Conformation and Orientation of Phospholipid Molecule in Pure Phospholipid Monolayer During Compressing

doi:10.1016/S1004-9541(13)60456-5

Abstract

Abstract: On the basis of energy conservation law and surface pressure isotherm, the conformation energy changes of dipalmitoylphosphatidylcholine (DPPC) and dipalmitoylphosphatidylglycerol (DPPG) in pure phospholipid monolayer at the air/water interface during compression are derived. The optimized conformations of phospholipids at absolute freedom state are simulated by Gaussian 98 software. Based on following assumptions: (1) the conformation energy change is mainly caused by the rotation of one special bond; (2) the atoms of glycerol near the water surface are active; (3) the rotation is motivated by hydrogen-bond action; (4) the rotation of bond is inertial, one simplified track of conformational change is suggested and the conformations of DPPC and DPPG at different states are determined by the plots of conformation energy change vs. dihedral angle. The thickness of the simulated phospholipid monolayer is consistent with published experimental result. According to molecular areas at different states, the molecular orientations in the compressing process are also developed.

Key words: dipalmitoylphosphatidylcholine, dipalmitoylphosphatidylglycerol, phospholipid monolayer, conformation, orientation

摘要： On the basis of energy conservation law and surface pressure isotherm, the conformation energy changes of dipalmitoylphosphatidylcholine (DPPC) and dipalmitoylphosphatidylglycerol (DPPG) in pure phospholipid monolayer at the air/water interface during compression are derived. The optimized conformations of phospholipids at absolute freedom state are simulated by Gaussian 98 software. Based on following assumptions: (1) the conformation energy change is mainly caused by the rotation of one special bond; (2) the atoms of glycerol near the water surface are active; (3) the rotation is motivated by hydrogen-bond action; (4) the rotation of bond is inertial, one simplified track of conformational change is suggested and the conformations of DPPC and DPPG at different states are determined by the plots of conformation energy change vs. dihedral angle. The thickness of the simulated phospholipid monolayer is consistent with published experimental result. According to molecular areas at different states, the molecular orientations in the compressing process are also developed.

关键词: dipalmitoylphosphatidylcholine, dipalmitoylphosphatidylglycerol, phospholipid monolayer, conformation, orientation

XUE Weilan, WANG Dan, ZENG Zuoxiang, GAO Xuechao. Conformation and Orientation of Phospholipid Molecule in Pure Phospholipid Monolayer During Compressing[J]. Chin.J.Chem.Eng., 2013, 21(2): 177-184.

薛为岚, 王丹, 曾作祥, 高雪超. Conformation and Orientation of Phospholipid Molecule in Pure Phospholipid Monolayer During Compressing[J]. Chinese Journal of Chemical Engineering, 2013, 21(2): 177-184.

References

1 Bi, X., Flach, C.R., Pérez-Gil, J., Plasencia, I., Andreu, D., Oliveira, E., Mendelsohn, R., “Secondary structure and lipid interactions of the N-terminal segment of pulmonary surfactant SP-C in Langmuir film: IR reflecton-adsorption spectroscopy and surface pressure studies”, Biochemistry, 41 (26), 8385-8395 (2002).

2 Dieudonné, D., Mendelsohn, R., Farid, R.S., Flach, C.R., “Secondary structure in lung surfactant SP-B peptides: IR and CD studies of bulk and monolayer phases”, Biochim. Biophys. Acta, 1511 (1), 99-112 (2001).

3 Veldhuizen, E.J.A., Haagasman, H.P., “Role of pulmonary surfactant components in surface film formation and dynamics”, Biochim. Biophys. Acta, 1467 (2), 255-270 (2000).

4 Brumm, T., Naumann, C., Sackmann, E., Rennie, A.R., Thomas, R.K., Kanellas, D., Penfold, J., Bayed, T.M., “Conformational changes of the lecithin headgroup in monolayers at the air/water interface”, Eur. Biophys. J., 23 (4), 289-295 (1994).

5 Brezesinski, G., Thoma, M., Struth, B., Möhwald, H., “Structural changes of monolayers at the air/water interface contacted with n-alkanes”, J. Phys. Chem., 100 (8), 3126-3130 (1996).

6 Gericke, A., Moore, D.J., Erukulla, R.K., Bittman, R., Mendelsohn, R., “Partially deuterated phospholipids as IR structure probes of conformational order in bulk and monolayer phases”, J. Mol. Struct., 379 (1-3), 227-239 (1996).

7 Ma, G., Allen, H.C., “DPPC Langmuir monolayer at the air-water interface: probing the tail and head groups by vibrational sum frequency generation spectroscopy”, Langmuir, 22 (12), 5341-5349 (2006).

8 Dominguez, H., Smondyrev, A.M., Berkowitz, M.L., “Computer simulations of phosphatidylcholine monolayers at air/water and CCl₄/water interfaces”, J. Phys. Chem. B, 103 (44), 9582-9588 (1999).

9 Adhangale, P.S., Gaver, D.P., “Equation of state for a coarse-grained DPPC monolayer at the air/water interface”, Mol. Phys., 104 (19), 3011-3019 (2006).

10 Laing C., Baoukina S., Tieleman D.P., “Molecular dynamics study of the effect of cholesterol on the properties of lipid monolayers at low surface tensions”, Phys. Chem. Chem. Phys., 11 (12), 1916-1922 (2009).

11 Mohammad-Aghaie, D., Mace, E., Sennoga, C.A., Seddon, J.M., Bresme, F., “Molecular dynamics simulations of liquid condensed to liquid expanded transitions in DPPC monolayers”, J. Phys. Chem. B, 114 (3), 1325-1335 (2010).

12 Shushkov, P., Tzvetanov, S., Velinova, M., Ivanova, A., Tadjer, A., “Structural aspects of lipid monolayers: computer simulation analyses”, Langmuir, 26 (11), 8081-8092 (2010).

13 Zeng Z.X., Chen Q., Xue W.L., Nie F., “Surface equation of state for pure phospholipid monolayer at the air/water interface”, Chin. J. Chem. Eng., 12 (2), 263-266 (2004).

14 Krüger, P., Schalke, M., Wang, Z., Notter, R.H., Dluhy, R.A., Lösche, M., “Effect of hydrophobic surfactant peptides SP-B and SP-C on binary phospholipid monolayers. I. Fluorescence and dark-field microscopy”, Biophys. J., 77 (2), 903-914 (1999).

15 Taneva, S., Keough, K.M., “Pulmonary surfactant protein SP-B and SP-C in spread monolayers at the air-water interface: I. Monolayers of pulmonary surfactant protein SP-B and phospholipids”, Biophys. J., 66 (4), 1137-1148 (1994).

16 Taneva, S., Keough, K.M., “Pulmonary surfactant protein SP-B and SP-C in spread monolayers at the air-water interface: II. Monolayers of pulmonary surfactant protein SP-C and phospholipids”, Biophys. J., 66 (4), 1149-1157 (1994).

17 Taneva, S., Keough, K.M., “Pulmonary surfactant protein SP-B and SP-C in spread monolayers at the air-water interface: III. Proteins SP-B plus SP-C with phospholipids in spread monolayers”, Biophys. J., 66 (4), 1158-1166 (1994).

18 Wüstneck, N., Wüstneck, R., Fainerman, V.B., Miller, R., Pison, U., “Interfacial behaviour and mechanical properties of spread lung surfactant protein/lipid layers”, Colloids Surf. B, 21 (1-3), 191-205 (2001).

19 Plasencia, I., Keough, K.M.W., Perez-Gil, J., “Interaction of the N-terminal segment of pulmonary surfactant protein SP-C with interfacial phospholipid films”, Biochim. Biophys. Acta, 1713 (2), 118-128 (2005).

20 Biswas, N., Shanmukh, S., Waring, A.J., Walther, F., Wang, Z., Chang, Y., Notter, R.H., Dluhy, R.A., “Structure and properties of phospholipid–peptide monolayers containing monomeric SP-B1-25 I. Phases and morphology by epifluorescence microscopy”, Biophys. Chem., 113 (3), 223-232 (2005).

21 Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Zakrzewski, V.G., Montgomery, J.A., Jr., 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, A.D., Raghavachari, K., Foresman, J.B., Cioslowski, J., Ortiz, J.V., Baboul, A.G., 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., Challacombe, M., Gill, P.M.W., Johnson, B.G., Chen, W., Wong, M.W., Andres, J.L., Gonzalez, C., Head-Gordon, M., Replogle, E.S., Pople, J.A., Gaussian 98, Revision A. 7, Gaussian, Inc., Pittsburgh, PA (1998).

22 Zeng, Z.X., Li, D., Xue, W.L., Sun, L., “Structural models and surface equation of state for pulmonary surfactant monolayers”, Biophys. Chem., 131 (1-3), 88-95 (2007).

23 Pimthon, J., Willumeit, R., Lendlein, A., Hofmann, D., “All-atom molecular dynamics simulation studies of fully hydrated gel phase DPPG and DPPE bilayers”, J. Mol. Struct., 921 (1-3), 38-50 (2009).

24 Li, D., Zeng, Z.X., Xue, W.L., Yao, Y.L., “The model of the action mechanism of SP-C in the lung surfactant monolayers”, Colloids Surf. B, 57 (1), 22-28 (2007).

25 Krüger, P., Baatz, J.E., Dluhy, R.A., Lösche, M., “Effects of hydrophobic surfactant protein SP-C on binary phospholipid monolayers. Molecular machinery at the air/water interface”, Biophys. Chem., 99 (3), 209-228 (2002).

26 Kohn, W., Sham, L.J., “Self-consistent equation including exchange and correlation effects”, Phys. Rev. A, 140 (4), 1135-1138 (1965).

27 Levy, M., “Universal variational functionals of electron densities, first-order density matrices, and natural spin-orbitals and solution of the v-representation problem”, PNAS, 76 (12), 6062-6065 (1979).

28 Becke, A.D., “Density-functional exchange-energy approximation with correct asymptotic behavior”, Phys. Rev. A, 38 (6), 3098-3100 (1998).

29 Vakinin, D., Kjaer, K., Als-Nielsen, J., Lösche, M., “Structural properties of phosphatidylcholine in a monolayer at the air/water interface: Neutron reflection study and reexamination of X-ray reflection measurements”, Biophys. J., 59 (6), 1325-1332 (1991).

30 Bayerl, T.M., Thomas, R.K., Penfold, J., Rennie, A., Sackmann, E., “Specular reflection of neutrons at phospholipid monolayers. Changes of monolayer structure and headgroup hydration at the transition from the expanded to the condensed phase state”, Biophys. J., 57 (5), 1095-1098 (1990).

31 Hauser, H., Pascher, I., Pearson, R.H., Sundell, S., “Preferred conformation and molecular packing of phosphatidylethanolamine and phosphatidylcholine”, Biochim. Biophys. Acta, 650 (1), 21-51 (1981).

32 Song, C.S., Ye, R.Q., Mu, B.Z, “Molecular behavior of a microbial lipopeptide monolayer at the air-water interface”, Colloids Surf. A, 302 (1-3), 82-87 (2007).

33 Baoukina, S., Monticelli, L., Risselada, H.J., Marrink, S.J., Tieleman, D.P., “The molecular mechanism of lipid monolayer collapse”, PNAS, 105 (31), 10803-10808 (2008).

[1]	Hamid Moradi, Bahamin Bazooyar, Ahmad Moheb, Seyed Gholamreza Etemad. Optimization of natural convection heat transfer of Newtonian nanofluids in a cylindrical enclosure [J]. Chin.J.Chem.Eng., 2015, 23(8): 1266-1274.
[2]	ZHAO Xiaofang, SHANG Yazhuo, LIU Honglai, HU Ying, JIANG Jianwen. Interaction of DNA with Cationic Gemini Surfactant Trimethylene-1, 3-bis(dodecyldimethyl-ammonium bromide) and Anionic Surfactant SDS Mixed System [J]. , 2008, 16(6): 923-928.
[3]	ZHANG ,Shanliang, ,LIN ,Jianzhong, ZHANG ,Weifeng. Numerical research on the fiber suspensions in a turbulent T-shaped branching channel flow [J]. , 2007, 15(1): 30-38.