Interactions of chlorpromazine with phospholipid monolayers: Effects of the ionization state of the drug

Biophysical Chemistry

Volumn 125, Issue 2-3, 2007, Pages 425-434

  Pickholz, Mónica ^a   Oliveira Jr , Osvaldo N ^b   Skaf, Munir S ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Chlorpromazine; DDPG; DPPC; Model membrane; Molecular dynamics; Monolayers

Indexed keywords

AMPHOLYTE; ANION; CHLORPROMAZINE; DIPALMITOYLPHOSPHATIDYLCHOLINE; DIPALMITOYLPHOSPHATIDYLGLYCEROL; LIPID; PHOSPHOLIPID; WATER;

ARTICLE; CHEMICAL INTERACTION; DRUG CONFORMATION; ELECTRIC POTENTIAL; ELECTRICITY; EXPERIMENTAL STUDY; HYDROGEN BOND; HYDROPHOBICITY; IONIZATION; LIPID MONOLAYER; MOLECULAR DYNAMICS; MOLECULAR MODEL; PRIORITY JOURNAL; PROTON TRANSPORT; QUALITATIVE ANALYSIS; SIMULATION; SURFACE PROPERTY;

1,2-DIPALMITOYLPHOSPHATIDYLCHOLINE; CHLORPROMAZINE; COMPUTER SIMULATION; ELECTROSTATICS; HYDROGEN BONDING; IONS; PHOSPHATIDYLGLYCEROLS; PHOSPHOLIPIDS;

EID: 33846302045     PISSN: 03014622     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bpc.2006.10.010     Document Type: Article

References (35)

1. Chen J.Y., Brunauer L.S., Chu F.C., Helsel C.M., Gedde M.M., and Huesti W.H. Selective amphipathic nature of chlorpromazine binding to plasma membrane bilayers. Biochim. Biophys. Acta 1616 (2003) 95-105 (1616)
2. Nerdal W., Gundersen S.A., Thorsen V., Hoiland H., and Holmsen H. Chlorpromazine interaction with glycerophospholipid liposomes studied by magic angle spinning solid state (13)C-NMR and differential scanning calorimetry. Biochim. Biophys. Acta 1464 (2000) 165-175
3. Agasøster A.V., Tungodden L.M., Cejka D., Bakstad E., Sydnes L.K., and Holmsen H. Chlorpromazine-induced increase in dipalmitoylphosphatidylserine surface area in monolayers at room temperature. Biochem. Pharmacol. 61 (2001) 817-825
4. Kuroda Y., and Kitamura K. Intra- and intermolecular proton-proton nuclear Overhauser effect studies on the interactions of chlorpromazine with lecithin vesicles. J. Am. Chem. Soc. 106 (1984) 1-6
5. Caetano W., and Tabak M. Interaction of chlorpromazine and tifluoperzine with anionic Sodium Dodecyl Sulfate (SDS) micelles: electronic absorption and fluorescence studies. J. Colloid Interface Sci. 225 (2000) 69-81
6. Ahyayauch H., Goñi F.M., and Bennouna M. pH-dependent effects of chlorpromazine on liposomes and erythrocyte membranes. J. Liposome Res. 13 (2003) 147-155
7. Römer J., and Bickel M.H. Biochem. Pharmacol. 28 (1979) 799
8. Jutila A., Söderlund T., Pakkanem A.L., Huttunen M., and Kinnunen P.K.J. Comparison of the effects of clozapine, chlorpromazine, and haloperidol on membrane lateral heterogeneity. Chem. Phys. Lipids 112 (2001) 151-163
9. Wisniewska A., and Wolnicka-Glubisz A. ESR studies on the effect of cholesterol on chlorpromazine interaction with saturated and unsaturated liposome membranes. Biophys. Chem. 111 (2004) 43-52
10. Pickholz M., Oliveira Jr. O.N., and Skaf M.S. Molecular dynamics simulations of neutral chlorpromazine in zwitterionic phospholipids monolayers. J. Phys. Chem., B 110 (2006) 8804-8814
11. Kaznessis Y.N., Kim S., and Larson R.G. Simulations of zwitterionic and anionic phospholipid monolayers. Biophys. J. 82 (2002) 1731-1742
12. Hidalgo A.A., Caetano W., Tabak M., and Oliveira Jr. O.N. Interaction of two phenothiazine derivatives with phospholipid monolayers. Biophys. Chem. 109 (2004) 85-104
13. Feller S.E., Zhang Y., and Pastor R.W. Computer simulation of liquid/liquid interfaces. II. Surface tension-area dependence of a bilayer and monolayer. J. Chem. Phys. 103 (1995) 10267-10276
14. Kalé L., Skeel R., Bhandarkar M., Brunner R., Gursoy A., Krawetz N., Phillips J., Shinozaki A., Varadarajan K., and Schulten K. NAMD2: greater scalability for parallel molecular dynamics. J. Comp. Physiol. 151 (1999) 283
15. Brooks B.R., Bruccoleri R.E., Olafson B.D., States D.J., Swaminathan S., and Karplus M. J. Comp. Chem. 4 (1983) 187
16. Jorgensen W.L., Chandrasekhar J., and Madura J.D. Comparison of simple potential functions for simulating liquid water. J. Chem. Phys. 79 (1983) 926-935
17. Becke A.D. J. Chem. Phys. 98 (1993) 5648
18. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Zakrzewski V.G., Montgomery J.J.A., Stratmann R.E., Burant J.C., Dapprich S., Millam J.M., Daniels A.D., Kudin K.N., Strain M.C., Farkas O., Tomasi J., Barone V., Cossi M., Cammi R., Mennucci B., Pomelli C., Adamo C., Clifford S., Ochterski J., Petersson G.A., Ayala P.Y., Cui Q., Morokuma K., Malick D.K., Rabuck D., Raghavachari K., Foresman J.B., Cioslowski J., Ortiz J.V., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Gomperts R., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Gonzalez C., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Andres J.L., Gonzalez C., Head-Gordon M., Replogle E.S., and Pople J.A. GAUSSIAN98 (Revision A.7) (1998), Gaussian Inc., Pittsburgh, PA
19. Singh U.C., and Kollman P.A. An approach to computing electrostatic charges for molecules. J. Comput. Chem. 5 (1984) 129-145
20. Cieplak P., and Kollman P.A. On the use of electrostatic potential derived charges in molecular mechanics force fields. The relative solvation free energy of cis- and trans-N-methyl-acetamide. J. Comput. Chem. 12 (1991) 1232-1236
21. Tuckerman M.E., Berne B.J., and Martyna G.J.J. Reversible multiple time scale molecular dynamics. Chem. Phys. 97 (1992) 1990-2001
22. Andersen H.C. Rattle: a "velocity" version of the shake algorithm for molecular dynamics calculations. J. Comput. Phys. 52 (1983) 24-34
23. Darden T., York D., and Pedersen L.J. Particle mesh Ewald: an N·log(N) method for Ewald sums in large systems. J. Chem. Phys. 98 (1993) 10089-10092
24. Constantinides P.P., Inouchi N., Tritton T.R., Sartorelli A.C., and Sturtevant J.M. A scanning calorimetric study of the interaction of anthracyclines with neutral and acidic phospholipids alone and in binary mixtures. J. Biol. Chem. 261 (1986) 10196-10203
25. 2/lipid agree suggests that both parameterization of the solute partial charges are reasonable and robust for the properties investigated here.
26. Ladanyi B.M., and Skaf M.S. Computer simulation of hydrogen-bonding liquids. Annu. Rev. Phys. Chem. 44 (1993) 335-368
27. Chen S., Gjerde A.U., Holmsen H., and Nerdal W. Inportance of polyunsaturated acyl chains in chlorpromazine interaction with phosphatidylserines: a 13C and 31P solid-state NMR study. Biophys. Chem. 117 (2005) 101-109
28. Seelig A., and Seelig J. The dynamic structure of fatty acyl chains in a phospholipid bilayer measured by deuterium magnetic Resonance. J. Biochem. 13 (1974) 4839-4845
29. Koubi L., Tarek M., Klein M.L., and Sharf D. Distribution of halothane in a dipalmitoyl phosphatidylcholine bilayer from molecular dynamics calculations. Biophys. J. 78 (2000) 800-811
30. de Vries A.H., Chandrasekhar I., van Gunsteren W.F., and Hünenberger P.H. Molecular dynamics simulations of phospholipid bilayers: influence of artificial periodicity, system size, and simulation time. J. Phys. Chem B, 109 (2005) 11643-11652
31. Skibinsky A., Venable R.M., and Pastor R.W. A molecular dynamics study of the response of lipid bilayers and monolayers to trehalose. Biophys. J. 89 (2005) 4111-4121
32. Lamoureux G., MacKerell Jr. A.D., and Roix B. A simple polarizable model of water based on classical drude oscillators. J. Chem. Phys. 119 (2003) 5185-5197
33. Feller S.E., Pastor R.W., Rojnuckarin A., Bogusz S., and Brooks B.R. Effect of electrostatic force truncation on interfacial and transport properties of water. J. Phys. Chem. 100 (1996) 17011-17020
34. Paluch M. Electrical properties of free surface of water and aqueous solutions. Adv. Colloid Interface Sci. 84 (2000) 27-45
35. Wajneberg E., Tabak M., Nussenzveig P.A., Lopes C.M., and Louro S.R. pH-dependent phase transition of chlorpromazine micellar solutions in the physiological range. Biochim. Biophys. Acta 944 (1988) 185-190