Effect of aggregation on bacteriochlorin a triplet-state formation: A laser flash photolysis study

[en] Bacteriochlorin a (BCA) is a potential photosensitizer for photodynamic therapy of cancer. It has been shown previously that the photoefficiency of the dye is mainly dependent on singlet oxygen (O-1(2)) generation. Nanosecond laser flash photolysis was used to produce and to investigate the excited triplet state of the dye in methanol, phosphate buffer and dimiristoyl-L-alpha-phosphatidylcholine (DMPC) liposomes. The transients were characterized in terms of their absorption spectra, decay kinetics, molar absorption coefficients and formation quantum yield of singlet-triplet intercrossing. The lifetime of the BCA triplet state was measured at room temperature. The triplet-state quantum yield is quite high in methanol (0.7) and in DMPC (0.4) but only 0.095 in phosphate buffer. In the last case, BCA is in a monomer-dimer equilibrium, and the low value of the quantum yield observed was ascribed to the fact the triplet state is only formed by the monomers.

Disciplines :

Biochemistry, biophysics & molecular biology

Author, co-author :

Damoiseau, Xavier

Tfibel, Francis

Hoebeke, Maryse ; Université de Liège - ULiège > Département de physique > Spectroscopie biomédicale

Fontaine-Aupart, Marie-Pierre

Language :

English

Title :

Effect of aggregation on bacteriochlorin a triplet-state formation: A laser flash photolysis study

Publication date :

November 2002

Journal title :

Photochemistry and Photobiology

ISSN :

0031-8655

Publisher :

Amer Soc Photobiology, Augusta, United States - Georgia

Volume :

Issue :

Pages :

480-485

Peer reviewed :

Peer Reviewed verified by ORBi

Available on ORBi :

since 13 May 2010

Statistics

Number of views

108 (2 by ULiège)

Number of downloads

190 (3 by ULiège)

More statistics

Scopus citations^®

Scopus citations^®
without self-citations

OpenCitations

OpenAlex citations

Bibliography

Beems, E. M., T. M. A. R. Dubbelman, J. Lugtenburg, J. A. Van Best, M. F. M. A. Smeets and J. P. Boegheim (1987) Photosensitizing properties of bacteriochlorophyllin a and bacteriochlorin a, two derivatives of bacteriochlorophyll a. Photochem. Photobiol. 46, 639-643.
Schuitmaker, J. J., J. A. Van Best, J. L. van Delft, T. M. A. R. Dubbelman, J. A. Oosterhuis and D. De Wolff-Rouendaal (1990) Bacteriochlorin a, a new photosensitizer in photodynamic therapy: in vivo results. Investig. Ophthalmol. Vis. Sci. 31, 1444-1450.
van Leengoed, H. L. L. M., J. J. Schuitmaker, N. Van der Veen, T. M. A. R. Dubbelman and W. M. Star (1991) Fluorescence and photodynamic effects of bacteriochlorin a observed in vivo in "sandwich" observation chambers. Br. J. Cancer 67, 467-471.
Schuitmaker, J. J., H. L. L. M. van Leengoed, N. Van der Veen, T. M. A. R. Dubbelman and W. M. Star (1993) Laser-induced in vivo fluorescence of bacteriochlorin a: preliminary results. Lasers Med. Sci. 8, 39-42.
Hoebeke, M., H. J. Schuitmaker, L. E. Jannink, T. M. A. R. Dubbelman, A. Jakobs and A. Van de Vorst (1997) 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, 502-508.
Hoebeke, M. and X. Damoiseau (2002) Determination of bacteriochlorin a singlet oxygen quantum yield: a comparative study in phosphate buffer and aqueous dispersion of dimiristoyl-L-a-phosphatidylcholine liposomes. Photochem. Photobiol. Sci. 1, 283-287.
Damoiseau, X., H. J. Schuitmaker, J. W. M. Lagerberg and M. Hoebeke (2000) Increase of the photosensitizing efficiency of the bacteriochlorin a by liposome-incorporation. J. Photochem. Photobiol. B: Biol. 60, 50-60.
Hoebeke, M., X. Damoiseau, H. J. Schuitmaker and A. Van de Vorst (1999) Fluorescence, absorption and electron spin resonance study of bacteriochlorin a incorporation into membrane models. Biochem. Biophys. Acta 1420, 73-85.
Omata, T. and N. Murata (1983) Preparation of chlorophyll a, chlorophyll b and bacteriochlorophyll a by column chromatography with DEAE Sepharose CL-6B and Sepharose CL-6B. Plant Cell Physiol. 25, 1093.
Oster, G., B. Broyde and J. S. Bellin (1964) Spectral properties of chlorophyllin a. J. Am. Chem. Soc. 5, 1309-1313.
Mayer, L., M. Hope and P. Cullis (1986) Vesicles of variable sizes produced by rapid extrusion procedure. Biochem. Biophys. Acta 858, 161-168.
Al Rabaa, A. R., F. Tfibel, F. Mérola, P. Pernot and M. P. Fontaine-Aupart (1999) Spectroscopic and photophysical study of an anthryl probe: DNA binding and chiral recognition. J. Chem. Soc., Perkin Trans. 2, 341-351.
Fontaine-Aupart, M. P., E. Renault, L. Brian, J. F. Delouis and M. Gardès-Albert (1995) Triplet excited-state characterization and determination of the photoionozation mechanism of the antitumoral drug pazelliptine. J. Photochem. Photobiol. A: Chem. 90, 95-102.
Bensasson, R. V., E. J. Land and T. G. Truscott (1993) Excited States and Free Radicals in Biology and Medicine. Oxford University Press, Oxford.
Bensasson, R. V., E. J. Land and T. G. Truscott (1983) Flash Photolysis and Pulse Radiolysis: Contributions to the Chemistry of Biology and Medicine. Pergamon Press, Exeter.
Bhattacharyya, B. and J. Wolff (1984) Immobilization-dependent fluorescence of colchicine. J. Biol. Chem. 249, 11836-11843.
Likhtenshtein, G. I. (1976) Spin Labeling Methods in Molecular Biology. Wiley-Interscience, New York.
Brault, D. (1990) Physical chemistry of porphyrins and their interactions with membranes: the importance of pH. J. Photochem. Photobiol. B: Biol. 6, 79-86.
Balny, C., S. S. Brody and G. Hui Bon Hoa (1969) Absorption and fluorescence spectra of chlorophyll-a in polar solvents as a function of temperature. Photochem. Photobiol. 9, 445-454.
Balteau, E., X. Damoiseau and M. Hoebeke (2002) Singlet oxygen involvement in bacteriochlorin a photosensitrization and photobleaching mechanisms. (In press)
Lampre, I., D. Markovitsi, A. Sharonov and M. Veber (1998) Triarylpyrylium salts: dynamics of the monomer-dimer equilibrium via a triplet absorption study. Chem. Phys. Lett. 293, 423-428.