Discovery and mutagenicity of a guanidinoformimine lesion as a new intermediate of the oxidative deoxyguanosine degradation pathway

Journal of the American Chemical Society
Dimitrios StathisThomas Carell

Abstract

Oxidative degradation of DNA is a major mutagenic process. Reactive oxygen species (ROS) produced in the course of oxidative phosphorylation or by exogenous factors are known to attack preferentially deoxyguanosine. The latter decomposes to give mutagenic lesions, which under physiological conditions are efficiently repaired by specialized maintenance systems in the cell. Although many intermediates of the degradation pathway are today well-known, we report in this study the discovery of a new intermediate with an interesting guanidinoformimine structure. The structure elucidation of the new lesion was possible by using HPLC-MS techniques and organic synthesis. Finally we report the mutagenic potential of the new lesion in comparison to the known lesions imidazolone and oxazolone using primer extension and pyrosequencing experiments.

References

Aug 15, 1998·Science·M RonaghiP Nyrén
Nov 17, 2001·Chemical Reviews·R V Williams
Feb 19, 2002·Chemical Reviews·Cynthia J. Burrows, James G. Muller
Jun 5, 2002·Annual Review of Biochemistry·Ulrich HubscherSilvio Spadari
Dec 20, 2002·Angewandte Chemie·Michael O DelaneyMarc M Greenberg
Jul 10, 2003·Angewandte Chemie·Orlando D Schärer
Nov 26, 2003·Mutation Research·Jean CadetJean-Luc Ravanat
Jan 7, 2005·Journal of Medicinal Chemistry·Guangping WeiRobert C Moschel
Mar 8, 2005·Mutation Research·Katsuhito Kino, Hiroshi Sugiyama
Mar 12, 2005·The Journal of Organic Chemistry·Peter K Freeman
Jun 15, 2005·Annual Review of Biochemistry·Satya PrakashLouise Prakash
Dec 22, 2005·Journal of the American Chemical Society·Matthias OberThomas Carell
Apr 13, 2006·Chemical Research in Toxicology·William L Neeley, John M Essigmann
Jun 23, 2006·Chemistry : a European Journal·Geneviève Pratviel, Bernard Meunier
Aug 1, 2008·Accounts of Chemical Research·Jean CadetJean-Luc Ravanat
Aug 12, 2008·Free Radical Biology & Medicine·Miral DizdarogluPawel Jaruga
Sep 26, 2009·Chembiochem : a European Journal of Chemical Biology·Katsuhito KinoFumio Hanaoka
Jan 12, 2010·Mutation Research·Olga A SedelnikovaWilliam M Bonner
Apr 7, 2010·Free Radical Biology & Medicine·Jean CadetJean-Luc Ravanat
May 21, 2010·Free Radical Biology & Medicine·Zsolt Radak, Istvan Boldogh

❮ Previous
Next ❯

Citations

Apr 8, 2014·Genes·Albino BacollaKaren M Vasquez
May 21, 2013·Nature Chemical Biology·Tim H GehrkeThomas Carell
Jan 16, 2014·The Journal of Biological Chemistry·Myong-Chul KoagSeongmin Lee
Oct 21, 2020·International Journal of Molecular Sciences·Katsuhito KinoHiroshi Miyazawa
Apr 9, 2015·Chemical Research in Toxicology·Aaron M FlemingCynthia J Burrows

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.

Related Papers

Chembiochem : a European Journal of Chemical Biology
Heiko MuellerThomas Carell
Journal of Computational Biology : a Journal of Computational Molecular Cell Biology
Yong Kong
Journal of Computational Chemistry
Kun SongCarlos Simmerling
© 2022 Meta ULC. All rights reserved