1-Alkyl-(N,N-dimethylamino)pyridinium bromides: Inhibitory effect on virulence factors of Candida albicans and on the growth of bacterial pathogens

Journal of Medical Microbiology

Volumn 62, Issue PART 2, 2013, Pages 241-248

  Sundararaman, Muthuraman ^a   Kumar, Radhakrishnan Rajesh ^a   Venkatesan, Perumal ^a   Ilangovan, Andivelu ^a  

^a BHARATHIDASAN UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

1 ALKYL (N,N DIMETHYLAMINO)PYRIDINIUM BROMIDE DERIVATIVE; ANTIBIOTIC AGENT; ANTIFUNGAL AGENT; ASPARTIC PROTEINASE; STREPTOMYCIN; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; BACTERIAL GROWTH; BACTERIAL STRAIN; CANDIDA; CANDIDA ALBICANS; CANDIDA GLABRATA; CANDIDA KRUSEI; CANDIDA TROPICALIS; CRYPTOCOCCUS NEOFORMANS; DISK DIFFUSION; DRUG STRUCTURE; DRUG SYNTHESIS; ESCHERICHIA COLI; HEMOLYSIS; MYCOBACTERIUM SMEGMATIS; NONHUMAN; PRIORITY JOURNAL; PROTEUS MIRABILIS; SALMONELLA TYPHI; STAPHYLOCOCCUS AUREUS; VIBRIO CHOLERAE;

ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; BACTERIA; CANDIDA ALBICANS; CRYPTOCOCCUS NEOFORMANS; DRUG RESISTANCE, MULTIPLE, BACTERIAL; DRUG RESISTANCE, MULTIPLE, FUNGAL; ESCHERICHIA COLI; MICROBIAL SENSITIVITY TESTS; MYCOBACTERIUM SMEGMATIS; PROTEUS MIRABILIS; PYRIDINIUM COMPOUNDS; SALMONELLA TYPHI; STAPHYLOCOCCUS AUREUS; VIBRIO CHOLERAE;

EID: 84872711789     PISSN: 00222615     EISSN: None     Source Type: Journal    
DOI: 10.1099/jmm.0.050070-0     Document Type: Article

References (39)

1. Alptüzün, V., Parlar, S., Taşli, H. & Erciyas, E. (2009). Synthesis and antimicrobial activity of some pyridinium salts. Molecules 14, 5203-5215.
2. Anwar, Kosuge, H., Okada, S., Oikawa, H. & Nakanishi, H. (2001). 4-(Dimethylamino)-1-ethylpyridinium iodide: a new colorless organic ionic crystal for second-order nonlinear optics. Jpn J Appl Phys 40 (Part 1, No. 6A), 4213-4216.
3. Arning, J., Stolte, S., Boschen, A., Stock, F., Pitner, W. R., Welz-Biermann, U., Jastorff, B. & Ranke, J. (2008). Qualitative and quantitative structure activity relationships for the inhibitory effects of cationic head groups, functionalised side chains and anions of ionic liquids on acetylcholinesterase. Green Chem 10, 47-58.
4. Bauer, A. W., Kirby, W. M. M., Sherris, J. C. & Turck, M. (1966). Antibiotic susceptibility testing by a standardized single disk method. Am J Clin Pathol 45, 493-496.
5. CLSI (2006). Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically, 7th edn. Approved standard M7-A7. Wayne, PA: Clinical and Laboratory Standards Institute.
6. CLSI (2008). Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts, 3rd edn. Approved standard M27-A3. Wayne, PA: Clinical and Laboratory Standards Institute.
7. Costa, C. R., Jesuíno, R. S., de Aquino Lemos, J., de Fátima Lisboa Fernandes, O., Hasimoto e Souza, L. K., Passos, X. S. & do Rosário Rodrigues Silva, M. (2010). Effects of antifungal agents in sap activity of Candida albicans isolates. Mycopathologia 169, 91-98.
8. Denny, B. J., Novotny, L., West, P. W., Blesova, M. & Zamocka, J. (2005). Antimicrobial activity of a series of 1-alkyl-2-(4-pyridyl)pyridinium bromides against Gram-positive and Gram-negative bacteria. Med Princ Pract 14, 377-381.
9. Ellepola, A. N. & Samaranayake, L. P. (1998). The effect of limited exposure to antifungal agents on the germ tube formation of oral Candida albicans. J Oral Pathol Med 27, 213-219.
10. Ezaki, S & Kokeguchi, N. (2006). Liquid crystal display medium containing bipolar fine particles. Kokai Tokkyo Koho, Japanese patent JP 2006171518.
11. Fábry, S., Gáborová, S., Bujdáková, H., Klobusický, M., Volleková, A. & Kuchta, T. (1999). Inhibition of germ tube formation, filamentation and ergosterol biosynthesis in Candida albicans treated with 6-amino-2-n-pentylthiobenzothiazole. Folia Microbiol (Praha) 44, 523-526.
12. Gama, Y., Suzuki, H. & Narasaki, H. (1981). Aminopyridine derivative and surface active agent comprising it. Japanese patent JP 56139463.
13. Holy, J., Kolomitsyna, O., Krasutsky, D., Oliveira, P. J., Perkins, E. & Krasutsky, P. A. (2010). Dimethylaminopyridine derivatives of lupane triterpenoids are potent disruptors of mitochondrial structure and function. Bioorg Med Chem 18, 6080-6088.
14. Hough-Troutman, W. L., Smiglak, M., Griffin, S., Reichert, W. M., Mirska, I., Jodynis-Liebert, J., Adamska, T., Nawrot, J., Stasiewicz, M. & other authors (2009). Ionic liquids with dual biological function: sweet and anti-microbial, hydrophobic quaternary ammonium-based salts. New J Chem 33, 26-33.
15. Ilangovan, A., Venkatesan, P., Sundararaman, M. & Rajesh Kumar, R. (2012). Synthesis, characterization and antimicrobial activity of 4-amino-1-alkylpyridinium salts. Med Chem Res 21, 694-702.
16. Kabara, J. J. (1978). Structurefunction relationships of surfactants as antimicrobial agents. J Soc Cosmet Chem 29, 733-741.
17. Kadir, T., Gümrü, B. & Uygun-Can, B. (2007). Phospholipase activity of Candida albicans isolates from patients with denture stomatitis: the influence of chlorhexidine gluconate on phospholipase production. Arch Oral Biol 52, 691-696.
18. Kupetis, G. K., Saduikis, G., Nivinskiene, O. & Eicher-Lorka, O. (2002). 1-Alkyl-4-dialkylaminopyridinium halides as phase-transfer catalysts in dichlorocarbene reactions. Monatsh Chem 133, 313-321.
19. Lyon, J. P., dos Santos, F. V., de Moraes, P. C. & Moreira, L. M. (2011). Inhibition of virulence factors of Candida spp. by different surfactants. Mycopathologia 171, 93-101.
20. Madaan, P. & Tyagi, V. K. (2008). Quaternary pyridinium salts: a review. J Oleo Sci 57, 197-215.
21. McDonnell, G. & Russell, A. D. (1999). Antiseptics and disinfectants: activity, action, and resistance. Clin Microbiol Rev 12, 147-179.
22. Muldoon, M., Brennecke, J. F., Maginn, E. J., Scriven, E. F. V., McAteer, C. H. & Murugan, R. (2010). Aminopyridinium ionic liquids. US patent 7687513, B1 20100330.
23. Neumann, J., Grundmann, O., Thöming, J., Schulte, M. & Stolte, S. (2010). Anaerobic biodegradability of ionic liquid cations under denitrifying condition. Green Chem 12, 620-627.
24. Ng, C. K. L., Obando, D., Widmer, F., Wright, L. C., Sorrell, T. C. & Jolliffe, K. A. J. (2006). Correlation of antifungal activity with fungal phospholipase inhibition using a series of bisquaternary ammonium salts. J Med Chem 49, 811-816.
25. Obando, D., Pantarat, N., Handke, R., Koda, Y., Widmer, F., Djordjevic, J. T., Ellis, D. H., Sorrell, T. C. & Jolliffe, K. A. (2009). Synthesis, antifungal, haemolytic and cytotoxic activities of a series of bis(alkylpyridinium)alkanes. Bioorg Med Chem 17, 6329-6339.
26. Patel, M., Gulube, Z. & Dutton, M. (2009). The effect of Dodonaea viscosa var. angustifolia on Candida albicans proteinase and phospholipase production and adherence to oral epithelial cells. J Ethnopharmacol 124, 562-565.
27. Petkovic, M., Seddon, K. R., Rebelo, L. P. & Silva Pereira, C. (2011). Ionic liquids: a pathway to environmental acceptability. Chem Soc Rev 40, 1383-1403.
28. Rajeshkumar, R. & Sundararaman, M. (2012). Emergence of Candida spp. and exploration of natural bioactive molecules for anticandidal therapy-status quo. Mycoses 55, e60-e73.
29. Samaranayake, L. P., Raeside, J. M. & MacFarlane, T. W. (1984). Factors affecting the phospholipase activity of Candida species in vitro. Sabouraudia 22, 201-207.
30. Sarkunam, K. & Nallu, M. (2004). Polymethylene bis(4-dimethylaminopyridinium bromide): synthesis, electrochemical and biological investigation. J Indian Chem Soc 81, 978-980.
31. Sayes, C. M., Reed, K. L. & Warheit, D. B. (2007). Assessing toxicity of fine and nanoparticles: comparing in vitro measurements to in vivo pulmonary toxicity profiles. Toxicol Sci 97, 163-180.
32. Schaller, M., Krnjaic, N., Niewerth, M., Hamm, G., Hube, B. & Korting, H. C. (2003). Effect of antimycotic agents on the activity of aspartyl proteinases secreted by Candida albicans. J Med Microbiol 52, 247-249.
33. Schaller, M., Borelli, C., Korting, H. C. & Hube, B. (2005). Hydrolytic enzymes as virulence factors of Candida albicans. Mycoses 48, 365-377.
34. Sugita, T., Kurosaka, S., Yajitate, M., Sato, H. & Nishikawa, A. (2002). Extracellular proteinase and phospholipase activity of three genotypic strains of a human pathogenic yeast, Candida albicans. Microbiol Immunol 46, 881-883.
35. Thorsteinsson, T., Másson, M., Kristinsson, K. G., Hjálmarsdóttir, M. A., Hilmarsson, H. & Loftsson, T. (2003). Soft antimicrobial agents: synthesis and activity of labile environmentally friendly long chain quaternary ammonium compounds. J Med Chem 46, 4173-4181.
36. Timm, C., Mordhorst, T. & Köck, M. (2010). Synthesis of 3-alkyl pyridinium alkaloids from the arctic sponge Haliclona viscosa. Mar Drugs 8, 483-497.
37. Vuillaume, P. Y., Brunelle, M., Bazuin, C. G., Talbot, B. G., Bégin, A., Van Calsteren, M.-R. & Laurent-Lewandowski, S. (2009). Tail-end amphiphilic dimethylaminopyridinium-containing polymethacrylates for gene delivery. New J Chem 33, 1941-1950.
38. Yamamoto, E., Yamaguchi, S. & Nagamune, T. (2011). Protein refolding by N-alkylpyridinium and N-alkyl-N-methylpyrrolidinium ionic liquids. Appl Biochem Biotechnol 164, 957-967.
39. Zhao, T. & Sun, G. (2008). Hydrophobicity and antimicrobial activities of quaternary pyridinium salts. J Appl Microbiol 104, 824-830.