Startseite Benzalkonium Salts of Amino Acids – Physicochemical Properties and Anti-Microbial Activity
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Benzalkonium Salts of Amino Acids – Physicochemical Properties and Anti-Microbial Activity

  • Paula Ossowicz , Ewa Janus , Magdalena Błaszak , Kinga Zatoń und Zbigniew Rozwadowski
Veröffentlicht/Copyright: 13. November 2017
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Tenside Surfactants Detergents
Aus der Zeitschrift Tenside Surfactants Detergents Band 54 Heft 6

Abstract

New salts combining a benzalkonium cation and chiral amino acid anions were synthesized and characterized. The identification was performed by NMR spectroscopy. Properties such as temperature of phase transformation, specific rotation, thermal stability and surface activity and antimicrobial activity were determined and compared with that of benzalkonium chloride. Benzalkonium amino acids salts can be used as conditioners in cosmetics. It has been shown they have weak impact on symbiotic microorganisms which occupy a wide range of skin, and this confirms that they do not disturb the biological balance of human skin.

Kurzfassung

Neue Salze, die aus einem Benzalkoniumkation und chiralen Aminosäureanionen bestehen, wurden synthetisiert und charakterisiert. Die Identifizierung erfolgte durch NMR-Spektroskopie. Eigenschaften wie die Phasenumwandlungstemperatur, die spezifische Rotation, die thermische Stabilität, die Oberflächenaktivität und die antimikrobielle Aktivität wurden bestimmt und mit denen von Benzalkoniumchlorid verglichen. Die Benzalkonium-Aminosäure-Salze können als Konditionierer in der Kosmetik verwendet werden. Es wurde gezeigt, dass sie einen schwachen Einfluss auf die symbiotischen Mikroorganismen haben, die einen weiten Bereich der Haut einnehmen. Dies bestätigt, dass sie das biologische Gleichgewicht der menschlichen Haut nicht stören.

Key words: Benzalkonium salts; amino acids; surface activity; biological activity
Stichwörter: Benzalkoniumsalze; Aminosäuren; Oberflächenaktivität; biologische Aktivität
*Correspondence address, Dr. Paula Ossowicz, Institute of Organic Chemical Technology, Faculty of Chemical Technology and Engineering, West Pomeranian University of Technology Szczecin, ul. Pułaskiego 10, 70-322 Szczecin, Poland, Tel.: +48914494584, Fax: +48914494365, E-Mail:

Paula Ossowicz – Ph. D., (Eng.), graduated from the Faculty of Chemical Engineering and Technology, West Pomeranian University of Technology in Szczecin (2011). In 2015, she received a degree of doctor from the same Faculty. Currently, she works as a researcher at the Institute of Organic Chemical Technology of West Pomeranian University of Technology in Szczecin. Her research interest encompasses novel compounds with application as medicinal and surface active remedies.

Ewa Janus – Ph. D., D. Sc., (Eng.), graduated from the Faculty of Chemical Technology and Engineering of Szczecin University of Technology (1994). She was granted the title of the Doctor of Technical Sciences in 1999, while in 2014 she was granted D.Sc. in the field of chemical technology. She works at the Institute of Organic Chemical Technology of West Pomeranian University of Technology in Szczecin. Scientific interests – ionic liquids – synthesis, properties and applications in technology and organic synthesis.

Magdalena Błaszak – Ph. D., D.Sc., (Eng.), works at the Department of Chemistry, Microbiology and Environmental Biotechnology of West Pomeranian University of Technology in Szczecin. She was granted the title of the Doctor of Agriculture Sciences, while in 2014 she was granted D.Sc. in the field of environmental microbiology.

Kinga Zatoń is Ph. D. student at the Department of Chemistry, Microbiology and Environmental Biotechnology of West Pomeranian University of Technology in Szczecin.

Zbigniew Rozwadowski – Ph. D., D.Sc., (Eng.), graduated from the Faculty of Chemical Technology and Engineering of Szczecin University of Technology (1993). He was granted the title of the Doctor of Chemical Sciences in 2000, while in 2010 he was granted D.Sc. in the field of chemistry. He works at the Department of Inorganic and Analytical Chemistry of West Pomeranian University of Technology in Szczecin. Specialty – organic chemistry.

References

1. 23rd Commission Directive 98/62/EC of 3 September 1998 adapting to technical progress Annexes II, III, VI and VII to Council Directive 76/768/EEC on the approximation of the laws of the Member States relating to cosmetic products.Suche in Google Scholar

2. Graf, P.: Adverse effects of benzalkonium chloride on the nasal mucosa: allergic rhinitis and rhinitis medicamentosa, Clin. Ther.21 (1999) 1749–1755. 10.1016/S0149-2918(99)80053-8Suche in Google Scholar

3. Sadakane, K. and Ichinose, T.: Effect of the Hand Antiseptic Agents Benzalkonium Chloride, Povidone-Iodine, Ethanol, and Chlorhexidine Gluconate on Atopic Dermatitis in NC/Nga Mice, Int. J. Med. Sci.12 (2015) 116–125. 10.7150/ijms.10322Suche in Google Scholar PubMed PubMed Central

4. Neza, E. and Centini, M.: Microbiologically Contaminated and Over-Preserved Cosmetic Products According Rapex 2008–2014, Cosmetics3 (2016) 1–11. 10.3390/cosmetics3010003Suche in Google Scholar

5. Adelson, L. and Sunshine, I.: Fatal poisoning due to a cationic detergent of the quaternary ammonium compound type, Am. J. Clin. Pathol.22 (1952) 656–661. 10.1093/ajcp/22.7.656Suche in Google Scholar PubMed

6. McDonnell, G. and Russell, A. D.: Antiseptics and disinfectants: activity, action, and resistance, Clin. Microbiol. Rev.12 (1999) 147–179. 10.1128/CMR.12.1.147Suche in Google Scholar PubMed PubMed Central

7. Chuanchuen, R., Beinlich, K., Hoang, T. T., Becher, A., Karkhoff-Schweizer, R. R. and Schweizer, H. P.: Cross-resistance between triclosan and antibiotics in Pseudomonas aeruginosa is mediated by multidrug efflux pumps: exposure of a susceptible mutant strain to triclosan selects nfxB mutants overexpressing MexCD-OprJ, Antimicrob. Agents Chemother.45 (2001) 428–432. 10.1128/AAC.45.2.428-432.2001Suche in Google Scholar PubMed PubMed Central

8. Sheldon, A. T.: Antiseptic “resistance”: real or perceived threat?, Clin. Infect. Dis.40 (2005) 1650–1656. 10.1086/430063Suche in Google Scholar PubMed

9. Fazlara, A. and Ekhtelat, M.: The Disinfectant Effects of Benzalkonium Chloride on Some Important Foodborne Pathogens, American-Eurasian J. Agric. & Environ. Sci.12 (2012) 23–29. 10.1186/1471-2334-14-292Suche in Google Scholar PubMed PubMed Central

10. Houari, A. and Di Martino, P.: Effect of chlorhexidine and benzalkonium chloride on bacterial biofilm formation, Lett. Appl. Microbiol.45 (2007) 652–656. 10.1111/j.1472-765X.2007.02249.xSuche in Google Scholar PubMed

11. Pernak, J., Materna, K. and Cybulski, J.: Pat. PL 207 844 (2010) “New quaternary ammonium salts of lactic acid and a method to obtain new quaternary ammonium salts of lactic acid”.Suche in Google Scholar

12. Cybulski, J., Wiśniewska, A., Kulig-Adamiak, A., Lewicka, L., Cieniecka-Rosłonkiewicz, A., Kita, K., Fojutowski, A., Nawrot, J., Materna, K. and Pernak, J.: Long-alkyl-chain quaternary ammonium lactate based ionic liquids, Chemistry – A European Journal14 (2008) 9305–9311. 10.1002/chem.200800973Suche in Google Scholar PubMed

13. Cybulski, J., Wisniewska, A., Kulig-Adamiak, A., Dabrowski, Z., Praczyk, T., Michalczyk, A., Walkiewicz, F., Materna, K. and Pernak, J.: Mandelate and prolinate ionic liquids: synthesis, characterization, catalytic and biological activity, Tetrahedron Lett.52 (2011) 1325–1328. 10.1016/j.tetlet.2011.01.069Suche in Google Scholar

14. Pernak, J., Smiglak, M., Griffin, S. T., Hough, W. L., Wilson, T. B., Pernak, A., Zabielska-Matejuk, J., Fojutowski, A., Kita, K. and Rogers, R. D.: Long alkyl chain quaternary ammonium-based ionic liquids and potential applications, Green Chem.8 (2006) 798–806. 10.1039/B604353DSuche in Google Scholar

15. Hough-Troutman, W. L., Smiglak, M., Griffin, S., Reichert, W. M., Mirska, I., Jodynis-Liebert, J., Adamska, T., Nawrot, J., Stasiewicz, M., Rogers, R. D. and Pernak, J.: Ionic liquids with dual biological function: sweet and anti-microbial, hydrophobic quaternary ammonium-based salts, New J. Chem.33 (2009) 26–33. 10.1039/B813213PSuche in Google Scholar

16. Sadakane, K. and Ichinose, T.: Effect of the Hand Antiseptic Agents Benzalkonium Chloride, Povidone-Iodine, Ethanol, and Chlorhexidine Gluconate on Atopic Dermatitis in NC/Nga Mice, Int. J. Med. Sci.12(2) (2015) 116–125. 10.7150/ijms.10322Suche in Google Scholar PubMed

17. Stanford, D. and Georgouras, K.: Allergic contact dermatitis from benzalkonium chloride in plaster of Paris, Contact Dermatitis35 (1996) 371–372. 10.1111/j.1600-0536.1996.tb02427.xSuche in Google Scholar

18. Lin, G. H. Y. and Hemming, M.: Ocular and dermal irritation studies of some quaternary ammonium compounds, Food Chem. Toxicol.34 (1996) 177–182. 10.1016/0278-6915(95)00099-2Suche in Google Scholar

19. Allouch, M., Infante, M. R., Seguer, J., Stebe, M. J. and Selve, C.: Nonionic Amphiphilic compounds from Aspartic and Glutamic acids as structural mimics of Lecithins, J. Am. Oil Chem. Soc.73 (1996) 87–96. 10.1007/BF02523453Suche in Google Scholar

20. Pérez, L., Pinazo, A., Vinardell, P., Clapés, P., Angelet, M. and InfanteM.R.: Synthesis and Biological properties of Dicationic arginine-diglycerides, New J. Chem.26 (2002) 1221–1227. 10.1039/B203896JSuche in Google Scholar

21. Pérez, L., Pinazo, A., Garcia, M. T., Morán, C. and Infante, M. R.: Monoglyceride surfactants from arginine: Synthesis and biological properties, New J. Chem.28 (2004) 1326–1334. 10.1039/B405733CSuche in Google Scholar

22. Singare, P. U. and Mhatre, J. D.: Cationic Surfactants from Arginine: Synthesis and Physicochemical Properties, American Journal of Chemistry2 (2012) 186–190. 10.5923/j.chemistry.20120204.02Suche in Google Scholar

23. Hough, W. L., Smiglak, M., Rodríguez, H., Swatloski, R. P., Spear, S. K., Daly, D. T., Pernak, J., Grisel, J. E., Carlis, R. D., Soutullo, M. D., Davis, J. H. and Rogers, R. D.: The third evolution of ionic liquids: active pharmaceutical ingredients, New J. Chem.31 (2007) 1429–1436. 10.1039/B706677PSuche in Google Scholar

24. Taylor, P. C., Schoenknecht, F. D., Sherris, J. C. and LinnerE.C.: Determination of minimum bactericidal concentrations of oxacillin for Staphylococcus aureus: influence and significance of technical factors, Antimicrob. Agents Chemotherapy23(1) (1983) 142–150. 10.1128/AAC.23.1.142Suche in Google Scholar PubMed PubMed Central

25. Yilmaz, M. T.: Minimum inhibitory and minimum bactericidal concentrations of boron compounds against several bacterial strains, Turk. J. Med. Sci.42 (2012) 1423–1429. 10.3906/sag-1205-83Suche in Google Scholar

26. Buffet-Bataillon, S., Tattevin, P., Bonnaure-Mallet, M. and Jolivet-Gougeon, A.: Emergence of resistance to antibacterial agents: the role of quaternary ammonium compounds – a critical review, Int. J. Antimicrob. Agents39 (2012) 381–389. 10.1016/j.ijantimicag.2012.01.011Suche in Google Scholar PubMed

27. French, G. L.: Bactericidal agents in the treatment of MRSA infections – the potential role of daptomycin, J. Antimicrob. Chemother.58 (2006) 1107–1117. 10.1093/jac/dkl393Suche in Google Scholar PubMed

28. Holla, G., Yeluri, R. and Munshi, A. K.: Evaluation of minimum inhibitory and minimum bactericidal concentration of nano-silver base inorganic anti-microbial agent Novaron® against Streptococcus mutans, Contemp. Clin. Dent.3 (2012) 288–293. 10.4103/0976-237X.103620Suche in Google Scholar PubMed PubMed Central

29. Joynson, J. A., Forbes, B. and Lambert, R. J. W.: Adaptive resistance to benzalkonium chloride, amikacin and tobramycin: the effect on susceptibility to other antimicrobials, J. Appl. Microbiol.93 (2002) 96–107. 10.1046/j.1365-2672.2002.01667.xSuche in Google Scholar PubMed

30. Ossowicz, P., Janus, E., Schroeder, G. and Rozwadowski, Z.: Spectroscopic Studies of Amino Acid Ionic Liquid-Supported Schiff Bases, Molecules18 (2013) 4986–5004. 10.3390/molecules18054986Suche in Google Scholar PubMed PubMed Central

31. Ossowicz, P., Janus, E., Szady-Chełmniecka, A. and Rozwadowski, Z.: Influence of modification of the amino acids ionic liquids on their physico-chemical properties: Ionic liquids versus ionic liquids-supported Schiff bases, J. Mol. Liq.224 (2016) 211–218. 10.1016/j.molliq.2016.09.111Suche in Google Scholar

32. Rozwadowski, Z.: Deuterium isotope effects on 13C chemical shifts of lithium salts of Schiff bases amino acids, J. Mol. Struct.753 (2006) 127–131. 10.1016/j.molstruc.2005.06.005Suche in Google Scholar

33. Breitmaier, E. and Voelter, W.: 13C NMR Spectroscopy, Methods and Applications in Organic Chemistry, in: EbelH. F. and VoelterW. (Eds.), Monographs in Modern Chemistry, Verlag Chemie, Weinheim (1978). 10.1002/prac.19813230630Suche in Google Scholar

34. Ossowicz, P., Janus, E., Rozwadowski, Z. and Pilawka, R.: Synthesis and properties of didecyldimethylammonium salts of amino acids, Przem. Chem.92 (2013) 1000–1003.Suche in Google Scholar

35. Brycki, B., Malecka, I., Kozirog, A. and Otlewska, A.: Synthesis, Structure and Antimicrobial Properties of Novel Benzalkonium Chloride Analogues with Pyridine Rings, Molecules22 (2017) 130–142. 10.3390/molecules22010130Suche in Google Scholar PubMed PubMed Central

36. Rosen, M. J. and Kunjappu, J. T.: Surfactants and Interfacial Phenomena, John Wiley&Sons, Hoboken (2012). 10.1002/9781118228920Suche in Google Scholar

37. Loughlin, M. F., Jones, M. V. and Lambert, P. A.: Pseudomonas aeruginosa cells adapted to benzalkonium chloride show resistance to other membrane-active agents but not to clinically relevant antibiotics, J. Antimicrob. Chemoth.49 (2002) 631–639. 10.1093/jac/49.4.631Suche in Google Scholar PubMed

38. Takahashi, T., Satoh, I. and Kikuchi, N.: Phylogenetic relationships of 38 taxa of the genus Staphylococcus based on 16S rRNA gene sequence analysis, Int. J. Syst. Bacteriol.49 (1999) 725–728. 10.1099/00207713-49-2-725Suche in Google Scholar PubMed

39. Chan, C. X., Beiko, R. G. and Ragan, M. A.: Lateral Transfer of Genes and Gene Fragments in Staphylococcus Extends beyond Mobile Elements, J. Bacteriol.193 (2011) 3964–3977. 10.1128/JB.01524-10Suche in Google Scholar PubMed PubMed Central

40. King, E. O., Ward, M. K. and Raney, D. E.: Two simple media for the demonstration of pyocyanin and fluorescin, J. Lab. Clin. Med.44 (1954) 301–307. Suche in Google Scholar PubMed

41. Egwuatu, T. O., Ogunsola, F. T., Okodugha, I. M., Jide, B., Arewa, D. G. and Osinupebi, O. A.: Effect of Blood Agar from Different Animal Blood on Growth Rates and Morphology of Common Pathogenic Bacteria, Adv. Microb.4 (2014) 1237–1241. 10.4236/aim.2014.416133Suche in Google Scholar

42. Peberdy, J. F.: Spore Formation in Bacteria, in: Peberdy, J. F. (Ed.) Developmental Microbiology, Springer, Boston (1980) MA. 88–114. 10.1007/978-1-4613-3927-4_5Suche in Google Scholar

43. Setlow, P.: Spores of Bacillus subtilis: their resistance to and killing by radiation, heat and chemicals, J Appl Microbiol.101 (2006) 514–525. 10.1111/j.1365-2672.2005.02736.xSuche in Google Scholar PubMed

44. Inamdar, S., Kanitkar, R. U. and Watve, M. G.: Longevity of Azotobacter cysts and a model for optimization of cyst density in liquid bioinoculants, Current Science78 (2000) 719–722, www.jstor.org/stable/24103888.Suche in Google Scholar

45. Lupo, M. P. and ColeA.L.: Cosmeceutical peptides, Dermatol. Ther.20 (2007) 343–349. 10.4103/0378-6323.186500Suche in Google Scholar PubMed

Received: 2017-05-11
Accepted: 2017-08-12
Published Online: 2017-11-13
Published in Print: 2017-11-15

© 2017, Carl Hanser Publisher, Munich

Artikel in diesem Heft

  1. Contents/Inhalt
  2. Contents
  3. Application
  4. The Influence of Natural and Synthetic Additives in Mitigating Calcium Phosphate Scale in Industrial Water Systems
  5. Preparation and Application of Double-Hydrophilic Copolymer as Scale and Corrosion Inhibitor for Industrial Water Recycling
  6. Removal of Insoluble Slimes from Potash Ore Using Flotation
  7. Ester-Based Pyridinium Gemini Surfactants as Novel Inhibitors for Mild Steel Corrosion in 1 M HCl Solution
  8. Novel Surfactants
  9. Benzalkonium Salts of Amino Acids – Physicochemical Properties and Anti-Microbial Activity
  10. Synthesis, Characterizations and Multifunctional Activities of New Thiourea-Based Non-Ionic Surfactants
  11. Environmental Chemistry
  12. Extraction of Natural Surfactant Saponin from Soapnut (Sapindus mukorossi) and its Utilization in the Remediation of Hexavalent Chromium from Contaminated Water
  13. Electrocatalytic Hydrogenolysis of Chlorophenolic Compounds by Modified Electrodes in Aqueous Medium in the Absence and the Presence of Ionic Surfactant
  14. Physical Chemistry
  15. Enzymatic Synthesis and Characterization of Sucrose Erucate
  16. Study of the Complex System of Fatty Alcohol Polyoxyethylene Ether Carboxylate and Alkyl Betaine for Heavy Oil Recovery
https://doi.org/10.3139/113.110524
Schlagwörter für diesen Artikel
Benzalkonium salts; amino acids; surface activity; biological activity

Artikel in diesem Heft

  1. Contents/Inhalt
  2. Contents
  3. Application
  4. The Influence of Natural and Synthetic Additives in Mitigating Calcium Phosphate Scale in Industrial Water Systems
  5. Preparation and Application of Double-Hydrophilic Copolymer as Scale and Corrosion Inhibitor for Industrial Water Recycling
  6. Removal of Insoluble Slimes from Potash Ore Using Flotation
  7. Ester-Based Pyridinium Gemini Surfactants as Novel Inhibitors for Mild Steel Corrosion in 1 M HCl Solution
  8. Novel Surfactants
  9. Benzalkonium Salts of Amino Acids – Physicochemical Properties and Anti-Microbial Activity
  10. Synthesis, Characterizations and Multifunctional Activities of New Thiourea-Based Non-Ionic Surfactants
  11. Environmental Chemistry
  12. Extraction of Natural Surfactant Saponin from Soapnut (Sapindus mukorossi) and its Utilization in the Remediation of Hexavalent Chromium from Contaminated Water
  13. Electrocatalytic Hydrogenolysis of Chlorophenolic Compounds by Modified Electrodes in Aqueous Medium in the Absence and the Presence of Ionic Surfactant
  14. Physical Chemistry
  15. Enzymatic Synthesis and Characterization of Sucrose Erucate
  16. Study of the Complex System of Fatty Alcohol Polyoxyethylene Ether Carboxylate and Alkyl Betaine for Heavy Oil Recovery
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