Skip to main content
Log in

Synthesis and Biological Activity of 8-Hydroxyquinoline and 2-Hydroxypyridine Quaternary Ammonium Salts

  • Original Article
  • Published:
Journal of Surfactants and Detergents

Abstract

Two series of quaternary cationic surfactant were synthesized by reaction of 8-hydroxyquinoline and 2-hydroxypyridine with long chain alkyl halides (dodecyl, tetradecyl- and hexadecyl-bromide). Surface tension was measured in aqueous solution for different concentrations at 25 °C. Various surface properties of the synthesized surfactants were evaluated, particularly critical micelle concentration (CMC), efficiency (ΠCMC) as well as maximum surface excess (Γmax) and minimum surface area (A min). Micellization and adsorption in liquid/air interfaces thermodynamics were investigated. The synthesized cationic surfactants were evaluated for their biocidal activity. All compounds prepared showed good antibacterial and antifungal activities.

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

Similar content being viewed by others

References

  1. Badawi AM, Marzibani MM, Haroun B, Soliman H (1983) Quaternary ammonium salts of potential biological activity. Curr Sci 52(24):1169–1171

    CAS  Google Scholar 

  2. Andrew J, Mc B, Ruth GL, Louiss EM, Carl C, Peter Gt (2004) Effects of quaternary-ammonium based formulation on bacterial community dynamics and antimicrobial susceptibility. Appl Environ Microbiol 70(6):3449–3456

    Article  Google Scholar 

  3. Mahmud SA, Ismail DA, Ghazy EA (2007) Surface properties and biological activity of select cationic surfactants. J Surfactants Detergents 10(4):191–194

    Article  Google Scholar 

  4. Shen AY, Chen CP, Roffler S (1999) A chelating agent possessing cytotoxicity and antimicrobial activity: 7-morpholinomethyl-8-hydroxyquinoline. Life Sci 64(9):813–825

    Article  CAS  Google Scholar 

  5. Bych JS, Middlesev NJ (1975) Antimicrobial hydroxyquinoline, ethylene-acrylic polymer composition. U.S. Patent 3,872,128

  6. Eric F, Scriven V, Murugan R (2005) Pyridine and pyridine derivatives, Kirk-Othmer encyclopedia of chemical technology

  7. Soldatenkov AT, Levov AN, Mobio IG, Polyakova EV, Kutyakov SV, Le Tuan An AI, Komarova KB, Polyanskii EI, Andreeva L (2004) Synthesis and biological activity of N- and O-acyl derivatives of 2,6-diphenyl-4-hydroxypiperidines and tetrahydropyridines. Heterocycl comp 35(10)

  8. Ismail DA, Mohamed AS, Mohamed MZ (2004) Synthesis of some new quaternary ammonium compounds: evaluation of their surface properties and solubilization activity. Trans Egypt Soc Chem Eng 30(2):1503–1511

    Google Scholar 

  9. Cooper RE (1972) In: Kavanagen FW (ed) Analytical microbiology, vols I, II. Academic press, New York

    Google Scholar 

  10. Gad EAM, El-Sukkary MMA, Ismail DA (1997) Surface and thermodynamic parameters of sodium N-acyl sarcosinate solutions. J Am Oil Chem Soc 74:34

    Article  Google Scholar 

  11. El-Sukary MMA, Ismail DA, Morsy SMI (2001) Preparation of some tourine derivatives from alkylhalo esters and evaluating them as surface active agents. Egypt J Petroleum 11(5):51–66

    Google Scholar 

  12. Mohamed AS, Mohamed MZ, Ismail DA (2004) Alanine-based surfactants: synthesis and some surface properties. J Surfactants Detergents 7(4):415–419

    Article  Google Scholar 

  13. Mohamed MZ, Ismail DA, Mohamed AS (2005) Synthesis and evaluation of new amphiphilic polyethylene glycol-based triblock copolymer surfactants. J Surfactants Detergents 8(4):175–180

    Article  Google Scholar 

  14. Augusta S, Gruber HF, Streichsbier F (2003) Synthesis and antibacterial activity of immobilized quaternary ammonium salts. J Appl Polymer Sci 53(9):1149–1163

    Article  Google Scholar 

  15. Negm NA, Morsy SMI, Said MM (2005) Biological activity of some Mannich base cationic derivatives. Bioorg Med Chem 13:5921–5926

    Article  Google Scholar 

  16. Badawi AM, Mekawi MA, Mohamed AS, Mohamed MZ, Khowdairy MM (2007) Surface and biological activity of some novel cationic surfactants. J Surfactants Detergents 10(4):243–25

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Dina A. Ismail.

About this article

Cite this article

Ahmed, S.M., Ismail, D.A. Synthesis and Biological Activity of 8-Hydroxyquinoline and 2-Hydroxypyridine Quaternary Ammonium Salts. J Surfact Deterg 11, 231–235 (2008). https://doi.org/10.1007/s11743-008-1078-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11743-008-1078-2

Keywords

Navigation