Skip to main content
SpringerLink
Log in

Cholic Acid-Derived Facial Surfactants with Long Side-Chain Quaternary Ammonium: Synthesis and Antimicrobial Activity Study

  • Original Article
  • Published:
Journal of Surfactants and Detergents

Abstract

Four cholic acid cationic surfactants containing a flexible long aliphatic chain were synthesized efficiently. A long aliphatic chain was introduced first on the side-chain carboxyl of cholic acid by one-pot condensation reaction of cholic acid and C12–C18 amines using DCC (Dicyclohexylcarbodiimide) and HOBt (N-hydroxybenzotrizole) as condensation agents for the formation of an amide framework. Then reduction of the amide and quaternization gave a cationic group for strengthening hydrophilicity. This strategy offered a very straightforward and efficient method for access to the designed surfactants in good overall yields. Preliminary results show that an increase both in the length of the hydrophobic tail and in the number of charged groups lowered the CMC of cholic acid-derived cationic surfactants. Cholic acid-based cationic surfactants containing a flexible longer aliphatic chain and a quaternary ammonium had the highest antimicrobial activity.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2

Similar content being viewed by others

References

  1. Simoesa SI, Marquesa CM, Cruza MEM, Cevcb G, Martins MBF (2004) The effect of cholate on solubilisation and permeability of simple and protein-loaded phosphatidylcholine/sodium cholate mixed aggregates designed to mediate transdermal delivery of macromolecules. Eur J Pharm Biopharm 58:509–519

    Article  Google Scholar 

  2. Michael S, Theolea M, Dillmanna R, Fahrb A, Drewec J, Fricker G (2000) Improvement of intestinal peptide absorption by a synthetic bile acid derivative, cholylsarcosine. Eur J Pharm Sci 10:133–140

    Article  CAS  Google Scholar 

  3. Garidel P, Lasch J (2007) Mixed vesicles and mixed micelles: formation, therm odynamic stability. In: Gregoriadis G (ed) Liposome technology: liposome preparation and related techniques. Informa Healthcare, New York

    Google Scholar 

  4. Madenci D, Egelhaaf SU (2010) Self-assembly in aqueous bile salt solutions. Curr Opin Coll Inter Sci 15:109–115

    Article  CAS  Google Scholar 

  5. Li C, Budge LP, Driscoll CD, Willardson BM, Allman GW, Savage PB (1999) Incremental conversion of outer-membrane permeabilizers into potent antibiotics for Gram-negative bacteria. J Am Chem Soc 121:931–940

    Article  CAS  Google Scholar 

  6. Willemen HM, de Smet LCPM, Koudijs A, Stuart MCA, Heikamp-de Jong IGAM, Marcelis ATM, Sudholter EJR (2002) Micelle formation and antimicrobial activity of cholic acid derivatives with three permanent ionic head groups. Angew Chem Int Ed 41:4275–4277

    Article  CAS  Google Scholar 

  7. Janout V, Zhang LH, Staina IV, Di Giorgio C, Regen SL (2001) Molecular umbrella-assisted transport of glutathione across a phospholipid membrane. J Am Chem Soc 123:5401–5406

    Article  CAS  Google Scholar 

  8. Taotafa U, McMullin DB, Lee SC, Hansen LD, Savage PB (2000) Anionic facial amphiphiles from cholic acid. Org Lett 2:4117–4120

    Article  CAS  Google Scholar 

  9. Stein TM, Gellman SH (1992) Synthesis and aggregation properties of a new family of amphiphiles with an unusual headgroup topology. J Am Chem Soc 114:3943–3950

    Article  CAS  Google Scholar 

  10. Loncle C, Brunel JM, Vidal N, Dherbomez M, Letourneux Y (2004) Synthesis and antifungal activity of cholesterol-hydrazone derivatives. Eur J Med Chem 39:1067–1071

    Article  CAS  Google Scholar 

  11. Vatmurge NS, Hazra BG, Pore VS, Shirazi F, Chavan PS, Deshpande MV (2008) Synthesis and antimicrobial activity of β-lactam–bile acid conjugates linked via triazole. Bioorg Med Chem Lett 18:2043–2047

    Article  CAS  Google Scholar 

  12. Aher NG, Pore VS, Mishra NN, Shukla PK, Gonnade RG (2009) Design and synthesis of bile acid-based amino sterols as antimicrobial agents. Bioorg Med Chem Lett 19:5411–5414

    Article  CAS  Google Scholar 

  13. Li H, Shinde PB, Lee HJ, YooES Lee CO, Hong J, Choi SH, Jung JH (2009) Bile acid derivatives from a sponge-associated bacterium Psychrobacter sp. Arch Pharm Res 32:857–862

    Article  CAS  Google Scholar 

  14. Savage PB (2002) Design, synthesis and characterization of cationic peptide and steroid antibiotics. Eur J Org Chem 5:759–768

    Article  Google Scholar 

  15. Savage PB, Li C, Taotafa U, Ding B, Guan Q (2002) Antibacterial properties of cationic steroid antibiotics. FEMS Microbiol Lett 217:1–7

    Article  CAS  Google Scholar 

  16. Zhang J, Jing B, Regen SL (2003) Kinetic evidence for the existence and mechanism of formation of a barrel stave structure from pore-forming dendrimers. J Am Chem Soc 125:13984–13987

    Article  CAS  Google Scholar 

  17. Chen WH, Regen SL (2005) Thermally gated liposomes. J Am Chem Soc 127:6538–6539

    Article  CAS  Google Scholar 

  18. Mehiri M, Chen WH, Janout V, Regen SL (2009) Molecular umbrella transport: exceptions to the classic size/lipophilicity rule. J Am Chem Soc 131:1338–1339

    Article  CAS  Google Scholar 

  19. Ronsin G, Kirby AJ, Rittenhouse S, Woodnutt G, Camilleri P (2002) Structure and antimicrobial activity of new bile acid-based gemini surfactants. J Chem Soc Perkin Trans 2:1302–1306

    Article  Google Scholar 

  20. Ye W, Li Y, Zhou Z, Wang X, Yao J, Liu J, Wang C (2013) Synthesis and antibacterial activity of new long-chain-alkyl bile acid-based amphiphiles. Bioorg Chem 51:1–7

    Article  CAS  Google Scholar 

  21. Kawamura H, Murata Y, Yamaguchi T, Igimi H, Tanaka M, Sugihara G, Kratovihil JP (1989) Spin label studies of bile salt micelles. J Phys Chem 93:3321–3326

    Article  CAS  Google Scholar 

  22. Rosen M (2004) Surfactants and interfacial phenomena, 3rd edn. Wiley, Hobaken

    Book  Google Scholar 

  23. Joondan N, Jhaumeer-Laulloo S, Caumul P (2014) A study of the antibacterial activity of l-Phenylalanine and l-Tyrosineesters in relation to their CMCs and their interactions with 1,2-dipalmitoyl-sn-glycero-3-phosphocholine, DPPC as model membrane. Microbiol Res 169:675–685

    Article  CAS  Google Scholar 

  24. Joondan N, Caumul P, Akerman M, Jhaumeer-Laulloo S (2015) Synthesis, micellisation and interaction of novel quaternary ammonium compounds derived from l-Phenylalanine with 1,2-dipalmitoyl-sn-glycero-3-phosphocholine as model membrane in relation to their antibacterial activity, and their selectivity over human red blood cells. Bioorg Chem 58:117–129

    Article  CAS  Google Scholar 

  25. Petrocci AN (1983) Surface-active agents: quaternary ammonium compounds. In: Block SS (ed) Disinfection, sterilization and preservation, 3rd edn. Lea and Febiger, Philadelphia

    Google Scholar 

  26. Coughlin RT, Tonsager S, McGroarty EJ (1983) Quantitation of metal-cations bound to membranes and extracted lipopolysaccharide of Escherichia coli. Biochemistry 22:2002–2007

    Article  CAS  Google Scholar 

  27. McDonnell G, Russell AD (2001) Antiseptics and disinfectants: activity, action, and resistance. Clin Microbiol Rev 14:227–228

    Google Scholar 

  28. Zhong X, Guo JW, Fu SQ, Zhu DY, Peng JP (2014) Synthesis, surface property and antimicrobial activity of cationic gemini surfactants containing adamantane and amide groups. J Surfact Deterg 17:943–950

    Article  CAS  Google Scholar 

  29. Balgavf P, Devinsky F (1996) Cut-off effects in biological activities of surfactants. Adv Colloid Interface Sci 66:23–63

    Article  Google Scholar 

Download references

Acknowledgments

Financial support of this research by the National Natural Science Foundation of China (NNSFC 21173181) is gratefully acknowledged by the authors. A Project Funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions.

Author information

Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Yangzhou University, 180 Siwangting Street, Yangzhou, 225002, People’s Republic of China

    Lanxiang Zhou, Yang Li, Shuangshuang Li & Cunde Wang

  2. Hangzhou Udragon Chemical Co., Ltd, Hangzhou, 311106, People’s Republic of China

    Xinliang Shen

Authors
  1. Lanxiang Zhou
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yang Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Shuangshuang Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Xinliang Shen
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Cunde Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Cunde Wang.

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zhou, L., Li, Y., Li, S. et al. Cholic Acid-Derived Facial Surfactants with Long Side-Chain Quaternary Ammonium: Synthesis and Antimicrobial Activity Study. J Surfact Deterg 19, 803–811 (2016). https://doi.org/10.1007/s11743-016-1837-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11743-016-1837-4

Keywords

Search

Navigation