VPA, a toxic metabolite of valproic acid
295. An unusual metabolite of testosterone. 17β-4,6-Androstadiene-3-one
296. Comparison of different forms of purified cytochrome P-450 from rat liver by immunological inhibition of regio- and stereoselective metabolism of warfarin
297. Biotransformation of lovastatin. IV. Identification of cytochrome P-450 3A proteins as the major enzymes responsible for the oxidative metabolism of lovastatin in rat and human liver microsomes
298. 6-ethenoadenosine
299. Cytochrome P-450-catalyzed desaturation of valproic acid in vitro
300. 3-valproic acid generated by baculovirus-expressed CYP3A1
301. S-(N-Methylcarbamoyl) glutathione: A reactive S-linked metabolite of methyl isocyanate
302. Glutathione: A vehicle for the transport of chemically reactive metabolites in vivo
303. N-Nitroso carcinogens
304. 13C NMR study of N-methyl-N-nitrosoaniline and its ring-substituted derivatives
305. Deuterium isotope effect on denitrosation and demethylation of N-nitrosodimethylamine by rat liver microsomes
306. Metabolic nitrite formation from N-nitrosamines: Evidence for a cytochrome P-450 dependent reaction
307. Demethylation and denitrosation of nitrosamines by cytochrome P-450 isozymes
308. Metabolic nitrite formation from N-nitrosamines: Are there other pathways than reductive denitrosation by cytochrome P-450?
309. Kinetics of N-nitrosation in oxygenated nitric oxide solutions at physiological pH: Role of nitrous anhydride and effects of phosphate and chloride
310. 9 desaturase complex
311. N-Acetyl-p-benzoquinoneimine: A cytochrome P450-mediated oxidation product of acetaminophen
312. Oxidative cleavage of carboxylic esters by cytochrome P-450
313. In vivo oxidative cleavage of a pyridine carboxylic acid ester of nifedipine
314. Oxidative cleavage of esters and amides to carbonyl products by cytochrome P450
315. 1-Phenylcyclobutylamine, the first in a new class of monoamine oxidase inactivators. Further evidence for a radical intermediate
316. Cytochrome P-450-dependent oxidation of the 17α-ethynyl group of synthetic steroids: D-homoannulation or enzyme inactivation
317. Self-catalyzed destruction of cytochrome P-450: Covalent binding of ethynyl sterols to prosthetic heme
318. The metabolism of the abortifacient terpene, (R)-(+)-pulegone, to a proximate toxin, menthofuran
319. Evidence for a cytochrome P450 catalyzed allylic rearrangement with double bond topomerization
320. Metabolic activation of (R)-(+)-pulegone to a reactive enonal that covalently binds to mouse liver proteins
321. Investigations of mechanisms of reactive metabolite formation from (R)-(+)-pulegone
322. Reactive intermediates in the oxidation of menthofuran by cytochromes P-450
323. Metabolism of(R)-(+)-pulegone and (R)(+)-menthofuran by human liver cytochrome P450s: Evidence for formation ora furan epoxide
324. Microsomal metabolism of furosemide evidence for the nature of the reactive intermediate involved in covalent binding
325. Studies on the activation of a model furan compound: Toxicity and covalent binding of 2-(N-ethyl-carbamoylhydroxymethyl)furan
326. Mechanism of metabolic cleavage of a furan ring
327. Reactive metabolites from the bioactivation of methylfurans
328. An unexpected product for the peracid oxidation of furan derivatives anda new ∈-lactone synthesis
329. Direct N.M.R. detection of an epoxyfuran intermediate in peracid oxidation of the fungicide methfuroxam
330. Synthesis of the 2,3-epoxy-2,3-dihydro-2,3dimethylbenzo[b]furan, the proposed ultimate mutagen of the benzofuran dioxetanes
331. Mechanism-based inactivation of cytochrome P450 2B4 by aldehydes: Relationship to aldehyde deformylation via a peroxyhemiacetal intermediate
332. Oxygenation mechanism in conversion of aldehyde to carboxylic acid catalyzed by a cytochrome P-450 isozyme
333. Dehydration of alkyl- and arylaldoximes as a new cytochrome P450catalyzed reaction: Mechanism and stereochemical characteristics
334. New catalytic properties of iron porphyrins: Model systems for cytochrome P450-catalyzed dehydration of aldoximes
335. TYR is a multifunctional heme-thiolate enzyme catalyzing the conversion of L-tyrosine to p-hydroxyphenylacetaldehyde oxime in the biosynthesis of cyanogenic glucoside dhurrin in Sorghum bicolor (L.) Moench
336. Relationships between toxicity and structure of aliphatic nitriles
337. In vivo acetylcholinesterase inhibition, metabolism, and toxicokinetics of aldicarb in channel catfish: Role of biotransformation in acute toxicity
338. Studies on the microsomal formation of arylating metabolites of acetaminophen and phenacetin
339. 18O]-phenacetin: The mechanism of activation of phenacetin to reactive intermediates in hamsters
340. Biological conversion of N-phenyl-2-naphthylamine to 2-naphthylamine in Sprague Dawley rat
341. A new hypothesis for the mechanism for cytochrome P-450 dependent aerobic conversion of hexahalogenated benzenes to pentahalogenated phenols
342. Novel metabolic pathway of arylethers by cytochrome P450: Cleavage of the oxygen-aromatic ring bond accompanying ipso-substitution by the oxygen atom ofthe active species in cytochrome P450 models and cytochrome P450
343. Cytochrome P450-catalyzed oxidation of halobenzene derivatives
344. Cytochrome P450-mediated oxidation of pentafluorophenol to tetrafluorobenzoquinone as the primary reaction product
345. Reaction pathways for biodehalogenation of fluorinated anilines
346. Occurrence of the NIH shift upon the cytochrome P450-catalyzed in vivo and in vitro aromatic ring hydroxylation of fluorobenzenes
347. Mechanisms of hydroxylation by cytochrome P-450: Metabolism of monohalobenzenes by phenobarbital-induced microsomes
348. Novel metabolic pathway of estrone and 17β-estradiol catalyzed by cytochrome P-450
349. One electrontransfer mechanism in the enzymatic oxygenation of sulfoxide to sulfone promoted by a reconstituted system with purified cytochrome P-450
350. Mechanisms of enzymatic S-oxygenation of thioanisole derivatives and O-demethylation of anisole derivatives promoted by both microsomes anda reconstituted system with purified cytochrome P-450
351. Isolation ofa high-valent 'oxo-like' manganese porphyrin complex obtained from NaOCl oxidation
352. Stabilization of higher-valent states of iron porphyrin by hydroxide and methoxide ligands: Electrochemical generation of iron(IV)-oxo porphyrins
353. Electrochemical generation of an iron(IV) porphyrin
354. Calculation of the cytochrome P-450 redox potential from kinetic data by the Marcus treatment; feasible or not?
355. Oxidation of polycyclic aromatic hydrocarbons and dibenzo[p]-dioxins by Phanerochaete chrysosporium ligninase
356. Oxidative degradation of phenanthrene by the ligninolytic fungus Phanerochaete chrysosporium
357. Inactivation of cytochrome P-450 by a catalytically generated cyclobutadiene species
358. The isolation of a cancer-producing hydrocarbon from coal tar. Parts I, II, and III
359. Polynuclear aromatic carcinogens
360. Metabolic activation of benzo[a]pyrene proceeds by a diolepoxide
361. 7-Sulfooxymethyl-12-methylbenz[a]anthracene is an exceptionally reactive electrophilic mutagen and ultimate carcinogen
362. 7-Sulfooxymethyl-12-methylbenz[a]anthracene is an electrophilic mutagen, bur does not appear to play a role in carcinogenesis by 7,12-dimethylbenz[a]anthracene or 7-hydroxymethyl 12methylbenz[a]anthracene
363. The microsomal metabolism of benzo[a]pyrene phenols
364. Central role of radical cations in metabolic activation of polycyclic aromatic hydrocarbons
365. Sulfotransferase-mediated mutagenicity of 1-hydroxymethylpyrene and 4H-cyclopenta [def]chrysen-4-ol and its enhancement by chloride anions
366. A 7-hydroxymethyl sulfate ester as an active metabolite of 7,12-dimethylbenz[a]anthracene
367. One electron-transfer oxidation of 7,12-dimethylbenz[a]anthracene, a model for the metabolic activation of carcinogenic hydrocarbons
368. One-electron oxidation of polycyclic aromatics as a model for the metabolic activation of carcinogenic hydrocarbons
369. The involvement of free radicals in chemical carcinogenesis
370. One-electron oxidation of 6-substituted benzo[a]pyrenes by manganic acetate. A model for metabolic activation
371. Induction of microsomal enzymes by foreign chemicals and carcinogenesis by polycyclic aromatic hydrocarbons: G. H. A. Clowes memorial lecture
372. Benzo[a]pyrene-7,8-dihydrodiol 9,10-oxide adenosine and deoxyadenosine adducts: Structure and stereochemistry
373. Binding of benzo[α]pyrene to DNA by cytochrome P-450 catalyzed one-electron oxidation in rat liver microsomes and nuclei
374. Identification and quantitation of 7-(benzo[a]pyren-6-yl)guanine in the urine and feces of rats treated with benzo[a]pyrene
375. Depurinating and stable benzo[α]pyrene-DNA adducts formed in isolated rat liver nuclei
376. Observation of ternary electron donor-acceptor complexes of anthracene by picosecond spectroscopy. Molecular structure of the anthracenophane-tetracyanoethylene complex
377. Dramatic solvent and stereoelectronic effects in a biomimetic oxidation: 9,10-dialky-lanthracenes
378. One-electron oxidation of 9-methylanthracene and 9-[(tri-methylsilyl)methyl]anthracene: Reversal of radical-cation selectivity by the trimethylsilyl group
379. The ligninase of Phanerochaete chrysosporium generates cation radicals from methoxybenzenes
380. Comparison of lignin peroxidase, horseradish peroxidase and laccase in the oxidation of methoxybenzenes
381. Oxidation of 1,2,4,5-tetramethoxybenzene to a cation radical by cytochrome P450
382. Correlation studies of anodic peak potentials and ionization potentials for polycyclic aromatic hydrocarbons
383. Voltammetry of acetaminophen and its metabolites
384. The anodic pyridination, dimerization, and fragmentation of some anilide structures
385. Identification of the convulsant opiate thebaine in mammalian brain
386. Synthesis of the skeleton of the morphine molecule by mammalian liver
387. Endogenous codeine and morphine in poor and extensive metabolisers of the CYP2D6 (debrisoquine/sparteine) polymorphism
388. Purification and characterization of a cytochrome P450 enzyme from pig liver, catalyzing the phenol oxidative coupling of (R)reticuline to salutaridine, the critical step in morphine biosynthesis
389. Oxidation of indole by cytochrome P450 enzymes
390. Structural determination of a mutagenic aminophenylnorharman produced by the co-mutagen norharman with aniline
391. Prostacyclin synthase, a cytochrome P450 enzyme
392. Isolation and characterization of thromboxane synthase from human platelets as a cytochrome P-450 enzyme
393. 2 biosynthesis
394. 2 analogues in the presence of iodosylbenzene
395. Xenobiotic metabolizing cytochromes P450 convert prostaglandin endoperoxide to hydroxyheptadecatrienoic acid and the mutagen, malondialdehyde
396. Xenobiotic metabolising enzyme expression in colonic neoplasia
397. P450-dependent transformations of 15R- and 15S-hydroperoxyeicosatetraenoic acids: Stereoselective formation of epoxyalcohol products
398. Purification of an allene oxide synthase and identification of the enzyme as a cytochrome P-450
399. Molecular cloning of a divinyl ether synthase: Identification as a CYP74 cytochrome P450
400. Interindividual variation in the isomerization of 4-hydroxytamoxifen by human liver microsomes: Involvement of cytochromes P450
401. Phospholipase D activity of cytochromes P450 in human liver endoplasmic reticulum
402. Tissue-specific distribution and subcellular distribution of phospholipase D in rat: Evidence for distinct RhoA- and ADP-ribosylation factor (ARF)-regulated isoenzymes
403. Analysis of human cytochrome P450 3A4 cooperativity: Construction and characterization of a site-directed mutant that displays hyperbolic steroid hydroxylation kinetics
404. 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
405. Cooperativity in oxidations catalyzed by cytochrome P450 3A4
406. Elucidation of distinct binding sites for cytochrome P450 3A4
407. Human liver carbamazepine metabolism: Role of CYP3A4 and CYP2C8 in 10,11-epoxide formation
408. Binding and oxidation of alkyl 4-nitrophenyl ethers by rabbit cytochrome P450 IA2: Evidence for two binding sites