Skip to main content
Log in

Synthesis and Antibacterial Activity of Novel Amido-Amine-Based Cationic Gemini Surfactants

  • Original Article
  • Published:
Journal of Surfactants and Detergents

Abstract

A series of novel cationic gemini surfactants were synthesized from corresponding amido-amines in a single step reaction. The amido-amines were obtained from long chain carboxylic acids and 3-N,N-dimethylamino-1-propyl-amine with excellent isolated yield (up to 95 %). All the synthesized quaternary ammonium compounds (QACs) were further investigated for surface active properties. The critical micelle concentration (CMC) and the effectiveness of surface tension reduction were determined. The surface tension measurements of newly synthesized gemini surfactants showed good water solubility, and low CMC values, had great efficiency in lowering the surface tension and a strong adsorption at the air/water interface than the corresponding monomeric surfactants. Further, the antibacterial activity of the synthesized QACs against both Gram-positive and Gram-negative bacteria was also investigated.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. Abbanat D, Macielag M, Bushrajesh K (2003) Novel antibacterial agents for the treatment of serious Gram-positive infection. Expert Opin Investig Drugs 12:379–399

    Article  CAS  Google Scholar 

  2. Pootoolal J, Neu J, Wright GD (2002) Glycopeptide antibiotic resistance. Annu Rev Pharmacol Toxicol 42:381–408

    Article  CAS  Google Scholar 

  3. Raad II, Hanna HA, Hachem RY, Dvorak T, Arbuckle RB, Chaiban G, Rice LB (2004) Clinical-use-associated decrease in susceptibility of vancomycin-resistant Enterococcus faecium to linezolid: comparison with quinupristin-dalfopristin. Antimicrob Agents Chemother 48:3583–3585

    Article  CAS  Google Scholar 

  4. Goldstein FW (2007) Combating resistance in a challenging, changing environment. Clin Microbiol Infect 13:2–6

    Article  CAS  Google Scholar 

  5. Fidler DF (1998) Legal issues associated with antimicrobial drug resistance. Emerg Infect Dis 4:169–177

    Article  CAS  Google Scholar 

  6. Macchiarulo A, Constantino G, Fringuelli D, Vecchiarelli A, Schiaffella F, Fringuelli R (2002) 1,4-Benzothiazine and 1,4-benzoxazine imidazole derivatives with antifungal activity: a docking study. Bioorg Med Chem 10:3415–3423

    Article  CAS  Google Scholar 

  7. 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 2:1871–1879

    Google Scholar 

  8. Kourai H, Yabuhara T, Shirai A, Maeda T, Nagamune H (2006) Synthesis and antimicrobial activities of a series of new bis-quaternary ammonium compounds. Eur J Med Chem 41:437–444

    Article  CAS  Google Scholar 

  9. Menger FM, Littau CA (1993) Gemini surfactants: a new class of self-assembling molecules. J Am Chem Soc 115:10083–10090

    Article  CAS  Google Scholar 

  10. Chunli X, Hailin Z, Tingting Z, Duanlin C, Zhiyong H (2011) Synthesis and properties of novel alkylbetaine zwitterionic gemini surfactants derived from cyanuric chloride. Colloid Surf A 375:141–146

    Article  Google Scholar 

  11. Oda R, Hac I, Candau SJ (1997) Gemini surfactants, the effect of hydrophobic chain length and dissymmetry. Chem Commun 21:2105–2106

    Article  Google Scholar 

  12. Garcia MY, Ribosa I, Guindulain T, Sanchez-Leal J, Vives-Rego J (2001) Fate and effect of monoalkyl quaternary ammonium surfactants in the aquatic environment. J. Environ Pollut 111:169–175

    Article  CAS  Google Scholar 

  13. Perez L, Torres JL, Manresa A, Solans C, Infante MR (1996) Synthesis, aggregation, and biological properties of a new class of gemini cationic amphiphilic compounds from arginine, bis(Args). Langmuir 12:5296–5301

    Article  CAS  Google Scholar 

  14. Weihs D, Danino D, Pinazo-Gassol A, Perez L, Franses EI, Talmon Y (2005) Self-aggregation in dimeric arginine-based cationic surfactants solutions. Colloid Surf A Physicochem Eng Asp 255:73–78

    Article  CAS  Google Scholar 

  15. Fisicaro E, Compari C, Duce E, Donofrio G, Rozycka-Roszak B, Wozniak E (2005) Biologically active bisquaternary ammonium chlorides: physico–chemical properties of long chain amphiphiles and their evaluation as non-viral vectors for gene delivery. Biochim Biophys Acta 1722:224–233

    Article  CAS  Google Scholar 

  16. Gaucheron J, Wong T, Wong KF, Maurer N, Cullis PR (2002) Synthesis and properties of novel tetraalkyl cationic lipids. Bioconjug Chem 1:671–675

    Article  Google Scholar 

  17. Zana R (2002) Dimeric (Gemini) surfactants: effect of the spacer group on the association behavior in aqueous solution. J Colloid Interface Sci 248:203–220

    Article  CAS  Google Scholar 

  18. Fielden ML, Perrin C, Kremer A, Bergsma M, Stuart MC, Camilleri Jan B, Engberts FN (2001) Sugar-based tertiary amino gemini surfactants with a vesicle-to-micelle transition in the endosomal pH range mediate efficient transfection in vitro. Eur J Biochem 268:1269–1279

    Article  CAS  Google Scholar 

  19. Bell PC, Bergsma M, Dolbnya IP, Bras W, Stuart MCA, Rowan AE, Feiters MC, Engberts Jan BFN (2003) Transfection mediated by gemini surfactants: engineered escape from the endosomal compartment. J Am Chem Soc 125:1551–1558

    Article  CAS  Google Scholar 

  20. Karlsson LV, Eijk MCP, Soderman O (2002) Interaction of bovine myelin basic protein with triphosphoinositide. J Colloid Interface Sci 252:290–296

    Article  CAS  Google Scholar 

  21. Sharkawy HE (2007) Cycloalkylation reactions of fatty amines with α,ω-dihaloalkanes: role of bis-quaternary ammonium salts as phase-transfer catalysts. Cat Commun 8:855–860

    Article  Google Scholar 

  22. Christine HF, Michael HC (1986) Comparative in vitro activities of ciprofloxacin and other 4-quinolones against mycobacterium tuberculosis and mycobacterium intracellular. Antimicrob Agents Chemother 29:386–388

    Article  Google Scholar 

  23. Paulo A, Pires R, Omar A, Seoud E (2006) Surfactants with an amide group “spacer”: synthesis of 3-(acylaminopropyl) trimethylammonium chlorides and their aggregation in aqueous solutions. J Colloid Interface Sci 304:474–485

    Article  Google Scholar 

  24. Cronin MTD, Aptula AO, Dearden JC, Duffy JC, Ntezeva TI, Patel H, Philip H, Rowe T, Wayne S, Andrew P, Worth, Konstantinos V, Gerrit S (2002) Structure-based classification of antibacterial activity. J Chem Inf Comput Sci 42:869–878

    CAS  Google Scholar 

Download references

Acknowledgments

The author (AKG) is greatly thankful to the UGC (University Grant Commission, India) for providing a fellowship. The authors would also extend their special thanks to Mr. Sharad Gaikwad and Mr. Chetan Pawar, K. T. H. M. College, Nashik, Maharashtra, India for carrying out antibacterial activity analysis during this work.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Sunil S. Bhagwat.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 1094 kb)

About this article

Cite this article

Ghumare, A.K., Pawar, B.V. & Bhagwat, S.S. Synthesis and Antibacterial Activity of Novel Amido-Amine-Based Cationic Gemini Surfactants. J Surfact Deterg 16, 85–93 (2013). https://doi.org/10.1007/s11743-012-1406-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11743-012-1406-4

Keywords

Navigation