New fluorescent octadecapentaenoic acids as probes of lipid membranes and protein-lipid interactions

Biophysical Journal

Volumn 71, Issue 4, 1996, Pages 2177-2191

  Mateo, C Reyes ^a   Souto, Andre A ^a,b   Amat Guerri, Francisco ^b   Acuña, A Ulises ^a  

^a INSTITUTO DE QUÍMICA FÍSICA ROCASOLANO   (Spain)

^b INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

DIMYRISTOYLPHOSPHATIDYLCHOLINE; FATTY ACID;

ABSORPTION SPECTROSCOPY; ARTICLE; CALORIMETRY; FLUORESCENCE SPECTROSCOPY; LIPID BILAYER; LIPID MEMBRANE; PARTITION COEFFICIENT; PROTEIN LIPID INTERACTION; THROMBOCYTE MEMBRANE;

EID: 0029839358     PISSN: 00063495     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-3495(96)79419-5     Document Type: Article

References (69)

1. Ameloot, M., H. Hendrickx, W. Herreman, H. Pottel, F. V. Cauwelaert, and B. W. Van der Meer. 1984. Effect of orientational order on the decay of the fluorescence anisotropy in membrane suspensions. Biophvs. J. 46:525-539.
2. Bañó, M. C., L. Braco, and C. Abad. 1991. Conformational transitions of gramicidin A in phospholipid model membranes. A high-performance liquid chromatography assessment. Biochemistry. 30:886-894.
3. Berde, C., B. S. Hudson, R. D. Simoni, and L. A. Sklar. 1979. Human serum albumin. Spectroscopic studies of binding and proximity relationships for fatty acids and bilirubin. J. Biol. Chem. 254:391-400.
4. Best, L., E. John, and F. Jáhnig. 1987. Order and fluidity of lipid membranes as determined by fluorescence anisotropy decay. Eur. Biophys. J. 15:87-102.
5. Bouwman, W. G., A. C. Jones, D. Phillips. P. Thibodeau, C. Friel, and R. L. Christensen. 1990. Fluorescence of gaseous tetraenes and pentaenes. J. Phys. Chem. 94:7429-7434.
6. Castanho, M., and M. E. Prieto. 1995. Filipin fluorescence quenching by spin-labelled probes. Studies in aqueous solution and in a membrane model system. Biophys. J. 69:155-168.
7. Castanho, M., M. E. Prieto, and A. U. Acuña. 1996. The transverse location of the fluorescence probe trans-parinaric acid in lipid bilayers. Biochim. Biophys. Acta. 1279:164-168.
8. Chattopadhyay, A., and E. London. 1987. Parallax method for direct measurement of membrane penetration depth utilising fluorescence quenching by spin-labelled phospholipids. Biochemistry. 26:39-45.
9. Cherry, R. J., and R. E. Godfrey. 1981. Anisotropic rotation of bacteriorhodopsin in lipid membranes. Biophys. J. 36:257-276.
10. Cross, A. J., and G. R. Fleming. 1984. Analysis of time-resolved fluorescence anisotropy decays. Biophys. J. 46:45-56.
11. Dale, R. E., L. A. Chen, and L. Brand. 1977. Rotational relaxation of the "microviscosity" probe diphenylhexatriene in paraffin oil and egg lecithin vesicles. J. Biol. Chem. 252:7500-7510.
12. Dote, J. L., D. Kivelson, and R. N. Schwartz. 1981. A molecular quasihydrodynamic free-space model for molecular rotational relaxation in liquids. J. Phys. Chem. 85:2169.
13. Engel, L. W., and F. G. Prendergast. 1981. Values for and significance of order parameters and "cone angles" of fluorophore rotation in lipid bilayers. Biochemistry: 20:7338-7345.
14. Förster, T. 1959. Transfer mechanism of electronic excitation. Discuss. Faraday Soc. 27:7-17.
15. Heyn, M. P. 1989. Order and viscosity of membranes. Analysis by timeresolved fluorescence depolarization. Methods Enzymol. 172:462-471.
16. Hope. M. J., M. B. Bally. G. Webb, and P. R. Cullis. 1985. Production of large unilamellar vesicles by a rapid extrusion procedure. Characterization of size distribution, trapped volume and ability to maintain a membrane potential. Biochim. Biophys. Acta. 812:55-65.
17. Hu, C. M., and R. Zwanzig. 1974. Rotational friction coefficients for spheroids with the slipping boundary condition. J. Chem. Phys. 60: 4354-4357.
18. Hudson. B. S., and S. Cavalier. 1988. Studies of membrane dynamics and lipid-protein interactions with parinaric acid. In Spectroscopic Membrane Probes, Vol. I. L. M. Loew. editor. CRC Press, Boca Raton, FL. 43-62.
19. Hudson. B. S., D. L. Harris, R. D. Ludescher. A. Ruggiero. A. Cooney-Fred, and S. A. Cavalier. 1986. Fluorescence probe studies of protein and membranes. In Applications of Fluorescence in the Biomedical Sciences. D. L. Taylor. A. S. Waggoner, F. Lanni, R. F. Murphy, and R. Birge, editors. Alan R. Liss, New York. 159-202.
20. Hudson. B., and B. Kohler. 1974. Linear polyene structure and spectroscopy. Anna. Rev. Phys. Chem. 25:437-460.
21. Hudson, B. S., B. E. Kohler, and K. Schulten. 1982. Linear polyene electronic structure and potential surfaces. In Excited States, Vol. 6. E. C. Lim, editor. Academic Press. New York. 1-95.
22. Kimelman. D., E. S. Tecona, P. K. Wolber, B. S. Hudson, W. T. Wickner, and R. D. Simoni. 1979. Protein-lipid interactions. Studies of M13 coat protein in dimyristoylphosphatidylcholine vesicles using parinaric acid. Biochemistry. 18:5874-5880.
23. Kinosita, K., Jr., A. Ikegami, and S. Kawato. 1982. On the wobbling-incone analysis of fluorescence anisotropy decay. Biophys. J. 37:461-464.
24. Kinosita, K., Jr., S. Kawato, and A. Ikegami. 1977. A theory of fluorescence polarization decay in membranes. Biophys. J. 20:289-305.
25. Kinosita, K., Jr., S. Kawato, and A. Ikegami. 1984. Dynamic structure of biological and model membranes: analysis by optical anisotropy decay measurements. Adv. Biophys. 17:147-203.
26. Knutson, J. R., J. M. Beechem, and L. Brand. 1983. Simultaneous analysis of multiple fluorescence decay curves: a global approach. Chem. Phys. Lett. 102:501-507.
27. α phase. Eur. Biophys. J. 19:55-62.
28. Lentz, B. R. 1993. Use of fluorescent probes to monitor molecular order and motions within liposome bilayers. Chem. Phys. Lipids. 64:99-116.
29. Lipari, G., and A. Szabo. 1980. Effect of librational motion on fluorescence depolarization and nuclear magnetic resonance relaxation in macromolecules and membranes. Biophys. J. 30:489-506.
30. Löfroth, J. E. 1985. Deconvolution of single photon counting data with a reference method and global analysis. Eur. Biophys. J. 13:45-48.
31. Lograsso, P. V., F. Moll, and T. A. Cross. 1988. The solvent history dependence of gramicidin A conformations in hydrated lipid bilayers. Biophys. J. 54:259-267.
32. López, M. C., and J. García de la Torre. 1987. Brownian dynamics simulation of restricted rotational diffusion. Biophys. J. 52:303-310.
33. Mabrey, S., and M. Sturtevant. 1976. Investigation of phase transitions of lipids and lipid mixtures by high sensitivity differential scanning calorimetry. Proc. Natl. Acad. Sci. USA. 73:3862-3866.
34. Macdonald, P. M., and J. Seelig. 1988. Dynamic properties of gramicidin A in phospholipid membranes. Biochemistry. 27:2357-2364.
35. Mateo, C. R., A. U. Acuña, and J. C. Brochon. 1995. Liquid-crystalline phases of cholesterol/lipid bilayers as revealed by the fluorescence of trans-parinaric acid. Biophys. J. 68:978-987.
36. Mateo, C. R., J. C. Brochon, M. P. Lillo, and A. U. Acuña. 1993a. Lipid clustering in bilayers detected by the fluorescence kinetics and anisotropy of trans-parinaric acid. Biophys. J. 65:2237-2247.
37. Mateo, C. R., M. P. Lillo, J. C. Brochon. M. Martínez-Ripoll, J. Sanz-Aparicio, and A. U. Acuña. 1993b. Rotational dynamics of 1,6-diphenyl-1,3,5-hexatriene and derivatives from fluorescence depolarization. J. Phys. Chem. 97:3486-3491.
38. Mateo, C. R., M. P. Lillo, J. González-Rodriguez, and A. U. Acuña. 1991. Molecular order and fluidity of the plasma membrane of human platelets from time-resolved fluorescence depolarization. Eur Biophys. J. 20: 41-52.
39. Mukherjee, S., and A. Chattopadhyay. 1994. Motionally restricted tryptophan environments at the peptide-lipid interface of gramicidin channels. Biochemistry. 33:5089-5097.
40. Muller, J. M., E. E. van Faassen, and G. van Ginkel. 1994. Experimental support for a novel compound motion model for the time-resolved fluorescence anisotropy decay of TMA-DPH in lipid vesicle bilayers. Chem. Phys. 185:393-404.
41. Naqvi, K. R. 1980. Photoselection in uniaxial liquid crystals: the effect of rotational Brownian motion on measurements of orientational distribution function. J. Chem. Phys 73:3019-3020.
42. Naqvi, K. R. 1981. Photoselection in uniaxial liquid crystals: the advantages of using saturating light pulses for the determination of orientational order. J. Chem. Phys. 74:2658-2659.
43. Naqvi, K. R., and A. U. Acuña. 1992. Polarized radiation and dynamics of biological systems. In Computational Chemistry: Structure. Interactions and Reactivity, Part B. S. Fraga, editor. Elsevier Science Publishers, Amsterdam. 246-267.
44. Parker, C. A. 1968. Photoluminescence of Solutions. Elsevier Publishing Company, Amsterdam. 222.
45. Rigler, R., and M. Ehrenberg. 1973. Molecular interactions and structure as analysed by fluorescence spectroscopy. Q. Rev. Biophys. 6:139-199.
46. Ruggiero, A., and B. Hudson. 1989a. Critical density fluctuations in lipid bilayers detected by fluorescence lifetime heterogeneity. Biophys. J. 55:1111-1124
47. Ruggiero, A., and B. Hudson. 1989b. Analysis of the anisotropy decay of trans-parinaric acid in lipid bilayers. Biophys. J. 55:1125-1135.
48. Seelig, J., and A. Seelig. 1980. Lipid conformation in model membranes and biological membranes. Q. Rev. Biophys. 13:19-61.
49. Shin, Y.-K., and J. H. Freed. 1989. Dynamic imaging of lateral diffusion by electron spin resonance and study of rotational dynamics in model membranes. Biophys. J. 55:537-550.
50. Sklar, L. A. 1980. The partition of cis-parinaric acid and trans-parinaric acid among aqueous, fluid lipid and solid lipid phases. Mol Cell. Biochem. 32:169-177.
51. Sklar, L. A., B. S. Hudson. M. Petersen, and J. Diamond. 1977a. Conjugated polyene fatty acids as fluorescent probes: spectroscopic characterisation. Biochemistry. 16:813-818.
52. Sklar, L. A., B. S. Hudson, and R. D. Simoni. 1977b. Conjugated polyene fatty acids as fluorescent probes: synthetic phospholipid membrane studies. Biochemistry. 16:819-828.
53. Sklar. L. A., G. P. Miljanich, S. L. Bursten, and E. A. Dratz. 1979. Thermal lateral phase separations in bovine retinal rod outer segment membranes and phospholipids as evidenced by parinaric acid fluorescence polarization and energy transfer. J. Biol. Chem. 254:9583-9591.
54. Souto, A. A., A. U. Acuña. and F. Amat-Guerri. 1994. A general and practical synthesis of linear conjugated pentaenoic acids. Tetrahedron Lett. 32:5907-5910.
55. Szabo, A. 1984. Theory of polarized fluorescent emission in uniaxial liquid crystals. J. Chem. Phys. 72:4620-4626.
56. Toptygin, D., and L. Brand. 1995. Determination of DPH order parameters in unoriented vesicles. J. Fluorescence. 5:39-50.
57. Valeur, B. 1993. Fluorescent probes for evaluation of local physical and structural parameters. In Molecular Luminescence Spectroscopy, Part 3. S. G. Schulman. editor. John Wiley and Sons, New York. 25-84.
58. Vanderkooi, J., and J. B. Callis. 1974. Pyrene. A probe of lateral diffusion in the hydrophobic region of membranes. Biochemistry. 13:4000-4006.
59. Van der Meer, B. W. 1991. "Membrane fluidity," more than one single parameter. Acta Pharm. Jugosl. 41:311-326.
60. Van der Meer, B. W., G. Coker III, and S. Y. S. Chen. 1994. Resonance Energy Transfer. Theory and Data. VCH Publishers, New York.
61. Van der Sijs, D. A., E. E. van Faassen, and Y. K. Levine. 1993. The interpretation of the fluorescence anisotropy decays of probe molecules in membrane systems. Chem. Phys. Lett. 216:559-565.
62. Van Ginkel, G., L. J. Korstanje, H. van Langen, and Y. K. Levine. 1986. The correlation between molecular orientational order and reorientational dynamics of probe molecules in lipid multibilayers. Faraday Discuss. Chem. Soc: 81:49-61.
63. Velapoldi, R. A. 1972. Considerations on organic compounds in solution and inorganic ions in glasses as fluorescent standard reference materials. J. Res. Natl. Bur. Stand. (U.S.). 76A:64I-654.
64. Wallace. B. A. 1990. Gramicidin channels and pores. Annu. Rev. Biophys. Biophys. Chem. 19:127-157.
65. Wang. S., E. Martin, J. Cimino, G. Omann, and M. Glaser. 1988. Distribution of phospholipids around gramicidin and D-β-hydrohybutyrate dehydrogenase as measured by resonance energy transfer. Biochemistry. 27:2033-2039.
66. Wardlaw, J. R., W. H. Sawyer, and K. P. Ghiggino. 1987. Vertical fluctuation of phospholipid acyl chains in bilayers. FEBS Lett. 231: 20-24.
67. Zachariasse, K. A., W. Kühnle, and A. Weller. 1980. Intramolecular excimer fluorescence as a probe of fluidity changes and phase transitions in phosphatidylcholine bilayers. Chem. Phys. Lett. 73:6-11.
68. Zachariasse, K. A., W. L. C. Vaz, C. Sotomayor, and W. Kühnle. 1982. Investigation of human erythrocyte ghost membranes with intramolecular excimer probes. Biochim. Biophys. Acta. 688:323-332.
69. Zannoni, C., A. Arcioni, and P. Cavatorta. 1983. Fluorescence depolarization in liquid crystals and membrane bilayers. Chem. Phys. Lipids. 32:179-250.