Cationic Bola Form Metallosurfactants Based on Isothiouronium, Synthesis and Anti-Microbial Activity
-
, , and
Abstract
Two series of well-defined dimeric metallo-bolaamphiphiles (bola surfactants) with the coordinated metal ions (Cu, Co, Zn) were prepared. These oligomeric surfactants consist of simple monomeric cationic surfactant fragments which are coupled via the hydrophilic ammonium chloride head groups by C6 and C12 spacer groups of different lengths. FTIR and 1HNMR identification techniques confirmed the obtained products. Measurements of surface tensions showed that the synthesized Bola amphiphiles have the desired, relatively low critical micelle formation concentrations (CMC). Bola amphiphiles with long spacer groups (C12) have a pronounced surface activity. The properties of these cationic surfactant oligomers in aqueous solution such as micellization and surface activity were discussed in relation to spacer group. In addition, the synthesized compounds were examined for their anti-microbial activity using the agar diffusion technique.
Kurzfassung
Es wurden zwei Serien gut definierter Metallo-Bolaamphiphile (Metallo-Bolatenside) mit den koordinierten Metallionen Cu, Co, Zn hergestellt. Diese oligomeren Tenside bestehen aus einfachen kationischen monomeren Tensidfragmenten, die über die hydrophilen Ammoniumchlorid-Kopfgruppen durch unterschiedlich lange C6- und C12-Spacergruppen gekoppelt sind. FTIR- und 1HNMR-Identifizierungstechniken bestätigten die erhaltenen Produkte. Messungen der Oberflächenspannungen zeigten, dass die synthetisierten Bola-Amphiphile die erwünschten, relativ niedrigen kritischen Mizellenbildungskonzentrationen (CMC) haben. Bolaamphiphile mit langen Spacergruppen (C12) haben eine ausgeprägte Oberflächenaktivität. Die Eigenschaften dieser kationischen Tensid-Oligomere in wässriger Lösung wie Mizellisierung und Oberflächenaktivität wurden in Bezug auf die Spacer-Gruppe diskutiert. Darüber hinaus wurden die synthetisierten Verbindungen mit Hilfe der Agardiffusionstechnik auf ihre antimikrobielle Aktivität untersucht.
References
1. Jain, M. F. A., Dhawan, V, Shah, S. and Nagarsenker, M. S.: Bolaamphiphiles, A Pharmaceutical Review. Adv Pharm Bull, 2015, 4 (Suppl 2), p. 483–491. 10.5681/apb.2014.072.Search in Google Scholar
2. Popov, M., Linder, C., Deckelbaum, R. J., Grinberg, S., Hansen, I. H., Shaubi, E., Waner, T. and Heldman, E.: Cationic vesicles from novel bolaamphiphilic compounds. Journal of Liposome Research, 2010; 20(2): 147–159. PMid:19848552; 10.3109/08982100903218900Search in Google Scholar
3. Meister, A. and Blume, A.: Self-assembly of bipolar amphiphiles. Curr Opin Colloid Interface Sci: 12 (3), 2007, p. 138–47. 10.1016/j.cocis.2007.05.003Search in Google Scholar
4. Macinnis, J., Boucher, G. D., Palepu, R. and Marangoni, G. D.: The properties of a family of two-headed surfactant systems: the 4-alkyl-3-sulfosuccinates 2. Surface properties of alkyl sulfosuccinate micelles. Canadian Journal of Chemistry.2011, 77(3):340–347. 10.1139/v99-008Search in Google Scholar
5. Hu, B.-B. Yuan, Y., Zhou, X.-P. and Li, S.-M.: Synthesis and properties of a novel bolaamphiphile surfactant derived from proline[J]. Chin. Chem. Lett., 2016, 27(03): 447–450. 10.1016/j.cclet.2015.12.019Search in Google Scholar
6. Asadov, Z. H., Nasibova, S. M., Rahimov, R. A., Gasimov, E. K., Muradova, S. A., Rzayev, F. H., Asadova, N. Z. and Zubkov, F. I.: Effects of head group on the properties of cationic surfactants containing hydroxyethyl- and hydroxyisopropyl fragments., Journal of Molecular Liquids274 (2019) 125–132. 10.1016/j.molliq.2018.10.100Search in Google Scholar
7. Lin, H.-X., Yang, M.-S., Li, J.Chen, X.-Y., Jiang, J.-X. and Han, C.-R.: A Novel Bola-Type Rosin-Based Functional Surfactant and Its Synergistic Effect with Natural Surfactant Saponin. J Surfact Deterg (2017) 20:1205–1212. 10.1007/s11743-017-1994-0Search in Google Scholar
8. Zeng, X., Wang, H., Chen, Y. and Wang, L.: Synthesis and Solution Properties of New Polysiloxane Bola Surfactants Containing Carbohydrate. Tenside Surfactants Detergents, 2014, 51, 5: 427–431. 10.3139/113.110325Search in Google Scholar
9. Yan, Y., Huang, J., Li, Z., Zhao, X., Zhu, B. and Ma, J.: Surface properties of cationic bolaamphiphiles and their mixed systems with oppositely charged conventional surfactant. Colloids and Surfaces A: Physicochemical and Engineering Aspects.215, 1–3, 2003, 263–275. 10.1016/S0927-7757(02)00486-7Search in Google Scholar
10. Yan, Y., Huang, J., Li, Z., Zhao, X., Zhu, B. and Ma, J.: Surface properties of cationic bolaamphiphiles and their mixed systems with oppositely charged conventional surfactant. Colloids and Surfaces A: Physicochem. Eng. Aspects215, (2003), 263–275. 10.1016/S0927-7757(02)00486-7Search in Google Scholar
11. Venkatachalam, T., Vassilev, A. O., Benyunov, A. and Grigoriants, O.: Stereochemistry as a Determinant of the Anti-Leukemic Potency of Halopyridyl and Thiazolyl Thiourea Compounds, Letters in Drug Design & Discovery4(5): 318–326. 2007. 10.2174/157018007780867870Search in Google Scholar
12. Ahmed, S. M.: Influence of chemical structure of Bis-isothiouronium surfactants on their surface and biological activities. Egyptian Journal of Petroleum18 (1), (2009), 11–20.Search in Google Scholar
13. Ismail, D. A., Ahmed, S. M.Ahmed, H. M., Awad, A. I. and El-Sharkawy, H. A.: Synthesis and Biological Activity of Alkyl Pyridinium Aldoxime Based Surfactants. Tenside Surf. Det.53 (2016) 4. 10.3139/113.110438Search in Google Scholar
14. Ismail, D. A., Mohamed, A. S. and Mohamed, M. Z.: “Synthesis of Some New Quarternary Ammonium Compounds: Evaluation of their Surface Surface.” properties and Solubilization Activity. Trans. Egypt. Soc. Chem. Eng., vol. 30, No. 2 (2004).Search in Google Scholar
15. Shaban, S. M., Aiad, I. and Ismail, A. R.: Surface Parameters and Biological Activity of N-(3- (Dimethyl Benzyl Ammonio) Propyl) Alkanamide Chloride Cationic Surfactants. J Surfact Deterg19 (3), (2016), 501–510. 10.1007/s11743-016-1795-xSearch in Google Scholar
16. Carroll, K. C., Pfaller, M. A., Landry, M. L, McAdam, A. J., Patel, R., Richter, S. S and Warnock, D. W.: Manual of Clinical Microbiology, Twelfth Edition. 2019. 10.1128/9781555819842Search in Google Scholar
17. Rosen, M. J.: Surface and Interfacial Phenomena, 2nd ed., John wiely & Sons: New York, (1989). ISBN 0-471-47818-0.Search in Google Scholar
18. El-Sukkary, M., Shaker, N. O., Ismail, D. A., Ahmed, S. M. and Awad, A.: “Preparation and evaluation of some amide ether carboxylate surfactants.” Egyptian Journal of Petroleum21 (1), (2012), 11–17. 10.1016/j.ejpe.2012.02.002Search in Google Scholar
19. EL-Sukkary, M., Ismail, D. A., Rayes, S. M. and Saad, M. A.: “Synthesis and Evaluation of some derivatives of polysiloxanes.” Published in: Egyptian Journal of Petroleum. 23, 4, 2014, 361–366. 10.1016/j.ejpe.2014.09.002Search in Google Scholar
20. Zana, R.: (2002) Dimeric (gemini) surfactants: effect of the spacer group on the association behaviour in aqueous solution. J Colloids Interface Sci248:203–220. PMid:16290524; 10.1006/jcis.2001.8104Search in Google Scholar PubMed
21. Ayad, M. I. and El- Boraey, H. A.: Characterization, Thermal and Electrical Conductivity of some Transition Metal Adducts. Int. J. ChemTech Res.2014, 6(1), 266–275.Search in Google Scholar
22. Shaban, S. M., Aiad, I. and Ismail, A. R.: Surface Parameters and Biological Activity of N-(3-(Dimethyl Benzyl Ammonio) Propyl) Alkanamide Chloride Cationic Surfactants. J Surfact Deterg19 (3), (2016), 501–510. 10.1007/s11743-016-1795-xSearch in Google Scholar
23. Tyagi, S. and TyagiV. K.: Novel cationic Gemini surfactants and methods for determination of their antimicrobial activity–review. Tenside, Surfactants, Detergents.2014; 51:379–386. 10.3139/113.110319Search in Google Scholar
24. Omurzak, E., Tegin, R. A. A., Kyzy, A. B., Satyvaldiev, A., Zhasnakunov, Z., Umetova, G., Kelgenbaeva, Z., Abdullaeva, Z. and Mashimo, T.: Effect of surfactant materials to nanoparticles formation under pulsed plasma conditions and their antibacterial properties, Materials Today: Proceedings5 (2018) 15686–15695. https://doi.org/10.1016/j.matpr.2018.04.179. 10.1016/j.matpr.2018.04.179Search in Google Scholar
25. Murguia, M. C., Vaillard, V. A., Sanchez, V. G., Conza, G. D. and Grau, R. J.: Synthesis, surface-active properties and antimicrobial activities of new double-chain gemini surfactants. J Oleo Sci57(5), (2008), 301–308. PMid:18391479; 10.5650/jos.57.301Search in Google Scholar PubMed
26. Bachrach, U. and Weinstein, A.: Effect of aliphatic polyamines on growth and macromolecular syntheses in bacteria. J Gen. microbiol.60, (1970), 159–165. PMid:4922668; 10.1099/00221287-60-2-159Search in Google Scholar PubMed
27. Shaban, S. M., Aiad, I., El-Sukkary, M. M., Soliman, E. A. and El-Awady, M. Y.: One step green synthesis of hexagonal silver nanoparticles and their biological activity. J Ind Eng Chem20, (2014), 4473–4481. 10.1016/j.jiec.2014.02.019Search in Google Scholar
28. Gilbert, P. and Moore, L. E.: Cationic antiseptics diversity of action under a common epithet. J Appl Microbiol99 (4), (2005), 703–715. PMid:16162221; 10.1111/j.1365-2672.2005.02664.xSearch in Google Scholar PubMed
29. Tavano, L., Infante, M. R., Abo Riya, M., Pinazo, A., Vinardell, M. P., Mitjans, M., Manresa, M. A. and Perez, L.: Role of aggregate size in the hemolytic and antimicrobial activity of colloidal solutions based on single and gemini surfactants from arginine. Soft Matter9, (2013), 306–319. 10.1039/C2SM26670ASearch in Google Scholar
30. Shaban, S. M, Aiad, I., Fetouh, H. A. and Maher, A.: Amidoamine double tailed cationic surfactant based on dimethyl amino propyl amine: synthesis, characterization and evaluation as Biocide. J Mol Liq212, (2015), 699–707. 10.1016/j.molliq.2015.10.024Search in Google Scholar
31. Badawi, A. M., Ali, H. El-Sh. and Ismail, D. A.: Synthesis, Characterization, and Antitumor Activity of Four Novel Sulphonamide compounds. Aust. J. Basic and Appl. Sci., 2(2) (2008) 301–309.Search in Google Scholar
© 2020, Carl Hanser Publisher, Munich
Articles in the same Issue
- Contents/Inhalt
- Contents
- Hygiene
- The Antimicrobial Activity of Herbal Soaps Against Selected Human Pathogens
- Detergent Properties of Coconut Oil Derived N-Acyl Prolinate Surfactant and the In silico Studies on its Effectiveness Against SARS-CoV-2 (COVID-19)
- Novel Surfactants
- Cationic Bola Form Metallosurfactants Based on Isothiouronium, Synthesis and Anti-Microbial Activity
- Application
- Effect of Inorganic Salt on Foam Properties of Nanoparticle and Surfactant Systems
- Effects of Surfactant Compounding on the Wettability Characteristics of Zhaozhuang Coal: Experiment and Molecular Simulation
- A Comparative Spectral Study on the Interaction of Organic Dye Congo-Red with Selective Aqueous Micellar Media of CPC, Rhamnolipids and Saponin
- Synthesis
- Development of a Gypsum Foaming Agent Based on Alkyl Polyglucosides
- Synthesis and Properties of Amide Gemini Surfactants
- Study of the Synthesis of Branched Chain Alkyl Polyglucosides from Guerbet Alcohol in an Acid/Phase Transfer Catalyst System and Their Properties
- Short Communication/Physical Chemistry
- Study of Methionine and Cumene Hydroperoxide Reaction Kinetics in the Presence of Nonionic Surfactant
Articles in the same Issue
- Contents/Inhalt
- Contents
- Hygiene
- The Antimicrobial Activity of Herbal Soaps Against Selected Human Pathogens
- Detergent Properties of Coconut Oil Derived N-Acyl Prolinate Surfactant and the In silico Studies on its Effectiveness Against SARS-CoV-2 (COVID-19)
- Novel Surfactants
- Cationic Bola Form Metallosurfactants Based on Isothiouronium, Synthesis and Anti-Microbial Activity
- Application
- Effect of Inorganic Salt on Foam Properties of Nanoparticle and Surfactant Systems
- Effects of Surfactant Compounding on the Wettability Characteristics of Zhaozhuang Coal: Experiment and Molecular Simulation
- A Comparative Spectral Study on the Interaction of Organic Dye Congo-Red with Selective Aqueous Micellar Media of CPC, Rhamnolipids and Saponin
- Synthesis
- Development of a Gypsum Foaming Agent Based on Alkyl Polyglucosides
- Synthesis and Properties of Amide Gemini Surfactants
- Study of the Synthesis of Branched Chain Alkyl Polyglucosides from Guerbet Alcohol in an Acid/Phase Transfer Catalyst System and Their Properties
- Short Communication/Physical Chemistry
- Study of Methionine and Cumene Hydroperoxide Reaction Kinetics in the Presence of Nonionic Surfactant