화학공학소재연구정보센터
홈 로그인 로그아웃 연락처 사이트맵
Journal of Industrial and Engineering Chemistry, Vol.47, 405-414, March, 2017
DOI10.1016/j.jiec.2016.12.013  Export Citation
Synthesis, characterization and antibacterial activity of novel heterocyclic quaternary ammonium surfactants
Mahantesh Jadhav, Rahul S. Kalhapure†, Sanjeev Rambharose, Chunderika Mocktar, and Thirumala Govender†
  • Discipline of Pharmaceutical Sciences, School of Health Sciences, University of KwaZulu-Natal, Private Bag X54001, Durban 4000, South Africa
E-mail:,
This work reports two new classes of non-toxic heterocyclic quaternary ammonium surfactants (HQASs) synthesized by condensation of a series of fatty acids with 2-morpholinoethan-1-amine and pyridin-4-ylmethanamine, followed by quaternization with benzyl bromide. Their critical micelle concentration (CMC), Krafft temperature (Tk), emulsion stability and foaming properties were determined. The CMC values of HQASs ranged from 0.24 to 0.55 mM/L. In vitro antibacterial activity studies revealed that the HQASs possessing unsaturated hydrocarbon chains exhibited activity against all the tested bacteria (minimum inhibitory concentration = 31.25-500 μg/mL) whereas, those possessing saturated hydrocar-bon chains did not exhibit any activity.
Keywords:Heterocyclic;Quaternary ammonium;Cationic surfactants;Synthesis;Antibacterial activity
  1. U.S. Department of Health & Human Services. https://www.cdc.gov/drugre-sistance/. (Accessed on 14 July 2016).
  2. Nikaido H, Annu. Rev. Biochem., doi:http://dx.doi.org/10.1146/annurev.biochem.78.082907.145923.(2), 119 (2010)
  3. Abraham EP, Chain E, Rev. Infect. Dis., doi:http://dx.doi.org/10.1038/146837a0., 677 (1940)
  4. Ghumare AK, Pawar BV, Bhagwat SS, J. Surfactants Deterg., doi:http://dx.doi.org/10.1007/s11743-012-1406-4., 85 (2013)
  5. Vieira DB, Carmona-Ribeiro AM, J. Antimicrob. Chemoter., doi:http://dx.doi.org/10.1093/jac/dkl312., 58(4), 760 (2006)
  6. Prez L, Pinazo A, Garca MT, Lozano M, Manresa A, Angelet M, Vinardell MP, Mitjans M, Pons R, Infante MR, Eur. J. Med. Chem., doi:http://dx.doi.org/10.1016/j.ejmech.2008.11.003., 44(5), 1884 (2009)
  7. Pinazo A, Manresa MA, Marques AM, Bustelo M, Espuny MJ, Prez L, Adv. Colloid Interface Sci., doi:http://dx.doi.org/10.1016/j.cis.2015.11.007., 228, 17 (2016)
  8. PE, lnfante M, Diz M, Manresa A, Pinazo A, J. Chem. Soc.-Perkin Trans., 1871 (1994)
  9. Akbas H, Kocaoglu S, Boz M, Dikmen A, Colloid Polym. Sci., doi:http://dx.doi.org/10.1007/s00396-016-3905-8., 294(9), 1439 (2016)
  10. Shaban SM, Aiad I, El-Sukkary MM, Soliman EA, El-Awady MY, J. Mol. Liq., doi:http://dx.doi.org/10.1016/j.molliq.2015.03.043., 207, 256 (2015)
  11. Kourai H, Yabuhara T, Shirai A, Maeda T, Nagamune H, Eur. J. Med. Chem., doi:http://dx.doi.org/10.1016/j.ejmech.2005.10.021., 41(4), 437 (2006)
  12. Zovko Z, Gabri MV, Sepi K, Pohleven F, Jakli D, Gunde-Cimerman N, Lu Z, Edrada-Ebel R, Houssen WE, Mancini I, Defant A, Jaspars M, Turk T, Int. Biodeterior. Biodegrad., doi:http://dx.doi.org/10.1016/j.ibiod.2011.10.014., 68, 71 (2012)
  13. Alptuzun V, Parlar S, Tasli H, Erciyas E, Molecules, doi:http://dx.doi.org/10.3390/molecules14125203., 14(12), 5203 (2009)
  14. Kharitonova EV, Zhuravlev OE, Chervinets VM, Voronchikhina LI, Demidova MA, Pharm. Chem. J., doi:http://dx.doi.org/10.1007/s11094-012-0776-2., 46(5), 266 (2012)
  15. Brycki B, Dega-Szafran Z, Mirska I, Polish J. Microbiol., 59(1), 49 (2010)
  16. Bhadani A, Misono T, Singh S, Sakai K, Sakai H, Abe M, Adv. Colloid Interface Sci., doi:http://dx.doi.org/10.1016/j.cis.2016.03.005., 231, 36 (2016)
  17. Patial P, Shaheen A, Ahmad I, J. Surfactants Deterg., doi:http://dx.doi.org/10.1007/s11743-013-1472-2., 17, 253 (2014)
  18. Kanjilal S, Sunitha S, Reddy PS, Kumar KP, Murty KPK, Prasad RBN, Eur. J. Lipid Sci. Technol., doi:http://dx.doi.org/10.1002/ejlt.200800292., 111(9), 941 (2009)
  19. Bartoloni A, Bombelli C, Borocci S, Bonicelli MG, Galantini L, Giansanti L, Ierino M, Mancini G, Muschietti A, Sperduto C, J. Colloid Interface Sci., doi:http://dx.doi.org/10.1016/j.jcis.2012.09.065., 392, 297 (2013)
  20. Chauhan V, Singh S, Mishra R, Kaur G, J. Colloid Interface Sci., doi:http://dx.doi.org/10.1016/j.jcis.2014.08.029., 436, 122 (2014)
  21. Bhadani A, Okano T, Ogura T, Misono T, Sakai K, Abe M, Sakai H, Colloids Surf. A: Physicochem. Eng. Asp., doi:http://dx.doi.org/10.1016/j.colsurfa.2015.11.073., 494, 147 (2016)
  22. Botequim D, Maia J, Lino MMF, Lopes LMF, Simoes PN, Ilharco LM, Ferreira L, Langmuir, doi:http://dx.doi.org/10.1021/la300948n., 28(20), 7646 (2012)
  23. Ma X, Lee NH, Oh HJ, Kim JW, Rhee CK, Park KS, Kim SJ, Colloids Surf. A: Physicochem. Eng. Asp., doi:http://dx.doi.org/10.1016/j.colsurfa.2010.01.051., 358(1-3), 172 (2010)
  24. Castillo JA, Pinazo A, Carilla J, Infante MR, Alsina MA, Haro I, Clapes P, Langmuir, doi:http://dx.doi.org/10.1021/la036452h., 20(8), 3379 (2004)
  25. Zakharova LY, Gabdrakhmanov DR, Ibragimova AR, Vasilieva EA, Nizameev IR, Kadirov MK, Ermakova EA, Gogoleva NE, Faizullin DA, Pokrovsky AG, Korobeynikov VA, Cheresiz SV, Zuev YF, Colloids Surf. B: Biointerfaces, doi:http://dx.doi.org/10.1016/j.colsurfb.2015.12.045., 140, 269 (2016)
  26. Lmery E, Brianon S, Chevalier Y, Bordes C, Oddos T, Gohier A, Bolzinger MA, Colloids Surf. A: Physicochem. Eng. Asp., doi:http://dx.doi.org/10.1016/j.colsurfa.2015.01.019., 469, 166 (2015)
  27. Kitahara T, Koyama N, Matsuda J, Aoyama Y, Hirakata Y, Kamihira S, Kohno S, Nakashima M, Sasaki H, Biol. Pharm. Bull., doi:http://dx.doi.org/10.1248/bpb.27.1321., 27(Septemb), 1321 (2004)
  28. Zheng CJ, Yoo JS, Lee TG, Cho HY, Kim YH, Kim WG, Febs Lett., doi:http://dx.doi.org/10.1016/j.febslet.2005.08.028., 579(23), 5157 (2005)
  29. Kalhapure RS, Mocktar C, Sikwal DR, Sonawane SJ, Kathiravan MK, Skelton A, Govender T, Colloids Surf. B: Biointerfaces, doi:http://dx.doi.org/10.1016/j.colsurfb.2014.02.045., 117, 303 (2014)
  30. Desbois AP, Lawlor KC, Mar. Drugs, doi:http://dx.doi.org/10.3390/md11114544., 11(11), 4544 (2013)
  31. Dilika F, Bremner PD, Meyer JJM, Fitoterapia, doi:http://dx.doi.org/10.1016/S0367-326X(00)00150-7., 71(4), 450 (2000)
  32. Huang CM, Chen CH, Pornpattananangkul D, Zhang L, Chan M, Hsieh MF, Zhang L, Biomaterials, doi:http://dx.doi.org/10.1016/j.biomaterials.2010.08.076., 32(1), 214 (2011)
  33. Sonawane SJ, Kalhapure RS, Jadhav M, Rambharose S, Mocktar C, Govender T, RSC Adv., doi:http://dx.doi.org/10.1039/C5RA16248C., 5(110), 90482 (2015)
  34. Suleman N, Kalhapure RS, Mocktar C, Rambharose S, Singh M, Govender T, RSC Adv., doi:http://dx.doi.org/10.1039/C5RA03179F., 5(44), 34967 (2015)
  35. Rambharose S, Kalhapure RS, Akamanchi KG, Govender T, J. Mater. Chem. B, doi:http://dx.doi.org/10.1039/C5TB00957J., 3(32), 6662 (2015)
  36. Xu D, Qi B, Fang D, Zhang X, Zhang T, J. Surfactants Deterg., doi:http://dx.doi.org/10.1007/s11743-015-1752-0., 19(1), 91 (2016)
  37. Kalhapure RS, Akamanchi KG, J. Surfactants Deterg., http://dx.doi.org/10.1007/s11743-015-1678-6., 18(3), 537 (2015)
  38. Tawfik SM, J. Ind. Eng. Chem., doi:http://dx.doi.org/10.1016/j.jiec.2015.02.011., 28, 171 (2015)
  39. Sayed GH, Ghuiba FM, Abdou MI, Badr EAA, Tawfik SM, Negm NAM, Colloids Surf. A: Physicochem. Eng. Asp., doi:http://dx.doi.org/10.1016/j.colsurfa.2011.11.006., 393, 96 (2012)
  40. Seedat N, Kalhapure RS, Mocktar C, Vepuri S, Jadhav M, Soliman M, Govender T, Mater. Sci. Eng. C-Biomimetic Supramol. Syst., doi:http://dx.doi.org/10.1016/j.msec.2015.12.053., 61, 616 (2016)
  41. Tadros TF, General classification of surfactants, An Introduction to Surfactants, Walter de Gruyter, 2014 (Chapter 2).
  42. Chang C, Zhang AQ, Kagan DB, Liu H, Hutnik CML, Clin. Exp. Ophthalmol., doi:http://dx.doi.org/10.1111/ceo.12390., 43(2), 16 (2015)
  43. Adriaens E, Dierckens K, Bauters TGM, Nelis HJ, Van Goethem F, Vanparys P, Remon JP, Pharm. Res., doi:http://dx.doi.org/10.1023/A:1010928025753., 18, 937 (2001)
  44. Uematsu M, Kumagami T, Shimoda K, Kusano M, Teshima M, Sasaki H, Kitaoka T, Cornea, doi:http://dx.doi.org/10.1097/ICO.0-b013e3181dc81b6., 29(11), 1296 (2010)
  45. Cao XL, Cheng C, Ma YL, Zhao CS, J. Mater. Sci. -Mater. Med., doi:http://dx.doi.org/10.1007/s10856-010-4133-2., 21(10), 2861 (2010)
  46. Kalhapure RS, Sonawane SJ, Sikwal DR, Jadhav M, Rambharose S, Mocktar C, Govender T, Colloids Surf. B: Biointerfaces, doi:http://dx.doi.org/10.1016/j.colsurfb.2015.10.003., 136, 651 (2015)
  47. Grant RL, Yao C, Gabaldon D, Acosta D, Toxicology, http://dx.doi.org/10.1016/0300-483X(92)90162-8., 76(2), 153 (1992)
  48. Hrab A, Antoni F, Szab MT, Bull. Environ. Contam. Toxicol., 28, 504 (1982)
  49. Comer J, Tam K, Pharmacokinet. Optim. Drug Res., doi:http://dx.doi.org/10.1002/9783906390437.ch17., 275 (2001)
  50. Shargel L, Wu-Pong S, Yu A, Physiological drug distribution and protein binding, Applied Biopharmaceutics & Pharmacokinetics, McGraw-Hill Medical, Secondary, New York, 2012 (Chapter 10).
  51. Sun YE, Xia W, Tang X, He Z, Chen J, Front. Chem. Eng. China, doi:http://dx.doi.org/10.1007/s11705-009-0255-9., 3(4), 407 (2009)
  52. Aiad I, El-Sukkary MM, Soliman EA, El-Awady MY, Shaban SM, J. Ind. Eng. Chem., doi:http://dx.doi.org/10.1016/j.jiec.2013.08.010., 20(4), 1633 (2014)
  53. Kumar B, Tikariha D, Ghosh KK, J. Dispersion Sci. Technol., doi:http://dx.doi.org/10.1080/01932691.2011.561178., 33, 265 (2012)
  54. Kim TS, Kida T, Nakatsuji Y, Hirao T, Ikeda I, J. Am. Oil Chem. Soc., doi:http://dx.doi.org/10.1007/BF02517994., 73(7), 907 (1996)
  55. Fekarcha L, Tazerouti A, J. Surfactants Deterg., doi:http://dx.doi.org/10.1007/s11743-012-1335-2., 15(4), 419 (2012)
  56. Tatsumi T, Zhang W, Nakatsuji Y, Miyake K, J. Surfactants Deterg., 4(3), 271 (2001)
  57. Dasari VRRK, Muthyala MKK, Nikku MY, Donthireddy SRR, Microbiol. Res., doi:http://dx.doi.org/10.1016/j.micres.2011.12.003., 167(6), 346 (2012)
  58. Jayatissa RN, Perera RP, Hettiarachchi CM, Weerawarna PM, Indian J. Microbiol., doi:http://dx.doi.org/10.1007/s12088-011-0234-y., 52(1), 83 (2012)
  59. Trkmen H, Ceyhan N, Yavaolu NIK, Zdemir G, Etinkaya B, Eur. J. Med. Chem., doi:http://dx.doi.org/10.1016/j.ejmech.2011.04.012., 46(7), 2895 (2011)
  60. Viscardi G, Quagliotto P, Barolo C, Savarino P, Barni E, Fisicaro E, J. Org. Chem., 65(24), 8197 (2000)
  61. Haldar J, Kondaiah P, Bhattacharya S, J. Med. Chem., doi:http://dx.doi.org/10.1021/jm049106l., 48(11), 3823 (2005)