Synthesis, surface-active properties, and antimicrobial activities of new double-chain gemini surfactants

Journal of Oleo Science

Volumn 57, Issue 5, 2008, Pages 301-308

  Murguía, Marcelo C ^a   Vaillard, Victoria A ^a   Sánchez, Victoria G ^a   Di Conza, José ^a   Grau, Ricardo J ^a  

^a UNIVERSIDAD NACIONAL DEL LITORAL   (Argentina)

Author keywords

Antimicrobial activity; Cationic dimeric compounds; Gemini surfactants; Neural dimeric compounds; Surface active properties

Indexed keywords

ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; SURFACTANT;

ARTICLE; BACTERIUM; CHEMISTRY; DIFFUSION; DIMERIZATION; DRUG EFFECT; FUNGUS; MICROBIOLOGICAL EXAMINATION; PH; SURFACE PROPERTY; SURFACE TENSION; SYNTHESIS;

ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; BACTERIA; DIFFUSION; DIMERIZATION; FUNGI; HYDROGEN-ION CONCENTRATION; MICROBIAL SENSITIVITY TESTS; SURFACE PROPERTIES; SURFACE TENSION; SURFACE-ACTIVE AGENTS;

EID: 43149111602     PISSN: 13458957     EISSN: 13473352     Source Type: Journal    
DOI: 10.5650/jos.57.301     Document Type: Article

References (29)

1. Menger, F.M.; Keiper, J.S. Gemini Surfactants, Angew. Chem. Int. Ed. Engl. 39, 1906-1920 (2000).
2. Zana, R. Dimeric (Gemini) surfactants: Effect of the spacer group on the association behavior in aqueous solution, J. Colloid Interface Sci. 248, 203-251 (2002).
3. Zana, R.; Xia, J. Gemini Surfactants, Surfactant Science Series, Marcel Dekker, New York (2004).
4. Menger, F.M.; Migulin, V.A. Synthesis and properties of multiarmed geminis. J. Org. Chem. 64, 8916-8921 (1999).
5. Menger F.M.; Mbadugha, B.N.A. Gemini surfactants with a disaccharide spacer. J. Am. Chem. Soc. 123, 875-885 (2001).
6. Devínsky, F.; Lacko, L.; Mlynarcik, D.; Racansky, V.; Krasnec, L. Relationship between critical micelle concentration and minimum inhibitory concentrations for some none-aromatic quaternary ammonium salts and amine oxides. Tenside Detergents 22, 10-15 (1985).
7. Kopecky, F. Micellization and other associations of amphiphilic antimicrobial quaternary ammonium salts in aqueous solutions. Pharmazie 51, 135-144 (1996).
8. Dubnicková M.; Pisárcik, M.; Lacko, I.; Devínsky, F.; Mlynarcik, D.; Balgavý, P. Gemini amphiphiles: Antimicrobial activity, micellization and interaction with phospholipid bilayers. XIIIth School on Biophysics of Membrane Transport. Cell. Mol. Biol. Lett. 2, (Suppl. 1), 215-216 (1997).
9. Dubnicková M.; Yaradaikin, S.; Lacko, I.; Devínsky, F.; Gordeliy, V.I.; Balgavý, P. Effects of gemini surfactants on egg phosphatidylcholine bilayers in the fluid lamellar phase, Colloids Surf. B: Biointerfaces 34, 161-164 (2004).
10. Horniak, L.; Ebringer, L.; Balgavý, P. Interaction of bactericidal bis-ammonium salts with model and bacterial membranes. IUMS Congress: Bacteriology and Mycology, Osaka, Japan. Septembre 16-22, Abstracts 171 (1990).
11. Iwamoto, S.; Otsuki, M.; Sasaki, Y.; Ikeda, A.; Kikuchi, J. Gemini peptide lipids with ditopic ion-recognition site. Preparation and functions as an inducer for assembling of liposomal membranes. Tetrahedron 60, 9841-9847 (2004).
12. Bell, P.C.; Bergsma, M.; Dolbnya, I.P.; Bras, W.; Stuart, M.C.A.; Rowan, A.E.; Feiters, M.C.; Engberts, J.B.F.N. Transfection mediated by gemini surfactants: Engineered escape from the endosomal compartment. J. Am. Chem. Soc. 125, 1551-1558 (2003).
13. David, S.; Pérez, L.; Infante, M.R. Sequestration of bacterial lipopolysaccharide by bis(args) gemini compounds. Bioorg. Med. Chem. Lett. 12, 357-360 (2002).
14. Diz, M.; Manresa, A.; Pinazo, A.; Erra, P.; Infante, M.R. Synthesis, surface active properties and antimicrobial activity of new bis-quaternary ammonium compounds. J. Chem. Soc. (Perkin Trans. 2) 1871-1876 (1994).
15. Okazaki, K.; Maeda, T.; Nagamune, H.; Manabe, Y.; Kourai, H. Synthesis and antimicrobial characteristics of 4,4′-(α,ω-Polymethylenedithio) bis(1-alkylpyridinium iodide)s. Chem. Pharm. Bull. (Tokyo) 45, 1970-1974 (1997).
16. Maeda, T.; Manabe, Y.; Yamamoto, M.; Yoshida, M.; Okazaki, K.; Nagamune, H. Synthesis and antimicrobial characteristics of novel biocides, 4,4′-(1,6-Hexamethylenedioxy dicarbonyl)bis(1-alkylpyridinium iodide)s. Chem. Pharm. Bull. (Tokyo) 47, 1020-1023 (1999).
17. Iyer, S.; Rele, S.M.; Baskaran, S.; Chaikof, E.L. Design and synthesis of hyaluronan-mimetic gemini disaccharides. Tetrahedron 59, 631-638 (2003).
18. Shirai, A.; Maeda, T.; Nagamune, H.; Matsuki, H.; Kaneshina, S.; Kourai, H. Biological and physicochemical properties of gemini quaternary ammonium compounds in which the positions of a cross-linking sulfur in the spacer differ. Euro. J. Med. Chem. 40, 113-123 (2005).
19. Chaudier, Y.; Zito, F.; Barthélémy, P.; Stroebel, D.; Améduri, B.; Popot, J-L.; Pucci, B. Synthesis and preliminary biochemical assessment of ethyl-terminated perfluoroalkylamine oxide surfactants. Bioorg. Med. Chem. Lett. 12, 1587-1590 (2002).
20. Massi, L.; Guittard, F.; Géribaldi, S.; Levy, R.; Duccini, Y. Antimicrobial properties of highly fluorinated bis-ammonium salts. Int. J. Antimicrobial Agents 21, 20-26 (2003).
21. Massi, L.; Guittard, F.; Géribaldi, S. Application en Tant que Biocides des Composés QUATERFLUO®, MC Patent Number 2452 (2000).
22. Ikeda, T.; Tazuke, S.; Suzuki, Y. Biologically active polycations. IV: Synthesis and antimicrobial activity of poly(trialkylvinylbenzylammonium chloride)s. Die Makromolekulare Chemie 185, 869-876 (1984).
23. Chlebicki, J.; Wegrzynska, J.; Maliszewska, I.; Oswiecimska, M. Preparation, surface-active properties, and antimicrobial activities of bis-quaternary ammonium salts from amines and epichlorhidrin. J. Surfact. Deterg. 8, 227-232 (2005).
24. Murguía M.C., Grau, R.J. Synthesis of new pentaerythritol-based gemini surfactants. Synlett 8, 1229-1232 (2001).
25. Murguía M.C.; Vaillard, S.E.; Grau, R.J. A Facile, Selective preparation of monoketals from pentaerythritol and ketones. Synthesis 7, 1093-1097 (2001).
26. Murguía M.C.: Cabrera, M.I.; Grau, R.J. Selective preparation of key intermediates for the synthesis of gemini surfactants by phase-transfer catalysis. React. Kinet. Catal. Lett. 75, 205-211 (2002).
27. Murguía M.C.; Cabrera, M.I.; Guastavino, J.F.; Grau, R.J. New oligomeric surfactants with multiple-ring spacers: Synthesis and tensioactive properties. Colloids and Surfaces A: Physicochem. Eng. Aspects 262, 1-7 (2005).
28. NF EN 1040: Chemical disinfectants and antiseptics-basic bactericidal activity-test methods and requeriments (phase 1). In: Antiseptiques et désinfectants, Paris: AFNOR, 131-159 (1998).
29. E 1054-91: Standard practices for evaluating inactivators of antimicrobial agents used in disinfectant, sanitizer, antiseptic, or preserved products. In ASTM standards on materials and environmental microbiology. 2nd ed. Philadelphia: ASTM, 198-199 (1993).