Reaction of endogenous Coenzyme Q₁₀ with nitrogen monoxide and its metabolite nitrogen dioxide

References

• Ernster L, Dallner G. Biochemical, physiological and medical aspects of ubiquinone function. Biochim Biophys Acta. 1995;1271:195–204. doi: 10.1016/0925-4439(95)00028-3
   PubMed Web of Science ®Google Scholar
• Dutton PL, Ohnishi T, Darrouzet E, et al. Coenzyme Q: molecular mechanism in health and disease. Kagan VE, Quinn PJ, editors. Boca Raton: CRC Press; 2000. p. 65–82.
   Google Scholar
• Okamoto T, Matsuya T, Fukunaga Y, et al. Human serum ubiquinol-10 levels and relationship to serum lipids. Int J Vitam Nutr Res. 1989;59(3):288–292.
   PubMed Web of Science ®Google Scholar
• Aberg F, Appelkvist EL, Dallner G, et al. Distribution and redox state of ubiquinones in rat and human tissues. Arch Biochem Biophys. 1992;295(2):230–234. doi: 10.1016/0003-9861(92)90511-T
   PubMed Web of Science ®Google Scholar
• Shindo Y, Witt E, Han D, et al. Enzymic and non-enzymic antioxidants in epidermis and dermis of human skin. J Invest Dermatol. 1994;102(1):122–124. doi: 10.1111/1523-1747.ep12371744
   PubMed Web of Science ®Google Scholar
• Frei B, Kim MC, Ames BN. Ubiquinol-10 is an effective lipid-soluble antioxidant at physiological concentrations. Proc Natl Acad Sci USA. 1990;87:4879–4883. doi: 10.1073/pnas.87.12.4879
   PubMed Web of Science ®Google Scholar
• James AM, Smith RAJ, Murphy MP. Antioxidant and prooxidant properties of mitochondrial Coenzyme Q. Arch Biochem Biophys. 2004;423:47–56. doi: 10.1016/j.abb.2003.12.025
   PubMed Web of Science ®Google Scholar
• Silvestri S, Orlando P, Armeni T, et al. Coenzyme Q10 and α-lipoic acid: antioxidant and pro-oxidant effects in plasma and peripheral blood lymphocytes of supplemented subjects. J Clin Biochem Nutr. 2015;57:21–26. doi: 10.3164/jcbn.14-130
   PubMed Web of Science ®Google Scholar
• Kagan V, Serbinova E, Packer L. Antioxidant effects of ubiquinones in microsomes and mitochondria are mediated by tocopherol recycling. Biochem Biophys Res Commun. 1990;169(3):851–857. doi: 10.1016/0006-291X(90)91971-T
   PubMed Web of Science ®Google Scholar
• Ernster L, Forsmark P, Nordenbrand K. The mode of action of lipid-soluble antioxidants in biological membranes: relationship between the effects of ubiquinol and vitamin E as inhibitors of lipid peroxidation in submitochondrial particles. BioFactors. 1992;3(4):241–248.
   PubMed Web of Science ®Google Scholar
• Maroz A, Anderson RF, Smith ASJ, et al. Reactivity of ubiquinone and ubiquinol with superoxide and hydroperoxyl radical: implications for in vivo antioxidant activity. Free Radical Biol Chem. 2009;46:105–109. doi: 10.1016/j.freeradbiomed.2008.09.033
   PubMed Web of Science ®Google Scholar
• Murphy MP. How mitochondria produce reactive oxygen species. Biochem J. 2009;417(1):1–13. doi: 10.1042/BJ20081386
   PubMed Web of Science ®Google Scholar
• Poderoso JJ, Carreras MC, Schöpfer F, et al. The reaction of nitric oxide with ubiquinol: kinetic properties and biological significance. Free Radical Biol Med. 1999;26(7/8):925–935. doi: 10.1016/S0891-5849(98)00277-9
   PubMed Web of Science ®Google Scholar
• Schöpfer F, Riobò NA, Carreras MC, et al. Oxidation of ubiquinol by peroxynitrite: implications for protection of mitochondria against nitrosative damage. Biochem J. 2000;349(1):35–42. doi: 10.1042/bj3490035
   PubMedGoogle Scholar
• Astolfi P, Charles L, Gigmes D, et al. Reaction of nitric oxide and nitrogen dioxide with coenzyme Q; involvement of the isoprenic chain. Org Biomol Chem. 2013;11:1399–1406. doi: 10.1039/c2ob27198b
   PubMed Web of Science ®Google Scholar
• Golding P, Powell JL, Ridd JH. Reaction of nitrogen dioxide with hexenes. The mechanistic and structural factors controlling the product composition. J Chem Soc Perkin Trans. 1996;2:813–819. doi: 10.1039/p29960000813
   Google Scholar
• Alberti A, Benaglia M, Macciantelli D. Mechanistic studies of radical-based processes. Use and misuse of EPR spectroscopy. Org Lett. 2000;2(11):1553–1555. doi: 10.1021/ol005741j
   PubMed Web of Science ®Google Scholar
• Park JSB, Walton JC. Reaction of nitric oxide and nitrogen dioxide with functionalised alkenes and dienes. J Chem Soc Perkin Trans. 1997;2:2579–2584. doi: 10.1039/a702295f
   Google Scholar
• Jassem W, Armeni T, Quiles JL, et al. Protection of mitochondria during cold storage of liver and following transplantation: comparison of the two solutions, University of Wisconsin and Eurocollins. J Bioenerg Biomemb. 2006;38:49–55. doi: 10.1007/s10863-006-9005-6
   PubMed Web of Science ®Google Scholar
• Bradford MM. A rapid and sensitive method for the quantification of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem. 1976;72:248–254. doi: 10.1016/0003-2697(76)90527-3
   PubMed Web of Science ®Google Scholar
• Mosca F, Fattorini D, Bompadre S, et al. Assay of coenzyme Q(10) in plasma by a single dilution step. Anal Biochem. 2002;305:49–54. doi: 10.1006/abio.2002.5653
   PubMed Web of Science ®Google Scholar
• Goldstein S, Czapski G. Mechansim of the nitrosation of thiols and amines by oxygenated NO solutins: the nature of the nitrosating intermediates. J Am Chem Soc. 1996;118:3419–3425. doi: 10.1021/ja9536680
   Web of Science ®Google Scholar
• Prütz WA, Mönig H, Butler J, et al. Reaction of nitrogen dioxide in aqueous model systems: oxidation of tyrosine units in peptides and proteins. Arch Biochem Biophys. 1985;243:125–134. doi: 10.1016/0003-9861(85)90780-5
   PubMed Web of Science ®Google Scholar
• Alberti A, Macciantelli D. in Electron paramagnetic resonance – a practitioner’s toolkit. Brustolon M, Giamello EJ, editors. Wiley and Sons, 2009. p. 285–324.
   Google Scholar
• Nicolescu AC. Mechanism of nitric oxide release from organic nitrates and nitrites: implications in the activation of soluble guanylyl cyclase and inhibition of lipid peroxidation [PhD thesis]. Kingston (ON): Queen’s University; January 2004.
   Google Scholar
• Bhagavan HN, Chopra RK. Coenzyme Q10: absorption, tissue uptake, metabolism and pharmacokinetics. Free Radical. Res. 2006;40:445–453. doi: 10.1080/10715760600617843
   PubMed Web of Science ®Google Scholar