A comparison of sulfur mustard and heptane penetrating a dipalmitoylphosphatidylcholine bilayer membrane

Journal of Hazardous Materials

Volumn 168, Issue 1, 2009, Pages 13-24

  Müller, Thomas J ^a   Müller Plathe, Florian ^a  

^a DARMSTADT UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

Diffusion; DPPC; Molecular dynamics; Mustard gas; Penetration; Sulfur mustard

Indexed keywords

ATOMIC CHARGE; BI-LAYER; CHEMICAL WARFARE AGENTS; DIPALMITOYL PHOSPHATIDYLCHOLINE; DIPALMITOYLPHOSPHATIDYLCHOLINE BILAYERS; DPPC; END-TO-END DISTANCES; EQUILIBRIUM SIMULATIONS; EXTERNAL FORCE; GENERIC MODELS; HEAD GROUPS; MOLECULAR DYNAMICS SIMULATIONS; MOLECULAR VOLUME; MUSTARD GAS; PENETRATION; SULFUR MUSTARD; TRANSPORT MECHANISM;

BIOLOGICAL MEMBRANES; CHEMICAL WARFARE; CYTOLOGY; DIFFUSION; HEPTANE; MOLECULAR DYNAMICS; PARAFFINS; SULFUR;

DYNAMICS;

DIPALMITOYLPHOSPHATIDYLCHOLINE; HEPTANE; MUSTARD GAS;

COMPUTER SIMULATION; DIFFUSION; MEMBRANE; MOLECULAR ANALYSIS; SULFUR;

ARTICLE; BILAYER MEMBRANE; COMPARATIVE STUDY; COMPUTER SIMULATION; DIFFUSION; MEMBRANE TRANSPORT; MOLECULAR DYNAMICS; MOLECULAR SIZE; POLARIZATION; SOLUTE;

1,2-DIPALMITOYLPHOSPHATIDYLCHOLINE; CELL MEMBRANE PERMEABILITY; CHEMICAL WARFARE AGENTS; COMPUTER SIMULATION; DIFFUSION; HEPTANES; LIPID BILAYERS; MOTION; MUSTARD GAS;

EID: 67349281940     PISSN: 03043894     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jhazmat.2009.01.140     Document Type: Article

References (45)

1. Duchowic R.J., and Vilensky J.A. Mustard gas: it's pre-World War I history. J. Chem. Educ. 84 (2007) 948-994
2. Harris J.C. Gassed. Arch. Gen. Psychiatry 62 (2005) 15-18
3. OPC Conference of the States Parties C-12/6: Report of the OPCW on the Implementation of the Convention of the Prohibition of the Development, Production, Stockpiling and Use of Chemical Weapons and on Their Destruction in 2006, Declaration under Article III.
4. Comption J.A.F. Military Chemical and Biological Agents: Chemical and Toxicological Properties (1987), The Telford Press, Caldwell, New Jersey
5. D.W. Riegle Jr., A.M. D'Amato, "The Riegle Report, U.S. Chemical and Biological Warfare-Related Dual Use Exports to Iraq and their Possible Impact on the Health Consequences of the Gulf War", United States Senate, 103d Congress, 2d Session, 1994.
6. Borak J., and Sidell F.R. Agents of chemical warfare: sulfur mustard. Ann. Emerg. Med. 21 (1992) 303-308
7. Shukla P.K., Mishra P.C., and Suhai S. Reactions of DNA bases with the anticancer nitrogen mustard mechlorethamine: a quantum chemical study. Chem. Phys. Lett. 449 (2007) 323-328
8. Wellert S., Imhof H., Dolle M., Altmann H.J., Richardt A., and Hellweg T. Colloid Polym. Sci. 286 (2008) 417-426
9. Berendsen H.J.C., and Marrink S.-J. Molecular dynamics of water transport through membranes: water from solvent to solute. Pure Appl. Chem. 65 (1993) 2513-2520
10. Marrink S.-J., and Berendsen H.J.C. Simulation of water transport through a lipid membrane. J. Phys. Chem. 98 (1994) 4155-4168
11. de Groot B.L., and Grubmüller H. Water permeation across biological membranes: mechanism and dynamics of Aquaporin-1 and GlpF. Science 294 (2001) 2353-2357
12. Sum A.K., Faller R., and de Pablo J.J. Molecular simulation study of phospholipid bilayers and insights of the interactions with disaccharides. Biophys. J. 85 (2003) 2830-2844
13. Pereira C.S., and Hünenberger P.H. Interaction of the sugars trehalose, maltose and glucose with a phospholipid bilayer: a comparative molecular dynamics study. J. Phys. Chem. B 110 (2006) 15572-15581
14. Pereira C.S., Lins R.D., Chandrasekhar I., Freitas L.C.G., and Hünenberger P.H. Interaction of the disaccharide trehalose with a phospholipid bilayer: a molecular dynamics study. Biophys. J. 86 (2004) 2273-2285
15. Tieleman D.P., Sansom M.S.P., and Berendsen H.J.C. Alamethicin helices in a bilayer and in solution: molecular dynamics simulations. Biophys. J. 76 (1999) 40-49
16. Pickholz M., Saiz L., and Klein M.L. Concentration effects of volatile anesthetics on the properties of model membrane: a coarse grain approach. Biophys. J. 88 (2005) 1524-1534
17. Lee B.W., Faller R., Sum A.K., Vattulainen I., Patra M., and Karttunen M. Structural effects of small molecules on phospholipid bilayers investigated by molecular simulations. Fluid Phase Equilib. 225 (2004) 63-68
18. MacCallum J.L., and Tieleman D.P. Interactions between small molecules and lipid bilayers. Curr. Top. Memb. 60 (2008) 227-256
19. Wang Y., Cohen J., Boron W.F., Schulten K., and Tajkhorshid E. Exploring gas permeability of cellular membranes and membrane channels with molecular dynamics. J. Struct. Biol. 157 (2007) 534-544
20. Müller-Plathe F. YASP: a molecular simulation package. Comput. Phys. Commun. 78 (1993) 77-94
21. Tarmyshov K., and Müller-Plathe F. Parallelizing a molecular dynamics algorithm on a multiprocessor workstation using OpenMP. J. Chem. Inf. Model. 45 (2005) 1943-1952
22. Müller-Plathe F. Reversion the perturbation in nonequilibrium molecular dynamics: an easy ways to calculate the shear viscosity of fluids. Phys. Rev. E 59 (1999) 4894-4899
23. Allen M.P., and Tildesley D.J. Computer Simulation of Liquids (1987), Clarendon, Oxford
24. Ryckaert J.-P., Ciccotti G., and Berendsen H.J.C. Numerical integration of the Cartesian equations of motion of a system with constraints: molecular dynamics of alkanes. J. Comput. Phys. 23 (1977) 327-341
25. Berendsen H.J.C., Postma J.P.M., van Gunsteren W.F., DiNola A., and Haak J.R. Molecular dynamics with coupling to an external bath. J. Chem. Phys. 81 (1984) 3684-3690
26. Müller-Plathe F., Rogers S.C., and van Gunsteren W.F. Gas sorbtion and transport in polybutylene: equilibrium and nonequilibrium molecular dynamics simulations. J. Chem. Phys. 98 (1993) 9895-9904
27. Evans D.J., and Moriss J.P. Statistical Mechanics of Nonequilibrium Liquids (1990), Academic Press, London
28. Chandrasekhar I., Kastenholz M., Lins R.D., Oostenbrink C., Schuler L.D., Tielemann D.P., and van Gunsteren W.F. A consistent potential energy parameter set for lipids: dipalmitoylphosphatidulcholine as a benchmark of the GROMOS96 45A3 force field. Eur. Biophys. J. 32 (2003) 67-77
29. van Gunsteren W.F., Billeter S.R., Eising A.A., Hünenberger P.H., Krüger P., Mark A.E., Scott W.R.P., and Tironi I.G. Biomolecular Simulation: The GROMOS96 Manual and User Guide (1996), VDF, Zürich
30. CRC Handbook of Chemistry and Physics, 73rd ed., CRC Press, London, 1992-1993.
31. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. Gaussian 03 Revision B. 01 (2003), Gaussian, Inc., Pittsburgh, PA
32. Berendsen H.J.C., Grigera J.R., and Straatsma T.P. The missing term in the effective pair potentials. J. Phys. Chem. 91 (1987) 6269-6271
33. Leonenko Z.V., Finot E., Ma H., Dahms T.E.S., and Cramb D.T. Investigation of temperature-induced phase transition in DOPC and DPPC phospholipid bilayers using temperature controlled scanning force microscopy. Biophys J. 86 3783 (2004) 3783-3793
34. Tristram-Nagle S., Moore T., Petrache H.I., and Nagle J.F. Specific volumes of lipids in fully hydrated bilayer dispersions. Biochim. Biophys. Acta 938 (1988) 135-142
35. Nagle J.F., and Tristram-Nagle S. Structure of bilayers, Structure of lipid bilayers. Biochim. Biophys. Acta 1469 (2000) 159-195
36. König S., Pfeiffer W., Bayerl T., Richter D., and Sackmann E.J. Molecular dynamics of lipid bilayers studied by incoherent quasi-elastic neutron scattering. J. Phys. II France 2 (1992) 1589-1616
37. Lipowski R., and Sackmann E. Structure and Dynamics of Membranes (1995), Elsevier, Amsterdam
38. Almeida P.F.F., Vaz W.L.C., and Thompson T.E. Lateral diffusion in the liquid phases of dimyristoylphosphatidylcholine/cholesterol lipid bilayers: a free volume analysis. Biochemistry 31 (1992) 6739-6747
39. Vijande J., Piñeiro J.J., García J., Valencia J.L., and Legido J.L. Density and surface tension variation with temperature for heptane + 1-alkanol. J. Chem. Eng. Data 51 (2006) 1778-1782
40. Report on Carcinogens, 11th ed., U.S. Department of Health and Human Services, Public Health Service, National Toxicology Program, 2005.
41. Glukhovtsev M., Bach R.D., and Nagel C.J. A high-level computational study of the thermochemistry and thermal decomposition of sulfur mustard (2,2′-dichlorethyl sulfide): chemical warfare agent. J. Phys. Chem. A 102 (1998) 3438-3446
42. Butterfoss G.L., and Hermans J. Boltzmann-type distribution of side-chain conformation in proteins. Protein Sci. 12 (2003) 2719-2731
43. Wolfe S., Weaver D.F., and Yang K. MMPEP: development and evaluation of peptide parameters for Allinger's MMP2(85) programme, including calculations of crambin and insulin. Can. J. Chem. 66 (1988) 2687-2702
44. Tsonopoulos C. Thermodynamic analysis of the mutual solubilities of normal alkanes and water. Fluid Phase Equilib. 156 (1999) 21-33
45. Müller T.J., Roy S., Zhao W., Maaß A., and Reith D. Economic simplex optimisation for broad range property prediction: strengths and weaknesses of an automated approach for tailoring of parameters. Fluid Phase Equilib. 274 (2008) 27-35