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Journal of Chemistry
Volume 2013, Article ID 473153, 7 pages
http://dx.doi.org/10.1155/2013/473153
Research Article

Antimicrobial Ionic Liquids with Fumarate Anion

School of Bioengineering, Jimei University, Xiamen 361021, China

Received 2 May 2013; Accepted 29 July 2013

Academic Editor: Tomokazu Yoshimura

Copyright © 2013 Biyan He et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. P. Wasserscheid and W. Keim, “Ionic liquids—new “solutions” for transition metal catalysis,” Angewandte Chemie, vol. 39, no. 21, pp. 3773–3789, 2000. View at Google Scholar · View at Scopus
  2. R. D. Rogers and K. R. Seddon, “Ionic liquids—solvents of the future?” Science, vol. 302, no. 5646, pp. 792–793, 2003. View at Publisher · View at Google Scholar · View at Scopus
  3. J. Pernak, K. Sobaszkiewicz, and I. Mirska, “Anti-microbial activities of ionic liquids,” Green Chemistry, vol. 5, no. 1, pp. 52–56, 2003. View at Publisher · View at Google Scholar · View at Scopus
  4. J. Pernak and A. Skrzypczak, “3-alkylthiomethyl-1-ethylimidazolium chlorides. Correlation between critical micelle concentrations and minimum inhibitory concentrations,” European Journal of Medicinal Chemistry, vol. 31, no. 11, pp. 901–903, 1996. View at Publisher · View at Google Scholar · View at Scopus
  5. M. Mora-Pale, L. Meli, T. V. Doherty, R. J. Linhardt, and J. S. Dordick, “Room temperature ionic liquids as emerging solvents for the pretreatment of lignocellulosic biomass,” Biotechnology and Bioengineering, vol. 108, no. 6, pp. 1229–1245, 2011. View at Publisher · View at Google Scholar · View at Scopus
  6. G. Ou, J. Yang, B. He, and Y. Yuan, “Buffer-mediated activation of Candida antarctica lipase B dissolved in hydroxyl-functionalized ionic liquids,” Journal of Molecular Catalysis B, vol. 68, no. 1, pp. 66–70, 2011. View at Publisher · View at Google Scholar · View at Scopus
  7. G. Ou, L. Xu, B. He, and Y. Yuan, “Enhanced stability of charged dendrimer-encapsulated Pd nanoparticles in ionic liquids,” Chemical Communications, no. 35, pp. 4210–4212, 2008. View at Publisher · View at Google Scholar · View at Scopus
  8. G.-N. Ou, M.-X. Zhu, J.-R. She, and Y.-Z. Yuan, “Ionic liquid buffers: a new class of chemicals with potential for controlling pH in non-aqueous media,” Chemical Communications, no. 44, pp. 4626–4628, 2006. View at Publisher · View at Google Scholar · View at Scopus
  9. D. Demberelnyamba, K.-S. Kim, S. Choi et al., “Synthesis and antimicrobial properties of imidazolium and pyrrolidinonium salts,” Bioorganic and Medicinal Chemistry, vol. 12, no. 5, pp. 853–857, 2004. View at Publisher · View at Google Scholar · View at Scopus
  10. J. Pernak, I. Goc, and I. Mirska, “Anti-microbial activities of protic ionic liquids with lactate anion,” Green Chemistry, vol. 6, no. 7, pp. 323–329, 2004. View at Publisher · View at Google Scholar · View at Scopus
  11. K. M. Docherty and C. F. Kulpa, “Toxicity and antimicrobial activity of imidazolium and pyridinium ionic liquids,” Green Chemistry, vol. 7, no. 4, pp. 185–189, 2005. View at Publisher · View at Google Scholar · View at Scopus
  12. M. T. Garcia, N. Gathergood, and P. J. Scammells, “Biodegradable ionic liquids—part 2. Effect of the anion and toxicology,” Green Chemistry, vol. 7, no. 1, pp. 9–14, 2005. View at Publisher · View at Google Scholar · View at Scopus
  13. J. Pernak, J. Feder-Kubis, A. Cieniecka-Rosłonkiewicz, C. Fischmeister, S. T. Griffin, and R. D. Rogers, “Synthesis and properties of chiral imidazolium ionic liquids with a (1R,2S,5R)-(−)-menthoxymethyl substituent,” New Journal of Chemistry, vol. 31, no. 6, pp. 879–892, 2007. View at Publisher · View at Google Scholar · View at Scopus
  14. K. Poole, “Overcoming antimicrobial resistance by targeting resistance mechanisms,” Journal of Pharmacy and Pharmacology, vol. 53, no. 3, pp. 283–294, 2001. View at Publisher · View at Google Scholar · View at Scopus
  15. V. Roy, B. L. Adams, and W. E. Bentley, “Developing next generation antimicrobials by intercepting AI-2 mediated quorum sensing,” Enzyme and Microbial Technology, vol. 49, no. 2, pp. 113–123, 2011. View at Publisher · View at Google Scholar · View at Scopus
  16. M. Ferrer, J. Soliveri, F. J. Plou et al., “Synthesis of sugar esters in solvent mixtures by lipases from Thermomyces lanuginosus and Candida antarctica B, and their antimicrobial properties,” Enzyme and Microbial Technology, vol. 36, no. 4, pp. 391–398, 2005. View at Publisher · View at Google Scholar · View at Scopus
  17. A. Skrzypczak, B. Brycki, I. Mirska, and J. Pernak, “Synthesis and antimicrobial activities of new quats,” European Journal of Medicinal Chemistry, vol. 32, no. 7-8, pp. 661–668, 1997. View at Publisher · View at Google Scholar · View at Scopus
  18. A. M. Hassan, A. M. Nassar, Y. Z. Hussien, and A. N. Elkmash, “Synthesis, characterization and biological evaluation of Fe (III), Co (II), Ni(II), Cu(II), and Zn(II) complexes with tetradentate schiff base ligand derived from protocatechualdehyde with 2-aminophenol,” Applied Biochemistry and Biotechnology, vol. 167, pp. 581–594, 2012. View at Google Scholar
  19. K. P. Deepa and K. K. Aravindakshan, “Synthesis, characterization, and antifungal studies of transition metal complexes of ω-bromoacetoacetanilide isonicotinylhydrazone,” Applied Biochemistry and Biotechnology Part A, vol. 118, no. 1-3, pp. 283–292, 2004. View at Publisher · View at Google Scholar · View at Scopus
  20. M. Diz, A. Manresa, A. Pinazo, P. Erra, and M. R. Infante, “Synthesis, surface active properties and antimicrobial activity of new bis quaternary ammonium compounds,” Journal of the Chemical Society, Perkin Transactions 2, no. 8, pp. 1871–1876, 1994. View at Google Scholar · View at Scopus
  21. G. Elegir, A. Kindl, P. Sadocco, and M. Orlandi, “Development of antimicrobial cellulose packaging through laccase-mediated grafting of phenolic compounds,” Enzyme and Microbial Technology, vol. 43, no. 2, pp. 84–92, 2008. View at Publisher · View at Google Scholar · View at Scopus
  22. J. Pernak, I. Mirska, and R. Kmiecik, “Antimicrobial activities of new analogues of benzalkonium chloride,” European Journal of Medicinal Chemistry, vol. 34, no. 9, pp. 765–771, 1999. View at Publisher · View at Google Scholar · View at Scopus
  23. J. Joseph and K. Nagashri, “Novel copper-based therapeutic agent for anti-inflammatory: synthesis, characterization, and biochemical activities of copper(II) complexes of hydroxyflavone Schiff bases,” Applied Biochemistry and Biotechnology, vol. 167, pp. 1446–1458, 2012. View at Google Scholar
  24. M. Dymicky, M. Bencivengo, R. L. Buchanan, and J. L. Smith, “Inhibition of Clostridium botulinum 62A by fumarates and maleates and relationship of activity to some physicochemical constants,” Applied and Environmental Microbiology, vol. 53, no. 1, pp. 110–113, 1987. View at Google Scholar · View at Scopus
  25. M. N. Islam, “Antimicrobial agents added to animal feeds,” US patent 4346118, 1982.
  26. W. Zecher and R. Merten, “Process for the preparation of fumaric acid monoesters,” US patent 4515974, 1985.
  27. J. J. Gavin, “Analytical microbiology—II. The diffusion methods,” Applied Microbiology, vol. 5, no. 1, pp. 25–33, 1957. View at Google Scholar · View at Scopus
  28. W. H. Schmidt and A. J. Moyer, “Penicillin—I. Methods of assay,” Journal of Bacteriology, vol. 47, pp. 199–209, 1944. View at Google Scholar
  29. M. Świtała-Zeliazkow, “Thermal degradation of copolymers of styrene with dicarboxylic acids—II: copolymers obtained by radical copolymerisation of styrene with maleic acid or fumaric acid,” Polymer Degradation and Stability, vol. 91, no. 6, pp. 1233–1239, 2006. View at Publisher · View at Google Scholar · View at Scopus
  30. J. G. Huddleston, A. E. Visser, W. M. Reichert, H. D. Willauer, G. A. Broker, and R. D. Rogers, “Characterization and comparison of hydrophilic and hydrophobic room temperature ionic liquids incorporating the imidazolium cation,” Green Chemistry, vol. 3, no. 4, pp. 156–164, 2001. View at Publisher · View at Google Scholar · View at Scopus
  31. L. C. Branco, J. N. Rosa, J. J. M. Ramos, and C. A. M. Afonso, “Preparation and characterization of new room temperature ionic liquids,” Chemistry, vol. 8, pp. 3671–3677, 2002. View at Google Scholar
  32. Z. Baker, R. W. Harrison, and B. F. Miller, “Action of synthetic detergents on the metabolism of bacteria,” The Journal of Experimental Method, vol. 73, pp. 249–271, 1941. View at Google Scholar
  33. T. J. Schmidt, M. Ak, and U. Mrowietz, “Reactivity of dimethyl fumarate and methylhydrogen fumarate towards glutathione and N-acetyl-l-cysteine-preparation of s-substituted thiosuccinic acid esters,” Bioorganic and Medicinal Chemistry, vol. 15, no. 1, pp. 333–342, 2007. View at Publisher · View at Google Scholar · View at Scopus
  34. E. Lueck, M. Jager, and S. F. Laichena, Antimicrobial Food Additives: Characteristics, Uses, Effects, Springer, Berlin, Germany, 1997.
  35. E. Freese, C. W. Sheu, and E. Galliers, “Function of lipophilic acids as antimicrobial food additives,” Nature, vol. 241, no. 5388, pp. 321–325, 1973. View at Publisher · View at Google Scholar · View at Scopus
  36. M. Dymicky, M. Bencivengo, R. L. Buchanan, and J. L. Smith, “Inhibition of Clostridium botulinum 62A by fumarates and maleates and relationship of activity to some physicochemical constants,” Applied and Environmental Microbiology, vol. 53, no. 1, pp. 110–113, 1987. View at Google Scholar · View at Scopus
  37. C. Morán, P. Clapés, F. Comelles et al., “Chemical structure/property relationship in single-chain arginine surfactants,” Langmuir, vol. 17, no. 16, pp. 5071–5075, 2001. View at Publisher · View at Google Scholar · View at Scopus
  38. T. J. Franklin and G. A. Snow, Biochemistry of Antimicrobial Action, Chapman and Hall, London, UK, 1985.
  39. R. T. W. Huang, K. C. Peng, H. N. Shih et al., “Antimicrobial properties of ethoxyether-functionalized imidazolium salts,” Soft Matter, vol. 7, no. 18, pp. 8392–8400, 2011. View at Publisher · View at Google Scholar · View at Scopus