Formation of ring-opened and rearranged products of guanine: mechanisms and biological significance

Free Radical Biology & Medicine
Nihar Ranjan Jena, Phool Chand Mishra

Abstract

DNA damage by endogenous and exogenous agents is a serious concern, as the damaged products can affect genome integrity severely. Damage to DNA may arise from various factors such as DNA base modifications, strand break, inter- and intrastrand crosslinks, and DNA-protein crosslinks. Among these factors, DNA base modification is a common and important form of DNA damage that has been implicated in mutagenesis, carcinogenesis, and many other pathological conditions. Among the four DNA bases, guanine (G) has the smallest oxidation potential, because of which it is frequently modified by reactive species, giving rise to a plethora of lethal lesions. Similarly, 8-oxo-7,8-dihydroguanine (8-oxoG), an oxidatively damaged guanine lesion, also undergoes various degradation reactions giving rise to several mutagenic species. The various products formed from reactions of G or 8-oxoG with different reactive species are mainly 2,6-diamino-4-oxo-5-formamidopyrimidine, 2,5-diamino-4H-imidazolone, 2,2,4-triamino-5-(2H)-oxazolone, 5-guanidino-4-nitroimidazole, guanidinohydantoin, spiroiminodihydantoin, cyanuric acid, parabanic acid, oxaluric acid, and urea, among others. These products are formed from either ring opening or ring opening and subs...Continue Reading

References

Oct 1, 1988·Proceedings of the National Academy of Sciences of the United States of America·J W Park, B N Ames
Feb 24, 1983·Nature·C S FooteR I Lehrer
Feb 7, 1998·Proceedings of the National Academy of Sciences of the United States of America·S S MarlaJ T Groves
Mar 5, 1999·Mutation Research·J CadetS Sauvaigo
May 18, 1999·Chemical Research in Toxicology·N Y TretyakovaS R Tannenbaum
Dec 22, 1999·Proceedings of the Society for Experimental Biology and Medicine·A E Aust, J F Eveleigh
Aug 30, 2000·Toxicology·J P Kehrer
Dec 6, 2001·Journal of the American Chemical Society·J C NilesS R Tannenbaum
Feb 2, 2002·Chemistry : a European Journal·Lars T Burgdorf, Thomas Carell
Feb 19, 2002·Chemical Reviews·Cynthia J. Burrows, James G. Muller
Mar 9, 2002·Nucleic Acids Research·Vadim I BruskovAnatoly V Chernikov
Apr 11, 2002·Journal of the American Chemical Society·Chimin SheuChristopher S Foote
May 7, 2002·Nature Reviews. Cancer·Laurence H Hurley
Jun 20, 2002·Journal of the American Chemical Society·Carissa J Wiederholt, Marc M Greenberg
Dec 31, 2002·Toxicology·Lawrence J Marnett
Jan 25, 2003·Journal of Biochemistry and Molecular Biology·Barbara Tudek
Oct 1, 1963·The Biochemical Journal·P D LAWLEY, P BROOKES
Aug 3, 2004·Nature Reviews. Cancer·Miriam C Poirier
Sep 3, 2004·Mutation Research·Mark D EvansMarcus S Cooke
May 14, 2005·Free Radical Biology & Medicine·Glaucia R MartinezPaolo Di Mascio
Sep 15, 2005·Nucleic Acids Research·Sriram Kanvah, Gary B Schuster
Dec 3, 2005·Chembiochem : a European Journal of Chemical Biology·Adam KupanBernard Meunier
Dec 20, 2005·Chemical Research in Toxicology·Hongbin YuSteven R Tannenbaum
Dec 22, 2005·Journal of the American Chemical Society·Matthias OberThomas Carell

❮ Previous
Next ❯

Citations

Jul 4, 2012·Journal of Biosciences·N R Jena
May 21, 2013·Nature Chemical Biology·Tim H GehrkeThomas Carell
Nov 1, 2015·Nucleic Acids Research·Nicholas C BauerPaul W Doetsch
Aug 13, 2013·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Nihar Ranjan Jena, Phool Chand Mishra
May 16, 2014·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Nihar R JenaPhool C Mishra
Nov 14, 2015·Archives of Toxicology·Ching-Fen WuThomas Efferth
Jun 24, 2015·Physical Chemistry Chemical Physics : PCCP·N R JenaP C Mishra
Apr 23, 2016·Physical Chemistry Chemical Physics : PCCP·N R JenaP C Mishra
Sep 2, 2016·Biochemistry·Safnas F AbdulSalamEdward J Merino
Aug 6, 2014·Bioorganic & Medicinal Chemistry·Joris IrvoasGeneviève Pratviel
Apr 25, 2017·Environmental and Molecular Mutagenesis·Yan ShaR Stephen Lloyd
Apr 1, 2018·Chemistry : a European Journal·Bruno Mattia BizzarriJuan Manuel García-Ruiz
Aug 16, 2017·Chembiochem : a European Journal of Chemical Biology·Safnas F AbdulSalamEdward J Merino
Nov 4, 2017·Oxidative Medicine and Cellular Longevity·Kazuya ShinmuraHaruhiko Sugimura
Jun 12, 2017·Journal of Molecular Biology·Anvesh DasariAnthony J Berdis
Oct 2, 2019·Chemical Research in Toxicology·Sebastien P Hebert, H Bernhard Schlegel
Mar 20, 2019·Analytical Chemistry·Casey A ChamberlainTimothy J Garrett

❮ 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.