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

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]

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

• Document type: Review article
• Source: CHEMICAL REVIEWS; v. 119, n. 3, p. 2043-2086, FEB 13 2019.
• Web of Science Citations: 22

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