Arene oxides and the NIH shift: the metabolism, toxicity and carcinogenicity of aromatic compounds. (Q54563707)

1 June 2018

title

Arene oxides and the NIH shift: the metabolism, toxicity and carcinogenicity of aromatic compounds. (English)

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1 June 2018

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J W Daly

1

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1 June 2018

D M Jerina

series ordinal

2

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1 June 2018

B Witkop

series ordinal

3

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1 June 2018

publication date

1 October 1972

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1 June 2018

published in

Experientia

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1 June 2018

volume

28

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1 June 2018

issue

10

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1 June 2018

page(s)

1129-1149

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1 June 2018

Solubilization, purification, and properties of a hepatic epoxide hydrase

cites work

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https://api.crossref.org/works/10.1007%2FBF01946135

Biochemical studies of toxic agents. 11. The occurrence of premercapturic acids

21 January 2018

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Studies in detoxication. 51. The determination of catechols in urine, and the formation of catechols in rabbits receiving halogenobenzenes and other compounds; dihydroxylation in vivo

21 January 2018

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Studies in detoxication; the metabolism of chlorobenzene in the rabbit; isolation of dihydrodihydroxychlorobenzene, p-chlorophenylglucuronide, 4-chlorocatechol glucuronide and p-chlorophenylmercapturic acid

21 January 2018

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Studies in detoxication. 68. The metabolism of [14C]nitrobenzene in the rabbit and guinea pig.

21 January 2018

1 reference

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Studies in detoxication. 62. The metabolism of halogenobenzenes. Ortho- and para-dichlorobenzenes

21 January 2018

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Studies in detoxication. 63. The metabolism of halogenobenzenes. (a) Meta-dichlorobenzene. (b) Further observations on the metabolism of chlorobenzene

21 January 2018

1 reference

https://api.crossref.org/works/10.1007%2FBF01946135

Biochemical studies of toxic agents. VII. The metabolism of naphthalene in animals of different species

21 January 2018

1 reference

https://api.crossref.org/works/10.1007%2FBF01946135

Metabolism of polycyclic compounds. 12. An acid-labile precursor of 1-naphthylmercapturic acid and naphthol: an N-acetyl-S-(1:2-dihydrohydroxy-naphthyl)-L-cysteine

21 January 2018

1 reference

https://api.crossref.org/works/10.1007%2FBF01946135

Metabolism of polycyclic compounds: Anthrylmercapturic acid

21 January 2018

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Metabolism of polycyclic compounds. 6. Conversion of phenanthrene into dihydroxydihydrophenanthrenes

21 January 2018

1 reference

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Metabolism of polycyclic compounds. 21. The metabolism of phenanthrene in rabbits and rats: dihydrodihydroxy compounds and related glucosiduronic acids

21 January 2018

1 reference

https://api.crossref.org/works/10.1007%2FBF01946135

Metabolism of polycyclic compounds. 20. The metabolism of phenanthrene in rabbits and rats: mercapturic acids and related compounds

21 January 2018

1 reference

https://api.crossref.org/works/10.1007%2FBF01946135

Metabolism of polycyclic compounds. 24. The metabolism of benz[α]anthracene

21 January 2018

1 reference

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The fate of diphenyl in the rat

21 January 2018

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12 December 2020

Carcnogenicity of epoxides, lactones, and peroxy compounds. VI. Structure and carcinogenic activity

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12 December 2020

The carcinogenic activities in mice of compounds related to 3-methylcholanthrene.

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12 December 2020

Enzymatic hydroxylation of benzopyrene and its relationship to cytotoxicity

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12 December 2020

Cis-1,2-dihydroxy-1,2-dihydronaphthalene: A bacterial metabolite from naphthalene

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12 December 2020

The role of arene oxide-oxepin systems in the metabolism of aromatic substrates. III. Formation of 1,2-naphthalene oxide from naphthalene by liver microsomes

1 reference

12 December 2020

Enzymic and nonenzymic hydroxylation and chlorination of p-deuteroanisole

1 reference

12 December 2020

Influence of "feeder cells" and inducers and inhibition of microsomal mixed-function oxidases on hydrocarbon-induced malignant transformation of cells derived from C3H mouse prostate

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12 December 2020

Epoxides as microsomal metabolites of polycyclic hydrocarbons

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12 December 2020

Metabolism of the acaricide chemical, fenazaflor(5,6-dichloro-1-phenoxycarbonyl-2-trifluoromethylbenzimidazole) in certain mammals, insects, and plants.

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12 December 2020

1,2-dihydro-1,2-dihydroxybenzene and several other substances in the metabolism of benzene

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12 December 2020

Bromobenzene-induced hepatic necrosis: species differences and protection by SKF 525-A

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12 December 2020

Oxygen activation by the iron(II)-2-mercaptobenzoic acid complex. A model for microsomal mixed function oxygenases

1 reference

12 December 2020

Arene oxides as intermediates in the oxidative metabolism of aromatic compounds. Isomerization of methyl-substituted arene oxides

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12 December 2020

Conversion of naphthalene to trans-naphthalene dihydrodiol: Evidence for the presence of a coupled aryl monooxygenase-epoxide hydrase system in hepatic microsomes

1 reference

12 December 2020

Intramolecular migration of deuterium and tritium during enzymic hydroxylation of p-deuteroacetanilide and p-tritioacetanilide

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12 December 2020

Isotope studies on the mechanism of action of adrenal tyrosine hydroxylase

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12 December 2020

Lack of hydroxylation-induced migration with 4-iodophenylalanine

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12 December 2020

Metabolic studies with deuterated phenobarbital

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12 December 2020

Reactivity of the K-region epoxides of some polycyclic hydrocarbons towards the nucleic acids and proteins of BHK 21 cells

1 reference

12 December 2020

Hepatic epoxide hydrase. Structure-activity relations for substrates and inhibitors

1 reference

12 December 2020

Hydroxylation of alkyl and halogen substituted anilines and acetanilides by microsomal hydroxylases

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12 December 2020

Quantitative studies on the hydroxylation-induced migration of deuterium and tritium during phenylalanine hydroxylation

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12 December 2020

Metabolism of polycyclic compounds. 5. Formation of 1:2-dihydroxy-1:2-dihydronaphthalenes.

1 reference

12 December 2020

Qualitative and quantitative studies on the metabolism of a series of aromatic hydrocarbons by rat-liver preparations

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12 December 2020

Metabolism of acetanilides and anisoles with rat liver microsomes

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12 December 2020

Aryl hydrocarbon hydroxylase, epoxide hydrase, and 7,12-dimethylbenz(a)anthracene-produced skin tumorigenesis in the mouse

1 reference

12 December 2020

The mechanism of enzymic formation of homogentisate from p-hydroxyphenylpyruvate

1 reference

12 December 2020

A simple radiometric assay for microsomal aryl hydroxylase activity

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12 December 2020

Low Carcinogenicity of the K-Region Epoxides of 7-Methylbenz(a)-anthracene and Benz (a) anthracene in the Mouse and Rat

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12 December 2020

Dimethylbenzanthracene Tumorigenesis and Aryl Hydrocarbon Hydroxylase in Mouse Skin: Inhibition by 7,8-Benzoflavone

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12 December 2020

Metabolism of Thiazole Acetic Acid Derivatives and the NIH Shift

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12 December 2020

Metabolism of iodobenzene

1 reference

12 December 2020

Hepatotoxic activity of retrorsine, senkirkine and hydroxysenkirkine in newborn rats, and the role of epoxides in carcinogenesis by pyrrolizidine alkaloids and aflatoxins

1 reference

12 December 2020

The conversion of phenanthrene 9, 10-oxide and dibenz[a, h]anthracene 5, 6-oxide into dihydrodiols by a rat-liver microsomal enzyme

1 reference

12 December 2020

Rearrangement of (1- 2 H)- and (2- 2 H)naphthalene 1,2-oxides to 1-naphthol. Mechanism of the NIH shift

1 reference

12 December 2020

N-hydroxy-2-acetylaminofluorene sulfotransferase: its probable role in carcinogenesis and in protein-(methion-S-yl) binding in rat liver

1 reference

12 December 2020

Substrate specificity of hepatic epoxide hydrase in microsomes and in a purified preparation: Evidence for homologous enzymes

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12 December 2020

Effect of superoxide generation and dismutation on hydroxylation reactions catalyzed by liver microsomal cytochrome P-450

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12 December 2020

Acetylation of the carcinogen N-hydroxy-2-acetylaminofluorene by acetyl Coenzyme A to form a reactive ester

1 reference

12 December 2020

Mixed functional oxygenations during the biosynthesis of cyclopenin and cyclopenol, benzodiazepine alkaloids of penicillium cyclopium westling. Incorporation of molecular oxygen and NIH-shift

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12 December 2020

Mutagenicity to mammalian cells of epoxides and other derivatives of polycyclic hydrocarbons

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12 December 2020

Labeling in vivo of rat liver proteins by tritium-labeled dimethylnitrosamine. Effect of prior treatment with 3-methylcholanthrene, phenobarbitone, dimethylformamide, diethyl-formamide, aminoacetonitrile, ethionine and carbon tetrachloride

1 reference

12 December 2020

Migration of substituents during hydroxylation of aromatic substrates (NIH shift). Oxidations with peroxytrifluoroacetic acid

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12 December 2020

A survey of molecular aspects of chemical carcinogenesis

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12 December 2020

Interactions of the K-region epoxides of phenanthrene and dibenz (a,h)anthracene with nucleic acids and histone

1 reference

12 December 2020

The intermediary metabolism of phenylalanine labeled with radioactive carbon

1 reference

12 December 2020

Decarboxylation of alpha-ketoglutarate coupled to collagen proline hydroxylase

1 reference

12 December 2020

The role of arene oxide-oxepin systems in the metabolism of aromatic substrates. II. Synthesis of 3,4-toluene-4-d oxide and subsequent "NIH shift" to 4-hydroxytoluene-3-H

1 reference

12 December 2020

Mutagenicity of epoxides of polycyclic hydrocarbons correlates with carcinogenicity of parent hydrocarbons.

1 reference

12 December 2020

[Microsomal oxidation of estradiol-17 beta. 2-hydroxylation and 1- respectively 4- thioether production with and without 17-hydroxy dehydrogenation]

1 reference

12 December 2020

Absence of isotope effects in the microsomal hydroxylation of acetanilide

1 reference

12 December 2020

Production of m-methyltyrosine and p-hydroxymethylphenylalanine from p-methylphenylalanine by phenylalanine hydroxylase

1 reference

12 December 2020

Ascorbic acid in aromatic hydroxylation. I. A model system for aromatic hydroxylation

1 reference

12 December 2020

Epoxy derivatives of aromatic polycyclic hydrocarbons. The preparation of benz[a]anthracene 8,9-oxide and 10,11-dihydrobenz[a]anthracene 8,9-oxide and their metabolism by rat liver preparations

1 reference

12 December 2020

Enzymic hydration of 8,9-indan oxide. Homoallylic addition of water

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12 December 2020

Migration of deuterium during aryl hydroxylation. 3. Effect of ortho- and meta- substituents

1 reference

12 December 2020

Incorporation of radioactive- -aminolevulinic acid into microsomal cytochrome P 450 : selective breakdown of the hemoprotein by allylisopropylacetamide and carbon tetrachloride

1 reference

12 December 2020

Epoxides of Carcinogenic Polycyclic Hydrocarbons Are Frameshift Mutagens

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12 December 2020

Possible mechanism of liver necrosis caused by aromatic organic compounds

1 reference

12 December 2020

Malignant transformation of cells derived from mouse prostate by epoxides and other derivatives of polycyclic hydrocarbons

1 reference

12 December 2020

A RAPID AND SIMPLE RADIOASSAY FOR TYROSINE HYDROXYLASE ACTIVITY

1 reference

12 December 2020

Rapid analysis of tryptophan hydroxylase in rat tissue using 5-3H-tryptophan

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12 December 2020

Incorporation of oxygen-18 into benzene by Pseudomonas putida

1 reference

12 December 2020

FUNGAL DETOXICATION. VII. METABOLISM OF 2,4-DICHLOROPHENOXYACETIC AND 4-CHLORO-2-METHYLPHENOXYACETIC ACIDS BY ASPERGILLUS NIGER

1 reference

12 December 2020

Ascorbic acid in aromatic hydroxylation. II. Products formed by reaction of substrates with ascorbic acid, ferrous ion, and oxygen

1 reference

12 December 2020

Aerobic aromatic hydroxylation catalyzed by horseradish peroxidase: Absence of NIH shift

1 reference

12 December 2020

[Non-enzymatic hydroxylation of phenylalanine to tyrosine using tetrahydrogenated pterines]

1 reference

12 December 2020

Arene Oxides as Intermediates in the Metabolism of Aromatic Substrates: Alkyl and Oxygen Migrations during Isomerization of Alkylated Arene Oxides

1 reference

12 December 2020

An epoxide is an intermediate in the microsomal metabolism of the chemical carcinogen, dibenz(a,h)anthracene.

1 reference

12 December 2020

Tyrosine hydroxylation catalyzed by mammalian tyrosinase: An improved method of assay

1 reference

12 December 2020

Aromatic ring hydroxylation of estradiol in man

1 reference

12 December 2020

Migration of deuterium during hydroxylation of aromatic substrates by liver microsomes: I. Influence of ring substituents

1 reference

12 December 2020

Oxotransition metal oxidants as mimics for the action of mixed-function oxygenases. "NIH shift" with chromyl reagents

1 reference

12 December 2020

Retention of deuterium in p-tyrosine formed enzymatically from p-deuterophenylalanine

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12 December 2020

7-Hydroxylation of thymine in a neurospora strain coupled to oxidative decarboxylation of 2-ketoglutarate

1 reference

12 December 2020

Hydroxylation-induced migration and retention of tritium on conversion of [4-3H] cinnamic acid to 4-hydroxycinnamic acid by an enzyme from pea seedlings

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12 December 2020

In vitro transformation of rodent cells by K-region derivatives of polycyclic hydrocarbons

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12 December 2020

The Mixed Function Oxygenation of 4-Halogenoacetanilides in Rat Liver Microsomes and Model Systems

1 reference

12 December 2020

Hydroxylation-induced migration: the NIH shift. Recent experiments reveal an unexpected and general result of enzymatic hydroxylation of aromatic compounds

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12 December 2020

Pharmacologic and metabolic studies with deuterated zoxazolamine

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12 December 2020

Selective Exchange of Nuclear Protons in Hydroxyindoles

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12 December 2020

Enzymic aromatization of 3,5-cyclohexadiene-1,2-diol

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12 December 2020

[Hydroxylation and defluorination of fluorinated derivatives of aniline]

1 reference

12 December 2020

Biosynthesis and metabolism of hydroxyphenylacetic acids in higher plants

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12 December 2020

Significance and rearrangements of quinol models of tyrosine metabolites

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12 December 2020

The metabolism of C14-ICI 54,450 (myalex) in various species--an in vivo NIH shift

1 reference

12 December 2020

A radiometric assay for hepatic epoxide hydrase activity with [7-3H] styrene oxide

1 reference

12 December 2020

A simple radioisotope assay for phenylalanine hydroxylase

1 reference

12 December 2020

Rapid loss of cytochrome P-450 and haem caused in the liver microsomes by the porphyrogenic agent 2-allyl-2-isopropylacetamide

1 reference

12 December 2020

C-2 Hydroxylation of 2-Deuterioestrogen in the Rat. Lack of “NIH Shift”

1 reference

12 December 2020

[Conversion of (4-3H)L-phenylalanine into (4-3H)pyrocatechol and (3-3H)hydroquinone in leaves of Bergenia crassifolia]

1 reference

12 December 2020

The production of meta-tritiotyrosine from p-tritiophenylalanine by phenylalanine hydroxylase

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12 December 2020

Biosynthetic studies on mescaline and related cactus alkaloids

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12 December 2020

FURTHER STUDIES ON PHENYLPYRUVATE OXIDASE. OCCURRENCE OF SIDE CHAIN REARRANGEMENT AND COMPARISON WITH P-HYDROXYPHENYLPYRUVATE OXIDASE

1 reference

12 December 2020

The migration of deuterium during aryl hydroxylation. II. Effect of induction of microsomal hydroxylases with phenobarbital or polycyclic aromatic hydrocarbons

1 reference

12 December 2020

A new metabolite of 5,5-diphenylhydantoin (Dilantin)

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12 December 2020

Identifiers

DOI

10.1007/BF01946135

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1 June 2018

PubMed ID

4117670

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1 June 2018