On the importance of anandamide structural features for its interactions with DPPC bilayers: Effects on PLA2 activity

Journal of Lipid Research

Volumn 46, Issue 9, 2005, Pages 1953-1961

  Ambrosi, S ^a   Ragni, L ^b   Ambrosini, A ^a   Paccamiccio, L ^a   Mariani, P ^a   Fiorini, R ^a   Bertoli, E ^a   Zolese, G ^a  

^a UNIVERSITÀ POLITECNICA DELLE MARCHE   (Italy)

^b UNIVERSITY OF CAMERINO   (Italy)

Author keywords

Dipalmitoylphosphatidylcholine; Laurdan; Phospholipase A2; X ray diffraction

Indexed keywords

ANANDAMIDE; CANNABINOID RECEPTOR; DIPALMITOYLPHOSPHATIDYLCHOLINE; ION CHANNEL; LAURDAN; MEMBRANE LIPID; PHOSPHOLIPASE A2; VANILLOID RECEPTOR;

ARTICLE; ENZYME ACTIVITY; FLUORESCENCE; LIPID BILAYER; MEMBRANE STRUCTURE; PRIORITY JOURNAL; X RAY DIFFRACTION;

1,2-DIPALMITOYLPHOSPHATIDYLCHOLINE; ARACHIDONIC ACIDS; CANNABINOIDS; DOSE-RESPONSE RELATIONSHIP, DRUG; FLUORESCENT DYES; LIPID BILAYERS; PHOSPHOLIPASES A; POLYUNSATURATED ALKAMIDES; SPECTROMETRY, FLUORESCENCE; STRUCTURE-ACTIVITY RELATIONSHIP; X-RAY DIFFRACTION;

EID: 24344502267     PISSN: 00222275     EISSN: None     Source Type: Journal    
DOI: 10.1194/jlr.M500121-JLR200     Document Type: Article

References (51)

1. Schuel, H., L. J. Burkman, J. Lippes, K. Crickard, E. Forester, D. Piomelli, and A. Giuffrida. 2002. N-Acylethanolamines in human reproductive fluids. Chem. Phys. Lipids. 121: 211-227.
2. Hansen, H. S., B. Moesgaard, H. H. Hansen, and G. Petersen. 2000. N-Acylethanolamines and precursor phospholipids-relation to cell injury. Chem. Phys. Lipids. 108: 135-150.
3. Hansen, H. H., C. Ikonomidou, P. Bittigau, S. H. Hansen, and H. S. Hansen. 2001. Accumulation of the anandamide precursor and other N-acylethanolamine phospholipids in infant rat models of in vivo necrotic and apoptotic neuronal death. J. Neurochem. 76: 39-46.
4. Leweke, F. M., A. Giuffrida, U. Wurster, H. M. Emrich, and D. Piomelli. 1999. Elevated endogenous cannabinoids in schizophrenia. Neuroreport. 10: 1665-1669.
5. Hillard, C. J., and W. B. Campbell. 1997. Biochemistry and pharmacology of arachidonylethanolamide, a putative endogenous cannabinoid. J. Lipid Res. 38: 2383-2398.
6. Howlett, A. C., and S. Mukhopadhyay. 2000. Cellular signal transduction by anandamide and 2-arachidonoylglycerol. Chem. Phys. Lipids. 108: 53-70.
7. Schmid, P. C., B. C. Paria, R. J. Krebsbach, H. H. Schmid, and S. K. Dey. 1997. Changes in anandamide levels in mouse uterus are associated with uterine receptivity for embryo implantation. Proc. Natl. Acad. Sci. USA. 94: 4188-4192.
8. Maccarrone, M., M. DeFelici, F. G. Klinger, N. Battista, F. Fezza, E. Dainese, G. Siracusa, and A. Finazzi-Agrò. 2004. Mouse blastocysts release a lipid which activates anandamide hydrolase in intact uterus. Mol. Hum. Reprod. 10: 215-221.
9. Parolaro, D., P. Massi, T. Rubino, and E. Monti. 2002. Endocannabinoids in the immune system and cancer. Prostaglandins Leukot. Essent. Fatty Acids. 66: 319-332.
10. Freund, T. F., I. Katona, and D. Piomelli. 2003. Role of endogenous cannabinoids in synaptic signaling. Physiol Rev. 83: 1017-1066.
11. Randall, M. D., D. Harris, D. A. Kendall, and V. Ralevic. 2002. Cardiovascular effects of cannabinoids. Pharmacol. Ther. 95: 191-202.
12. Pate, D. W., K. Jarvinen, A. Urtti, V. Mahadevan, and T. Jarvinen. 1998. Effect of the CB1 receptor antagonist, SR141716A, on cannabinoid-induced ocular hypotension in normotensive rabbits. Life Sci. 63:2181-2188.
13. De Petrocellis, L., D. Melck, T. Bisogno, and V. Di Marzo. 2000. Endocannabinoids and fatty acid amides in cancer, inflammation and related disorders. Chem. Phys. Lipids. 108: 191-209.
14. Berdyshev, E. V., P. C. Schmid, R. J. Krebsbach, C. J. Hillard, C. Huang, N. Chen, Z. Dong, and H. H. O. Schmid. 2001. Cannabinoid-receptor-independent cell signalling by N-acylethanolamines. Biochem. J. 360: 67-75.
15. Schmid, H. H. O., P. C. Schmid, and V. Natarajan. 1990. N-Acylated glycerophospholipids and their derivatives. Prog. Lipid Res. 29: 1-43.
16. Ambrosini, A., E. Bertoli, P. Mariani, F. Tanfani, M. Wozniak, and G. Zolese. 1993. N-Acylethanolamines as membrane topological stress compromising agents. Biochim. Biophys. Acta. 1148: 351-355.
17. Ambrosini, A., F. Tanfani, E. Bertoli, M. Wozniak, Z. Wypych, and G. Zolese. 1993. Effect of N-acylethanolamines with different acyl-chains on DPPC multilamellar liposomes. Chem. Phys. Lipids. 65: 165-169.
18. 2 activity by saturated and monounsaturated N-acylethanolamines. J. Lipid Res. 44: 742-753.
19. Bloom, A. S., W. S. Edgemond, and J. C. Moldvan. 1997. Nonclassical and endogenous cannabinoids: effects on the ordering of brain membranes. Neurochem. Res. 22: 563-568.
20. Makriyannis, A., and R. S. Rapaka. 1990. The molecular basis of cannabinoid activity. Life Sci. 47: 2173-2184.
21. Schuel, H., L. J. Burkman, J. Lippes, K. Crickard, M. C. Mahony, A. Giuffrida, R. P. Picone, and A. Makriyannis. 2002. Evidence that anandamide-signaling regulates human sperm functions required for fertilization. Mol. Reprod. Dev. 63: 376-387.
22. Jain, M. K., M. H. Gelb, J. Rogers, and O. G. Berg. 1995. Kinetic bases for interfacial catalysis by phospholipase A2. Methods Enzymol. 249: 567-614.
23. Bell, J. D., and R. L. Biltonen. 1992. Molecular details of the activation of soluble phospholipase A2 on lipid bilayers. Comparison of computer simulations with experimental results. J. Biol. Chem. 267: 11046-11056.
24. Bell, J. D., M. Burnside, J. A. Owen, M. L. Royall, and M. L. Baker. 1996. Relationships between bilayer structure and phospholipase A2 activity: interactions among temperature, diacylglycerol, lysolecithin, palmitic acid, and dipalmitoylphosphatidylcholine. Biochemistry. 35: 4945-4955.
25. Vermehren, C., T. Kielber, I. Hylander, T. H. Callisen, and K. Jørgensen. 1998. Increase in phospholipase A2 activity towards lipopolymer-containing liposomes. Biochim. Biophys. Acta. 1373: 27-36.
26. Laye, J. P., and J. H. Gill. 2003. Phospholipase A2 expression in tumours: a target for therapeutic intervention? DrugDiscov. Today. 8: 710-716.
27. Burack, W. R., A. R. Dibble, M. M. Allietta, and R. L. Biltonen. 1997. Changes in vesicle morphology induced by lateral phase separation modulate phospholipase A2 activity. Biochemistry. 36: 10551-10557.
28. Callisen, T. H., and Y. Talmon. 1998. Direct imaging by cryo-TEM shows membrane break-up by phospholipase A2 enzymatic activity. Biochemistry. 37: 10987-10993.
29. Parasassi, T., G. De Stasio, G. Ravagnan, R. M. Rusch, and E. Gratton. 1991. Quantitation of lipid phases in phospholipid vesicles by the generalized polarization of Laurdan fluorescence. Biophys. J. 60:179-189.
30. Parasassi, T., G. De Stasio, A, D'Ubaldo, and E. Gratton. 1990. Phase fluctuation in phospholipid membranes revealed by Laurdan fluorescence. Biophys. J. 57: 1179-1186.
31. Hirsch-Lerner, D., and Y. Barenholz. 1999. Hydration of lipoplexes commonly used in gene delivery: follow-up by Laurdan fluorescence changes and quantification by differential scanning calorimetry. Biochim. Biophys. Acta. 1461: 47-57.
32. Parasassi, T., M. Loiero, M. Raimondi, G. Ravagnan, and E. Gratton. 1993. Absence of lipid gel-phase domains in seven mammalian cell lines and in four primary cell types. Biochim. Biophys. Acta. 1153:143-154.
33. Mariani, P., V. Luzzati, and H. Delacroix. 1988. Cubic phases of lipid-containing systems. Structure analysis and biological implications. J. Mol. Biol. 204: 165-189.
34. Luzzati, V. 1968. X-ray diffraction studies of lipid-water systems. In Biological Membranes. D. Chapman and F. H. Wallah, editors. Academic Press, London. 71-123.
35. Heimburg, T. 2000. A model for the lipid pretransition: coupling of ripple formation with the chain-melting transition. Biophys. J. 78: 1154-1165.
36. Høyrup, P., O. G. Mouritsen, and J. Jorgensen. 2001. Phospholipase A(2) activity towards vesicles of DPPC and DMPC-DSPC containing small amounts of SMPC. Biochim. Biophys. Acta. 1515: 133-143.
37. Heimburg, T. 1998. Mechanical aspects of membrane thermodynamics. Estimation of the mechanical properties of lipid membranes close to the chain melting transition from calorimetry. Biochim. Biophys. Acta. 1415: 147-162.
38. Mason, P. C., B. D. Gaulin, R. M. Epand, G. D. Wignall, and J. S. Lin. 1999. Small angle neutron scattering and calorimetric studies of large unilamellar vesicles of the phospholipid dipalmitoylphosphatidylcholine. Phys. Rev. E. 59: 3361-3367.
39. Hafez, I. M., and P. R. Cullis. 2001. Roles of lipid polymorphism in intracellular delivery. Adv. Drug Deliv. Rev. 47: 139-148.
40. Janiak, M. J., D. M. Small, and G. G. Shipley. 1976. Nature of the thermal pretransition of synthetic phospholipids: dimyristolyl- and dipalmitoyllecithin. Biochemistry. 15: 4575-4580.
41. Hønger, T., K. Jørgensen, D. Stokes, R. L. Biltonen, and O. G. Mouritsen. 1997. Phospholipase A2 activity and physical properties of lipid-bilayer substrates. Methods Enzymol. 286: 168-190.
42. 2. Biophys. J. 74: 2398-2404.
43. 2 hydrolysis of DPPC bilayers visualized by atomic force microscopy. Biochim. Biophys. Acta. 1420: 266-271.
44. Hønger, T., K. Jorgensen, R. L. Biltonen, and O. G. Mouritsen. 1996. Systematic relationship between phospholipase A2 activity and dynamic lipid bilayer microheterogeneity. Biochemistry. 35: 9003-9006.
45. Leidy, C., O. G. Mouritsen, K. Jorgensen, and G. H. Peters. 2004. Evolution of a rippled membrane during phospholipase A2 hydrolysis studied by time-resolved AFM. Biophys. J. 87: 408-418.
46. Semmler, K., H. W. Meyer, and P. J. Quinn. 2000. The structure and thermotropic phase behavior of dipalmitoylphosphatidylcholine codispersed with a branched-chain phosphatidylcholine. Biochim. Biophys. Acta. 1509: 385-396.
47. Cunningham, B. A., A-D. Brown, D. H. Wolfe, W. P. Williams, and A. Brain. 1998. Ripple phase formation in phosphatidylcholine: effect of acyl chain relative length, position, and unsaturation. Phys. Rev. E. 58: 3662-3672.
48. Meyer, H. W., B. Dobner, and K. Semmler. 1996. Macroripple-structures induced by different branched-chain phosphatidylcholines in bilayers of dipalmitoylphosphatidylcholine. Chem. Phys. Lipids. 82: 179-189.
49. Piomelli, D., M. Beltramo, S. Glasnapp, S. Y. Lin, A. Goutopoulos, X. Q. Xie, and A. Makriyannis. 1999. Structural determinants for recognition and translocation by the anandamide transporter. Proc. Natl. Acad. Sci. USA. 96: 5802-5807.
50. Ramirez, F., and M. K. Jain. 1991. Phospholipase A2 at the bilayer interface. Proteins. 9: 229-239.
51. Bahnson, B. J. 2005. Structure, function and interfacial allosterism in phospholipase A2: insight from the anion-assisted dimer. Arch. Biochem. Biophys. 433: 96-106.