Location of chlorhexidine in DMPC model membranes: A neutron diffraction study

Chemistry and Physics of Lipids

Volumn 163, Issue 6, 2010, Pages 480-487

  Komljenović, Ivana ^a   Marquardt, Drew ^a   Harroun, Thad A ^a   Sternin, Edward ^a  

^a BROCK UNIVERSITY   (Canada)

Author keywords

Cell lysis; Chlorhexidine; DMPC; Lipid water interface; Model membrane; Neutron diffraction

Indexed keywords

CHLORHEXIDINE; GLYCEROL; HYDROCARBON; PHOSPHATIDYLCHOLINE; ANTIINFECTIVE AGENT; DEUTERIUM; DIMYRISTOYLPHOSPHATIDYLCHOLINE; LIPID BILAYER;

ARTICLE; ARTIFICIAL MEMBRANE; HUMAN; MEMBRANE DAMAGE; MEMBRANE STRUCTURE; NEUTRON DIFFRACTION; PRIORITY JOURNAL; CHEMICAL STRUCTURE; CHEMISTRY; LIPID BILAYER;

ANTI-BACTERIAL AGENTS; CHLORHEXIDINE; DEUTERIUM; DIMYRISTOYLPHOSPHATIDYLCHOLINE; LIPID BILAYERS; MODELS, MOLECULAR; NEUTRON DIFFRACTION;

BACTERIA (MICROORGANISMS);

EID: 77954214471     PISSN: 00093084     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemphyslip.2010.03.007     Document Type: Article

References (45)

1. K.H. Abu-Elteen, and P.A. Whittaker Effect of sub-inhibitory concentration of chlorhexidine on lipid and sterol composition of Candida albicans Mycopathologia 140 1998 69 76
2. K.L. Audus, M.R. Tavakoli-Saberi, H. Zheng, and E.N. Boyce Chlorhexidine effects on membrane lipid domains of human buccal epithelial cells J. Dent. Res. 71 6 1992 1298 1303
3. K. Barrett-Bee, L. Newboult, and S. Edwards The membrane destabilising action of the antibacterial agent chlorhexidine FEMS Microbiol. Lett. 119 1994 249 254 (Pubitemid 24185662)
4. R.S. Blackburn, A. Harvey, L.L. Kettle, A.P. Manian, J.D. Payne, and S.J. Russell Sorption of chlorhexidine on cellulose: mechanism of binding and molecular recognition J. Phys. Chem. B 111 2007 8775 8784
5. R. Brasseur Molecular Description of Biological Membranes by Computer Aided Conformational Analysis 1990 CRC Press
6. J.A. Castillo, P. Clapés, M.R. Infante, J. Comas, and Á. Manresa Comparative study of the antimicrobial activity of bis (N α-caproyl-L-arginine)-1,3-propanediamine dihydrochloride and chlorhexidine dihydrochloride against Staphylococcus aureus and Escherichia coli J. Antimicrob. Chemother. 57 2006 691 698
7. J.A. Castillo, A. Pinazo, J. Carilla, M.R. Infante, M. Ásunción Alsina, I. Haro, and P. Clapés Interaction of antimicrobial arginine-based cationic surfactants with liposomes and lipid monolayers Langmuir 20 2004 3379 3387
8. F.-Y. Chen, M.-T. Lee, and H.W. Huang Evidence for membrane thinning effect as the mechanism for peptide-induced pore formation Biophys. J. 84 2003 3751 3758
9. L. Chen, L. Bromberg, T.A. Hatton, and G.C. Rutledge Electrospun cellulose acetate fibers containing chlorhexidine as a bactericide Polymer 49 2008 1266 1275
10. D.M. Deng, M.A. Hoogenkamp, J.M.T. Cate, and W. Crielaard Novel metabolic activity indicator in Streptococcus mutans biofilms J. Microbiol. Methods 77 2009 67 71
11. J.J. Dynes, J.R. Lawrence, D.R. Korber, G.D.W. Swerhone, G.G. Leppard, and A.P. Hitchcock Morphological and biochemical changes in Pseudomonas flourescens biofilms induced by sub-inhibitory exposure to antimicrobial agents Can. J. Microbiol. 55 2009 163 178
12. T. El-Moug, D. Rogers, J. Furr, B. El-Falaha, and A. Russell Antiseptic-induced changes in the cell surface of a chlorhexidine-sensitive and a chlorhexidine-resistant strain of Providencia stuartii J. Antimicrob. Chemother. 16 1985 685 689 (Pubitemid 16212206)
13. R.G. Fisher, and R.P. Quintana Surface-chemical studies on chlorhexidine and related compounds: II. Interactions with monomolecular-film systems J. Dent. Res. 54 1975 25 31
14. K. Fitzgerald, A. Davies, and A. Russell Uptake of C 14-chlorhexidine diacetate to Escherichia coli and Pseudomonas aeruginosa and its release by azolectin FEMS Microbiol. Lett. 60 1989 327 332
15. P. Gilbert, and L.E. Moore Cationic antiseptics: diversity of action under a common epithet J. Appl. Microbiol. 99 2005 703 715
16. V.I. Gordeliy, and N.I. Chernov Accuracy of determination of position and width of molecular groups in biological and lipid membranes via neutron diffraction Acta Crystallogr. D D53 1997 377 384
17. X. Han, M. Mihailescu, and K. Hristova Neutron diffraction studies of fluid bilayers with transmembrane proteins: structural consequences of the achondroplasia mutation Biophys. J. 91 2006 3736 3747
18. F. Harold, J. Baarda, C. Baron, and A. Abrams Dio 9 and chlorhexidine: inhibitors of membrane-bound ATP ase and of cation transport in Streptococcus faecalis Biochim. Biophys. Acta 183 1969 129 136
19. T. Harroun, J. Katsaras, and S. Wassall Cholesterol is found to reside in the center of a polyunsaturated lipid membrane Biochemistry 47 2008 7090 7096
20. T. Harroun, M. Koslowsky, M.-P. Nieh, V. Raghunathan, and J. Katsaras Finite-size effects do not reduce the repeat spacing of phospholipid multibilayer stacks on a rigid substrate Eur. Phys. J. E 13 2004 359 362
21. D.D. Heard, and R.W. Ashworth The colloidal properties of chlorhexidine and its interaction with some macromolecules J. Pharm. Pharmacol. 20 1968 505 512
22. S. Hiom, J. Furr, A. Russell, and J. Dickinson Effects of chlorhexidine diacetate and cetylpyridinium chloride on whole cells and protoplasts of Saccharomyces cerevisiae Microbios 74 1993 111 120
23. W. Hugo, and A. Longworth Some aspects of the mode of action of chlorhexidine J. Pharm. Pharmacol. 16 1964 655 662
24. T. Ikeda, S. Tazuke, and M. Watanabe Interaction of biologically active molecules with phospholipid membranes: fluorescence depolarization studies on the effect of polymeric biocide bearing biguanide groups in the main chain Biochim. Biophys. Acta 735 1983 380 386
25. M.N. Jones, Y.-H. Song, M. Kaszuba, and M.D. Reboiras The interaction of phospholipid liposomes with bacteria and their use in the delivery of bactericides J. Drug Target 5 1 1997 25 34
26. M. Kiselev, D. Lombardo, P. Lesieur, A. Kisselev, S. Borbely, T. Simonova, and L. Barsukov Membrane self assembly in mixed DMPC/NaC systems by SANS Chem. Phys. 345 2008 173 180
27. N. Kucerka, J.F. Nagle, J.N. Sachs, S.E. Feller, J. Pencer, A. Jackson, and J. Katsaras Lipid bilayer structure determined by the simultaneous analysis of neutron and X-ray scattering data Biophys. J. 95 2008 2356 2367
28. T. Kuyyakanond, and L. Quesnel The mechanism of action of chlorhexidine FEMS Microbiol. Lett. 100 1992 211 216
29. J.R. Lawrence, B. Zhu, G.D.W. Swerhone, E. Topp, J. Roy, L.I. Wassenaar, T. Rema, and D.R. Korber Community-level assessment of the effects of the broad-spectrum antimicrobial chlorhexidine on the outcome of river microbial biofilm development Appl. Environ. Microbiol. 74 11 2008 3541 3550
30. M. Moser, T. Hudlicky, S. Sadeghi, and E. Sternin Synthesis of deuterium-labelled chlorhexidine J. Label. Compd. Radiopharm. 50 2007 671 674
31. J.F. Nagle Lipid bilayer phase transition: density measurements and theory Proc. Natl. Acad. Sci. U.S.A. 70 12 1973 3443 3444
32. T. Ooi, and M. Oobatake Effects of hydrated water on protein unfolding J. Biochem. 103 1988 114 120
33. J.B. Park, and N.-H. Park Effect of chlorhexidine on the in vitro and in vivo herpes simplex virus infection Oral Surg. 67 1989 149 153
34. H.I. Petrache, S.W. Dodd, and M.F. Brown Area per lipid and acyl length distributions in fluid phosphatidylcholines determined by H 2 NMR spectroscopy Biophys. J. 79 2000 3172 3192
35. A. Russell, and M. Day Antibacterial activity of chlorhexidine J. Hosp. Infect. 25 1993 229 238
36. T. Salditt Thermal fluctuations and stability of solid-supported lipid membranes J. Phys.: Condens. Matter 17 2005 R287 R314
37. D. Stopar, R.B. Spruijt, and M.A. Hemminga Anchoring mechanisms of membrane-associated M13 major coat protein Chem. Phys. Lipids 141 1-2 2006 83 93
38. M. Swart, T. van der Wijst, C.F. Guerra, and F.M. Bickelhaupt π-π stacking tackled with density functional theory J. Mol. Model. 13 2007 1245 1257
39. J.M. Tanzer, A.M. Slee, and B.A. Kamay Structural requirements of guanide, biguanide, and bisbiguanide agents for antiplaque activity Antimicrob. Agents Chemother. 12 6 1977 721 729
40. A. Thomas, and R. Brasseur Tilted peptides: the history Curr. Protein Pept. Sci. 7 6 2006 523 527
41. P.C.A. van der Wel, N.D. Reed, D.V. Greathouse, and R.E. Koeppe Orientation and motion of tryptophan interfacial anchors in membrane-spanning peptides Biochemistry 46 25 2007 7514 7524
42. M.C. Wiener, and S.H. White Fluid bilayer structure determination by the combined use of X-ray and neutron diffraction. I. Fluid bilayer models and the limits of resolution Biophys. J. 59 1991 162 173
43. M.C. Wiener, and S.H. White Fluid bilayer structure determination by the combined use of X-ray and neutron diffraction. II. "Composition-space" refinement method Biophys. J. 59 1991 174 185
44. D.L. Worcester, and N.P. Franks Structural analysis of hydrated egg lecithin and cholesterol bilayers. II. Neutron diffraction J. Mol. Biol. 100 1976 359 378
45. W. Zhang, E. Crocker, S. McLaughlin, and S.O. Smith Binding of peptides with basic and aromatic residues to bilayer membranes J. Biol. Chem. 278 2003 21459 21466