Home Alkyl glycosides as potential anti-Candida albicans growth agents
Article
Licensed
Unlicensed Requires Authentication

Alkyl glycosides as potential anti-Candida albicans growth agents

  • Tomáš Klunda , Eva Machová , Alžbeta Čížová , Radim Horák , Monika Poláková EMAIL logo and Slavomír Bystrický
Published/Copyright: April 22, 2016
Become an author with De Gruyter Brill

Abstract

Candida infections are becoming increasingly prevalent and many clinical isolates are resistant to common azole derivatives treatment. Accordingly, the capacity of a series of 19 alkyl glycosides, mainly mannosides and glucosides but also a cellobioside with aglycone chain-length from C-6 to C-20, to inhibit the growth of laboratory and clinically isolated strains of Candida albicans, was investigated. The study showed that only glycosides with the C-10 and C-12 aglycones were effective growth inhibitors of both types of Candida strains, whose metabolic activity was also significantly reduced as revealed by an XTT assay.

Acknowledgements

This work was supported by the Slovak Research and Development Agency (project no. APVV-0484-12), the Scientific Grant Agency of the Ministry of Education of the Slovak Republic and the Slovak Academy of Sciences (project nos. VEGA-2/0064/15 and 2/0026/13), and by the European Social Fund (project no. CZ. 1.07/2.4.00/31.0130) and IGA (IGAPrF2014026)

References

Adasch, V., Hoffmann, B., Milius, W., Platz, G., & Voss, G. (1998). Preparation of alkyl α- and β-D-glucopyranosides, thermotropic properties and X-ray analysis. Carbohydrate Research, 314, 177-187. DOI: 10.1016/s0008-6215(98)00302-4. 10.1016/s0008-6215(98)00302-4Search in Google Scholar

Boyd, B. J., Drummond, C. J., Krodkiewska, I., & Grieser, F. (2000). How chain length, headgroup polymerization, and anomeric configuration govern the thermotropic and ly-otropic crystalline phase behavior and the air-water interfacial adsorption of glucose-based surfactants. Langmuir, 16, 7359-7367. DOI: 10.1021/la991573w.10.1021/la991573wSearch in Google Scholar

Compain, P., & Martin, O. R. (2001). Carbohydrate mimetics-based glycosyltransferase inhibitors. Bioorganic & Medicinal Chemistry, 9, 3077-3092. DOI: 10.1016/s0968-0896(01) 00176-6.10.1016/s0968-0896(01) 00176-6Search in Google Scholar

Feigel, M., Ladberg, R., Winter, M., Blaeser, D., & Boese, R. (2006). Synthesis and structure of macrolactams of 3α-aminodeoxycholanic acid. European Journal of Organic Chemistry, 2, 371-377. DOI: 10.1002/ejoc.200500408.10.1002/ejoc.200500408Search in Google Scholar

Karthaus, O., Shoda, S. I., Takano, H., Obata, K., & Kobayashi, S. J. (1994). Cellulase-catalyzed glycosylation reactions: simple route towards a highly selective synthesis of oligosaccharides. Journal of Chemical Society, Perkin Transaction 1, 13, 1851-1857. DOI: 10.1039/p19940001851.10.1039/p19940001851Search in Google Scholar

Koto, S., Hirooka, M., Tashiro, T., Sakashita, M., Hatachi, M., Kono, T., Shimizu, M., Yoshida, N., Kurasawa, S., Sakuma, N., Sawazaki, S., Takeuchi, A., Shoya, N., & Nakamura, E. (2004). Simple preparations of alkyl and cycloalkyl α-glycosides of maltose, cellobiose, and lactose. Carbohydrate Research, 339, 2415-2424. DOI: 10.1016/j.carres.2004.07.016.10.1016/j.carres.2004.07.016Search in Google Scholar PubMed

Kuhn, D. M., Balkis, M., Chandra, J., Mukherjee, P. K., & Ghannoum, M. A. (2003). Uses and limitations of the XTT assay in studies of Candida growth and metabolism. Journal of Clinical Microbiology, 41, 506-508. DOI: 10.1128/jcm.41. 1.506-508.2003.10.1128/jcm.41. 1.506-508.2003Search in Google Scholar

Machová, E., & Bystrický, S. (2008). Growth inhibition of Candida albicans in the presence of antiserum elicited in rabbits by mannan-protein conjugate. Zeitschrift fur Natur-forschung, 63, 909-91210.1515/znc-2008-11-1222Search in Google Scholar PubMed

Poláková, M., Beláňová, M., Petruš, L., & Mikušová, K. (2010). Synthesis of alkyl and cycloalkyl α-D-mannopyranosides and derivatives thereof and their evaluation in the mycobacterial mannosyltransferase assay. Carbohydrate Research, 345, 1339-1347. DOI: 10.1016/j.carres.2010.03.011.10.1016/j.carres.2010.03.011Search in Google Scholar PubMed

Rauter, A. P., Lucas, S., Almeida, T., Sacoto, D., Ribeiro, V., Justino, J., Neves, A., Silva, F. V. M., Oliveira, M. C., Ferreira, M. J., Santos, M. S., & Barbosa, E. (2005). Synthesis, surface active and antimicrobial properties of new alkyl 2,6-dideoxy-L-arabino-hexopyranosides. Carbohydrate Research, 340, 191-201. DOI: 10.1016/j.carres.2004.11.020.10.1016/j.carres.2004.11.020Search in Google Scholar PubMed

Sabah, K. J., & Hashim, R. (2013). Novel mixed-heteroatom macrocycles via templating: a new protocol. Tetrahedron Letters, 54, 1534-1537. DOI: 10.1016/j.tetlet.2013.01.025.10.1016/j.tetlet.2013.01.025Search in Google Scholar

Schmidt-Lassen, J., & Lindhorst, T. K. (2014). Exploring the meaning of sugar configuration in a supramolecular environment: comparison of six octyl glycoside micelles by ITC and NMR spectroscopy. MedChemComm, 5, 1218-1226. DOI: 10.1039/c4md00122b.10.1039/c4md00122bSearch in Google Scholar

Silva, F. V. M., Goulart, M., Justino, J., Neves, A., Santos, F., Caio, J., Lucas, S., Newton, A., Sacoto, D., Barbosa, E., Santos, M. S., & Rauter, A. P. (2008). Alkyl deoxy-arabino-hexopyranosides: Synthesis, surface properties, and biological activities. Bioorganic & Medicinal Chemistry, 16, 4083–4092. DOI: 10.1016/j.bmc.2008.01.020.10.1016/j.bmc.2008.01.020Search in Google Scholar

van Doren, H. A., van der Geest, R., Kellogg, R. M., & Wyn-berg, H. (1989). Synthesis and liquid crystalline properties of the n-alkyl 1-thio-α-D-glucopyranosides, a new homologous series of carbohydrate mesogens. Carbohydrate Research, 194, 71-77. DOI: 10.1016/0008-6215(89)85007-4.10.1016/0008-6215(89)85007-4Search in Google Scholar

Williams, R. J., Paul, C. E., & Nitz, M. (2014). Protecting-group-free O-glycosidation using p-toluenesulfonohydrazide and glycosyl chloride donors. Carbohydrate Research, 386, 73-77. DOI: 10.1016/j.carres.2013.08.019.10.1016/j.carres.2013.08.019Search in Google Scholar PubMed

Xie, J., & Bogliotti, N. (2014). Synthesis and applications of carbohydrate-derived macrocyclic compounds. Chemical Reviews, 114, 7678-7739. DOI: 10.1021/cr400035j.10.1021/cr400035jSearch in Google Scholar PubMed

Received: 2015-6-17
Revised: 2016-2-3
Accepted: 2016-2-7
Published Online: 2016-4-22
Published in Print: 2016-9-1

© 2016 Institute of Chemistry, Slovak Academy of Sciences

Articles in the same Issue

  1. Review
  2. Plant extracts as “green” corrosion inhibitors for steel in sulphuric acid
  3. Original Paper
  4. Use of 6-O-mono-substituted derivatives of β-cyclodextrin-bearing substituent with two permanent positive charges in capillary electrophoresis
  5. Original Paper
  6. Development of ICP-MS and ICP-OES methods for determination of gadolinium in samples related to hospital waste water treatment
  7. Original Paper
  8. Alkyl glycosides as potential anti-Candida albicans growth agents
  9. Original Paper
  10. Preparation of corn stalk-based adsorbents and their specific application in metal ions adsorption
  11. Original Paper
  12. Treatment of metal-plating waste water by modified direct contact membrane distillation
  13. Original Paper
  14. Influence of pH and cationic surfactant on stability and interfacial properties of algerian bitumen emulsion
  15. Original Paper
  16. Synthesis, structural and spectroscopic properties of asymmetric schiff bases derived from 2,3-diaminopyridine
  17. Original Paper
  18. Syntheses of cardanol-based cationic surfactants and their use in emulsion polymerisation
  19. Original Paper
  20. Synthesis of urethane—acrylic multi-block copolymers via electrochemically mediated ATRP
  21. Original Paper
  22. Diazene sulphonate as a cross-linking agent for polymers with pendant triarylamine hole-conducting units
  23. Original Paper
  24. Leaching test for calcined kaolinite and kaolinite/TiO2 photoactive composite
  25. Original Paper
  26. Chitosan sponge matrices with β-cyclodextrin for berberine loadinging
  27. Original Paper
  28. Ageing of plasticized poly(lactic acid)/poly(β-hydroxybutyrate) blend films under artificial UV irradiation and under real agricultural conditions during their application as mulches
  29. Original Paper
  30. Synthesis, in-vitro cytotoxicity of 4H-benzo[h]chromene derivatives and structure–activity relationships of 4-aryl group and 3-, 7-positions
  31. Original Paper
  32. Chemoselective synthesis of 1,2-disubstituted benzimidazoles in lactic acid without additive
  33. Original Paper
  34. Sorption properties of sheep wool irradiated by accelerated electron beam
Downloaded on 27.10.2025 from https://www.degruyterbrill.com/document/doi/10.1515/chempap-2016-0051/html
Scroll to top button