DNA Adduct Formation from Metabolic 5'-Hydroxylation of the Tobacco-Specific Carcinogen N'-Nitrosonornicotine in Human Enzyme Systems and in Rats (Q34510694)

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English	DNA Adduct Formation from Metabolic 5'-Hydroxylation of the Tobacco-Specific Carcinogen N'-Nitrosonornicotine in Human Enzyme Systems and in Rats	scientific article

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scholarly article

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Europe PubMed Central

PubMed publication ID

2 August 2017

DNA Adduct Formation from Metabolic 5'-Hydroxylation of the Tobacco-Specific Carcinogen N'-Nitrosonornicotine in Human Enzyme Systems and in Rats (English)

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Europe PubMed Central

PubMed publication ID

2 August 2017

1

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Europe PubMed Central

PMC publication ID

https://www.ebi.ac.uk/europepmc/webservices/rest/search?query=EXT_ID:26808005%20AND%20SRC:MED&resulttype=core&format=json

11 June 2020

author name string

Pramod Upadhyaya

2

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https://www.ebi.ac.uk/europepmc/webservices/rest/search?query=EXT_ID:26808005%20AND%20SRC:MED&resulttype=core&format=json

11 June 2020

Jing Yang

3

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Europe PubMed Central

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https://www.ebi.ac.uk/europepmc/webservices/rest/search?query=EXT_ID:26808005%20AND%20SRC:MED&resulttype=core&format=json

11 June 2020

Stephen S Hecht

4

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https://www.ebi.ac.uk/europepmc/webservices/rest/search?query=EXT_ID:26808005%20AND%20SRC:MED&resulttype=core&format=json

11 June 2020

publication date

25 January 2016

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2 August 2017

Chemical Research in Toxicology

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https://www.ebi.ac.uk/europepmc/webservices/rest/search?query=EXT_ID:26808005%20AND%20SRC:MED&resulttype=core&format=json

11 June 2020

29

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https://www.ebi.ac.uk/europepmc/webservices/rest/search?query=EXT_ID:26808005%20AND%20SRC:MED&resulttype=core&format=json

11 June 2020

3

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https://www.ebi.ac.uk/europepmc/webservices/rest/search?query=EXT_ID:26808005%20AND%20SRC:MED&resulttype=core&format=json

11 June 2020

380-389

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PMC publication ID

https://www.ebi.ac.uk/europepmc/webservices/rest/search?query=EXT_ID:26808005%20AND%20SRC:MED&resulttype=core&format=json

11 June 2020

Entrapment of a Histone Tail by a DNA Lesion in a Nucleosome Suggests the Lesion Impacts Epigenetic Marking: A Molecular Dynamics Study

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4805523

7 July 2018

Analysis of O(6)-[4-(3-Pyridyl)-4-oxobut-1-yl]-2'-deoxyguanosine and Other DNA Adducts in Rats Treated with Enantiomeric or Racemic N'-Nitrosonornicotine.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4805523

7 July 2018

Analysis of the benzene oxide-DNA adduct 7-phenylguanine by liquid chromatography-nanoelectrospray ionization-high resolution tandem mass spectrometry-parallel reaction monitoring: application to DNA from exposed mice and humans

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4805523

7 July 2018

Quantitation of pyridyloxobutyl-DNA adducts in tissues of rats treated chronically with (R)- or (S)-N'-nitrosonornicotine (NNN) in a carcinogenicity study

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4805523

7 July 2018

(S)-N'-Nitrosonornicotine, a constituent of smokeless tobacco, is a powerful oral cavity carcinogen in rats

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4805523

7 July 2018

Levels of (S)-N'-nitrosonornicotine in U.S. tobacco products.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4805523

7 July 2018

Personal habits and indoor combustions. Volume 100 E. A review of human carcinogens

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4805523

7 July 2018

Quantitation of pyridyloxobutyl DNA adducts in nasal and oral mucosa of rats treated chronically with enantiomers of N'-nitrosonornicotine.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4805523

7 July 2018

Identification of adducts formed in the reactions of 5'-acetoxy-N'-nitrosonornicotine with deoxyadenosine, thymidine, and DNA.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4805523

7 July 2018

Smokeless tobacco and some tobacco-specific N-nitrosamines

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4805523

7 July 2018

Analysis of pyridyloxobutyl DNA adducts in F344 rats chronically treated with (R)- and (S)-N'-nitrosonornicotine

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4805523

7 July 2018

Identification of adducts formed in the reaction of 5'-acetoxy-N'-nitrosonornicotine with deoxyguanosine and DNA

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4805523

7 July 2018

Cytochrome P450 2A-catalyzed metabolic activation of structurally similar carcinogenic nitrosamines: N'-nitrosonornicotine enantiomers, N-nitrosopiperidine, and N-nitrosopyrrolidine

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4805523

7 July 2018

Tobacco smoke and involuntary smoking

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4805523

7 July 2018

DNA adduct burden and tobacco carcinogenesis

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4805523

7 July 2018

Expression of cytochrome P450 2A3 in rat esophagus: relevance to N-nitrosobenzylmethylamine

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4805523

7 July 2018

Evidence for cytochrome P450 2A6 and 3A4 as major catalysts for N'-nitrosonornicotine alpha-hydroxylation 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=4805523

7 July 2018

DNA conformation mediates aflatoxin B1-DNA binding and the formation of guanine N7 adducts by aflatoxin B1 8,9-exo-epoxide

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4805523

7 July 2018

DNA adducts of chemical carcinogens

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4805523

7 July 2018

Enantiospecificity of covalent adduct formation by benzo[a]pyrene anti-diol epoxide with human serum albumin.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4805523

7 July 2018

Metabolism of tobacco-specific N-nitrosamines by cultured human tissues

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4805523

7 July 2018

Comparative mutagenicity of 4-(carbethoxynitrosamino)-4-(3-pyridyl)butanal and 4-(carbethoxynitrosamino)-1-(3-pyridyl)-1-butanone, model compounds for alpha-hydroxylation of N'-nitrosonornicotine

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4805523

7 July 2018

Solvolysis of model compounds for alpha-hydroxylation of N'-nitrosonornicotine and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone: evidence for a cyclic oxonium ion intermediate in the alkylation of nucleophiles.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4805523

7 July 2018

Stereoselective formation of in vitro nucleic acid adducts by 2,3-epoxy-4-hydroxynonanal

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4805523

7 July 2018

Metabolic alpha-hydroxylation of the tobacco-specific carcinogen, N'-nitrosonornicotine

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4805523

7 July 2018

Identification of adducts formed by pyridyloxobutylation of deoxyguanosine and DNA by 4-(acetoxymethylnitrosamino)-1-(3-pyridyl)-1-butanone, a chemically activated form of tobacco specific carcinogens

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4805523

27 October 2018

Metabolism and pharmacokinetics of N'-nitrosonornicotine in the patas monkey

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4805523

27 October 2018

Enantiomeric composition of N'-nitrosonornicotine and N'-nitrosoanatabine in tobacco.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4805523

27 October 2018

Metabolism of N'-nitrosonornicotine enantiomers by cultured rat esophagus and in vivo in rats.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4805523

27 October 2018

Biochemistry, biology, and carcinogenicity of tobacco-specific N-nitrosamines

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4805523

27 October 2018

Comparative metabolism of the tobacco-related carcinogens benzo[a]pyrene, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol, and N'- nitrosonornicotine in human hepatic microsomes.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4805523

27 October 2018

Comparative carcinogenicity and metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and N'-nitrosonornicotine in Syrian golden hamsters

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4805523

27 October 2018

Comparative carcinogenicity in A/J mice and metabolism by cultured mouse peripheral lung of N'-nitrosonornicotine, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, and their analogues.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=4805523

27 October 2018

Double-stranded DNA stereoselectively binds benzo(a)pyrene diol epoxides

1 reference

https://pubmed.ncbi.nlm.nih.gov/26808005

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Metabolism of N'-nitrosonornicotine by cultured rat esophagus

1 reference

https://pubmed.ncbi.nlm.nih.gov/26808005

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Metabolism of N'-nitrosonornicotine by adult and fetal human oesophagal cultures

1 reference

https://pubmed.ncbi.nlm.nih.gov/26808005

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

An improved synthesis of (+/-)-N'-nitrosonornicotine 5'-acetate

1 reference

https://pubmed.ncbi.nlm.nih.gov/26808005

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Identifiers

10.1021/ACS.CHEMRESTOX.5B00520

1 reference

Europe PubMed Central

PMC publication ID

https://www.ebi.ac.uk/europepmc/webservices/rest/search?query=EXT_ID:26808005%20AND%20SRC:MED&resulttype=core&format=json

11 June 2020

release_dmr2cnxmvrbpfmf3vqpp5divkq

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24 November 2022

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mapped directly with Wikidata item

PMC publication ID

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Europe PubMed Central

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https://www.ebi.ac.uk/europepmc/webservices/rest/search?query=EXT_ID:26808005%20AND%20SRC:MED&resulttype=core&format=json

11 June 2020

PubMed publication ID

1 reference

Europe PubMed Central

PMC publication ID

https://www.ebi.ac.uk/europepmc/webservices/rest/search?query=EXT_ID:26808005%20AND%20SRC:MED&resulttype=core&format=json

11 June 2020

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