Salicylhydroxamic Acid Inhibits the Growth of Candida albicans
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Salicylhydroxamic Acid Inhibits the Growth of Candida albicans

Authors: Shu-Ying Marissa Pang, Stephen Tristram, Simon Brown

Abstract:

Candida spp. are common and aggressive pathogens. Because of the growing resistance of Candida spp. to current antifungals, novel targets, found in Candida spp. but not in humans or other flora, have to be identified. The alternative oxidase (AOX) is one such possibility. This enzyme is insensitive to cyanide, but is sensitive to compounds such as salicylhydroxamic acid (SHAM), disulfiram and n-alkyl gallates. The growth Candida albicans was inhibited by SHAM (Ki = 9-15 mM) and cyanide (Ki = 2-4 mM), albeit to differing extents. The rate of O2 uptake was inhibited by less than 10% by 25 mM SHAM and by about 90% by 250 μM KCN. Although SHAM substantially inhibited the growth of C. albicans, it is unlikely that the inhibition of AOX was the cause. Salicylhydroxamic acid is used therapeutically in the treatment of urinary tract infections and urolithiasis, but it also has some potential in the treatment of C. albicans infection.

Keywords: alternative oxidase, Candida albicans, growth, respiration, salicylhydroxamic acid.

Digital Object Identifier (DOI): doi.org/10.5281/zenodo.1059699

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References:


[1] A. M. Tortorano, J. Peman, H. Bernhardt, L. Klingspor, C. C. Kibbler, O. Faure, E. Biraghi, E. Canton, K. Zimmermann, S. Seaton, and R. Grillot, "Epidemiology of candidaemia in Europe: results of 28-month European Confederation of Medical Mycology (ECMM) hospital-based surveillance study," European Journal of Clinical Microbiology and Infectious Diseases, vol. 23, pp. 317-322, 2004.
[2] M. A. Pfaller, R. N. Jones, G. V. Doern, H. S. Sader, S. A. Messer, A. Houston, S. Coffman, and R. J. Hollis, "Bloodstream infections due to Candida species: SENTRY Antimicrobial Surveillance Program in North America and Latin America, 1997-1998," Antimicrobial Agents and Chemotherapy, vol. 44, pp. 747-751, 2000.
[3] O. Gudlaugsson, S. Gillespie, K. Lee, J. Vande Berg, J. Hu, S. Messer, L. Herwaldt, M. Pfaller, and D. Diekema, "Attributable mortality of nosocomial candidemia, revisited," Clinical Infectious Diseases, vol. 37, pp. 1172-1177, 2003.
[4] G. R. Schonbaum, W. D. Bonner, Jr., B. T. Storey, and J. T. Bahr, "Specific inhibition of the cyanide-insensitive respiratory pathway in plant mitochondria by hydroxamic acids," Plant Physiology, vol. 47, pp. 124-128, 1971.
[5] J. N. Siedow and M. E. Girvin, "Alternative Respiratory Pathway: Its role in seed respiration and its inhibition by propyl gallate.," Plant Physiology, vol. 65, pp. 669-674, 1980.
[6] J. N. Siedow and D. M. Bickett, "Structural features required for inhibition of cyanide-insensitive electron transfer by propyl gallate," Archive of Biochemistry and Biophysics, vol. 207, pp. 32-39, 1981.
[7] L. Yan, M. Li, Y. Cao, P. Gao, Y. Cao, Y. Wang, and Y. Jiang, "The alternative oxidase of Candida albicans causes reduced fluconazole susceptibility," Journal of Antimicrobial Chemotherapy, vol. to be published, 2009.
[8] N. Sen and H. K. Majumder, "Mitochondrion of protozoan parasite emerges as potent therapeutic target: exciting drugs are on the horizon," Current Pharmaceutical Design, vol. 14, pp. 839-846, 2008.
[9] A. Veiga, J. D. Arrabaca, and M. C. Loueiro-Dias, "Stress situations induce cyanide-resistant respiration in spoilage yeasts," Journal of Applied Microbiology, vol. 95, pp. 364-371, 2003.
[10] V. N. Popov, R. A. Simonian, V. P. Skulachev, and A. A. Starkov, "Inhibition of the alternative oxidase stimulates H2O2 production in plant mitochondria," FEBS Letters, vol. 415, pp. 87-90, 1997.
[11] S.-Y. M. Pang, S. Tristram, and S. Brown, "An in silico model of the alternative oxidase," International Journal of Biosciences and Technology, vol. submitted for publication, 2009.
[12] R. M. Nervig and S. Kadis, "Effect of hydroxamic acids on growth and urease activity in Corynebacterium renale," Canadian Journal of Microbiology, vol. 22, pp. 544-551, 1976.
[13] C. Y. Wang and L. H. Lee, "Mutagenicity and antibacterial activity of hydroxamic acids," Antimicrobial Agents and Chemotherapy, vol. 11, pp. 753-755, 1977.
[14] J. J. Gavin, "Analytical microbiology. II. The diffusion methods," Applied Microbiology, vol. 5, pp. 25-33, 1957.
[15] S. Budavari, "The Merck Index," 12 ed. Whitehouse Station: Merck & Co., Inc., 1996.
[16] A.-E. A. Salem and M. M. Omar, "Atomic absorption and spectrophotometric determinations of salicylhydroxamix acid in its pure and pharmeceutical dosage forms," Turkish Journal of Chemistry, vol. 27, pp. 383-393, 2003.
[17] B. Gompertz, "On the nature of the function expressive of the law of human mortality, and on a new mode of determining the value of life contingencies.," Philosophical Transactions of the Royal Society of London, vol. 115, pp. 513-585, 1825.
[18] M. H. Zweitering, I. Jongenburger, F. M. Rombouts, and K. van't Riet, "Modeling of the bacterial growth curve.," Applied and Environmental Microbiology, vol. 56, pp. 1875-1881, 1990.
[19] R Development Core Team, "R: A language and environment for statistical computing." Vienna, Austria: R Foundation for Statistical Computing, 2006.
[20] R. K. Finn, "Theory of agar diffusion methods of assay.," Analytical Chemistry, vol. 31, pp. 975-977, 1959.
[21] M. L. Delignette-Muller and J. P. Flandrois, "An accurate diffusion method for determining bacterial sensitivity to antibiotics.," Journal of Antimicrobial Chemothrapy, vol. 34, pp. 73-81, 1994.
[22] A. L. Koch, "Diffusion through agar blocks of finite dimensions: a theoretical analysis of three systems of practical significance in microbiology.," Microbiology, vol. 145, pp. 643-654, 1999.
[23] S. Brown and N. L. Taylor, "Inhibition of mitochondrial electron transfer by antipsychotic medication," Human and Veterinary Toxicology, vol. 42, pp. 209-211, 2000.
[24] J. B. Hiskey and V. M. Sanchez, "Mechanistic and kinetic aspects of silver dissolution in cyanide solutions.," Journal of Applied Electrochemistry, vol. 20, pp. 479-487, 1990.
[25] B. K. Davis, "Diffusion in polymer gel implants.," Proceedings of the National Academy of Sciences of the USA, vol. 71, pp. 3120-3123, 1974.
[26] L. Friedman, "Structure of agar gels from studies of diffusion.," Journal of the American Chemical Society, vol. 52, pp. 1311-1314, 1930.
[27] N. Fatin-Rogue, K. Starchev, and J. Buffle, "Size effects on diffusion processes within agarose gels.," Biophysical Journal, vol. 86, pp. 2710- 2719, 2004.
[28] E. J. Schantz and M. A. Lauffer, "Diffusion measurements in agar gel.," Biochemistry, vol. 1, pp. 658-663, 1962.
[29] W. G. Bardsley, P. Leff, J. Kavanagh, and R. D. Waight, "Deviations from Michaelis-Menten kinetics. The possibility of complicated curves for simple kinetic schemes and the computer fitting of experimental data for acetylcholinesterase, acid phosphatase, adenosine deaminase, arylsulphatase, benzylamine oxidase, chymotrypsin, fumarase, galactose dehydrogenase, β-galactosidase, lactate dehydrogenase, peroxidase and xanthine oxidase.," Biochemical Journal, vol. 187, pp. 739-765, 1980.
[30] R. Battino, T. R. Rettich, and T. Tominaga, "The solubility of oxygen and ozone in liquids," Journal of Physical and Chemical Reference Data, vol. 12, pp. 163-178, 1983.
[31] S. Aoki and S. Ito-Kuwa, "Respiration of Candida albicans in relation to its morphogenesis," Plant and Cell Physiology, vol. 23, pp. 721-726, 1982.
[32] Nomenclature Committee of the International Union of Biochemistry, "Symbolism and terminology in enzyme kinetics.," European Journal of Biochemistry, vol. 128, pp. 281-291, 1982.
[33] O. Schabenberger, B. E. Tharp, J. J. Kells, and D. Penner, "Statistical tests for hormesis and effective dosages in herbicide dose response.," Agronomy Journal, vol. 91, pp. 713-721, 1999.
[34] P. R. Rich, N. K. Wiegand, H. Blum, A. L. Moore, and W. D. Bonner, Jr., "Studies on the mechanism of inhibition of redox enzymes by substituted hydroxamic acids," Biochimica et Biophysica Acta, vol. 525, pp. 325-337, 1978.
[35] J. Hase and K. Kobashi, "Inhibition of Proteus vulgaris urease by hydroxamic acids.," Journal of Biochemistry, vol. 62, pp. 293-299, 1967.
[36] K. Kobashi, J. Hase, and K. Uehara, "Specific inhibition of urease by hydroxamic acids," Biochimica et Biophysica Acta, vol. 65, pp. 380-383, 1962.
[37] W. N. Fishbein and P. P. Carbone, "Urease Catalysis. Ii. Inhibition of the Enzyme by Hydroxyurea, Hydroxylamine, and Acetohydroxamic Acid," Journal of Biological Chemistry, vol. 240, pp. 2407-2414, 1965.
[38] B. Davies and D. W. Edwards, "Inhibition of myeloperoxidase by salicylhydroxamic acid.," Biochemical Journal, vol. 258, pp. 801-806, 1989.
[39] T. Jones, N. A. Federspiel, H. Chibana, J. Dungan, S. Kalman, B. B. Magee, G. Newport, Y. R. Thorstenson, N. Agabian, P. T. Magee, R. W. Davis, and S. Scherer, "The diploid genome sequence of Candida albicans," Proceedings of the National Academy of Sciences of the USA, vol. 101, pp. 7329-7334, 2004.
[40] J. H. Bell and R. F. Pratt, "Mechanism of inhibition of the betalactamase of Enterobacter cloacae P99 by 1:1 complexes of vanadate with hydroxamic acids," Biochemistry, vol. 41, pp. 4329-4338, 2002.
[41] G. R. Gale, "Selective inhibition of deoxyribonucleic acid synthesis by salicylhydroxamic acid.," Proceedings of the Society for Experimental Biology and Medicine., vol. 122, pp. 1236-1240, 1966.
[42] I. Khozin-Goldberg, C. Bigogno, and Z. Cohen, "Salicylhydroxamic acid inhibits D6 desaturation in the microalga Porphyridium cruentum.," Biochimica et Biophysica Acta, vol. 1439, pp. 384-394, 1999.
[43] D. Leung, G. Abbenante, and D. P. Fairlie, "Protease inhibitors: current status and future prospects," Journal of Medicinal Chemistry, vol. 43, pp. 305-341, 2000.
[44] J. B. Summers, K. H. Kim, H. Mazdiyasni, J. H. Holms, J. D. Ratajczyk, A. O. Stewart, R. D. Dyer, and G. W. Carter, "Hydroxamic acid inhibitors of 5-lipoxygenase: quantitative structure-activity relationships," Journal of Medicinal Chemistry, vol. 33, pp. 992-998, 1990.
[45] E. C. O'Brien, S. Le Roy, J. Levaillain, D. J. Fitzgerald, and K. B. Nolan, "Metal complexes of salicylhydroxamic acid and Oacetylsalicylhydroxamic acid," Inorganica Chimica Acta, vol. 266, pp. 117-120, 1997.
[46] C. J. Marmion, D. Griffith, and K. B. Nolan, "Hydroxamic acids - an intriguing family of enzyme inhibitors and biomedical ligands," European Journal of Inorganic Chemistry, vol. 2004, pp. 3003-3017, 2004.
[47] V. Špringer, M. Hornácková, R. Karlícek, and B. Kopecká, "Salicylhydroxamic acids and its iron(III) complexes.," Collection of Czechoslovak Chemical Communications, vol. 52, pp. 602-608, 1987.
[48] B. Coyle, K. Kavanagh, M. McCann, M. Devereux, and M. Geraghty, "Mode of anti-fungal activity of 1,10-phenanthroline and its Cu(II), Mn(II) and Ag(I) complexes," Biometals, vol. 16, pp. 321-329, 2003.
[49] P. R. Rich, A. L. Moore, and W. D. Bonner, Jr, "The effects of bathophenanthroline, bathophenanthrolinesulphonate and 2- thenoyltrifluoroacetone on mung-bean mitochondria and submitochondrial particles," Biochemical Journal, vol. 162, pp. 205-208, 1977.
[50] H. J. Harmon and F. L. Crane, "Inhibition of mitochondrial electron transport by hydrophilic metal chelators. Determination of dehydrogenase topography," Biochimica et Biophysica Acta, vol. 440, pp. 45-58, 1976.
[51] N. Schnell and K. D. Entian, "Identification and characterization of a Saccharomyces cerevisiae gene (PAR1) conferring resistance to iron chelators," European Journal of Biochemistry, vol. 200, pp. 487-493, 1991.