Rational discovery and development of a mitochondria-targeted antioxidant based on cinnamic acid scaffold

References

• Sheu SS., Nauduri D, Anders MW. Targeting antioxidants to mitochondria: a new therapeutic direction. Biochim Biophys Acta 2006;1762:256–265.
   PubMed Web of Science ®Google Scholar
• Beal MF. Energetics in the pathogenesis of neurodegenerative diseases. Trends Neurosci 2000;23:298–304.
   PubMed Web of Science ®Google Scholar
• Brookes PS., Yoon Y, Robotham JL., Anders MW., Sheu SS. Calcium, ATP, and ROS: a mitochondrial love-hate triangle. Am J Physiol Cell Physiol 2004;287:C817–C833.
   PubMed Web of Science ®Google Scholar
• Simonian N A, Coyle JT. Oxidative stress in neurodegenerative diseases. Annu Rev Pharmacol Toxicol 1996;36:83–106.
   PubMed Web of Science ®Google Scholar
• Halliwell B, Whiteman M. Measuring reactive species and oxidative damage in vivo and in cell culture: how should you do it and what do the results mean? Br J Pharmacol 2004;142:231–255.
   PubMed Web of Science ®Google Scholar
• Antolovich M, Prenzler PD, Patsalides E, McDonald S, Robards K. Methods for testing antioxidant activity. Analyst 2002;127:183–198.
   PubMed Web of Science ®Google Scholar
• Valko M, Rhodes CJ, Moncol J, Izakovic M, Mazur M. Free radicals, metals and antioxidants in oxidative stress-induced cancer. Chem Biol Interact 2006;160:1–40.
   PubMed Web of Science ®Google Scholar
• Aydin A, Arsova-Sarafinovska Z, Sayal A, Eken A, Erdem O, Erten K, . Oxidative stress and antioxidant status in non-metastatic prostate cancer and benign prostatic hyperplasia. Clin Biochem 2006;39:176–179.
   PubMed Web of Science ®Google Scholar
• Firoozrai M, Nourbakhsh M, Razzaghy-Azar M. Erythrocyte susceptibility to oxidative stress and antioxidant status in patients with type 1 diabetes. Diabetes Res Clin Pract 2007;77:427–432.
   PubMed Web of Science ®Google Scholar
• Pasupathi P, Chandrasekar V, Kumar US. Evaluation of oxidative stress, enzymatic and non-enzymatic antioxidants and metabolic thyroid hormone status in patients with diabetes mellitus. Diabetes Metab Syndr: Clin Res Rev 2009;3:160–165.
   Google Scholar
• Gilgun-Sherki Y, Melamed E, Offen D. Oxidative stress induced-neurodegenerative diseases: the need for antioxidants that penetrate the blood brain barrier. Neuropharmacology 2001;40:959–975.
   PubMed Web of Science ®Google Scholar
• Annunziato L, Amoroso S, Pannaccione A, Cataldi M, Pignataro G, D'Alessio A, . Apoptosis induced in neuronal cells by oxidative stress: role played by caspases and intracellular calcium ions. Toxicol Lett 2003;139:125–133.
   PubMed Web of Science ®Google Scholar
• Cui K, Luo X, Xu K, Ven Murthy MR. Role of oxidative stress in neurodegeneration: recent developments in assay methods for oxidative stress and nutraceutical antioxidants. Prog Neuropsychopharmacol Biol Psychiatry 2004;28:771–799.
   PubMed Web of Science ®Google Scholar
• Kasapoglu M, Ozben T. Alterations of antioxidant enzymes and oxidative stress markers in aging. Exp Gerontol 2001;36:209–220.
   PubMed Web of Science ®Google Scholar
• Del Valle LG. Oxidative stress in aging: Theoretical outcomes and clinical evidences in humans. Biomed Aging Pathol 2011;1:1–7.
   Google Scholar
• Smith RAJ, Hartley RC, Murphy MP. Mitochondria-targeted small molecule therapeutics and probes. AntioxidRedox Signal 2011;15:3021–3038.
   PubMed Web of Science ®Google Scholar
• Yang CS, Landau JM, Huang MT, Newmark HL. Inhibition of carcinogenesis by dietary polyphenolic compounds. Annu Rev Nutr 2001;21:381–406.
   PubMed Web of Science ®Google Scholar
• Esteves M, Siquet C, Gaspar A, Rio V, Sousa JB, Reis S, . Antioxidant versus cytotoxic properties of hydroxycinnamic acid derivatives-a new paradigm in phenolic research. Arch Pharm (Weinheim) 2008;341:164–173.
   PubMed Web of Science ®Google Scholar
• Menezes JC, Kamat SP, Cavaleiro JA, Gaspar A, Garrido J, Borges F, . Synthesis and antioxidant activity of long chain alkyl hydroxycinnamates. Eur J Med Chem 2011;46:773–777.
   PubMed Web of Science ®Google Scholar
• Manach C, Scalbert A, Morand C, Remesy C, Jimenez L. Polyphenols: food sources and bioavailability. Am J Clin Nutr 2004;79:727–747.
   PubMed Web of Science ®Google Scholar
• Murphy MP. Targeting lipophilic cations to mitochondria. Biochim Biophys Acta 2008;1777:1028–1031.
   PubMed Web of Science ®Google Scholar
• Guan L-P, Wei C-X, Deng X-Q, Sui X, Piao H-R, Quan Z-S, . Synthesis and anticonvulsant activity of N-(2-hydroxyethyl) cinnamamide derivatives. Eur J Med Chem 2009;44: 3654–3657.
   Google Scholar
• Brown SE, Ross MF, Sanjuan-Pla A, Manas AR, Smith RA, Murphy MP, . Targeting lipoic acid to mitochondria: synthesis and characterization of a triphenylphosphonium-conjugated alpha-lipoyl derivative. Free Radic Biol Med 2007;42:1766–1780.
   PubMed Web of Science ®Google Scholar
• Milhazes N Cunha-Oliveira T, Martins P, Garrido J, Oliveira C, Rego AC, . Synthesis and cytotoxic profile of 3,4-methylenedioxymethamphetamine (“ecstasy”) and its metabolites on undifferentiated PC12 cells: a putative structure-toxicity relationship. Chem Res Toxicol 2006;19:1294–1304.
   Google Scholar
• Kelso GF, Porteous CM, Coulter CV, Hughes G, Porteous WK, Ledgerwood EC, . Selective targeting of a redox-active ubiquinone to mitochondria within cells: antioxidant and antiapoptotic properties. J Biol Chem 2001;276: 4588–4596.
   PubMed Web of Science ®Google Scholar
• Brand-Williams W, Cuvelier ME, Berset C. Use of a free radical method to evaluate antioxidant activity. LWT-Food Science and Technology 1995;28:25–30.
   Web of Science ®Google Scholar
• Re R, Pellegrini N, Proteggente A, Pannala A, Yang M, Rice-Evans C, . Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radic Biol Med 1999;26:1231–1237.
   PubMed Web of Science ®Google Scholar
• Chappell JB, Hansford RG. 1972. Preparation of mitochondria from animal tissues and yeast. In: Subcellular components: preparation and fractionation. London: Butterworths.
   Google Scholar
• Gornall AG, Bardawill CJ, David MM. Determination of serum proteins by means of the biuret reaction. J Biol Chem 1949;177:751–766.
   PubMed Web of Science ®Google Scholar
• Smith RA, Kelso GF, James AM, Murphy MP. Targeting coenzyme Q derivatives to mitochondria. Methods Enzymol 2004;382:45–67.
   PubMed Web of Science ®Google Scholar
• Kamo N, Muratsugu M, Hongoh R, Kobatake Y. Membrane potential of mitochondria measured with an electrode sensitive to tetraphenyl phosphonium and relationship between proton electrochemical potential and phosphorylation potential in steady state. J Membr Biol 1979;49:105–121.
   PubMed Web of Science ®Google Scholar
• Montalbetti CAGN, Falque V. Amide bond formation and peptide coupling. Tetrahedron 2005;61:10827–10852.
   Web of Science ®Google Scholar
• Roleira FM, Siquet C, Orru E, Garrido EM, Garrido J, Milhazes N, . Lipophilic phenolic antioxidants: correlation between antioxidant profile, partition coefficients and redox properties. Bioorg Med Chem 2010;18:5816–5825.
   PubMed Web of Science ®Google Scholar
• Gaspar A, Garrido EM, Esteves M, Quezada E, Milhazes N, Garrido J, . New insights into the antioxidant activity of hydroxycinnamic acids: synthesis and physicochemical characterization of novel halogenated derivatives. Eur J Med Chem 2009;44:2092–2099.
   Google Scholar
• Trabelsi SK, Tahar NB, Abdelhedi R. Electrochemical behavior of caffeic acid. Electrochimica Acta 2004;49:1647–1654.
   Google Scholar
• Yakovleva K, Kurzeev S, Stepanova E, Fedorova T, Kuznetsov B, Koroleva O, . Characterization of plant phenolic compounds by cyclic voltammetry. App Biochem Microbiol 2007;43:661–668.
   Web of Science ®Google Scholar
• Yang B, Kotani A, Arai K, Kusu F. Relationship of electrochemical oxidation of catechins on their antioxidant activity in microsomal lipid peroxidation. Chem Pharm Bull (Tokyo) 2001;49:747–751.
   PubMed Web of Science ®Google Scholar
• Brown GC, Brand MD. Thermodynamic control of electron flux through mitochondrial cytochrome bc1 complex. Biochem J 1985;225:399–405.
   Google Scholar
• Ross MF, Prime TA, Abakumova I, James AM, Porteous CM, Smith RA, . Rapid and extensive uptake and activation of hydrophobic triphenylphosphonium cations within cells. Biochem J 2008;411:633–645.
   PubMed Web of Science ®Google Scholar
• Cocheme HM, Quin C, McQuaker SJ, Cabreiro F, Logan A, Prime TA, . Measurement of H2O2 within living Drosophila during aging using a ratiometric mass spectrometry probe targeted to the mitochondrial matrix. Cell Metab 2011;13:340–350.
   PubMedGoogle Scholar
• Ross MF, Kelso GF, Blaikie FH, James AM, Cocheme HM, Filipovska A, . Lipophilic triphenylphosphonium cations as tools in mitochondrial bioenergetics and free radical biology. Biochemistry (Mosc) 2005;70:222–230.
   PubMed Web of Science ®Google Scholar
• Asin-Cayuela J, Manas AR, James AM, Smith RA, Murphy MP. Fine-tuning the hydrophobicity of a mitochondria-targeted antioxidant. FEBS Lett 2004;571:9–16.
   PubMed Web of Science ®Google Scholar
• Smith RA, Porteous CM, Coulter CV, Murphy MP. Selective targeting of an antioxidant to mitochondria. Eur J Biochem 1999;263:709–716.
   PubMedGoogle Scholar