[en] Analysis of the bacteriochlorin a absorption spectra suggests the existence of a monomer-dimer equilibrium, particularly intense in phosphate buffer and favored by a decrease of the pH. The dye in methanolic solution is predominantly in monomeric form. Fluorescence and electron spin resonance nitroxide spin labeling measurements indicate that incorporation into the lipid phase of dimyristoyl-L-alpha-phosphatidylcholine liposomes induces dye monomerization. Moreover, the molecules are bound in the external surface of the vesicles and a complete incorporation is ensured by a lipid-to-dye ratio greater than 125.
Disciplines :
Physics
Author, co-author :
Hoebeke, Maryse ; Université de Liège - ULiège > Département de physique > Spectroscopie biomédicale
Damoiseau, X.
Schuitmaker, H. J.
Van de Vorst, A.
Language :
English
Title :
Fluorescence, Absorption and Electron Spin Resonance Study of Bacteriochlorin a Incorporation into Membrane Models
M. Ochsner, Photophysical and photobiology processes in the photodynamic therapy of tumours, J. Photochem. Photobiol. Biol. 39 (1997) 1-18.
M. Hoebeke, H. Schuitmaker, L. Jannink, M. Dubbelman, A. Jacobs, A. Van de Vorst, Electron spin resonance evidence of the generation of superoxide anion, hydroxyl radical and singlet oxygen during the photohemolysis of human erythrocytes with bacteriochlorin a, Photochem. Photobiol. 66 (1997) 502-508.
J.J. Schuitmaker, J.A. Van Best, J.L. Van Delft, T.M.A.R. Dubbelman, J.A. Oosterhuis, D. de Wolff-Rouendull, Bacteriochlorin a, a new photosensitizer in photodynamic therapy: in vivo results, Invest. Ophthalmol. Vis. Sci. 31 (1990) 1444-1450.
H.L.L.M. Van Leengoed, J.J. Schuitmaker, N. Van der Veen, T.M.A.R. Dubbelman, W.M. Star, Fluorescence and photodynamic effects of bacteriochlorin a observed in vivo in 'sandwich observation' chambers, Br. J. Cancer 67 (1993) 898-903.
J.J. Schuitmaker, H.L.L.M. Van Leengoed, N. Van der Veen, T.M.A.R. Dubbelman, W.M. Star, Laser-induced in vivo fluorescence of bacteriochlorin a; preliminary results, Laser Med. Sci. 8 (1993) 39-42.
I.P.J. Van Geel, H. Oppelaar, Y.G. Oussoren, J.J. Schuitmaker, F.A. Stewart, Mechanisms for optimizing PDT: second generation photosensitizers in combination with mitomycin C, Br. J. Cancer 72 (1995) 344-350.
J.J. Schuitmaker, B.M. Koster, J.G.R. Elferink, The effects of photodynamic therapy on human neutrophil migration using bacteriochlorin a, Photochem. Photobiol. 68 (1998) 841-845.
J.J. Schuitmaker, E.W. Vogel, J.F. Nagelkerke, R.P. Bos, Mutagenicity and dark toxicity of the second-generation photosensitizer bacteriochlorin a, J. Photochem. Photobiol. B. Biol. 47 (1998) 211-215.
H.P. Van Iperen, H.J. Schuitmaker, G.M.J. Beijersbergen van Henegouwen, Non specific systemic immune suppression induced by photodynamic treatment of lymph node cells with bacteriochlorin a, J. Photochem. Photobiol. B: Biol. 28 (1995) 197-202.
T.H. Foster, R.S. Murant, R.G. Bryant, R.S. Knox, S.L. Gibson, R. Hief, Oxygen consumption and diffusion effects in photodynamic therapy, Radiat. Res. 126 (1991) 296-303.
J.P. Henning, R.L. Fourier, J.A. Hampton, A transient mathematical model of oxygen depletion during photodynamic therapy, Radiat. Res. 142 (1995) 221-226.
A. Baker, J.R. Kanofsky, Quenching of singlet oxygen by biomolecules from L1210 leukemia cells, Photochem. Photobiol. 55 (1992) 523-528.
J.R. Kanofsky, Quenching of singlet oxygen by human red cell ghosts, Photochem. Photobiol. 53 (1991) 93-99.
M. Ochsner-Bruderer, Zinc (II) - phthalocyanine, a photosensitizer for photodynamic therapy of tumours, Inaugural Dissertation, University of Basle, Basle, 1994.
C.S. Foote, Type I and Type II mechanisms of photodynamic action, in: J.R. Heitz, K.R. Downum (Eds.), Light-Activated Pesticides, American Chemical Society, Washington, DC, 1987, pp. 22-38.
F. Riccheli, G. Jori, S. Gobbo, M. Tronckin, Liposomes as models to study the distribution of porphyrins in cell membranes, Biochim. Biophys. Acta 1065 (1991) 42-48.
A. Losi, Fluorescence and time-resolved photoacoustics of hypericin inserted in liposomes : dependence on pigment concentration and bilayer phase, Photochem. Photobiol. 65 (1997) 791-801.
F. Riccheli, S. Gobbo, G. Jori, G. Moreno, F. Vinzens, C. Salet, Photosensitization of mitochondria by liposomes bound porphyrins, Photochem. Photobiol. 58 (1993) 53-58.
L. Mayer, M. Hope, P. Cullis, Vesicles of variable sizes produced by rapid extrusion procedure, Biochim. Biophys. Acta 858 (1986) 161-168.
M. Hoebeke, A. Seret, J. Piette, A. Van de Vorst, Destruction of stearic acid nitroxyl radicals mediated by photoexcited Merocyanine 540 in liposomal and micellar systems, Biochemistry 32 (1993) 2730-3736.
W. West, S. Pearce, The dimeric state of cyanine dye, J. Phys. Chem. 69 (1965) 1894-1903.
K. Sauer, J. Smith, A. Schultz, The dimerization of chlorophyll a, chlorophyll b and bacteriochlorophyll in solution, J. Am. Chem. Soc. 88 (1996) 2681-2688.
D. Brault, C. Vever-Bizet, T. Le Doan, Spectrofluorimetric study of porphyrin incorporation into membrane models -evidence for pH effects, Biochim. Biophys. Acta 857 (1986) 238-250.
L. Sikurova, I. Haban, D. Chorvat, Dimers of merocyanine 540, I. In aqueous solutions, Stud. Biophys. 125 (1988) 197-201.
L. Sikura, I. Haban, R. Frankova, Dimers of merocyanine 540, II. In egg lecithin liposomes, Stud. Biophys. 128 (1988) 103-108.
L. Sikura, R. Frankova, D. Chorvat, Dimers of merocyanine 540, III. In dimyristoyl lecithin liposomes, Stud. Biophys. 133 (1989) 67-72.
B. Ehrenberg, E. Pevzner, Spectroscopic properties of the potentiometric probe merocyanine 540 in solutions and in liposomes, Photochem. Photobiol. 57 (1993) 228-234.
K. Chen, P. Morse II, M. Swartz, Kinetics of enzyme-mediated reduction of lipid soluble nitroxide spin labels by living cells, Biochim. Biophys. Acta 943 (1988) 477-484.
M. Takahashi, J. Tsuchiya, E. Niki, S. Urano, Action of vitamin E as antioxidant in phospholipid liposomal membranes as studied by spin label technique, J. Nutr. Sci. Vitaminol. 34 (1988) 25-34.
J. Feix, B. Kalyanaraman, An electron spin resonance study of merocyanine 540- mediated type I reactions in liposomes, Photochem. Photobiol. 53 (1991) 39-45.
R. Bensasson, E. Land, T. Truscott, Flash Photolysis and Pulse Radiolysis, Pergamon Press, Oxford, 1983, pp. 20-66.
C. Balny, S. Seymour, G. Hui Bon Hoa, Absorption and fluorescence spectra of chlorophyll-a in polar solvents as a function of temperature, Photochem. Photobiol. 9 (1969) 445-454.
D. Brault, Physical chemistry of porphyrins and their interactions with membranes: the importance of pH, J. Photochem. Photobiol. B: Biol. 6 (1990) 79-86.
D. Brault, C. Vever-Bizet, K. Kuzelova, Interactions of dicarboxylic porphyrins with membranes in relation to their ionization state, J. Photochem. Photobiol. B: Biol. 20 (1993) 191-195.
J. Connolly, E. Samuel, F. Janzen, Effect of solvent on the fluorescence properties of bacteriochlorophyll a, Photochem. Photobiol. 36 (1982) 565-574.
F. Richelli, G. Jori, Distribution of porphyrins in the various compartments of unilamellar liposomes of dipalmitoyl-phosphatidylcholine as probed by fluorescence spectroscopy, Photochem. Photobiol. 44 (1986) 151-157.
H. Toledano, R. Edrei, S. Kimel, Photodynamic damage by liposome-bound porphycenes: comparison between in vitro and in vivo models, J. Photochem. Photobiol. B: Biol. 42 (1998) 20-27.