Synthesis and characterization of a 5-membered ring cyclic hydroxylamine coupled to triphenylphosphonium to detect mitochondrial superoxide by EPR spectrometry

References

• Payen VL, Zampieri LX, Porporato PE, et al. Pro- and antitumor effects of mitochondrial reactive oxygen species. Cancer Metastasis Rev. 2019;38(1-2):189–203.
   PubMed Web of Science ®Google Scholar
• Porporato PE, Payen VL, Pérez-Escuredo J, et al. A mitochondrial switch promotes tumor metastasis. Cell Rep. 2014;8(3):754–766.
   PubMed Web of Science ®Google Scholar
• Zhelev Z, Bakalova R, Aoki I, et al. Imaging of superoxide generation in the dopaminergic area of the brain in Parkinson’s disease, using Mito-TEMPO. ACS Chem Neurosci. 2013;4(11):1439–1445.
   PubMed Web of Science ®Google Scholar
• Dikalova AE, Bikineyeva AT, Budzyn K, et al. Therapeutic targeting of mitochondrial superoxide in hypertension. Circ Res. 2010;107(1):106–116.
   PubMed Web of Science ®Google Scholar
• Zielonka J, Joseph J, Sikora A, et al. Mitochondria-targeted triphenylphosphonium-based compounds: syntheses, mechanisms of action, and therapeutic and diagnostic applications. Chem Rev. 2017;117(15):10043–10120.
   PubMed Web of Science ®Google Scholar
• Murphy MP, Smith R. Targeting antioxidants to mitochondria by conjugation to lipophilic cations. Annu Rev Pharmacol Toxicol. 2007;47(1):629–656.
   PubMed Web of Science ®Google Scholar
• Reily C, Mitchell T, Chacko BK, et al. Mitochondrially targeted compounds and their impact on cellular bioenergetics. Redox Biol. 2013;1(1):86–93.
   PubMed Web of Science ®Google Scholar
• Rossman MJ, Santos-Parker JR, Steward CAC, et al. Chronic supplementation with a mitochondrial antioxidant (MitoQ) improves vascular function in healthy older adults. Hypertension. 2018;71(6):1056–1063.
   PubMed Web of Science ®Google Scholar
• Smith RAJ, Murphy MP. Animal and human studies with the mitochondria-targeted antioxidant MitoQ. Ann N Y Acad Sci. 2010;1201(1):96–103.
   PubMedGoogle Scholar
• Cheng G, Zielonka J, McAllister D, et al. Antiproliferative effects of mitochondria-targeted cationic antioxidants and analogs: role of mitochondrial bioenergetics and energy-sensing mechanism. Cancer Lett. 2015;365(1):96–106.
   PubMed Web of Science ®Google Scholar
• Dikalova AE, Kirilyuk IA, Dikalov SI. Antihypertensive effect of mitochondria-targeted proxyl nitroxides. Redox Biol. 2015;4:355–362.
   PubMed Web of Science ®Google Scholar
• Cheng G, Zielonka J, Ouari O, et al. Mitochondria-targeted analogues of metformin exhibit enhanced antiproliferative and radiosensitizing effects in pancreatic cancer cells. Cancer Res. 2016;76(13):3904–3915.
   PubMed Web of Science ®Google Scholar
• Hardy M, Rockenbauer A, Vásquez-Vivar J, et al. Detection, characterization, and decay kinetics of ROS and thiyl adducts of Mito-DEPMPO spin TRAP. Chem Res Toxicol. 2007;20(7):1053–1060.
   PubMed Web of Science ®Google Scholar
• Hardy M, Poulhés F, Rizzato E, et al. Mitochondria-targeted spin traps: synthesis, Superoxide spin trapping, and mitochondrial uptake. Chem Res Toxicol. 2014;27(7):1155–1165.
   PubMed Web of Science ®Google Scholar
• Dikalov SI, Kirilyuk IA, Voinov M, et al. EPR detection of cellular and mitochondrial superoxide using cyclic hydroxylamines. Free Radic Res. 2011;45(4):417–430.
   PubMed Web of Science ®Google Scholar
• Abbas K, Hardy M, Poulhès F, et al. Detection of superoxide production in stimulated and unstimulated living cells using new cyclic nitrone spin traps. Free Radic Biol Med. 2014;71:281–290.
   PubMed Web of Science ®Google Scholar
• Scheinok S, Leveque P, Sonveaux P, et al. Comparison of different methods for measuring the superoxide radical by EPR spectroscopy in buffer, cell lysates and cells. Free Radic Res. 2018;52(10):1182–1196.
   PubMed Web of Science ®Google Scholar
• Yordanov AT, Yamada K, Krishna MC, et al. Acyl-protected hydroxylamines as spin label generators for EPR brain imaging. J Med Chem. 2002;45(11):2283–2288.
   PubMed Web of Science ®Google Scholar
• Dikalov SI, Li W, Mehranpour P, et al. Production of extracellular superoxide by human lymphoblast cell lines: comparison of electron spin resonance techniques and cytochrome C reduction assay. Biochem Pharmacol. 2007;73(7):972–980.
   PubMed Web of Science ®Google Scholar
• Frezza C, Cipolat S, Scorrano L. Organelle isolation: functional mitochondria from mouse liver, muscle and cultured fibroblasts. Nat Protoc. 2007;2(2):287–295.
   PubMed Web of Science ®Google Scholar
• Driesschaert B, Bobko AA, Khramtsov VV, et al. Nitro-triarylmethyl radical as dual oxygen and superoxide probe. Cell Biochem Biophys. 2017;75(2):241–246.
   PubMed Web of Science ®Google Scholar
• Klug D, Rabani J, Fridovich I. A direct demonstration of the catalytic action of superoxide dismutase through the use of pulse radiolysis. J Biol Chem. 1972;247(15):4839–4842.
   PubMed Web of Science ®Google Scholar
• Dhanasekaran A, Kotamraju S, Karunakaran C, et al. Mitochondria superoxide dismutase mimetic inhibits peroxide-induced oxidative damage and apoptosis: role of mitochondrial superoxide. Free Radic Biol Med. 2005;39(5):567–583.
   PubMed Web of Science ®Google Scholar
• Cochemé HM, Murphy MP. Complex I is the major site of mitochondrial superoxide production by paraquat. J Biol Chem. 2008;283(4):1786–1798.
   PubMed Web of Science ®Google Scholar
• Soule BP, Hyodo F, Matsumoto K, et al. The chemistry and biology of nitroxide compounds. Free Radic Biol Med. 2007;42(11):1632–1650.
   PubMed Web of Science ®Google Scholar
• Hawkins CL, Davies MJ. Detection and characterisation of radicals in biological materials using EPR methodology. Biochim Biophys Acta. 2014;1840(2):708–721.
   PubMed Web of Science ®Google Scholar
• Zhang R, Goldstein S, Samuni A. Kinetics of superoxide-induced exchange among nitroxide antioxidants and their oxidized and reduced forms. Free Radic Biol Med. 1999;26(9-10):1245–1252.
   PubMed Web of Science ®Google Scholar
• Krishna MC, Grahame DA, Samuni A, et al. Oxoammonium cation intermediate in the nitroxide-catalyzed dismutation of superoxide. Proc Natl Acad Sci U S A. 1992;89(12):5537–5541.
   PubMed Web of Science ®Google Scholar
• Wilcox CS. Effects of tempol and redox-cycling nitroxides in models of oxidative stress. Pharmacol Ther. 2010;126(2):119–145.
   PubMed Web of Science ®Google Scholar