Interaction of dicarboxylic metalloporphyrins with liposomes. The effect of pH on membrane binding revisited

Photochemistry and Photobiology

Volumn 76, Issue 5, 2002, Pages 486-492

  Kȩpczyński, Mariusz ^a,b   Ehrenberg, Benjamin ^a  

^a BAR ILAN UNIVERSITY   (Israel)

^b JAGIELLONIAN UNIVERSITY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID; CHEMICAL COMPOUND; DICARBOXYLIC ACID; HEMATOPORPHYRIN; LIPID; LIPOSOME; METALLOPORPHYRIN; PORPHYRIN; PYRROLE DERIVATIVE; WATER; ZINC;

ACID BASE BALANCE; ARTICLE; BINDING AFFINITY; CALCULATION; CHEMICAL ANALYSIS; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; IONIZATION; MEMBRANE; MEMBRANE BINDING; MOLECULE; PH; PROTON TRANSPORT;

DICARBOXYLIC ACIDS; HYDROGEN-ION CONCENTRATION; KINETICS; LIPOSOMES; MESOPORPHYRINS; METALLOPORPHYRINS; MOLECULAR STRUCTURE; SPECTROMETRY, FLUORESCENCE; THERMODYNAMICS; ZINC;

EID: 0036877536     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1562/0031-8655(2002)076<0486:IODMWL>2.0.CO;2     Document Type: Article

References (34)

1. Srivastava, R. C., V. D. Anand and W. R. Carper (1973) A fluorescence study of hematoporphyrin. Appl. Spectrosc. 27, 444-449.
2. Savitski, A. P., E. V. Vorobyora, I. V. Berezin and N. N. Ugarova (1981) Acid-base properties of protoporphyrin IX; its dimethyl ester and heme solubilized on surfactant micelles: spectrophotometric and fluorimetric titration. J. Colloid Interface Sci. 84, 175-181.
3. Brault, D., C. Vever-Bizet and T. Le Doan (1986) Spectrofluorimetric study of porphyrin incorporation into membrane models - evidence for pH effects. Biochim. Biophys. Acta 857, 238-250.
4. Pottier, R. H., J. C. Kennedy, Y. F. A. Chow and F. Cheung (1988) The pKa values of hematoporphyrin IX as determined by absorbance and fluorescence spectroscopy. Can. J. Spectrosc. 33, 57-62.
5. Barrett, A. J., J. C. Kennedy, R. A. Jones, P. Nadeau and R. H. Pottier (1990) The effect of tissue and cellular pH on the selective biodistribution of porphyrin-type photochemotherapeutic agents: a volumetric titration study. J. Photochem. Photobiol. B: Biol. 6, 309-323.
6. Chapados, C., D. Girard, M. Trudel and M. Ringuet (1995) Separation of overlapping spectra from evolving systems using factor-analysis. 4. Fluorescence-spectra of hematoporphyrin-IX. Biophys. Chem. 55, 289-300.
7. Chapados, C., D. Girard, M. Trudel and M. Ringuet (1995) Separation of overlapping spectra from evolving systems using factor-analysis. 3. Fluorescence-spectra of hematoporphyrin-IX di-n-propylether diethanolamide. Biophys. Chem. 54, 165-174.
8. Cunderlíková, B., L. Gangeskar and J. Moan (1999) Acid-base properties of chlorin e6: relation to cellular uptake. J. Photochem. Photobiol. B: Biol. 53, 81-90.
9. Cunderlíková, B., E. G. Bjørklund, E. O. Pettersen and J. Moan (2001) pH dependent spectral properties of HP IX, TPPS2a, mTHPP and mTHPC. Photochem. Photobiol. 74, 246-252.
10. Brault, D. and C. Vever-Bizet (1992) Protonation equilibria of hematoporphyrin as studied by fluorescence lifetime analysis. J. Chem. Soc. Faraday Trans. 88, 1519-1524.
11. Brault, D., C. Vever-Bizet and K. Kuzelova (1993) Interactions of dicarboxylic porphyrins with membranes in relation to their ionization state. J. Photochem. Photobiol. B: Biol. 20, 191-195.
12. Kuzelova, K. and D. Brault (1995) Interactions of dicarboxylic porphyrins with unilamellar lipidic vesicles - drastic effects of pH and cholesterol on kinetics. Biochemistry 34, 11245-11255.
13. Brault, D. (1990) Physical chemistry of porphyrins and their interactions with membranes: the importance of pH. J. Photochem. Photobiol. B: Biol. 6, 79-86.
14. Hoebeke, M. (1995) The importance of liposomes as models and tools in the understanding of photosensitization mechanisms. J. Photochem. Photobiol. B: Biol. 28, 189-196.
15. Kepczynski, M., R. P. Pandian, K. M. Smith and B. Ehrenberg (2002) Do liposome-binding constants of porphyrins correlate with their measured and predicted partitioning between octanol and water? Photochem. Photobiol. 76, 127-134.
16. Malinowski, E. R. (1991) Factor Analysis in Chemistry. Wiley-Interscience Publication, New York.
17. Phillips, J. N. (1960) The ionization and coordination behaviour of porphyrins. Rev. Pure Appl. Chem. 10, 35-60.
18. Bárdos-Nagy, I., R. Galántai, A. D. Kaposi and J. Fidy (1998) Difference in the transport of metal and free-base porphyrins. Steady-state and time-resolved fluorescence studies. Int. J. Pharm. 175, 255-267.
19. Buchler, J. W. (1975) Static coordination chemistry of metalloporphyrins. In Porphyrins and Metalloporphyrins, (Edited by K. M. Smith), pp. 157-231. Elsevier Scientific Publishing Company, Amsterdam.
20. Pottier, R. and T. G. Truscott (1986) The photochemistry of hematoporphyrin and related systems. Int. J. Radiat. Biol. 50, 421-452.
21. Hambright, P. (1975) Dynamic coordination chemistry of metalloporphyrins. In Porphyrins and Metalloporphyrins, (Edited by K. M. Smith), p. 265. Elsevier Scientific Publishing Company, Amsterdam.
22. Margalit, R., N. Shaklai and S. Cohen (1983) Fluorimeteic studies on the dimerization equlibrium of protoporphyrin IX and its haemato derivative. Biochem. J. 209, 547-552.
23. Margalit, R. and M. Rotenberg (1984) Thermodynamics of porphyrin dimerization in aqueous solutions. Biochem. J. 219, 445-450.
24. Šašic, S. (2001) Eigenvalues and principal component loadings of heavily overlapped vibrational spectra. Spectrochim. Acta, A 57, 323-336.
25. Shen, C., T. J. Vickers and C. K. Mann (1992) Abscissa error-detection and correction in Raman-spectroscopy. Appl. Spectrosc. 46, 772-777.
26. Shen, C., A. J. Peacock, R. G. Alamo, T. J. Vickers, L. Mandelkern and C. K. Mann (1992) Structural studies of crystalline linear polyethylenes as revealed by factor-analysis of their Raman-spectra. Appl. Spectrosc. 46, 1226-1230.
27. Lavi, A., H. Weitman, R. T. Holmes, K. M. Smith and B. Ehrenberg (2002) The depth of a porphyrin in a membrane and the membrane's physical properties strongly affect the photosensitizing efficiency. Biophys. J. 82, 2101-2110.
28. Ehrenberg, B. (1992) Assessment of the partitioning of probes to membranes by spectroscopic titration. J. Photochem. Photobiol. B: Biol. 14, 383-386.
29. Roslaniec, M., H. Weitman, D. Freeman, Y. Mazur and B. Ehrenberg (2000) Liposome binding constants and singlet oxygen quantum yields of hypericin, tetrahydroxy helianthrone and their derivatives: studies in organic solutions and in liposomes. J. Photochem. Photobiol. B: Biol. 57, 149-158.
30. Gennis, R. B. (1989) Biomembranes - Molecular Structure and Function. Springer Verlag, New York.
31. Galántai, R., I. Bárdos-Nagy, K. Módos, J. Kardos, P. Závodszky and J. Fidy (2000) Serum albumin-lipid membrane interaction influencing the uptake of porphyrins. Arch. Biochem. Biophys. 373, 261-270.
32. Kuzelová, K. and D. Brault (1995) Interactions of dicarboxylic porphyrins with unilamellar lipidic vesicles: drastic effect of pH and cholesterol on kinetics. Biochemistry 34, 11245-11255.
33. Maman, N. and D. Brault. (1998) Kinetics of the interactions of a dicarboxylic porphyrin with unilamellar lipidic vesicles: interplay between bilayer thickness and pH in rate control. Biochim. Biophys. Acta 1414, 31-42.
34. McLaughlin, S. (1977) Electrostatic potentials at membrane-solution interfaces. Curr. Top. Membr. Transp. 9, 71-144.