(Q37593926)

English

Tumorigenicity of the optical enantiomers of the diastereomeric benzo[a]pyrene 7,8-diol-9,10-epoxides in newborn mice: exceptional activity of (+)-7beta,8alpha-dihydroxy-9alpha,10alpha-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene

scientific article published on November 1, 1978

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scholarly article

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Europe PubMed Central

21 August 2017

Tumorigenicity of the optical enantiomers of the diastereomeric benzo[a]pyrene 7,8-diol-9,10-epoxides in newborn mice: exceptional activity of (+)-7beta,8alpha-dihydroxy-9alpha,10alpha-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene (English)

1 reference

Europe PubMed Central

21 August 2017

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Europe PubMed Central

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20 February 2023

author name string

M. K. Buening

1

1 reference

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20 February 2023

P. G. Wislocki

2

1 reference

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20 February 2023

W. Levin

3

1 reference

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20 February 2023

H. Yagi

4

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20 February 2023

D. R. Thakker

5

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20 February 2023

H. Akagi

6

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20 February 2023

M. Koreeda

7

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20 February 2023

D. M. Jerina

8

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20 February 2023

A. H. Conney

9

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20 February 2023

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publication date

1 November 1978

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Europe PubMed Central

21 August 2017

full work available at URL

https://europepmc.org/articles/PMC392962

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Europe PubMed Central

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Europe PubMed Central

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20 February 2023

https://europepmc.org/articles/PMC392962?pdf=render

Portable Document Format

online access status

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Europe PubMed Central

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Europe PubMed Central

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20 February 2023

https://pnas.org/doi/pdf/10.1073/pnas.75.11.5358

1 reference

10.1073/PNAS.75.11.5358

https://api.crossref.org/works/10.1073/PNAS.75.11.5358

20 February 2023

Proceedings of the National Academy of Sciences of the United States of America

1 reference

Europe PubMed Central

21 August 2017

75

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Europe PubMed Central

21 August 2017

11

1 reference

Europe PubMed Central

21 August 2017

5358-5361

1 reference

Europe PubMed Central

21 August 2017

Effects of Inducers and Epoxide Hydrase on the Metabolism of Benzo[ a ]pyrene by Liver Microsomes and a Reconstituted System: Analysis by High Pressure Liquid Chromatography

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=392962

23 August 2017

Lung Tumors in Mice: Application to Carcinogenesis Bioassay

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=392962

23 August 2017

(+/-)-trans-7,8-dihydroxy-7,8-dihydrobenzo (a)pyrene: a potent skin carcinogen when applied topically to mice

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=392962

23 August 2017

Metabolism of benzo[a]pyrene: conversion of (+/-)-trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene to highly mutagenic 7,8-diol-9,10-epoxides

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=392962

23 August 2017

(+/-)-7alpha,8beta-dihydroxy-9beta,10beta-epoxy-7,8,9,10-tetrahydrobenzo(a)-pyrene is an intermediate in the metabolism and binding to DNA of benzo(a)pyrene

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=392962

23 August 2017

Enzymatic conversion of benzo(a)pyrene leading predominantly to the diol-epoxide r-7,t-8-dihydroxy-t-9,10-oxy-7,8,9,10-tetrahydrobenzo(a)pyrene through a single enantiomer of r-7, t-8-dihydroxy-7,8-dihydrobenzo(a)pyrene

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=392962

23 August 2017

Identification of mutagenic metabolites of benzo(a)pyrene in mammalian cells

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=392962

23 August 2017

Comparison of the tumor-initiating activities of benzo(a)pyrene arene oxides and diol-epoxides

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=392962

23 August 2017

Carcinogenicity of benzo-ring derivatives of benzo(a)pyrene on mouse skin

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=392962

23 August 2017

A bacteriophage system for screening and study of biologically active polycyclic aromatic hydrocarbons and related compounds

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=392962

23 August 2017

Modification of DNA by the benzo[a]pyrene metabolite diol-epoxide r-7,t-8-dihydroxy-t-9,10-oxy-7,8,9,10-tetrahydrobenzo[a]pyrene

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=392962

23 August 2017

Changes of mechanisms and product distributions in the hydrolysis of benzo[a]pyrene-7,8-diol 9,10,-epoxide metabolites induced by changes in pH

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=392962

6 September 2017

A critical review of experiments in chemical carcinogensis using newborn animals

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=392962

14 September 2017

Epoxides in polycyclic aromatic hydrocarbon metabolism and carcinogenesis.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=392962

14 September 2017

Differences in mutagenicity of the optical enantiomers of the diastereomeric benzo[a]pyrene 7,8-diol-9,10-epoxides

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=392962

28 September 2017

In vitro reaction of radioactive 7beta, 8alpha, --dihydroxy--9alpha, 10alpha-epoxy--7,8,9,10--tetrahydrobenzo (A) pyrene and 7beta,8alpha--dihydroxy--9beta, 10beta--epoxy--7,8,9,10--tetrahydrobenzo (A) pyrene with DNA.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=392962

28 September 2017

Metabolic conversion of benzo[a]pyrene by Syrian hamster liver microsomes and binding of metabolites to deoxyribonucleic acid

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=392962

25 June 2018

Synthesis of (+-)-7.beta.,8.alpha.-dihydroxy-9.beta.,10.beta.-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene, a potential metabolite of the carcinogen benzo[a]pyrene with stereochemistry related to the antileukemic triptolides

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=392962

25 June 2018

Microsomal mixed-function oxidases and epoxide hydratase convert benzo(a)pyrene stereospecifically to optically active dihydroxydihydrobenzo(a)pyrenes

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=392962

25 June 2018

Absolute sterochemistry of the highly mutagenic 7,8-diol 9,10-epoxides derived from the potent carcinogen trans-7,8-dihydroxy-7,8-dihydrobenzol[a]pyrene

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=392962

25 June 2018

Metabolism of benzo[a]pyrene. VI. Stereoselective metabolism of benzo[a]pyrene and benzo[a]pyrene 7,8-dihydrodiol to diol epoxides

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=392962

25 June 2018

Benzo[a]pyrene 7,8-dihydrodiol is more carcinogenic than benzo[a]pyrene in newborn mice

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=392962

25 June 2018

Epidermal hyperplasia after topical application of benzo (a) pyrene, benzo (a) pyrene diol epoxides, and other metabolites

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=392962

25 June 2018

Synthesis and reactions of the highly mutagenic 7,8-diol 9,10-epoxides of the carcinogen benzo[a]pyrene

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=392962

25 June 2018

Absolute configuration of a ribonucleic acid adduct formed in vivo by metabolism of benzo[a]pyrene

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=392962

25 June 2018

Mutagenicity and cytotoxicity of benzo(a)pyrene benzo-ring epoxides

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=392962

25 June 2018

High mutagenicity and toxicity of a diol epoxide derived from benzo(a)pyrene

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=392962

25 June 2018

Tumorigenicity studies with diol-epoxides of benzo(a)pyrene which indicate that (+/-)-trans-7beta,8alpha-dihydroxy-9alpha,10alpha-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene is an ultimate carcinogen in newborn mice

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=392962

25 June 2018

Skin tumor initiating ability of benzo(a)pyrene 4,5- 7,5- and 7,8-diol-9,10-epoxides and 7,8-diol

1 reference

https://pubmed.ncbi.nlm.nih.gov/281685

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Benzo(a)pyrene diol epoxides as intermediates in nucleic acid binding in vitro and in vivo

1 reference

https://pubmed.ncbi.nlm.nih.gov/281685

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Metabolic activation of benzo(a)pyrene proceeds by a diol-epoxide

1 reference

https://pubmed.ncbi.nlm.nih.gov/281685

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

High-pressure liquid chromatographic analysis of benzo(alpha)pyrene metabolism and covalent binding and the mechanism of action of 7,8-benzoflavone and 1,2-epoxy-3,3,3-trichloropropane

1 reference

https://pubmed.ncbi.nlm.nih.gov/281685

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Exceptional mutagenicity of a benzo[a]pyrene diol epoxide in cultured mammalian cells

1 reference

https://pubmed.ncbi.nlm.nih.gov/281685

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

High-pressure liquid chromatographic separation of 10 benzo(a)pyrene phenols and the identification of 1-phenol and 7-phenol as new metabolites

1 reference

https://pubmed.ncbi.nlm.nih.gov/281685

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Substrate-induced synthesis and other properties of benzpyrene hydroxylase in rat liver

1 reference

https://pubmed.ncbi.nlm.nih.gov/281685

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Binding of Nenzo[ a ]pyrene 7,8-Diol-9,10-Epoxides to DNA, RNA, and Protein of Mouse Skin Occurs with High Stereoselectivity

1 reference

https://pubmed.ncbi.nlm.nih.gov/281685

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Structures of benzo(a)pyrene–nucleic acid adducts formed in human and bovine bronchial explants

1 reference

https://pubmed.ncbi.nlm.nih.gov/281685

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

The nature of benzo(a)pyrene-DNA adducts formed in hamster embryo cells depends on the length of time of exposure to benzo(a)pyrene

1 reference

https://pubmed.ncbi.nlm.nih.gov/281685

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Identifiers

10.1073/PNAS.75.11.5358

1 reference

Europe PubMed Central

21 August 2017

1978PNAS...75.5358B

0 references

1 reference

Europe PubMed Central

21 August 2017

1 reference

Europe PubMed Central

21 August 2017

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