Literature DB >> 15606116

Synthesis of the N2-deoxyguanosine adduct of the potent dietary mutagen IQ.

James S Stover1, Carmelo J Rizzo.   

Abstract

[structure: see text] After bioactivation, the potent dietary mutagen 2-amino-3-methylimidazo[4,5-f]-quinoline (IQ) reacts with DNA to give two regioisomeric adducts of deoxyguanosine. The synthesis of the minor N2-adduct has been achieved utilizing the Buchwald-Hartwig palladium-catalyzed N-arylation reaction as the key step.

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Year:  2004        PMID： 15606116     DOI： 10.1021/ol047851m

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  10 in total

1.  1,5-Disubstituted benzimidazoles that direct cardiomyocyte differentiation from mouse embryonic stem cells.

Authors:  Karl J Okolotowicz; Paul Bushway; Marion Lanier; Cynthia Gilley; Mark Mercola; John R Cashman
Journal:  Bioorg Med Chem       Date:  2015-08-04       Impact factor: 3.641

2.  Translesion synthesis past the C8- and N2-deoxyguanosine adducts of the dietary mutagen 2-Amino-3-methylimidazo[4,5-f]quinoline in the NarI recognition sequence by prokaryotic DNA polymerases.

Authors:  James S Stover; Goutam Chowdhury; Hong Zang; F Peter Guengerich; Carmelo J Rizzo
Journal:  Chem Res Toxicol       Date:  2006-11       Impact factor: 3.739

3.  Zn2+-dependent deoxyribozymes that form natural and unnatural RNA linkages.

Authors:  Kelly A Hoadley; Whitney E Purtha; Amanda C Wolf; Amber Flynn-Charlebois; Scott K Silverman
Journal:  Biochemistry       Date:  2005-06-28       Impact factor: 3.162

4.  DNA-catalyzed reductive amination.

Authors:  On Yi Wong; Amanda E Mulcrone; Scott K Silverman
Journal:  Angew Chem Int Ed Engl       Date:  2011-10-12       Impact factor: 15.336

5.  Synthesis of oligonucleotides containing the N2-deoxyguanosine adduct of the dietary carcinogen 2-amino-3-methylimidazo[4,5-f]quinoline.

Authors:  James S Stover; Carmelo J Rizzo
Journal:  Chem Res Toxicol       Date:  2007-10-04       Impact factor: 3.739

6.  Palladium-catalyzed synthesis of nucleoside adducts from bay- and fjord-region diol epoxides.

Authors:  Elise Champeil; Padmanava Pradhan; Mahesh K Lakshman
Journal:  J Org Chem       Date:  2007-06-09       Impact factor: 4.354

7.  Palladium-Catalyzed Aryl Amination Reactions of 6-Bromo- and 6-Chloropurine Nucleosides.

Authors:  Paul F Thomson; Pallavi Lagisetty; Jan Balzarini; Erik De Clercq; Mahesh K Lakshman
Journal:  Adv Synth Catal       Date:  2010-07-05       Impact factor: 5.837

8.  Base-Displaced Intercalated Conformation of the 2-Amino-3-methylimidazo[4,5-f]quinoline N(2)-dG DNA Adduct Positioned at the Nonreiterated G(1) in the NarI Restriction Site.

Authors:  Kallie M Stavros; Edward K Hawkins; Carmelo J Rizzo; Michael P Stone
Journal:  Chem Res Toxicol       Date:  2015-06-17       Impact factor: 3.739

Review 9.  Metabolism and biomarkers of heterocyclic aromatic amines in humans.

Authors:  Medjda Bellamri; Scott J Walmsley; Robert J Turesky
Journal:  Genes Environ       Date:  2021-07-16

10.  Base-displaced intercalation of the 2-amino-3-methylimidazo[4,5-f]quinolone N2-dG adduct in the NarI DNA recognition sequence.

Authors:  Kallie M Stavros; Edward K Hawkins; Carmelo J Rizzo; Michael P Stone
Journal:  Nucleic Acids Res       Date:  2013-12-23       Impact factor: 16.971
  10 in total

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