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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Singlet Molecular Oxygen Reactions with Nucleic Acids, Lipids, and Proteins

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Author(s):
Di Mascio, Paolo [1] ; Martinez, Glaucia R. [2] ; Miyamoto, Sayuri [1] ; Ronsein, Graziella E. [1] ; Medeiros, Marisa H. G. [1] ; Cadet, Jean [3]
Total Authors: 6
Affiliation:
[1] Univ Sao Paulo, Inst Quim, Dept Bioquim, CP 26077, BR-05508000 Sao Paulo, SP - Brazil
[2] Univ Fed Parana, Setor Ciencias Biol, Dept Bioquim & Biol Mol, BR-81531990 Curitiba, PR - Brazil
[3] Univ Sherbrooke, Fac Med Sci Sante, Dept Med Nucl & Radiobiol, Sherbrooke, PQ J1H 5N4 - Canada
Total Affiliations: 3
Document type: Review article
Source: CHEMICAL REVIEWS; v. 119, n. 3, p. 2043-2086, FEB 13 2019.
Web of Science Citations: 15
Abstract

Singlet oxygen (O-1(2)) is a biologically relevant reactive oxygen species capable of efficiently reacting with cellular constituents. The resulting oxidatively generated damage to nucleic acids, membrane unsaturated lipids, and protein components has been shown to be implicated in several diseases, including arthritis, cataracts, and skin cancer. Singlet oxygen may be endogenously produced, among various possibilities, by myeloperoxidase, an enzyme implicated in inflammation processes, and also efficiently in skin by the UVA component of solar radiation through photosensitization reactions. Emphasis is placed in this Review on the description of the main oxidation reactions initiated by O-1(2), and the resulting modifications within key cellular targets, including guanine for nucleic acids, unsaturated lipids, and targeted amino acids. Most of these reactions give rise to peroxides and dioxetanes, whose formation has been rationalized in terms of {[}4+2] cycloaddition and 1,2-cycloaddition with dienes + olefins, respectively. The use of {[}O-18]-labeled thermolabile endoperoxides as a source of {[}O-18] -labeled O-1(2) has been applied to study mechanistic aspects and preferential targets of O-1(2) in biological systems. A relevant major topic deals with the search for the molecular signature of the O-1(2) formation in targeted biomolecules within cells. It may be anticipated that {[}O-18] -labeled O-1(2) and labeled peroxides in association with sensitive mass spectrometric methods should constitute powerful tools for this purpose. (AU)

FAPESP's process: 12/12663-1 - Singlet molecular oxygen and peroxides in chemical biology
Grantee:Paolo Di Mascio
Support type: Research Projects - Thematic Grants
FAPESP's process: 16/00696-3 - Proteomic as a tool to understand HDL function and composition
Grantee:Graziella Eliza Ronsein
Support type: Research Grants - Young Investigators Grants
FAPESP's process: 13/07937-8 - Redoxome - Redox Processes in Biomedicine
Grantee:Ohara Augusto
Support type: Research Grants - Research, Innovation and Dissemination Centers - RIDC