Photophysical studies of zinc phthalocyanine and chloroaluminum phthalocyanine incorporated into liposomes in the presence of additives

Brazilian Journal of Medical and Biological Research

Volumn 37, Issue 2, 2004, Pages 273-284

  Nunes, S M T ^a   Sguilla, F S ^a   Tedesco, A C ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Bovine serum albumin; Cardiolipin; Chloroaluminum phthalocyanine; Cholesterol; Dimyristoyl phosphatidycholine; Liposomes; Zinc phthalocyanine

Indexed keywords

BOVINE SERUM ALBUMIN; CARDIOLIPIN; CHLOROALUMINUM PHTHALOCYANINE; CHOLESTEROL; DIMYRISTOYLPHOSPHATIDYLCHOLINE; DRUG ADDITIVE; DRUG CARRIER; LIPOSOME; PHOTOSENSITIZING AGENT; PHTHALOCYANINE DERIVATIVE; PHTHALOCYANINE SILICON; PHTHALOCYANINE ZINC; UNCLASSIFIED DRUG;

ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DIMERIZATION; DRUG DELIVERY SYSTEM; DRUG PROTEIN BINDING; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG TARGETING; FLUORESCENCE; HYDROPHOBICITY; INTERNALIZATION; LASER; PHOTOLYSIS; STEADY STATE;

BOVINAE;

EID: 1442306692     PISSN: 0100879X     EISSN: 1414431X     Source Type: Journal    
DOI: 10.1590/S0100-879X2004000200016     Document Type: Article

References (40)

1. Pandey RK (2000). Recent advances in photodynamic therapy. Journal of Porphyrins and Phthalocyanines, 4: 368-373.
2. Owens JW, Smith R, Robinson R & Robins M (1998). Photophysical properties of porphyrins, phthalocyanines and benzochlorins. Inorganica Chimica Acta, 279: 226-231.
3. Cahn W-S, Brasseur N, La Madeleine C, Quellet R & van Lier JE (2001). Current status of phthalocyanines in the photodynamic therapy of cancer. European Journal of Cancer, 33: 1855-1860.
4. Urizzi P, Allen CM, Langlois R, Quellet B, La Madeleine C & van Lier JE (2001). Low density lipoprotein-bound aluminium sulphophthalocyanine: targeting tumor cells for photodynamic therapy. Journal of Porphyrins and Phthalocyanines, 5: 154-160.
5. Ruch A, Beck G, Bachor R, Akgun N, Gschwence MH & Steiner R (1996). Dynamic fluorescence changes during photodynamic therapy in vivo and in vitro of hydrophilic Al(III) phthalocyanine tetrasulphonated and lipophilic Zn(II) phthalocyanine administered in liposomes. Journal of Photochemistry and Photobiology. B, Biology, 36: 127-134.
6. Soncin M, Polo L, Reddi E, Jori G, Kenney ME, Cheng G & Rodgers MAJ (1995). Effect of the delivery system on the biodistribution of Ge(IV)octabutoxy-phthalocyanines in tumour-bearing mice. Cancer Letters, 89: 101-106.
7. Storm G & Crommelin DJA (1998). Liposomes: quo vadis. Pharmaceutical Science Technology Today, 1: 19-31.
8. Aveline BM, Hasan T & Redmond RW (1995). The effects of aggregation, protein binding and cellular incorporation on the photophysical properties of benzoporphyrin derivative mono acid ring A (BPDMA). Journal of Photochemistry and Photobiology. B, Biology, 30: 161-169.
9. Sil S, Kar M & Chakraborti AS (1997). Studies on the interaction of hematoporphyrin with hemoglobin. Journal of Photochemistry and Photobiology. B, Biology, 41: 67-72.
10. Ball DJ, Wood SR, Vernon DI, Griffiths J, Dubbelman MAR & Brown SB (1998). The characterization of three substituted zinc phthalocyanines of different charge for use in photodynamic therapy. A comparative study of their aggregation and photosensitizing ability in relation to mTHPC and polyhaematoporphyrin. Journal of Photochemistry and Photobiology. B, Biology, 45: 28-35.
11. Dhami S & Phillips D (1996). Comparison of the photophysics of an aggregation and non-aggregating aluminium phthalocyanine system incorporated into unilamellar vesicles. Journal of Photochemistry and Photobiology. A, Chemistry, 100: 77-84.
12. Damoiseau X, Schuitmaker HJ, Lagerberg JW & Hoebeke M (2001). Increase of the photosensitizing efficiency of the Bacteriochlorin a by liposome-incorporation. Journal of Photochemistry and Photobiology. B, Biology, 60: 50-60.
13. Tanielian C & Heinrich G (1995). Effect of aggregation on the hematoporphyrin-sensitized production of singlet molecular oxygen. Photochemistry and Photobiology, 61: 131-135.
14. Ford WE & Tollin G (1984). Chlorophyll photosensitized electron transfer in phospholipid bilayer vesicle systems: effects of cholesterol on radical yields and kinetic parameters. Photochemistry and Photobiology, 40: 249-259.
15. Kremer JMH, Esker MWJ, Pathmamanoharan C & Wiersema PH (1977). Vesicles of variable diameter prepared by a modified injection method. Biochemistry, 16: 3932-3936.
16. Oulmi D, Maillard P, Vever-Bizet C, Momenteau M & Brault D (1998). Glycosylated porphyrins: characterization of association in aqueous solutions by absorption and fluorescence spectroscopies and determination of singlet oxygen yield in organic media. Photochemistry and Photobiology, 67: 511-518.
17. Lakiwicz JR (1999). Principles of Fluorescence Spectroscopy. 2nd edn. Kluwer Academic Publishing/Plenum, New York.
18. Bárdos-Nagy I, Galántai R, Kaposi AD & Fidy J (1998). Difference in the transport of metal and free-base porphyrins. Steady-state and time-resolved fluorescence studies. International Journal of Pharmacology, 175: 255-267.
19. Lehrer S & Fashman GD (1966). The fluorescence of lysozyme and lysozyme substrate complexes. Biochemical and Biophysical Research Communications, 23: 133-138.
20. Chipman DM, Grisaro V & Shanon N (1967). The binding of oligosaccharides containing N-acetylglucosamine and N-acetylmaramic acid to lysozyme. Journal of Biological Chemistry, 242: 4388-4394.
21. Damoiseau X, Tfibel F, Hoebeke M & Fontaine-Aupart MP (2002). Effect of aggregation on bacteriochlorin a triplet-state formation: a laser flash photolysis study. Photochemistry and Photobiology, 76: 480-485.
22. Monahan AR, Brado JA & DeLuca AF (1972). The association of copper (II), vanadyl and zinc (II) 4,4′, 4′,-tetraalkylphthalocyanine dyes in benzene. Journal of Physical Chemistry, 76: 1994-1996.
23. Ricchelli F, Jori G, Gobbo S & Tronchin M (1991). Liposomes as models to study the distribution of porphyrins in cell membranes. Biochimica et Biophysica Acta, 1065: 42-48.
24. Bittman R, Kasireddy CR, Mattjus P & Slotte JP (1994). Interaction of cholesterol with sphingomyelin in monolayers and vesicles. Biochemistry, 33: 11776-11781.
25. Slotte JP (1992). Enzyme-catalysed oxidation of cholesterol in mixed phospholipid monolayers reveals the stoichiometry at which free cholesterol clusters disappear. Biochemistry, 31: 5472-5477.
26. Epand RM (2003). Cholesterol in bilayers of sphingomyelin or dihydrosphingomyelin at concentrations found in ocular lens membranes. Biophysical Journal, 84: 3102-3110.
27. Guo W & Hamilton JA (1995). A multinuclear solid-state NMR study of phospholipid-cholesterol interaction. Dipalmitoylphosphatidylcholine-cholesterol binary system. Biochemistry, 34: 14174-14184.
28. Guo W, Kurze V, Huber T, Afdhal NH, Beyer K & Hamilton JA (2002). A solid state NMR study of phospholipid-cholesterol interactions: sphingomyelin-cholesterol binary systems. Biophysical Journal, 83: 1465-1478.
29. Huang J, Buboltz JT & Feigenson GW (1999). Maximum solubility of cholesterol in phosphatidylcholine and phosphatidylethanolamine bilayers. Biochimica et Biophysica Acta, 1417: 89-100.
30. Morrow MR, Singh D, Lu D & Grant CW (1995). Glycosphingolipid fatty acid arrangement in phospholipid bilayers: cholesterol effects. Biophysical Journal, 68: 179-186.
31. O'Leary TJ (1993). Vibrational spectroscopy of cholesterol-lipid interactions. In: Finegold L (Editor), Cholesterol in Membrane Models. CRC Press, Boca Raton, FL, USA, 175-196.
32. Bittman R (1997). Has nature designed the cholesterol side chain for optimal interaction with cholesterol? In: Bittman R (Editor), Subcellular Biochemistry Series. Vol. 28: Cholesterol: Its Functions and Metabolism in Biology and Medicine. Plenum Press, New York, 145-172.
33. Davis JH (1993). The molecular dynamics, orientational order and thermodynamic phase equilibria of cholesterol/phosphatidylcholine mixtures: 2H nuclear magnetic resonance. In: Finegold L (Editor), Cholesterol in Membrane Models. CRC Press, Boca Raton, FL, USA, 67-136.
34. Ohvo-Rekilã H, Ramstedt B, Leppimäki P & Slotte JP (2002). Cholesterol interactions with phospholipids in membranes. Progress in Lipid Research, 41: 66-97.
35. Jacobson J, Duchen MR & Heales SJR (2002). Intracellular distribution of the fluorescent dye nonyl acridine orange responds to the mitochondrial membrane potential: implications for assays of cardiolipin and mitochondrial mass. Journal of Neurochemistry, 82: 224-233.
36. Gantchev TG, Oullet R & van Lier JE (1999). Binding interactions and conformational changes induced by sulfonated aluminum phthalocyanines in human serum albumin. Archives of Biochemistry and Biophysics, 366: 21-30.
37. Filyasova AI, Kudelina IA & Feafanov AV (2001). A spectroscopic study of the interaction of tetrasulfonated aluminum phthalocyanine with human serum albumin. Journal of Molecular Structure, 565-566: 173-176.
38. Bárdos-Nagy I, Galántai R & Fidy J (2001). Effect of trehalose in low concentration on the binding and transport of porphyrins in liposome-human serum albumin system. Biochimica et Biophysica Acta, 1512: 125-134.
39. Dimitrova MN, Matsumura H, Dimitrova A & Neitchev V (2000). Interaction of albumins from different species with phospholipid liposomes. Multiple binding sites system. International Journal of Biological Macromolecules, 27: 187-194.
40. Wohrle D, Muller S, Shopova M, Mantareva V, Spassova GVF, Ricchelli F & Jori G (1999). Effects of delivery system on the pharmacokinetic and phototerapeutic properties of bis(methyloxyethyleneoxy) silicon-phthalocyanine in tumour-bearing mice. Journal of Photochemistry and Photobiology. B, Biology, 50: 124-128.