Mixed monolayer of DPPC and lysine-based cationic surfactants: An investigation into the antimicrobial activity

Langmuir

Volumn 29, Issue 25, 2013, Pages 7912-7921

  Colomer, Aurora ^a   Perez, Lourdes ^a   Pons, Ramon ^a   Infante, Maria Rosa ^a   Perez Clos, Dani ^a   Manresa, Angels ^b   Espuny, Maria Jose ^b   Pinazo, Aurora ^a  

^a INSTITUTE OF ADVANCED CHEMISTRY OF CATALONIA IQAC CSIC   (Spain)

^b UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ANTI-MICROBIAL ACTIVITY; CELL DESTRUCTION; HYDROPHOBIC INTERACTIONS; MEMBRANE MODELS; MIXED MONOLAYERS; STAPHYLOCOCCUS AUREUS; STRUCTURAL ALTERATIONS; SURFACTANT STRUCTURE;

AMINO ACIDS; BACTERIA; DYES; ESCHERICHIA COLI; MONOLAYERS; TRANSMISSION ELECTRON MICROSCOPY;

CATIONIC SURFACTANTS;

ANTIINFECTIVE AGENT; DIPALMITOYLPHOSPHATIDYLCHOLINE; LYSINE; SURFACTANT;

AIR; ARTICLE; CHEMISTRY; DRUG EFFECT; ESCHERICHIA COLI; STAPHYLOCOCCUS AUREUS; TRANSMISSION ELECTRON MICROSCOPY;

1,2-DIPALMITOYLPHOSPHATIDYLCHOLINE; AIR; ANTI-INFECTIVE AGENTS; ESCHERICHIA COLI; LYSINE; MICROSCOPY, ELECTRON, TRANSMISSION; STAPHYLOCOCCUS AUREUS; SURFACE-ACTIVE AGENTS;

EID: 84879537013     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la401092j     Document Type: Article

References (45)

1. Moellering, R. C., Jr. NDM-1 A cause for Worldwide Concern N. Engl. J. Med. 2010, 363, 2377-2379
2. Moellering, R. C., Jr. Advances in Antibacterial Therapy Transplant. Proc. 2011, 43, 2441-2442
3. Moellering, R. C., Jr. Discovering new antimicrobial agents Int. J. Antimicrob. Agents 2011, 363, 2377-2379
4. M. R. Porter. Handbook of Surfactants, 2 nd ed.; Blackie Academic and Professional: London, U.K, 1994; pp 248-257.
5. Hugo, W.B.; Russel, A.D. Principles and Practice of Disinfection. In Types of Antimicrobial Agents, 2 nd ed.; Russel, A. D.; Hugo, W. B.; Ayliffe, G. A. J., Eds.; Blackwell Scientific Publications: Oxford, U.K., 1992; pp 7-86.
6. Llies, M. A.; Seitz, W. A.; Johnson, B. H.; Ezell, E. L.; Miller, A. L.; Thompson, E. B.; Balaban, A. T. Lipophilic Pyrylium Salts in the Sinthesis of Efficien Pyridinium-Based Cationic Lipids, Gemini Surfactants, and Lipophilic Oligomers for Gene Delivery J. Med. Chem. 2006, 49, 3872-3887
7. Vyas, S. M.; Turánek, J.; Knötigová, P.; Kasná, A.; Kvardova, V.; Rankin, E.; Knutson, L.; Lehmler, H. J. Synthesis and Biocompatibility Evaluation of Partially Fluorinated Pyridinium Bromides New J. Chem. 2006, 30, 944-951
8. Heyes, J. A.; Nicolescu-Duvaz, D.; Cooper, R. G.; Springer, C. J. Synthesis of Novel Cationic Lipids: Effect of Structural Modification on the Efficiency of Gene Transfer J. Med. Chem. 2002, 45, 99-114
9. Stephenson, B. C.; Rangel-Yagui, C. O.; Pessoa, A.; Tavares, L. C.; Beers, K.; Blankschtein, D. Experimental and Theoretical Investigation of the Micellar-Assisted Solubilization of Ibuprofen in Aqueous Media Langmuir 2006, 22, 1514-1525
10. Bramer, T.; Dew, N.; Edsman, K. Pharmaceutical Applications for Catanionic Mixtures J. Pharm. Pharmacol. 2007, 59, 1319-1334
11. Wang, W.; Lu, W.; Jiang, L. Influence of pH on the Aggregation Morphology of a Novel Surfactant with Single Hydrocarbon Chain and Multi-Amine Headgroups J. Phys. Chem. B 2008, 112, 1409-1413
12. Pérez, N.; Pérez, L.; Infante, M. R.; García, M. T. Biological Properties of Arginine-Based Glycerolipidic Cationic Surfactants Green Chem. 2005, 7, 540-546
13. Morán, C.; Clapés, P.; Comelles, F.; García, T.; Pérez, L.; Vinardell, P.; Mitjans, M.; Infante, M. R. Chemical Structure/Property Relationship in Single Chain Arginine Surfactants Langmuir 2001, 17, 5071-5075
14. Pérez, L.; García, M. T.; Ribosa, I.; Vinardell, M. P.; Manresa, A.; Infante, M. R. Biological Properties of Arginine-Based Gemini Cationic Surfactants Environ. Toxicol. Chem. 2002, 21, 570-577
15. Morán, M. C.; Pinazo, A.; Pérez, L.; Clapés, P.; Angelet, M.; García, M. T.; Vinardell, P.; Infante, M. R. Green Amino-Acid Surfactants Green Chem. 2004, 6, 233-240
16. Sanchez, L.; Mitjans, M.; Infante, M. R.; Vinardell, M. P. Potential Irritation of Lysine Derivative Surfactants by Hemolisis and Hacat Cell viavility Toxicol. Lett. 2006, 161, 53-60
17. Sen, J.; Chaudhuri, A. Gene Transfer Efficacies of Novel Cationic Amphiphiles with Alanine, β-Alanine, And Serine Headgroups: A Structure-Activity Investigation Bioconjugate Chem. 2005, 16, 903-912
18. Roy, S.; Das, P.-K. Antibacterial Hydrogels of Amino Acid-Based Cationic Amphiphiles Biotechnol. Bioeng. 2008, 100, 756-764
19. Colomer, A.; Pinazo, A.; Mitjans, M.; Vinardell, P.; Manresa, A.; Perez, L. Cationic Surfactants Derived from Lysine: Effects of Their Structure and Charge Type on Antimicrobial and Hemolytic Activities J. Med. Chem. 2011, 54, 989-1002
20. Colomer, A.; Pinazo, A.; García, M. T.; Martinez, V.; Mitjans, M.; Vinardell, P.; Infante, M. R.; Pérez, L. pH Sensitive Surfactants from Lysine: Assessment of Their Cytotoxicity and Environmental Behavior Langmuir 2012, 28, 5900-5912
21. Mezei, A.; Pérez, L.; Pinazo, A.; Comelles, F.; Infante, M. R.; Pons, R. Self Assembly of pH-Sensitive Lysine Surfactants Langmuir 2012, 28, 16761-16771
22. Jones, R. N.; Barry, A. L.; Gavan, T. L.; Washington, J. A. In II Manual of Clinical Microbiology; Lennette, E.H.; Ballows, A.; Hauser, W.J.; Shadomy, H.J., Eds.; American Society for Microbiology: Washington D.C., 1980.
23. Pinazo, A.; Pérez, L.; Infante, M. R.; Pons, R. Unconventional Vesicle-to-Ribbon Transition Behaviour of Diacyl Glicerol Amino Acid Based Surfactants in Extremely Diluted Systems Induced by pH-Concentration Effects Phys. Chem. Chem. Phys. 2004, 6, 1475-1481
24. Boullanger, P.; Chevalier, Y. Surface Active Properties and Micellar Aggregation of Alkyl 2-Amino-2-Deoxy-B-D-Glucopyranosides Langmuir 1996, 12, 1771-1776
25. Tabohashi, T.; Tobita, K.; Sakamoto, K.; Kouchi, J.; Ykoyama, S.; Sakai, H.; Abe, M. Solution Properties of Amino Acid-Type New Surfactants Colloids Surf., B 2001, 20, 79-86
26. Goldsipe, A.; Blankschtein, D. Tritation of Mixed Micelles Containing a pH-Sensitive Surfactant and Conventional (pH-insensitive) Surfactant: A Regular Solution Theory Modeling Approach Langmuir 2006, 22, 9894-9904
27. Söderman, O.; Jönsson, B.; Olofsson, G. Tritation of Fatty Acids Solubilized in Cationic and Anionic Micelles. Calorimetry and Thermodynamic Modeling J. Phys. Chem. B 2006, 110, 3288-3293
28. Brockman, H. Lipid Monolayers: Why Use Half a Membrane to Characterize Protein-Membrane Interactions? Curr. Opin. Struct. Biol. 1999, 9, 438-443
29. Kim, S. H.; Franses, E. I. New Protocols for Preparing Dipalmitoylphosphatidylcholine Dispersions and Controling Surface Tension and Competitive Adsorption at the Air/Water Interface Colloids Surf., B 2005, 43, 256-266
30. Infante, M. R.; Juliá, M. R.; Erra, P.; Molinero, J.; García-Domíngez, J.; Alsina, M. A. Correlation between the Antimicrobial Activity of Acyl-Bis Amino Acids and Their Structural Arrangement in the Monolayers Tenside, Surfactants, Deterg. 1984, 21, 39
31. Goracci, L.; Germani, R.; Rathman, J. F.; Savelli, G. Anomalous Behavior of Amine Oxide Surfactants at the Air/Water Interface Langmuir 2007, 23, 10525-10532
32. Gaines, G.L. Insoluble Monolayers at Liquid-Gas Interface; John Wiley & Sons: New York, 1966.
33. Brzozowska, I.; Figaszewski, Z. A. The influence of pH on phosphatidylcholine monolayer at the air/aqueous solution interface Colloids Surf., B 2003, 27, 303-309
34. Brzozowska, A. M.; Duits, M. H. G.; Mugele, F. Stability of Stearic Acid Monolayers on Artificial Sea Water Colloids Surf., A 2012, 407, 38-48
35. McFate, C.; Ward, D.; Olmsted, J. Organized Collapse of Fatty-Acid Monolayers Langmuir 1993, 9, 1036-1039
36. Miñones, J., Jr.; Pais, S.; Miñones, J.; Conde, O.; Dynarowicz-Latka, P. Interactions between Membrane Sterols and Phospholipids in Model Mammalian and Fungi Cellular Membranes: A Langmuir Monolayer Study Biophys. Chem. 2009, 140, 69-77
37. Finer, E. G.; Phillips, M. C. Factors Affecting Molecular Packing in Mixed Lipid Monolayers and Bilayers Chem. Phys. Lipids 1973, 10, 237-252
38. Bakshi, M. S.; Sing, J.; Kaur, G. Mixed Micelles of Monomeric and Dimeric Cationic Surfactants with Phospholipids: Effect of Hydrophobic Interactions Characterization of Mixed Micelles of Cationic Twin Tail Surfactants with Phospholipids Using Fluorescence Spectroscopy Chem. Phys. Lipids 2005, 138, 81-92
39. Lohner, K.; Sevcsik, E.; Pabst, G. Liposome-Based Biomembrane Mimetic Systems: Implications for Lipid-Peptide Interactions Adv. Planar Lipid Bilayers Liposomes 2008, 6, 103-137
40. Nikaido, H. Molecular Basis of Bacterial Outer Membrane Permeability Revisited Microbiol. Mol. Biol. Rev. 2003, 67, 593-656
41. Denyer, S. P. Mechanism of Action of Antibacterial Biocides Biodeterior. Biodegrad. 1995, 36, 227-245
42. McDonnell, G.; Rusell, A. D. Antiseptics and Disinfectants. Activity, action and resistance Clin. Microbiol. Rev. 1999, 12, 147-179
43. Rodríguez, E.; Seguer, J.; Rocabayera, X.; Manresa, A. Cellular Effects of Monohydrochloride of L-Arginine, N-Lauroyl Ethylester (LAE) on Exposure to Salmonella Typhimurium and Staphylococcus Aureous J. Appl. Microbiol. 2004, 96, 903-912
44. Papanastasiou, E. A.; Hua, Q.; Sandouk, A.; Son, U.; Christenson, A. J.; Van Hoek, M. L.; Bishop, B. M. Role of Acetylation and Charge in Antimicrobial Peptides Based on Human ß-Defensin-3 APMIS 2009, 492-499
45. Valko, E. I.; DuBois, A. S. Correlation between Antibacterial Power and Chemical Structure of Higher Alkyl Ammonium Ions J. Bacteriol. 1945, 50, 481-490