Fjord-region benzo[g]chrysene-11,12-dihydrodiol and benzo[c]phenanthrene-3,4-dihydrodiol as substrates for rat liver dihydrodiol dehydrogenase (AKR1C9): structural basis for stereochemical preference (Q28757855)

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scientific article (publication date: March 2008)

Language	Label	Description	Also known as
English	Fjord-region benzo[g]chrysene-11,12-dihydrodiol and benzo[c]phenanthrene-3,4-dihydrodiol as substrates for rat liver dihydrodiol dehydrogenase (AKR1C9): structural basis for stereochemical preference	scientific article (publication date: March 2008)

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scholarly article

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Fjord-region benzo[g]chrysene-11,12-dihydrodiol and benzo[c]phenanthrene-3,4-dihydrodiol as substrates for rat liver dihydrodiol dehydrogenase (AKR1C9): structural basis for stereochemical preference (English)

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author name string

Carol A Shultz

1

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Nisha T Palackal

2

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Dipti Mangal

3

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Ronald G Harvey

4

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Ian A Blair

5

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Trevor M Penning

6

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language of work or name

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publication date

March 2008

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Chemical Research in Toxicology

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21

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3

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668-77

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Crystal structure of human type III 3alpha-hydroxysteroid dehydrogenase/bile acid binding protein complexed with NADP(+) and ursodeoxycholate

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Tobacco smoke carcinogens and lung cancer

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16 March 2017

Steroid recognition and regulation of hormone action: crystal structure of testosterone and NADP+ bound to 3 alpha-hydroxysteroid/dihydrodiol dehydrogenase

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16 March 2017

Analysis of automobile exhaust condensates

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Dibenzanthracenes and benzochrysenes elicit both genotoxic and nongenotoxic events in rat liver 'stem-like' cells

1 reference

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20 June 2018

Benzo[a]pyrene-7,8-quinone-3'-mononucleotide adduct standards for 32P postlabeling analyses: detection of benzo[a]pyrene-7,8-quinone-calf thymus DNA adducts.

1 reference

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20 June 2018

Polycyclic aromatic hydrocarbon (PAH) o-quinones produced by the aldo-keto-reductases (AKRs) generate abasic sites, oxidized pyrimidines, and 8-oxo-dGuo via reactive oxygen species

1 reference

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20 June 2018

Competing roles of aldo-keto reductase 1A1 and cytochrome P4501B1 in benzo[a]pyrene-7,8-diol activation in human bronchoalveolar H358 cells: role of AKRs in P4501B1 induction

1 reference

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20 June 2018

Formation of 8-oxo-7,8-dihydro-2'-deoxyguanosine (8-oxo-dGuo) by PAH o-quinones: involvement of reactive oxygen species and copper(II)/copper(I) redox cycling

1 reference

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20 June 2018

Identification and characterization of novel stable deoxyguanosine and deoxyadenosine adducts of benzo[a]pyrene-7,8-quinone from reactions at physiological pH.

1 reference

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20 June 2018

Activation of polycyclic aromatic hydrocarbon trans-dihydrodiol proximate carcinogens by human aldo-keto reductase (AKR1C) enzymes and their functional overexpression in human lung carcinoma (A549) cells

1 reference

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20 June 2018

Metabolic activation of benzo[g]chrysene in the human mammary carcinoma cell line MCF-7.

1 reference

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20 June 2018

Benzo[alpha]pyrene metabolism, activation and carcinogenesis: role and regulation of mixed-function oxidases and related enzymes

1 reference

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Induction of microsomal enzymes by foreign chemicals and carcinogenesis by polycyclic aromatic hydrocarbons: G. H. A. Clowes Memorial Lecture.

1 reference

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20 June 2018

Use of newborn and infant animals in carcinogenicity testing

1 reference

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20 June 2018

Carcinogenesis in AKR mice injected at birth with benzo(a)pyrene and dimethylnitrosamine.

1 reference

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20 June 2018

Spectroscopic identification of ortho-quinones as the products of polycyclic aromatic trans-dihydrodiol oxidation catalyzed by dihydrodiol dehydrogenase. A potential route of proximate carcinogen metabolism.

1 reference

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20 June 2018

Non-K-region o-quinones as enzyme-generated inactivators of dihydrodiol dehydrogenase

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2440589

20 June 2018

Regulation of drug metabolism in man by environmental chemicals and diet.

1 reference

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20 June 2018

Molecular docking simulations of steroid substrates into human cytosolic hydroxysteroid dehydrogenases (AKR1C1 and AKR1C2): insights into positional and stereochemical preferences

1 reference

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27 November 2018

Role of cytochrome p4501 family members in the metabolic activation of polycyclic aromatic hydrocarbons in mouse epidermis

1 reference

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Alanine scanning mutagenesis of the testosterone binding site of rat 3 alpha-hydroxysteroid dehydrogenase demonstrates contact residues influence the rate-determining step

1 reference

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Synthesis of the o-quinones and other oxidized metabolites of polycyclic aromatic hydrocarbons implicated in carcinogenesis

1 reference

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27 November 2018

Steroid-binding site residues dictate optimal substrate positioning in rat 3alpha-hydroxysteroid dehydrogenase (3alpha-HSD or AKR1C9).

1 reference

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27 November 2018

Reactive oxygen species generated by PAH o-quinones cause change-in-function mutations in p53.

1 reference

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27 November 2018

The ubiquitous aldehyde reductase (AKR1A1) oxidizes proximate carcinogen trans-dihydrodiols to o-quinones: potential role in polycyclic aromatic hydrocarbon activation

1 reference

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27 November 2018

Stable expression of rat dihydrodiol dehydrogenase (AKR1C9) in human breast MCF-7 cells results in the formation of PAH-o-quinones and enzyme mediated cell death

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2440589

27 November 2018

Dihydrodiol dehydrogenases and polycyclic aromatic hydrocarbon activation: generation of reactive and redox active o-quinones.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2440589

27 November 2018

Covalent DNA adducts formed in mouse epidermis by benzo[g]chrysene.

1 reference

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27 November 2018

Reactivity of benzo[a]pyrene-7,8-dione with DNA. Evidence for the formation of deoxyguanosine adducts.

1 reference

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27 November 2018

Tumorigenicity in newborn mice of fjord region and other sterically hindered diol epoxides of benzo[g]chrysene, dibenzo[a,l]pyrene (dibenzo[def,p]chrysene), 4H-cyclopenta[def]chrysene and fluoranthene.

1 reference

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27 November 2018

Regio- and stereoselectivity of hepatic cytochrome P-450 toward polycyclic aromatic hydrocarbon substrates.

1 reference

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27 November 2018

The arginine 276 anchor for NADP(H) dictates fluorescence kinetic transients in 3 alpha-hydroxysteroid dehydrogenase, a representative aldo-keto reductase

1 reference

https://pubmed.ncbi.nlm.nih.gov/18251511

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Carcinogenicity of polycyclic aromatic hydrocarbons.

1 reference

https://pubmed.ncbi.nlm.nih.gov/18251511

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Aldo-keto reductase- and cytochrome P450-dependent formation of benzo[a]pyrene-derived DNA adducts in human bronchoalveolar cells

1 reference

https://pubmed.ncbi.nlm.nih.gov/18251511

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/18251511

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Sex differences in indomethacin-sensitive 3 alpha-hydroxysteroid dehydrogenase of rat liver cytosol

1 reference

https://pubmed.ncbi.nlm.nih.gov/18251511

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Stereoselective metabolism of the (+)-(S,S)- and (-)-(R,R)-enantiomers of trans-3,4-dihydroxy-3,4-dihydrobenzo[c]-phenanthrene by rat and mouse liver microsomes and by a purified and reconstituted cytochrome P-450 system

1 reference

https://pubmed.ncbi.nlm.nih.gov/18251511

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Generation of Reactive Oxygen Species during the Enzymatic Oxidation of Polycyclic Aromatic Hydrocarbontrans-Dihydrodiols Catalyzed by Dihydrodiol Dehydrogenase

1 reference

https://pubmed.ncbi.nlm.nih.gov/18251511

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

DNA strand scission by polycyclic aromatic hydrocarbon o-quinones: role of reactive oxygen species, Cu(II)/Cu(I) redox cycling, and o-semiquinone anion radicals,

1 reference

https://pubmed.ncbi.nlm.nih.gov/18251511

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Identifiers

10.1021/TX7003695

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