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Synthesis, interfacial properties, and antimicrobial activity of a new cationic gemini surfactant

  • Maneedaeng, Atthaphon (School of Chemical Engineering, Institute of Engineering, Suranaree University of Technology) ;
  • Phoemboon, Sakonwan (School of Chemical Engineering, Institute of Engineering, Suranaree University of Technology) ;
  • Chanthasena, Panjamaphon (Faculty of Medical Science, Nakhon Ratchasima College) ;
  • Chudapongse, Nuannoi (School of Preclinical Sciences, Institute of Science, Suranaree University of Technology)
  • 투고 : 2018.05.13
  • 심사 : 2018.07.26
  • 발행 : 2018.11.30

초록

Tetramethylene-1,4-bis(N,N-dodecylammonium bromide), cationic gemini surfactant, (12-4-12) was first synthesized with an one-step and shortened procedure and its interfacial and antimicrobial properties were compared with a conventional single-chain cationic surfactant, cetyltrimethylammonium bromide (CTAB). The interfacial and thermodynamic properties of both surfactants reveal that critical micelle concentration (CMC) of this novel synthetic cationic dimeric surfactant is lower than that of cationic monomeric surfactant at almost 15 times of its magnitude, which is due to the increase in hydrophobicity of the surfactant molecules by having dual hydrocarbon chains. In comparison with CTAB, the produced compound 12-4-12 yields much better interfacial and thermodynamic properties. The antimicrobial activities of the synthesized gemini surfactant were tested against eight strains of bacteria, as well as two strains of fungi. The results showed that both 12-4-12 compound and CTAB exhibited higher inhibitory effects on the growth of Gram-positive bacteria and fungi than that of Gram-negative bacteria. The minimum inhibitory concentrations in molar of 12-4-12 against all tested Gram-negative bacteria were lower than those of CTAB, which is hypothetically due to the lower HLB together with smaller CMC values of our gemini surfactant.

키워드

과제정보

연구 과제 주관 기관 : Thailand Research Fund (TRF)

참고문헌

  1. A. Colomer, A. Pinazo, M. A. Manresa, M. P. Vinardell, M. Mitjans, M. R. Infante and L. Perez, J. Med. Chem., 54, 989 (2011). https://doi.org/10.1021/jm101315k
  2. D. N. Rubingh and P. M. Holland, Cationic surfactant: Physical chemistry; Surfactant Science Series 37, Marcel Dekker, New York (1991).
  3. T. Geng, C. Zhang, Y. Jiang, H. Ju and Y. Wang, J. Mol. Liq., 232, 36 (2017). https://doi.org/10.1016/j.molliq.2017.02.055
  4. M. J. Rosen and J. T. Kunjappu, Surfactants and interfacial phenomena, Wiley, New Jersey (2012).
  5. V. Pradines, C. Bijani, J. L. Stigliani, M. Blanzat, I. Rico-Lattes and G. Pratviel, ChemPhysChem, 16, 3877 (2015). https://doi.org/10.1002/cphc.201500783
  6. M. Lechuga, M. Fernandez-Serrano, E. Jurado, J. Nunez-Olea and F. Rios, Ecotoxicol. Environ. Saf., 125, 1 (2016). https://doi.org/10.1016/j.ecoenv.2015.11.027
  7. M. G. Mondal and A. P. Pratap, J. Oleo Sci., 65, 663 (2016). https://doi.org/10.5650/jos.ess15276
  8. L. Zhi, Q. Li, Y. Sun and S. Yao, J. Surfactants Deterg., 19, 337 (2016). https://doi.org/10.1007/s11743-015-1773-8
  9. M.C. Galan-Jimenez, E. Gomez-Pantoja, E. Morillo and T. Undabeytia, Sci. Total Environ., 538, 262 (2015). https://doi.org/10.1016/j.scitotenv.2015.08.008
  10. M. Ronald and F. P. Luis, Constr. Build. Mater., 123, 162 (2016). https://doi.org/10.1016/j.conbuildmat.2016.06.129
  11. M. A. Hegazy, A. Y. El-Etre, M. El-Shafaie and K. M. Berry, J. Mol. Liq., 214, 347 (2016). https://doi.org/10.1016/j.molliq.2015.11.047
  12. J. Falbe, Surfactants in consumer products: theory, technology and application, Springer-Verlag, Heidelberg (1986).
  13. Z. Huang, H. Zhong, S. Wang, L. Xia, W. Zou and G. Liu, Chem. Eng. J., 257, 218 (2014). https://doi.org/10.1016/j.cej.2014.07.057
  14. A. Donauerova, J. Bujdak, M. Smolinska and H. Bujdakova, J. Photochem. Photobiol. B, 151, 135 (2015). https://doi.org/10.1016/j.jphotobiol.2015.07.018
  15. M. A. Migahed, N. A. Negm, M. M. Shaban, T. A. Ali and A. A. Fadda, J. Surfactants Deterg., 19, 119 (2016). https://doi.org/10.1007/s11743-015-1749-8
  16. D. H. Deck and L. G. Winston, in Basic and clinical pharmacology, B. G. Katzung, S. B. Masters and A. J. Trevor, Eds., Lange Medical Books (2012).
  17. Z. Jia and W. Xu, Carbohydr. Res., 333, 1 (2001). https://doi.org/10.1016/S0008-6215(01)00112-4
  18. Y. Liu, K. Ma, R. Li, X. Ren and T. S. Huang, Cellulose, 20, 3123 (2013). https://doi.org/10.1007/s10570-013-0056-7
  19. G. C. Daniels, E. B. Iezzi and P. A. Fulmer, Prog. Org. Coat., 95, 91 (2016). https://doi.org/10.1016/j.porgcoat.2016.02.021
  20. K. Kuperkar, J. Modi and K. Patel, J. Surfactants Deterg., 15, 107 (2012). https://doi.org/10.1007/s11743-011-1269-0
  21. F. M. Menger and C. A. Littau, J. Am. Chem. Soc., 115, 10083 (1993). https://doi.org/10.1021/ja00075a025
  22. S. M. Tawfik, J. Ind. Eng. Chem., 28, 171 (2015). https://doi.org/10.1016/j.jiec.2015.02.011
  23. I. Aiad, S. M. Shaban, H. Y. Moustafa and A. Hamed, Prot. Met. Phys. Chem. Surf., 54, 135 (2018). https://doi.org/10.1134/S2070205118010173
  24. A. Pinazo, M. A. Manresa, A. M. Marques, M. Bustelo, M. J. Espuny and L. Perez, Adv. Colloid Interface Sci., 228, 17 (2016). https://doi.org/10.1016/j.cis.2015.11.007
  25. N. A. Negm and A. S. Mohamed, J. Surfactants Deterg., 11, 215 (2008). https://doi.org/10.1007/s11743-008-1071-9
  26. B. Brycki, K. Kowalczyk and A. Kozirog, Molecules, 16, 319 (2011). https://doi.org/10.3390/molecules16010319
  27. Y. Wang, Y. Han, X. Huang, M. Cao and Y. Wang, J. Colloid Interface Sci., 319, 534 (2008). https://doi.org/10.1016/j.jcis.2007.11.021
  28. F. R. Cockerill, M. A. Wikler, J. Alder, M. N. Dudley, G. M. Eliopoulos, M. J. Ferraro, D. J. Hardy, D. W. Hecht, J. A. Hindler, J. B. Patel, M. Powell, J. M. Swenson, R. B. Thomson, M. M. Traczewski, J. D. Turnidge, M. P. Weinstein and B. L. Zimmer, Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically: Approved standard - 9th Ed., Clinical and Laboratory Standards Institute, Pennsylvania (2012).
  29. J. L. Rodriguez-Tudela, M. Cuenca-Estrella, T. M. Diaz-Guerra and E. Mellado, J. Clin. Microbiol., 39, 2513 (2001). https://doi.org/10.1128/JCM.39.7.2513-2517.2001
  30. J. H. Oh, Y. J. Jeong, H. J. Koo, D. W. Park, S. C. Kang, H. V. Khoa, L. B. Le, J. H. Cho and J. Y. Lee, Molecules, 19, 3607 (2014). https://doi.org/10.3390/molecules19033607
  31. W. H. Himratul-Aznita, N. Mohd-Al-Faisal and A. R. Fathilah, J. Med. Plants Res., 5, 878 (2011).
  32. B. Senhaji, D. Ben Hmamou, R. Salghi, A. Zarrouk, B Chebli, H. Zarrok, I. Warad, B. Hammouti and S. S. Al-Deyab, Int. J. Electrochem. Sci., 8, 6033 (2013).
  33. M. Balouiri, M Sadiki and S. K. Ibnsouda, J. Pharm. Anal., 6, 71 (2016). https://doi.org/10.1016/j.jpha.2015.11.005
  34. M. M. El-Sukkary, N. O. Shaker, D. A. Ismail, S. M. Ahmed, M. F. Zaki and A. I. Awad, Egypt. J. Pet., 21, 37 (2012). https://doi.org/10.1016/j.ejpe.2012.02.006
  35. T. F. Tadros, Surfactants in agrochemicals, Marcel Dekker, New York (1994).
  36. M. J. Rosen and D. J.Tracy, J. Surfactants Deterg., 1, 547 (1998). https://doi.org/10.1007/s11743-998-0057-8
  37. A. Maneedaeng and A. E. Flood, J. Surfactants Deterg., 20, 263 (2017). https://doi.org/10.1007/s11743-016-1902-z
  38. J. T. Davies in Proceedings of 2nd International Congress Surface Activity Vol. I: Gas/Liquid and Liquid/Liquid Interface, J. H. Schulman Ed., Butterworths (1957).
  39. D. B. Miraglia, J. L. Rodriguez, R. M. Minardi and P. C. Schulz, J. Surfactants Deterg., 14, 401 (2011). https://doi.org/10.1007/s11743-010-1239-y
  40. D. Manko, A. Zdziennicka and B. Janczuk, Colloids Surf., B., 114, 170 (2014). https://doi.org/10.1016/j.colsurfb.2013.10.012
  41. T. Lu, Y. Lan, C. Liu, J. Huang and Y. Wang, J. Colloid Interface Sci., 377, 222 (2012). https://doi.org/10.1016/j.jcis.2012.03.044
  42. X. Wang, J. Wang, Y. Wang, J. Ye, H. Yan and R. K. Thomas, J. Phys. Chem. B, 107, 11428 (2003). https://doi.org/10.1021/jp035198z
  43. M. S. Borse and S. Devi, Adv. Colloid Interface Sci., 123, 387 (2006).
  44. K. Ghosh and P. Quagliotto, Indian J. Chem., Sect. A: Inorg., Bioinorg., Phys., Theor. Anal. Chem., 48, 1522 (2009).
  45. T. Tsuchido, A. Svarachorn, H. Soga and M. Takano, Antimicrob. Agents Chemother., 34, 78 (1990). https://doi.org/10.1128/AAC.34.1.78
  46. G. Wu, Q. Yang, M. Long, L. Guo, B. Li, Y. Meng, A. Zhang, H. Wang, S. Liu and L. Zou, J. Antibiot., 68, 661 (2015). https://doi.org/10.1038/ja.2015.51
  47. S. Ishikawa, Y. Matsumura, F. Yoshizako and T. Tsuchido, J. Appl. Microbiol., 92, 261 (2002). https://doi.org/10.1046/j.1365-2672.2002.01526.x
  48. M. Vaara, Antimicrob. Agents Chemother., 37, 2255 (1993). https://doi.org/10.1128/AAC.37.11.2255
  49. N. Fatma, M. Panda, Kabir-ud-Din and M. Beg, J. Mol. Liq., 222, 390 (2016). https://doi.org/10.1016/j.molliq.2016.07.044
  50. M. A. Migahed, N. A. Negm, M. M. Shaban, T. A. Ali and A. A. Fadda, J. Surfactants Deterg., 19, 119 (2015).
  51. A. Cornellas, L. Perez, F. Comelles, I. Ribosa, A. Manresa and M. T. Garcia, J. Colloid Interface Sci., 355, 164 (2011). https://doi.org/10.1016/j.jcis.2010.11.063
  52. K. Kuperkar, J. Modi and K. Patel, J. Surfactants Deterg., 15, 107 (2011).
  53. G. McDonnell and A. D. Russell, Clin. Microbiol. Rev., 12, 147 (1999). https://doi.org/10.1128/CMR.12.1.147
  54. G. Harkes, H. Van der Mei, P. Rouxhet, J. Dankert, H. Busscher and J. Feijen, Cell. Biochem. Biophys., 20, 17 (1992).
  55. M. Vaara, Microbiol. Rev., 56, 395 (1992).
  56. M. Diz, A. Manresa, A. Pinazo, P. Erra and M. Infante, J. Chem. Soc. Perkin Trans., 2, 1871 (1994).

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