MALDI-TOF mass spectrometric analysis for the characterization of the 5,10,15,20-tetrakis- (m-hydroxyphenyl)bacteriochlorin (m-THPBC) photoproducts in biological environment. - 2005
MALDI-TOF mass spectrometric analysis for the characterization of the 5,10,15,20-tetrakis- (m-hydroxyphenyl)bacteriochlorin (m-THPBC) photoproducts in biological environment.
2005 MALDI-TOF mass spectrometric analysis for the characterization of the 5,10,15,20-tetrakis-(m-hydroxyphenyl)bacteriochlorin (m-THPBC) photoproducts in biological environment.pdf
[en] Photoproducts formation upon irradiation (739 nm) of 5,10,15,20-tetrakis(m-hydroxyphenyl)bacteriochlorin (m-THPBC) in phosphate buffer saline (PBS) supplemented with human serum albumin (HSA) were studied by means of absorption spectroscopy and MALDI-TOF mass spectrometry. The experiments were performed with a freshly prepared PBS-HSA solution of m-THPBC and with a PBS-HSA m-THPBC solution incubated for 6 h at 37 degrees C. The incubation of m-THPBC solution leads to the dye monomerisation, whereas in the freshly prepared solution, m-THPBC is under an aggregated form. Regardless of the incubation condition, photobleaching experiments carried out by absorption spectroscopy demonstrate the degradation of the photosensitizer and its phototransformation in m-THPC. Moreover, m-THPC was the sole photoproduct detected using absorption spectroscopy. Together with a degradation of m-THPBC and formation of m-THPC, MALDI-TOF mass spectrometry evidenced several other photoinduced modifications. Photoproducts such as dihydroxy m-THPBC and dihydroxy m-THPC were detected in both conditions; however, the formation of hydroxylated photoproducts was significantly greater in incubated solution. In addition, small molecules arising from the degradation of the photosensitizer and identified as dipyrin derivatives and dipyrrolic synthon were observed.
Disciplines :
Chemistry
Author, co-author :
Lassalle, Henri-Pierre; Centre Alexis Vautrin, CRAN CNRS UMR 7039 INPL UHP, Vandoeuvre les Nancy, France. h.lassalle@nancy.fnclcc.fr
Lourette, Natacha ; Laboratoire de Spectrométrie de Masse et de Chimie Laser, Metz, France
Maunit, Benoît; Laboratoire de Spectrométrie de Masse et de Chimie Laser, Metz, France
Muller, Jean-François; Laboratoire de Spectrométrie de Masse et de Chimie Laser, Metz, France
Guillemin, François; Centre Alexis Vautrin, CRAN CNRS UMR 7039-INPL-UHP, Vandœuvre-les-Nancy, France
Bezdetnaya-Bolotine, Lina; Centre Alexis Vautrin, CRAN CNRS UMR 7039-INPL-UHP, Vandœuvre-les-Nancy, France
Language :
English
Title :
MALDI-TOF mass spectrometric analysis for the characterization of the 5,10,15,20-tetrakis- (m-hydroxyphenyl)bacteriochlorin (m-THPBC) photoproducts in biological environment.
Moan J. Effect of bleaching of porphyrin sensitizers during photodynamic therapy. Cancer Lett. 1986; 33: 45.
Bonnett R, Martinez G. Photobleaching of Sensitisers Used in Photodynamic Therapy. Tetrahedron. 2001; 57: 9513.
Bonnett R, White RD, Winfield UJ, Berenbaum MC. Hydroporphyrins of the meso-tetra(hydroxyphenyl)porphyrin series as tumour photosensitizers. Biochem. J. 1989; 261: 277.
Bonnett R, charlesworth P, Djelal BD, Foley S, McGarvey DJ, Truscott TG. Photophysical properties of 5,10,15,20-tetrakis(m-hydroxyphenyl) porphyrin (m-THPP), 5,10,15,20-tetrakis(m-hydroxyphenyl)chlorin (m-THPC) and 5,10,15,20-tetrakis(m-hydroxyphenyl)bacteriochlorin (m-THPBC): a comparative study. J. Chem. Soc., Perkin Trans. 2. 1999; 2: 325.
Engelmann K, Mack MG, Eichler K, Straub R, Zangos S, Vogl TJ. Interstitial photodynamic laser therapy for liver metastases: first results of a clinical phase I-study. Rofo. Fortschr. Geb. Rontgenstr. Neuen. Bildgeb. Verfahr. 2003; 175: 682.
Beato B, Yost R, Quirke J. Doubly charged porphyrin ion tandem mass spectrometry: implications for structure elucidation. Org. Mass. Spectrom. 1989; 24: 875.
Shaw GJ, Eglinton G, Quirke JME. Structural analysis of tetrapyrroles by hydrogen chemical ionization mass spectrometry. Anal. Chem. 1981; 53: 2014.
Miller JM. Fast atom bombardment mass spectrometry of organometallic, coordination, and related compounds. Mass Spectrom. Rev. 1990; 9: 319.
Lindsey JS, Chaudhary T, Chait BT. 252Cf plasma desorption mass spectrometry in the synthesis of porphyrin model systems. Anal. Chem. 1992; 64: 2804.
Ha J, Hogan JD, Laude J, David A. Competitive ionization of tetraphenylporphyrin in a laser-generated metal ion plasma. J. Am. Soc., Mass Spectrom. 1993; 4: 159.
McLuckey SA, Glish GL, Van Berkel GJ. Charge determination of product ions formed from collision-induced dissociation of multiply protonated molecules via ion/molecule reactions. Anal. Chem. 1991; 63: 1971.
Kasselouri A, Bourdon O, Demore D, Blais JC, Prognon P, Bourg-Heckly G, Blais J. Fluorescence and mass spectrometry studies of meta-tetra(hydroxyphenyl) chlorin photoproducts. Photochem. Photobiol. 1999; 70: 275.
Angotti M, Maunit B, Muller JF, Bezdetnaya L, Guillemin F. Characterization by matrix-assisted laser desorption/ionization Fourier transform ion cyclotron resonance mass spectrometry of the major photoproducts of temoporfin (m-THPC) and bacteriochlorin (m-THPBC). J. Mass Spectrom. 2001; 36: 825.
Bartlett MG, Busch KL, Wells CA, Schey KL. Use of 2-hydroxy-1-naphthoic acid as a matrix for matrix-assisted laser desorption/ionization mass spectrometry of low molecular weight porphyrins and peptides. J. Mass Spectrom. 1996; 31: 275.
Green MK, Medforth CJ, Muzzi CM, Nurco DJ, Shea KM, Smith KM, Lebrilla CB. Application of matrix-assisted laser desorption/ionization Fourier transform mass spectrometry to the analysis of planar porphyrins and highly substituted nonplanar porphyrins. Eur. J. Mass Spectrom. 1997; 3: 439.
Lassalle HP, Bezdetnaya L, Iani V, Juzeniene A, Guillemin F, Moan J. Photodegradation and phototransformation of 5,10,15,20-tetrakis-(m- hydroxyphenyl)bacteriochlorin (m-THPBC) in solution. Photochem. Photobiol. Sci. 2004; 3: 999.
Brown SB, Shillcock M, Jones P. Equilibrium and kinetic studies of the aggregation of porphyrins in aqueous solution. Biochem. J. 1976; 153: 279.
Bonnett R, Djelal BD, Nguyen A. Physical and chemical studies related to the development of m-THPC (FOSCAN®) for the photodynamic therapy (PDT) of tumours. J. Porphyrins Phtalocyanines 2001; 5: 652.
Aveline BM, Hasan T, Redmond RW. The effects of aggregation, protein binding and cellular incorporation on the photophysical properties of benzoporphyrin derivative monoacid ring A (BPDMA). J. Photochem. Photobiol. B. 1995; 30:161.
Bezdetnaya L, Zeghari N, Belitchenko I, Barberi-Heyob M, Merlin JL, Potapenko A, Guillemin F. Spectroscopic and biological testing of photobleaching of porphyrins in solutions. Photochem. Photobiol. 1996; 64: 382.
Belitchenko I, Melnikova V, Bezdetnaya L, Rezzoug H, Merlin JL, Potapenko A, Guillemin F. Characterization of photodegradation of meta- tetra(hydroxyphenyl)chlorin (mTHPC) in solution: biological consequences in human tumor cells. Photochem. Photobiol. 1998; 67: 584.
Hadjur C, Lange N, Rebstein J, Monnier P, van den Bergh H, Wagnières G. Spectroscopic studies of photobleaching and photoproduct formation of meta(tetrahydroxyphenyl) chlorin (m-THPC) used in photodynamic therapy. The production of singlet oxygen by m-THPC. J. Photochem. Photobiol B. 1998; 45: 170.
Rotomskis R, Bagdonas S, Streckyte G. Spectroscopic studies of photobleaching and photoproduct formation of porphyrins used in tumour therapy. J. Photochem. Photobiol. B. 1996; 33: 61.
Ma LW, Moan J, Grahn MF, Iani V. Comparison of mesotetrahydroxyphenyl- chlorin and meso-tetrahydroxyphenyl-bacteriochlorin with respect to photobleaching and PCT efficiency in vivo. Proc. SPIE 1996; 2924: 219.
Grahn MF, McGuinness A, Benzie R, Boyle R, de Jode ML, Dilkes MG, Abbas B, Williams NS. Intracellular uptake, absorption spectrum and stability of the bacteriochlorin photosensitizer 5,10,15,20-tetrakis (m-hydroxyphenyl) bacteriochlorin (mTH-PBC). Comparison with 5,10,15,20-tetrakis(m-hydroxyphenyl)- chlorin (mTHPC). J. Photochem. Photobiol. B. 1997; 37: 261.
Jones RM, Wang Q, Lamb JH, Djelal BD, Bonnett R, Lim CK. Identification of photochemical oxidation products of 5,10,15,20-tetra(m-hydroxyphenyl)chlorin by on-line high-performance liquid chromatography-electrospray ionization tandem mass spectrometry. J Chromatogr., A. 1996; 722: 257.
Bonnett R. Chemical Aspects of Photodynamic Therapy. CRC Press: London, 2000.
Spikes JD. Quantum yields and kinetics of the photobleaching of hematoporphyrin, Photofrin II, tetra(4-sulfonatophenyl)-porphine and uroporphyrin. Photochem. Photobiol. 1992; 55: 797.
Angotti M, Maunit B, Muller JF, Bezdetnaya L, Guillemin F. Matrix-assisted laser desorption/ionization coupled to Fourier transform ion cyclotron resonance mass spectrometry: a method to characterize temoporpfin photoproducts. Rapid Commun. Mass Spectrom. 1999; 13: 597.
Lourette N, Maunit B, Bezdetnaya L, Lassalle HP, Guillemin F, Muller JF. Characterization of photoproducts of m-THPP in aqueous solution. Photochem. Photobiol. 2005; in press.
Bonnett R, Martinez G. Photobleaching of compounds of the 5,10,15,20-Tetrakis(m-hydroxyphenyl)porphyrin Series (m-THPP, m-THPC, and m-THPBC). Org. Lett. 2002; 4: 2013.