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5′,8-Cyclopurine Lesions in DNA Damage: Chemical, Analytical, Biological, and Diagnostic Significance

1
Istituto per la Sintesi Organica e la Fotoreattività, Consiglio Nazionale delle Ricerche, Via P. Gobetti 101, 40129 Bologna, Italy
2
Center for Advanced Technologies, Adam Mickiewicz University, 61-614 Poznań, Poland
3
Department of Chemistry, New York University, 31 Washington Place, New York, NY 10003-5180, USA
4
Institute of Nanoscience and Nanotechnology, N.C.S.R. “Demokritos”, 15310 Agia Paraskevi Attikis, Greece
5
Department of Chemistry and Biochemistry, Florida International University, 11200 SW 8th Street, Miami, FL 33199, USA
6
Biochemistry Ph.D. Program, Florida International University, Miami, FL 33199, USA
7
Biomolecular Sciences Institute, Florida International University, Miami, FL 33199, USA
8
Laboratory of Chemical and Environmental Technology, Department of Chemistry, Aristotle University of Thessaloniki, 54124 Thessaloniki, Greece
*
Author to whom correspondence should be addressed.
Cells 2019, 8(6), 513; https://doi.org/10.3390/cells8060513
Received: 13 April 2019 / Revised: 18 May 2019 / Accepted: 22 May 2019 / Published: 28 May 2019
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Abstract

Purine 5′,8-cyclo-2′-deoxynucleosides (cPu) are tandem-type lesions observed among the DNA purine modifications and identified in mammalian cellular DNA in vivo. These lesions can be present in two diasteroisomeric forms, 5′R and 5′S, for each 2′-deoxyadenosine and 2′-deoxyguanosine moiety. They are generated exclusively by hydroxyl radical attack to 2′-deoxyribose units generating C5′ radicals, followed by cyclization with the C8 position of the purine base. This review describes the main recent achievements in the preparation of the cPu molecular library for analytical and DNA synthesis applications for the studies of the enzymatic recognition and repair mechanisms, their impact on transcription and genetic instability, quantitative determination of the levels of lesions in various types of cells and animal model systems, and relationships between the levels of lesions and human health, disease, and aging, as well as the defining of the detection limits and quantification protocols. View Full-Text
Keywords: reactive oxygen species; free radicals; DNA damage; cyclopurines; DNA and RNA polymerases; nucleotide excision repair; LC-MS/MS; xeroderma pigmentosum; cancer reactive oxygen species; free radicals; DNA damage; cyclopurines; DNA and RNA polymerases; nucleotide excision repair; LC-MS/MS; xeroderma pigmentosum; cancer
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Chatgilialoglu, C.; Ferreri, C.; Geacintov, N.E.; Krokidis, M.G.; Liu, Y.; Masi, A.; Shafirovich, V.; Terzidis, M.A.; Tsegay, P.S. 5′,8-Cyclopurine Lesions in DNA Damage: Chemical, Analytical, Biological, and Diagnostic Significance. Cells 2019, 8, 513.

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