Literature DB >> 15355100

Site-specific synthesis and properties of oligonucleotides containing C8-deoxyguanosine adducts of the dietary mutagen IQ.

C Eric Elmquist1, James S Stover, Zhiwei Wang, Carmelo J Rizzo.   

Abstract

The site-specific synthesis of oligonucleotides containing the C8-deoxyguanosine adduct of the highly mutagenic heterocyclic amine 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) has been achieved, and the oligonucleotides were characterized by UV melting temperature analysis, circular dichroism, and UV absorption spectroscopy. Examination of these data indicated that the IQ-adduct is accommodated in dramatically different environments. This sequence-dependent conformational preference is likely to play a key role in the mutagenicity and repair of IQ-modified oligonucleotides.

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Year:  2004        PMID： 15355100     DOI： 10.1021/ja0487022

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  27 in total

1.  The C8-2'-deoxyguanosine adduct of 2-amino-3-methylimidazo[1,2-d]naphthalene, a carbocyclic analogue of the potent mutagen 2-amino-3-methylimidazo[4,5-f]quinoline, is a block to replication in vitro.

Authors:  Plamen P Christov; Goutam Chowdhury; Craig A Garmendia; Feng Wang; James S Stover; C Eric Elmquist; Albena Kozekova; Karen C Angel; Robert J Turesky; Michael P Stone; F Peter Guengerich; Carmelo J Rizzo
Journal:  Chem Res Toxicol       Date:  2010-06-21       Impact factor: 3.739

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.  Site specific synthesis and polymerase bypass of oligonucleotides containing a 6-hydroxy-3,5,6,7-tetrahydro-9H-imidazo[1,2-a]purin-9-one base, an intermediate in the formation of 1,N2-etheno-2'-deoxyguanosine.

Authors:  Angela K Goodenough; Ivan D Kozekov; Hong Zang; Jeong-Yun Choi; F Peter Guengerich; Thomas M Harris; Carmelo J Rizzo
Journal:  Chem Res Toxicol       Date:  2005-11       Impact factor: 3.739

4.  Chemical and electrochemical oxidation of C8-arylamine adducts of 2'-deoxyguanosine.

Authors:  James S Stover; Madalina Ciobanu; David E Cliffel; Carmelo J Rizzo
Journal:  J Am Chem Soc       Date:  2007-01-26       Impact factor: 15.419

Review 5.  Biological properties of single chemical-DNA adducts: a twenty year perspective.

Authors:  James C Delaney; John M Essigmann
Journal:  Chem Res Toxicol       Date:  2007-12-12       Impact factor: 3.739

6.  Site-specific synthesis and characterization of oligonucleotides containing an N6-(2-deoxy-D-erythro-pentofuranosyl)-2,6-diamino-3,4-dihydro-4-oxo-5-N-methylformamidopyrimidine lesion, the ring-opened product from N7-methylation of deoxyguanosine.

Authors:  Plamen P Christov; Kyle L Brown; Ivan D Kozekov; Michael P Stone; Thomas M Harris; Carmelo J Rizzo
Journal:  Chem Res Toxicol       Date:  2008-12       Impact factor: 3.739

7.  Synthesis of oligonucleotides containing 2'-deoxyguanosine adducts of nitropyrenes.

Authors:  Laureen C Colis; Debasis Chakraborti; Pablo Hilario; Christopher McCarty; Ashis K Basu
Journal:  Nucleosides Nucleotides Nucleic Acids       Date:  2009-02       Impact factor: 1.381

8.  Synthesis of G-N2-(CH2)3-N2-G Trimethylene DNA interstrand cross-links.

Authors:  Francesca Gruppi; Tracy L Johnson Salyard; Carmelo J Rizzo
Journal:  Curr Protoc Nucleic Acid Chem       Date:  2014-03-26

9.  The abundant DNA adduct N 7-methyl deoxyguanosine contributes to miscoding during replication by human DNA polymerase η.

Authors:  Olive J Njuma; Yan Su; F Peter Guengerich
Journal:  J Biol Chem       Date:  2019-05-17       Impact factor: 5.157

10.  Base-displaced intercalated structure of the food mutagen 2-amino-3-methylimidazo[4,5-f]quinoline in the recognition sequence of the NarI restriction enzyme, a hotspot for -2 bp deletions.

Authors:  Feng Wang; Nicholas E DeMuro; C Eric Elmquist; James S Stover; Carmelo J Rizzo; Michael P Stone
Journal:  J Am Chem Soc       Date:  2006-08-09       Impact factor: 15.419
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