Evaluation of the antifungal and plasma membrane H⁺-ATPase inhibitory action of ebselen and two ebselen analogs in S. cerevisiae cultures

References

• Sheppard D, Lampiris HW. Antifungal agents. In: Katzung B, ed. Basic and Clinical Pharmacology, 10th ed. New York: McGraw-Hill, 2007:814–22.
   Google Scholar
• Mavor AL, Thewes S, Hube B. Systemic fungal infections caused by Candida species: epidemiology, infection process and virulence attributes. Curr Drug Targets 2005;6:863–74.
   PubMed Web of Science ®Google Scholar
• Dimopoulos G, Karabinis A, Samonis G, Falagas ME. Candidemia in immunocompromised and immunocompetent critically ill patients: a prospective comparative study. Eur J Clin Microbiol Infect Dis 2007;26: 377–84.
   PubMed Web of Science ®Google Scholar
• Perlroth J, Choi B, Spellberg B. Nosocomial fungal infections: epidemiology, diagnosis, and treatment. Med Mycol 2007;45:321–46.
   PubMed Web of Science ®Google Scholar
• Młochowski J, Kloc K, Lisiak R, Potaczek P, Wójtowicz H. Developments in the chemistry of selenaheterocyclic compounds of practical importance in synthesis and medicinal biology. ARKIVOC 2007;6:14–46.
   Google Scholar
• Narajji C, Karvekar MD, Das AK. Biological importance of organoselenium compounds. Indian J Pharm Sci 2007;69:344–51.
   Google Scholar
• Schewe T. Molecular actions of ebselen—an antiinflammtory antioxidant. Gen Pharmacol 1995;26:1153–69.
   PubMedGoogle Scholar
• Mugesh G, du Mont W-W, Sies H. Chemistry of biologically important synthetic organoselenium compounds. Chem Rev 2001;101:2125–79.
   PubMed Web of Science ®Google Scholar
• Soteropoulos P, Vaz T, Santangelo R, Paderu P, Huang DY, Tamas MJ, et al. Molecular characterization of the plasma membrane H(+)-ATPase, an antifungal target in Cryptococcus neoformans. Antimicrob Agents Chemother 2000;44:2349–55.
   PubMed Web of Science ®Google Scholar
• Chan G, Hardej D, Santoro M, Lau-Cam C, Billack B. Evaluation of the antimicrobial activity of ebselen: role of the yeast plasma membrane H+-ATPase. J Biochem Mol Toxicol 2007;21:252–64.
   PubMed Web of Science ®Google Scholar
• Piętka-Ottlik M, Wójtowicz-Młochowska H, Kołodziejczyk K, Piasecki E, Młochowski J. New organoselenium compounds active against pathogenic bacteria, fungi and viruses. Chem Pharm Bull 2008;56:1423–7.
   PubMed Web of Science ®Google Scholar
• Bień M, Blaszczyk B, Kalinowska K, Młochowski J, Inglot AD. Antifungal activity of 2-(4-chlorophenyl)-1,2-benzisoselenazol-3(2H)-one, the analog of ebselen. Arch Immunol Ther Exp (Warsz) 1999;47:185–93.
   PubMedGoogle Scholar
• Wójtowicz H, Kloc K, Maliszewska I, Młochowski J, Piętka M, Piasecki E. Azaanalogues of ebselen as antimicrobial and antiviral agents: synthesis and properties. Farmaco 2004;59:863–8.
   PubMedGoogle Scholar
• Nozawa K, Yokota T, Fujimoto T. Susceptibility of methicillin-resistant Staphylococcus aureus to the selenium-containing compound 2-phenyl-1,2-benzoisoselenazol-3(2H)-one (PZ51). Antimicrob Agents Chemother 1989;33:1388–90.
   PubMed Web of Science ®Google Scholar
• Yamaguchi T, Sano K, Takakura K, Saito I, Shinohara Y, Asano T, et al. Ebselen in acute ischemic stroke: a placebo-controlled, double-blind clinical trial. Ebselen Study Group. Stroke 1998;29:12–17.
   PubMed Web of Science ®Google Scholar
• Bouhafs RK, Jarstrand C. Effects of antioxidants on surfactant peroxidation by stimulated human polymorphonuclear leukocytes. Free Radic Res 2002;36:727–34.
   PubMed Web of Science ®Google Scholar
• Serrano R, Kielland-Brandt MC, Fink GR. Yeast plasma membrane ATPase is essential for growth and has homology with (Na+-K+), K+-, and Ca2+- ATPases. Nature 1986;319:689–93.
   PubMed Web of Science ®Google Scholar
• Monk BC, Perlin DS. Fungal plasma membrane proton pumps as promising new antifungal targets. Crit Rev Microbiol 1994;20:209–23.
   PubMed Web of Science ®Google Scholar
• Perlin DS, Seto-Young D, Monk BC. The plasma membrane H(+)-ATPase of fungi. A candidate drug target? Ann NY Acad Sci 1997;834:609–17.
   PubMed Web of Science ®Google Scholar
• Cotgreave IA, Morgenstern R, Engman L, Ahokas J. Characterisation and quantitation of a selenol intermediate in the reaction of ebselen with thiols. Chem Biol Interact 1992;84:69–76.
   PubMed Web of Science ®Google Scholar
• Glass RS, Farooqui F, Sabahi M, Ehler KW. Formation of thiocarbonyl compounds in the reaction of ebselen oxide with thiols. J Org Chem 1989;54:1092–7.
   Web of Science ®Google Scholar
• Młochowski J, Kloc K, Syper L, Inglot AD, Piasecki E. Aromatic and azoaromatic diselenides, benzisoselenazolones and related compounds as immunomodulators active in humans: synthesis and properties. Liebigs Ann Chem 1993;12:1239–44.
   Google Scholar
• Palus J, Młochowski J, Juchniewicz L. 2,2′-Diselenobisbenzoates and 2,2′-diselenobisbenzenesulfonates: new chiral aryl diselenides. Pol J Chem 1998;72:1931–6.
   Google Scholar
• Wang G, Tamas MJ, Hall MJ, Pascual-Ahuir A, Perlin DS. Probing conserved regions of the cytoplasmic LOOP1 segment linking transmembrane segments 2 and 3 of the Saccharomyces cerevisiae plasma membrane H+-ATPase. J Biol Chem 1996;271:25438–45.
   PubMed Web of Science ®Google Scholar
• Emsley J. Very strong hydrogen bonding. Chem Soc Rev 1980;9:91–124.
   Web of Science ®Google Scholar
• Morin D, Zini R, Ligeret H, Neckameyer W, Labidalle S, Tillement JP. Dual effect of ebselen on mitochondrial permeability transition. Biochem Pharmacol 2003;65:1643–51.
   PubMed Web of Science ®Google Scholar
• Porciúncula LO, Rocha JB, Ghisleni G, Tavares RG, Souza DO. The effects of ebselen on [3H]glutamate uptake by synaptic vesicles from rat brain. Brain Res 2004;1027:192–5.
   PubMed Web of Science ®Google Scholar
• Sarma BK, Mugesh G. Glutathione peroxidase-like antioxidant activity of the organoselenium drug ebselen: unexpected complications with thiol exchange reactions. J Am Chem Soc 2005;127:11477–85.
   PubMed Web of Science ®Google Scholar
• Lisiak R, Mlochowski J, Palus J. Nucleophilic cleavage of selenaheterocyclic ring in benzisoselenaol-3(2H)-ones and 1,3,2-benzodiselenazoles. Pol J Chem 2007;81:1403–11.
   Google Scholar