(Q34311334)

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Potent Mutagenicity of 3-Methylindole Requires Pulmonary Cytochrome P450-Mediated Bioactivation: A Comparison to the Prototype Cigarette Smoke Mutagens B(a)P and NNK

scientific article published on August 26, 2010

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1 August 2017

Potent Mutagenicity of 3-Methylindole Requires Pulmonary Cytochrome P450-Mediated Bioactivation: A Comparison to the Prototype Cigarette Smoke Mutagens B(a)P and NNK (English)

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10.1021/TX100147Z

https://api.crossref.org/works/10.1021/TX100147Z

2 July 2024

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Garold S Yost

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1 August 2017

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Jaime D'Agostino

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1 August 2017

Xinxin Ding

4

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1 August 2017

Jessica M. Weems

1

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Europe PubMed Central

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https://www.ebi.ac.uk/europepmc/webservices/rest/search?resulttype=core&format=json&query=SRC%3AMED%20AND%20EXT_ID%3A20795680

2 July 2024

John G. Lamb

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26 August 2010

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2 July 2024

https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/20795680/pdf/?tool=EBI

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https://www.ebi.ac.uk/europepmc/webservices/rest/search?resulttype=core&format=json&query=SRC%3AMED%20AND%20EXT_ID%3A20795680

2 July 2024

https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/20795680/?tool=EBI

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https://www.ebi.ac.uk/europepmc/webservices/rest/search?resulttype=core&format=json&query=SRC%3AMED%20AND%20EXT_ID%3A20795680

2 July 2024

https://europepmc.org/articles/PMC2981624

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Europe PubMed Central

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https://www.ebi.ac.uk/europepmc/webservices/rest/search?resulttype=core&format=json&query=SRC%3AMED%20AND%20EXT_ID%3A20795680

2 July 2024

https://europepmc.org/articles/PMC2981624?pdf=render

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Europe PubMed Central

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Europe PubMed Central

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https://www.ebi.ac.uk/europepmc/webservices/rest/search?resulttype=core&format=json&query=SRC%3AMED%20AND%20EXT_ID%3A20795680

2 July 2024

https://doi.org/10.1021/tx100147z

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Europe PubMed Central

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https://www.ebi.ac.uk/europepmc/webservices/rest/search?resulttype=core&format=json&query=SRC%3AMED%20AND%20EXT_ID%3A20795680

2 July 2024

https://pubs.acs.org/doi/pdf/10.1021/tx100147z

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10.1021/TX100147Z

https://api.crossref.org/works/10.1021/TX100147Z

2 July 2024

Chemical Research in Toxicology

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Europe PubMed Central

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1 August 2017

23

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Europe PubMed Central

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1 August 2017

11

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Europe PubMed Central

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1 August 2017

1682-1690

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Europe PubMed Central

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1 August 2017

3-Methylindole metabolites induce lung CYP1A1 and CYP2F1 enzymes by AhR and non-AhR mechanisms, respectively

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2981624

6 July 2018

3-Methylindole is mutagenic and a possible pulmonary carcinogen

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2981624

6 July 2018

The pneumotoxin 3-methylindole is a substrate and a mechanism-based inactivator of CYP2A13, a human cytochrome P450 enzyme preferentially expressed in the respiratory tract

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2981624

6 July 2018

Single mutations change CYP2F3 from a dehydrogenase of 3-methylindole to an oxygenase

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2981624

6 July 2018

Effects of 8-methoxypsoralen on cytochrome P450 2A13.

1 reference

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6 July 2018

The case of the disappearing nitrosamines: a potentially global phenomenon

1 reference

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6 July 2018

Characterization of the human lung CYP2F1 gene and identification of a novel lung-specific binding motif

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2981624

6 July 2018

3-methylindole-induced toxicity to human bronchial epithelial cell lines

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2981624

6 July 2018

CYP1A1 and GSTM1 genotypes affect benzo[a]pyrene DNA adducts in smokers' lung: comparison with aromatic/hydrophobic adduct formation.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2981624

6 July 2018

Smoking molecular damage in bronchial epithelium

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2981624

6 July 2018

Human extrahepatic cytochromes P450: function in xenobiotic metabolism and tissue-selective chemical toxicity in the respiratory and gastrointestinal tracts

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2981624

6 July 2018

The less harmful cigarette: a controversial issue. a tribute to Ernst L. Wynder

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2981624

6 July 2018

Human cytochrome P450 CYP2A13: predominant expression in the respiratory tract and its high efficiency metabolic activation of a tobacco-specific carcinogen, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2981624

6 July 2018

Tobacco smoke carcinogens and lung cancer

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2981624

6 July 2018

Specific dehydrogenation of 3-methylindole and epoxidation of naphthalene by recombinant human CYP2F1 expressed in lymphoblastoid cells

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2981624

6 July 2018

Mechanistic studies on the cytochrome P450-catalyzed dehydrogenation of 3-methylindole.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2981624

6 July 2018

Metabolism of 3-methylindole by vaccinia-expressed P450 enzymes: correlation of 3-methyleneindolenine formation and protein-binding.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2981624

6 July 2018

Metabolism and bioactivation of 3-methylindole by Clara cells, alveolar macrophages, and subcellular fractions from rabbit lungs.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2981624

6 July 2018

Decreased pneumotoxicity of deuterated 3-methylindole: bioactivation requires methyl C-H bond breakage

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2981624

6 July 2018

Mechanisms of 3-methylindole pneumotoxicity

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2981624

6 July 2018

Detection of carcinogens as mutagens in the Salmonella/microsome test: assay of 300 chemicals

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2981624

6 July 2018

Detection of carcinogens as mutagens: bacterial tester strains with R factor plasmids

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2981624

6 July 2018

The genotoxicity of mainstream and sidestream marijuana and tobacco smoke condensates

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2981624

28 October 2018

Genotoxicity of 10 cigarette smoke condensates in four test systems: comparisons between assays and condensates

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2981624

28 October 2018

Mechanism-based inactivation of lung-selective cytochrome P450 CYP2F enzymes

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2981624

28 October 2018

Metabolism and bioactivation of 3-methylindole by human liver microsomes.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2981624

28 October 2018

CYP2A13 in human respiratory tissues and lung cancers: an immunohistochemical study with a new peptide-specific antibody.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2981624

28 October 2018

Mechanisms of chemopreventive effects of 8-methoxypsoralen against 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone-induced mouse lung adenomas

1 reference

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28 October 2018

Pretreatment with 8-methoxypsoralen, a potent human CYP2A6 inhibitor, strongly inhibits lung tumorigenesis induced by 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in female A/J mice.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2981624

28 October 2018

IARC carcinogens reported in cigarette mainstream smoke and their calculated log P values

1 reference

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28 October 2018

Genotoxicity of naturally occurring indole compounds: correlation between covalent DNA binding and other genotoxicity tests

1 reference

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28 October 2018

Detection and characterization of DNA adducts of 3-methylindole.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2981624

28 October 2018

Selective dehydrogenation/oxygenation of 3-methylindole by cytochrome p450 enzymes

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2981624

28 October 2018

Bacterial mutagenicity of some tobacco aromatic nitrogen bases and their mixtures

1 reference

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28 October 2018

Thioether adducts of a new imine reactive intermediate of the pneumotoxin 3-methylindole.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2981624

28 October 2018

Evidence supporting the formation of 2,3-epoxy-3-methylindoline: a reactive intermediate of the pneumotoxin 3-methylindole

1 reference

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28 October 2018

Purification and characterization of heterologously expressed mouse CYP2A5 and CYP2G1: role in metabolic activation of acetaminophen and 2,6-dichlorobenzonitrile in mouse olfactory mucosal microsomes

1 reference

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28 October 2018

Structure of the glutathione adduct of activated 3-methylindole indicates that an imine methide is the electrophilic intermediate

1 reference

https://pubmed.ncbi.nlm.nih.gov/20795680

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Isolation of a mercapturate adduct produced subsequent to glutathione conjugation of bioactivated 3-methylindole

1 reference

https://pubmed.ncbi.nlm.nih.gov/20795680

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Carcinogens in tobacco smoke: benzo[a]pyrene from Canadian cigarettes and cigarette tobacco

1 reference

https://pubmed.ncbi.nlm.nih.gov/20795680

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Identification of a cysteinyl adduct of oxidized 3-methylindole from goat lung and human liver microsomal proteins

1 reference

https://pubmed.ncbi.nlm.nih.gov/20795680

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Activation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in human lung microsomes by cytochromes P450, lipoxygenase, and hydroperoxides

1 reference

https://pubmed.ncbi.nlm.nih.gov/20795680

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

CYP2A13: variable expression and role in human lung microsomal metabolic activation of the tobacco-specific carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone

1 reference

https://pubmed.ncbi.nlm.nih.gov/20795680

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Profiling gene expression of whole cytochrome P450 superfamily in human bronchial and peripheral lung tissues: Differential expression in non-small cell lung cancers

1 reference

https://pubmed.ncbi.nlm.nih.gov/20795680

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Drug Metabolism and Disposition

11

29

950

author name string

Lanza D. L.

publication date

2001

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10.1021/TX100147Z

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2 July 2024

Drug Metabolism and Disposition

19

13

690

author name string

Nocerini M. R.

publication date

1985

1 reference

10.1021/TX100147Z

https://api.crossref.org/works/10.1021/TX100147Z

2 July 2024

Cancer Research

26

60

5074

author name string

Su T.

publication date

2000

1 reference

10.1021/TX100147Z

https://api.crossref.org/works/10.1021/TX100147Z

2 July 2024

Journal of Pharmacology and Experimental Therapeutics

27

285

1287

author name string

Gu J.

publication date

1998

1 reference

10.1021/TX100147Z

https://api.crossref.org/works/10.1021/TX100147Z

2 July 2024

Drug Metabolism and Disposition

34

27

798

author name string

Lanza D. L.

publication date

1999

1 reference

10.1021/TX100147Z

https://api.crossref.org/works/10.1021/TX100147Z

2 July 2024

Journal of Pharmacology and Experimental Therapeutics

43

276

21

author name string

Thornton-Manning J.

publication date

1996

1 reference

10.1021/TX100147Z

https://api.crossref.org/works/10.1021/TX100147Z

2 July 2024

Cancer Research

44

55

5566

author name string

Smith T. J.

publication date

1995

1 reference

10.1021/TX100147Z

https://api.crossref.org/works/10.1021/TX100147Z

2 July 2024

Cancer Research

46

63

7581

author name string

Takeuchi H.

publication date

2003

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10.1021/TX100147Z

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2 July 2024

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10.1021/TX100147Z

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Europe PubMed Central

PubMed publication ID

1 August 2017

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Europe PubMed Central

PubMed publication ID

1 August 2017

PubMed publication ID

1 reference

Europe PubMed Central

PubMed publication ID

1 August 2017

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