Synthesis, surface-active properties, and antimicrobial activities of new neutral and cationic trimeric surfactants

Journal of Surfactants and Detergents

Volumn 11, Issue 1, 2008, Pages 41-48

  Murguía, Marcelo C ^a   Cristaldi, Mariano D ^a   Porto, Ayelén ^b   Conza, José Di ^b   Grau, Ricardo J ^a  

^a Instituto de Desarrollo Tecnologico para la Industria Quimica   (Argentina)

^b UNIVERSIDAD NACIONAL DEL LITORAL   (Argentina)

Author keywords

Antimicrobial activity; Cationic trimeric compounds; Neutral trimeric compounds; Surface active properties

Indexed keywords

AMINES; COLUMN CHROMATOGRAPHY; REDUCTION; REGIOSELECTIVITY; SURFACE ACTIVE AGENTS;

ANTIMICROBIAL ACTIVITIES; CRITICAL MICELLE CONCENTRATION (CMC); TERTIARY AMINES;

SYNTHESIS (CHEMICAL);

EID: 41049090051     PISSN: 10973958     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11743-007-1052-4     Document Type: Article

References (31)

1. Menger FM, Keiper JS (2000) Gemini surfactants. Angew Chem Int Ed Engl 39:1906-1920
2. Zana R (2002) Dimeric (gemini) surfactants: effect of the spacer group on the association behavior in aqueous solution. J Colloid Interface Sci 248:203-251
3. Zana R, Xia J (2004) Gemini surfactants, surfactant science series. Marcel Dekker, New York
4. Menger FM, Migulin VA (1999) Synthesis and properties of multiarmed geminis. J Org Chem 64:8916-8921
5. Menger FM, Mbadugha BNA (2001) Gemini surfactants with a disaccharide spacer. J Am Chem Soc 123:875-885
6. Devínsky F, Lacko L, Mlynarcik D, Racansky V, Krasnec L (1985) Relationship between critical micelle concentration and minimum inhibitory concentrations for some none-aromatic quaternary ammonium salts and amine oxides. Tenside Detergents 22:10-15
7. Kopecky F (1996) Micellization and other associations of amphiphilic antimicrobial quaternary ammonium salts in aqueous solutions. Pharmazie 51:135-144
8. Dubnicková M, Pisárcik M, Lacko I., Devínsky F, Mlynarcik D, Balgavý P (1997) 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
9. Dubnicková M, Yaradaikin S, Lacko I, Devínsky F, Gordeliy VI, Balgavý P (2004) Effects of gemini surfactants on egg phosphatidylcholine bilayers in the fluid lamellar phase. Colloids Surf B Biointerfaces 34:161-164
10. Horniak L, Ebringer L, Balgavý P (1990) Interaction of bactericidal bis-ammonium salts with model and bacterial membranes. In: IUMS Congress: Bacteriology and Mycology, Osaka (1990), Japan, September 16-22, Book of Abstracts, 171
11. Iwamoto S, Otsuki M, Sasaki Y, Ikeda A, Kikuchi J (2004) Gemini peptide lipids with ditopic ion-recognition site. Preparation and functions as an inducer for assembling of liposomal membranes. Tetrahedron 60:9841-9847
12. Bell PC, Bergsma M, Dolbnya IP, Bras W, Stuart MCA, Rowan AE, Feiters MC, Engberts JBFN (2003) Transfection mediated by gemini surfactants: engineered escape from the endosomal compartment. J Am Chem Soc 125:1551-1558
13. David S, Pérez L, Infante MR (2002) Sequestration of bacterial lipopolysaccharide by bis(args) gemini compounds. Bioorg Med Chem Lett 12:357-360
14. Diz M, Manresa A, Pinazo A, Erra P, Infante MR (1994) Synthesis, surface active properties and antimicrobial activity of new bis-quaternary ammonium compounds. J Chem Soc (Perkin Trans 2)1871-1876
15. Okazaki K, Maeda T, Nagamune H, Manabe Y, Kourai H (1997) Synthesis and antimicrobial characteristics of 4,4′-(α,ω- polymethylenedithio) bis(1-alkylpyridinium iodide)s. Chem Pharm Bull (Tokyo) 45:1970-1974
16. Maeda T, Manabe Y, Yamamoto M, Yoshida M, Okazaki K, Nagamune H (1999) 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
17. Iyer S, Rele SM, Baskaran S, Chaikof EL (2003) Design and synthesis of hyaluronan-mimetic gemini disaccharides. Tetrahedron 59:631-638
18. Shirai A, Maeda T, Nagamune H, Matsuki H, Kaneshina S, Kourai H (2005) Biological and physicochemical properties of gemini quaternary ammonium compounds in which the positions of a cross-linking sulfur in the spacer differ. Eur J Med Chem 40:113-123
19. Chaudier Y, Zito F, Barthélémy P, Stroebel D, Améduri B, Popot J-L, Pucci B (2002) Synthesis and preliminary biochemical assessment of ethyl-terminated perfluoroalkylamine oxide surfactants. Bioorg Med Chem Lett 12:1587-1590
20. Massi L, Guittard F, Géribaldi S, Levy R, Duccini Y (2003) Antimicrobial properties of highly fluorinated bis-ammonium salts. Int J Antimicrobial Agents 21:20-26
21. ®, MC Patent Number 2452
22. Ikeda T, Tazuke S, Suzuki Y (1984) Biologically active polycations. IV: synthesis and antimicrobial activity of poly(trialkylvinylbenzylammonium chloride)s. Die Makromolekulare Chemie 185:869-876
23. Chlebicki J, Wegrzynska J, Maliszewska I, Oswiecimska M (2005) Preparation, surface-active properties, and antimicrobial activities of bis-quaternary ammonium salts from amines and epichlorhidrin. J Surfact Deterg 8:227-232
24. Murguía MC, Grau RJ (2001) Synthesis of new pentaerythritol-based gemini surfactants. Synlett 8:1229-1232
25. Murguía MC, Vaillard SE, Grau RJ (2001) A facile, Selective preparation of monoketals from pentaerythritol and ketones. Synthesis 7:1093-1097
26. Murguía MC, Cabrera MI, Grau RJ (2002) Selective preparation of key intermediates for the synthesis of gemini surfactants by phase-transfer catalysis. React Kinet Catal Lett 75:205-211
27. Murguía MC, Cabrera MI, Guastavino JF, Grau RJ (2005) New oligomeric surfactants with multiple-ring spacers: synthesis and tensioactive properties. Colloids Surf A Physicochem Eng Aspects 262:1-7
28. Kida T, Yokota M, Masuyama A, Nakatsuji Y, Okahara M (1993) A facile synthesis of polyglycidyl ethers from polyols and epichlorohydrin. Synthesis 74:487-489
29. NF EN 1040 (1998) Chemical disinfectants and antiseptics-basic bactericidal activity-test methods and requirements (phase 1). In: Antiseptiques et désinfectants, AFNOR, Paris, pp 131-159
30. E 1054-91 (1993) 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 edn. ASTM, Philadelphia, pp 198-199
31. Tewari N, Tiwari VK, Tripathi RP, Chaturvedi V, Srivastava A, Srivastava R, Shukla PK, Chaturvedi AK, Gaikwad A, Sinha S, Srivastava BS (2004) Synthesis of galactopyranosyl amino alcohols as new class of antitubercular and antifungal agents. Bioorg Med Chem Letters 14:329-332