Synthesis, Surface and Biological Activities of Cationic Surfactants Based on Glycine Moiety
-
Fatma H. Abdel-Salam
Abstract
Two series of cationic surfactants based on glycine molecule as sulfonate salt of N,N-diethyl glycine fatty esters having a hydrocarbon chain length of C12,C16 and C18 followed by quaternerization with ethyl iodide were synthesized. Their chemical structures were confirmed using IR,1H-NMR, and mass spectroscopy. The surface activity of these amphiphiles has been determined by measurement of their surface tension. Parameters like surface tension (γ), critical micelle concentration (cmc), effectiveness (Πcmc), efficiency (pC20), maximum surface excess (Γmax), minimum surface area (Amin) and Gibbs free energy of the micellization (ΔGmic) and adsorption (ΔGads) have been determined from the measurements obtained by surface tension method. All these surfactants showed much lower CMC values compared to the similar hydrophobic chain length surfactant. All synthesized compounds have been evaluated for their biological activity against bacteria and fungi.
Kurzfassung
Es wurde eine Reihe kationischer Tenside aus Glycin als Sulfonatsalz der N,N-Diethylglycinfettsäureester mit Kohlenstoffkettenlängen von C12, C16 und C18 bei nachfolgender Quaternisierung mit Ethyliodid synthetisiert. Ihre Strukturen wurden mittels IR, 1H-NMR und Massenspektrometrie bestätigt. Die Oberflächenaktivität dieser Amphiphile wurde bestimmt mittels Messung der Oberflächenspannung. Aus den Messungen der Oberflächenspannung wurden Parameter wie die Oberflächenspannung (γ), die kritische Mizellenbildungskonzentration (CMC), die Effektivität (ΠCMC), die Effizienz (pC20), der maximale Oberflächenüberschuss (Γmax), der minimale Oberflächenplatzbedarf (Amin), die freie Gibbs Energie der Mizellenbildung (ΔGmic) und die der Adsorption (ΔGads) ermittelt. Alle untersuchten Tenside hatten kleinere CMCs als Tenside mit einem vergleichbar langen Kohlenwasserstoffrest. Des Weiteren wurden die Tenside hinsichtlich ihrer biologischen Aktivität gegenüber Bakterien und Pilzen untersucht.
References
1. Rico-Lattes, I. and Lattes, A.: Synthesis of new sugar-based surfactants having biological applications: key role of their self- association, Colloids Surf. A123 (1997) 37–48. 10.1016/S0927-7757(96)03778-8Suche in Google Scholar
2. Pinazo, A., Pons, R., Perez, L. and Infante, M. R.: Amino Acids as Raw Material for Biocompatible Surfactants, Ind. Eng. Chem. Res.50 (2011) 4805–4817. 10.1021/ie1014348Suche in Google Scholar
3. Tehrani-Bagha, A. R. and Holmberg, K.: Cationic Ester-Containing Gemini Surfactants: Physical–Chemical Properties, Langmuir26 (2010) 9276–9282. 10.1021/la1001336Suche in Google Scholar PubMed
4. Infante, M. R., Molinero, J., Erra, P., Julia, R. and Garcia, J. J.: A Comparative Study on Surface Active and Antimicrobial Properties of Some Nα-Lauroyl-L-α,ω-Dibasic Amino acids Derivatives, Fette. Seifen. Anstrichmittel.87 (8) (1983) 309–313. 10.1002/lipi.19850870805Suche in Google Scholar
5. Pegiadou, S., Perez, L. and Infante, M. R.: Synthesis, characterization and surface properties of N-tryptophan-glycerol-ether surfactants, J. Surfactants Deterg.3 (4) (2000) 517–525. 10.1007/s11743-000-0151-ySuche in Google Scholar
6. Seguer, J., Selve, C., Allouch, M. and Infante, M. R.: Nonionic amphiphilic compounds from lysine as molecular mimics of lecithins, Journal of the American Oil Chemists' Society73 (1) (1996) 79–86. 10.1007/BF02523452Suche in Google Scholar
7. Allouch, M., Infante, M.R., Seguer, J., Stebe, M.J. and Selve, C.: Nonionic amphiphilic compounds from aspartic and glutamic acids as structural mimics of lecithins, J. Am. Oil Chem. Soc.73 (1) (1996) 87–96. 10.1007/BF02523453Suche in Google Scholar
8. Pravin, U. S. and Jyoti, D. M.: Cationic Surfactants from Arginine: Synthesis and Physicochemical Properties, American Journal of Chemistry2 (4) (2012) 186–190. 0.5923/j.chemistry.20120204.02Suche in Google Scholar
9. Perez, L., Pinazo, A., Vinardell, P., Clapes, P., Angelet, M., and Infante, M. R.: Synthesis and biological properties of dicationic arginine–diglycerides, New J. Chem.26 (2002) 1221–1227. 10.1039/b203896jSuche in Google Scholar
10. Perez, L., Infante, M. R., Angelet, M., Clapes, P. and Pinazo, A.: Presented at the XV Conference European Colloid and Interface Society, Coimbra, Portugal, September(2001).Suche in Google Scholar
11. Brigham, K. L., Meyrick, B., Christman, B., Magnuson, M., King, G. and Berry, L. C.: In vivo transfection of murine lungs with a functioning prokaryotic gene using a liposome vehicle, Am. J. Med. Sci.298 (4) (1989) 278–281. 10.1097/00000441-198910000-00013Suche in Google Scholar PubMed
12. Tang, F. X. and Hughes, J. A.: Synthesis of a single-tailed cationic lipid and investigation of its transfection, J. Controlled Release62 (3) (1999) 45–358. 10.1016/S0168-3659(99)00158-3Suche in Google Scholar
13. Schulze, U., Schmidt, H. W. and Safinya, C. R.: Synthesis of Novel Cationic Poly(Ethylene Glycol) Containing Lipids, Bioconjugate Chem.10 (3) (1999) 548–552. 10.1021/bc9801068Suche in Google Scholar PubMed
14. Heyes, J., Niculescu-Duvaz, D., Cooper, R. G. and Springer, J. C.: Synthesis of Novel Cationic Lipids: Effect of Structural Modification on the Efficiency of Gene Transfer, J. Med. Chem.45 (1) (2002) 99–114. 10.1021/jm010918gSuche in Google Scholar PubMed
15. Kiehlbauch, J. A., Hannett, G. E, Salfinger, M., ArchinalW., Monserrai, C. and Clint, J.: Use of the national committee for clinical laboratory standards guidelines for disk diffusion susceptibility testing in New York state laboratories, Microbiol38 (2000) 3341–3348. 0095-1137/00/04.0010Suche in Google Scholar
16. Zhang, Q., Gao, Z. N., Xu, F., Tai, S. X., Liu, X. G., Mo, S. B. and Niu, F.: Surface tension and aggregation properties of novel cationic Gemini surfactants with diethylammonium head groups and a diamido spacer, Langmuir28 (2012) 11979–11987. 10.1021/la3011212Suche in Google Scholar PubMed
17. Kamboj, R., Singh, S., Bhadani, A., Kataria, H. and Kaur, G.: Gemini imidazolium surfactants: synthesis and their biophysiochemical study, Langmuir28 (2012) 11969–11978. 10.1021/la300920pSuche in Google Scholar PubMed
18. Kamboj, R., Singh, S. and Chauhan, V.: Synthesis, characterization and surface properties of N-(2-hydroxyalkyl)-N-(2-hydroxyethyl) imidazolium surfactants, Colloids and Surfaces A: Physicochem. Eng. Aspects441 (2014) 233–241. 10.1016/j.colsurfa.2013.08.063Suche in Google Scholar
19. Ren, C., Wang, F., Zhang, Z., Nie, H., Li, N. and Cui, M.: Synthesis, surface activity and aggregation behavior of Gemini imidazolium surfactants 1,3-bis(3-alkylimidazolium-1-yl)propane bromide, Colloids and Surfaces A: Physicochem. Eng. Aspects467 (2015) 1–8. 10.1016/j.colsurfa.2014.11.031Suche in Google Scholar
20. Nabel, A. N. and Salah, M. T.: Characterization, surface properties and biological activity of some synthesized anionic surfactants, Journal of Industrial and Engineering Chemistry20 (2014) 4463–4472. 10.1016/j.jiec.2014.02.018Suche in Google Scholar
21. Rongqiang, L., Fengmei, Y., Junli, Z., Chenfeng, X. and Jinben, W.: The self-assembly properties of a series of polymerizable cationic gemini surfactants: Effect of the acryloxyl group, Colloids and Surfaces A: Physicochem. Eng. Aspects444 (2014) 276–282. 10.1016/j.colsurfa.2013.12.079Suche in Google Scholar
22. Pérez, L, Pinazo, A, Pons, R. and Infante, M.: Gemini surfactants from natural amino acids, Advances in Colloid and Interface Science205 (2014) 134–155. 10.1016/j.cis.2013.10.020Suche in Google Scholar PubMed
23. Patial, P., Shaheen, A. and Ahmada, I.: Synthesis, surface active and thermal properties of novel imidazolium cationic monomeric surfactants, J. of Industrial and Engineering Chemistry20 (2014) 4267–4275. 10.1016/j.jiec.2014.01.032Suche in Google Scholar
24. Ismail, A. A., Abdelfatah, M. B., Mohammed, M., Abdallah, A. E. and Ahmed, I. A.: Synthesis and Biocidal Activity of Some Naphthalene- Based Cationic Surfactants, J Surfact Deterg.15 (2012) 223–234. 10.1007%2Fs11743-011-1286-zSuche in Google Scholar
25. Cronin, M. T., Aptula, A. O., Dearden, J. C., Duffy, J. C., Ntezeva, T. I., Patel, H. P, Philip, H. R., Wayne, S. T., Andrew, P. W., Konstantinos, V. and Gerrit, S.: Structure-based classification of antibacterial activity, J. Chem. Inf. Comput. Sci.42 (2002) 869–878. 10.1021/ci025501dSuche in Google Scholar PubMed
26. Li, F., Rosen, M. J., Morrall, S. W. M. and Versteeg, D. J.: The relationship between the interfacial properties of surfactants and their toxicity to aquatic organisms. Environ Sci Technol35 (2001) 954–959. 10.1021/es0015141Suche in Google Scholar PubMed
© 2016, Carl Hanser Publisher, Munich
Artikel in diesem Heft
- Contents/Inhalt
- Contents
- Application
- Flotation Selectivity of Novel Alkyl Dicarboxylate Reagents for Calcite-Fluorite Separation
- Physical Chemistry
- Investigation of Phase States, Thermo-Morphologic, Magneto-Morphologic and Refractive Properties of Mesophases in Dodecyltrimethyl Ammonium Bromide – Water Lyotropic Liquid Crystalline System
- Lyotropic Liquid Crystal Formed in Aqueous Lecithin Solutions with IPM and AEO20 Additives
- Micelle Formation of Morpholinium Bromide Surfactants in Aqueous Solution
- Hygiene
- Antimicrobial Efficacy of Laundry Detergents with Regard to Time and Temperature in Domestic Washing Machines
- Hygienic Performance of Commercial Dishwashers with Water-Change System – An Experimental Study
- Laundry Washing
- Study of Different Hueing Dyes Deposition on Fabrics during Home Laundry
- Consumer Behaviour
- Consumer Behavior and Fascinating Challenges on Household Laundry and Dishwashing
- Practices in Using and Handling Household Cleaning Products in Egypt
- Synthesis
- Synthesis, Surface and Biological Activities of Cationic Surfactants Based on Glycine Moiety
- Synthesis and Surface/Interfacial Properties of Novel Dialkyl Disulfonate Gemini Surfactants Derived from 1,3,5-triazine
Artikel in diesem Heft
- Contents/Inhalt
- Contents
- Application
- Flotation Selectivity of Novel Alkyl Dicarboxylate Reagents for Calcite-Fluorite Separation
- Physical Chemistry
- Investigation of Phase States, Thermo-Morphologic, Magneto-Morphologic and Refractive Properties of Mesophases in Dodecyltrimethyl Ammonium Bromide – Water Lyotropic Liquid Crystalline System
- Lyotropic Liquid Crystal Formed in Aqueous Lecithin Solutions with IPM and AEO20 Additives
- Micelle Formation of Morpholinium Bromide Surfactants in Aqueous Solution
- Hygiene
- Antimicrobial Efficacy of Laundry Detergents with Regard to Time and Temperature in Domestic Washing Machines
- Hygienic Performance of Commercial Dishwashers with Water-Change System – An Experimental Study
- Laundry Washing
- Study of Different Hueing Dyes Deposition on Fabrics during Home Laundry
- Consumer Behaviour
- Consumer Behavior and Fascinating Challenges on Household Laundry and Dishwashing
- Practices in Using and Handling Household Cleaning Products in Egypt
- Synthesis
- Synthesis, Surface and Biological Activities of Cationic Surfactants Based on Glycine Moiety
- Synthesis and Surface/Interfacial Properties of Novel Dialkyl Disulfonate Gemini Surfactants Derived from 1,3,5-triazine
