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Chemistry and biology of DNA containing 1,N(2)-deoxyguanosine adducts of the alpha,beta-unsaturated aldehydes acrolein, crotonaldehyde, and 4-hydroxynonenal.

Minko IG, Kozekov ID, Harris TM, Rizzo CJ, Lloyd RS, Stone MP.

Chem Res Toxicol. 2009 May;22(5):759-78. doi: 10.1021/tx9000489. Review.


Stereospecific formation of interstrand carbinolamine DNA cross-links by crotonaldehyde- and acetaldehyde-derived alpha-CH3-gamma-OH-1,N2-propano-2'-deoxyguanosine adducts in the 5'-CpG-3' sequence.

Cho YJ, Wang H, Kozekov ID, Kurtz AJ, Jacob J, Voehler M, Smith J, Harris TM, Lloyd RS, Rizzo CJ, Stone MP.

Chem Res Toxicol. 2006 Feb;19(2):195-208.


Spectroscopic characterization of interstrand carbinolamine cross-links formed in the 5'-CpG-3' sequence by the acrolein-derived gamma-OH-1,N2-propano-2'-deoxyguanosine DNA adduct.

Cho YJ, Kim HY, Huang H, Slutsky A, Minko IG, Wang H, Nechev LV, Kozekov ID, Kozekova A, Tamura P, Jacob J, Voehler M, Harris TM, Lloyd RS, Rizzo CJ, Stone MP.

J Am Chem Soc. 2005 Dec 21;127(50):17686-96.


Interstrand DNA cross-links induced by alpha,beta-unsaturated aldehydes derived from lipid peroxidation and environmental sources.

Stone MP, Cho YJ, Huang H, Kim HY, Kozekov ID, Kozekova A, Wang H, Minko IG, Lloyd RS, Harris TM, Rizzo CJ.

Acc Chem Res. 2008 Jul;41(7):793-804. doi: 10.1021/ar700246x.


Replication bypass of N2-deoxyguanosine interstrand cross-links by human DNA polymerases η and ι.

Klug AR, Harbut MB, Lloyd RS, Minko IG.

Chem Res Toxicol. 2012 Mar 19;25(3):755-62. doi: 10.1021/tx300011w.


Formation of deoxyguanosine cross-links from calf thymus DNA treated with acrolein and 4-hydroxy-2-nonenal.

Kozekov ID, Turesky RJ, Alas GR, Harris CM, Harris TM, Rizzo CJ.

Chem Res Toxicol. 2010 Nov 15;23(11):1701-13. doi: 10.1021/tx100179g.


Stereospecific formation of the (R)-gamma-hydroxytrimethylene interstrand N2-dG:N2-dG cross-link arising from the gamma-OH-1,N2-propano-2'-deoxyguanosine adduct in the 5'-CpG-3' DNA sequence.

Huang H, Kim HY, Kozekov ID, Cho YJ, Wang H, Kozekova A, Harris TM, Rizzo CJ, Stone MP.

J Am Chem Soc. 2009 Jun 24;131(24):8416-24. doi: 10.1021/ja809543j.


Orientation of the crotonaldehyde-derived N2-[3-Oxo-1(S)-methyl-propyl]-dG DNA adduct hinders interstrand cross-link formation in the 5'-CpG-3' sequence.

Cho YJ, Wang H, Kozekov ID, Kozekova A, Kurtz AJ, Jacob J, Voehler M, Smith J, Harris TM, Rizzo CJ, Lloyd RS, Stone MP.

Chem Res Toxicol. 2006 Aug;19(8):1019-29.


Comparative evaluation of the bioreactivity and mutagenic spectra of acrolein-derived alpha-HOPdG and gamma-HOPdG regioisomeric deoxyguanosine adducts.

Sanchez AM, Minko IG, Kurtz AJ, Kanuri M, Moriya M, Lloyd RS.

Chem Res Toxicol. 2003 Aug;16(8):1019-28.


Replication bypass of the acrolein-mediated deoxyguanine DNA-peptide cross-links by DNA polymerases of the DinB family.

Minko IG, Yamanaka K, Kozekov ID, Kozekova A, Indiani C, O'Donnell ME, Jiang Q, Goodman MF, Rizzo CJ, Lloyd RS.

Chem Res Toxicol. 2008 Oct;21(10):1983-90. doi: 10.1021/tx800174a.


Repair kinetics of acrolein- and (E)-4-hydroxy-2-nonenal-derived DNA adducts in human colon cell extracts.

Choudhury S, Dyba M, Pan J, Roy R, Chung FL.

Mutat Res. 2013 Nov-Dec;751-752:15-23. doi: 10.1016/j.mrfmmm.2013.09.004.


Mutagenic properties of 3-(deoxyguanosin-N2-yl)-2-acetylaminofluorene, a persistent acetylaminofluorene-derived DNA adduct in mammalian cells.

Yasui M, Dong H, Bonala RR, Suzuki N, Ohmori H, Hanaoka F, Johnson F, Grollman AP, Shibutani S.

Biochemistry. 2004 Nov 30;43(47):15005-13.


Translesion synthesis past acrolein-derived DNA adducts by human mitochondrial DNA polymerase γ.

Kasiviswanathan R, Minko IG, Lloyd RS, Copeland WC.

J Biol Chem. 2013 May 17;288(20):14247-55. doi: 10.1074/jbc.M113.458802.


DNA interchain cross-links formed by acrolein and crotonaldehyde.

Kozekov ID, Nechev LV, Moseley MS, Harris CM, Rizzo CJ, Stone MP, Harris TM.

J Am Chem Soc. 2003 Jan 8;125(1):50-61.


γ-Hydroxy-1,N2-propano-2'-deoxyguanosine DNA adduct conjugates the N-terminal amine of the KWKK peptide via a carbinolamine linkage.

Huang H, Wang H, Voehler MW, Kozekova A, Rizzo CJ, McCullough AK, Lloyd RS, Stone MP.

Chem Res Toxicol. 2011 Jul 18;24(7):1123-33. doi: 10.1021/tx200113n.


Translesional synthesis past acetylaminofluorene-derived DNA adducts catalyzed by human DNA polymerase kappa and Escherichia coli DNA polymerase IV.

Suzuki N, Ohashi E, Hayashi K, Ohmori H, Grollman AP, Shibutani S.

Biochemistry. 2001 Dec 18;40(50):15176-83.


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