pH-Dependent Modification of Lipophilicity of Porphyrin-type Photosensitizers

Photochemistry and Photobiology

Volumn 79, Issue 3, 2004, Pages 242-247

  Čunderlíková, Beata ^a,b   Kaalhus, Olav ^a   Čunderlík, Róbert ^c   Mateášik, Anton ^b   Moan, Johan ^a,d   Kongshaug, Magne ^a  

^a Center of Clinical Epidemiology   (Norway)

^b INTERNATIONAL LASER CENTER   (Slovakia)

^c SLOVAK UNIVERSITY OF TECHNOLOGY   (Slovakia)

^d UNIVERSITY OF OSLO   (Norway)

Author keywords

[No Author keywords available]

Indexed keywords

BUFFER; HEMATOPORPHYRIN; IMINE; MESO TETRA(3 HYDROXYPHENYL)CHLORIN; MESO TETRA(3 HYDROXYPHENYL)PORPHINE; NITROGEN; OCTANOL; PHOSPHATE; PHOTOSENSITIZING AGENT; PORPHYRIN DERIVATIVE; TETRAPHENYLPORPHINESULFONIC ACID; UNCLASSIFIED DRUG;

ACIDITY; ALKALINITY; ARTICLE; CALCULATION; CHEMICAL MODIFICATION; DRUG STRUCTURE; ENVIRONMENTAL FACTOR; FLUOROMETRY; INFORMATION PROCESSING; LIPOPHILICITY; MODEL; PARTITION COEFFICIENT; PH; PKA; PROTON TRANSPORT; TITRIMETRY;

1-OCTANOL; BUFFERS; COUNTERCURRENT DISTRIBUTION; FLUOROMETRY; HEMATOPORPHYRINS; HYDROGEN-ION CONCENTRATION; PHOTOSENSITIZING AGENTS; PORPHYRINS; SIGNAL PROCESSING, COMPUTER-ASSISTED; TITRIMETRY;

EID: 11144356446     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1562/0031-8655(2004)79<242:PMOLOP>2.0.CO;2     Document Type: Article

References (31)

1. Tannock, I. F. and D. Rotin (1989) Acid pH in tumors and its potential for therapeutic exploitation. Cancer Res. 49, 4373-4384.
2. Martin, G. R. and R. K. Jain (1994) Noninvasive measurement of interstitial pH profiles in normal and neoplastic tissue using fluorescence imaging microscopy. Cancer Res. 54, 5670-5674.
3. Wike-Hooley, J., L. J. Haverman and H. S. Reinhold (1984) The relevance of tumor pH to the treatment of malignant diseases. Radiother. Oncol. 2, 343-366.
4. Moan, J. and T. Christensen (1981) Cellular uptake and photodynamic effect of hematoporphyrin. Photochem. Photobiol. 2, 291-299.
5. Moan, J., Q. Peng, J. F. Evensen, K. Berg, A. Western and C. Rimington (1987) Photosensitizing efficiencies, tumor- and cellular uptake of different photosensitizing drugs relevant for photodynamic therapy of cancer. Photochem. Photobiol. 46, 713-721.
6. 2a, mTHPP and mTHPC. Photochem. Photobiol. 74, 246-252.
7. 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.
8. 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.
9. Brault, D. and C. Vever-Bizet (1992) Protonation equilibria of haematoporphyrin as studied by fluorescence lifetime analysis. J. Chem. Soc. Faraday Trans. 88, 1519-1524.
10. a values of hematoporphyrin IX as determined by absorbance and fluorescence spectroscopy. Can. J. Spectrosc. 33, 57-62.
11. Srivastava, R. C., V. D. Anand and W. R. Carper (1973) A fluorescence study of hematoporphyrin. Appl. Spectrosc. 27, 444-449.
12. Bjørklund, E. G. (1998) pH-effekter innen Fotodynamisk Terapi av Kreft. MD Thesis. pp. 43-45. Oslo, Norway.
13. Kessel, D. (1977) Effects of photoactivated porphyrins at the cell surface of leukemia L1210 cells. Biochemistry 16, 3443-3449.
14. Sørensen, S. P. L. (1909) Ergänzung zu der Abhandlung: Enzymstudien II: Über die Messung und die Bedeutung der Wasserstoffionekonzentration bei enzymatischen Prozessen. Biochem. Z. 21, 1-131.
15. March, J. (1992) Advanced Organic Chemistry: Reactions, Mechanisms and Structure, 4th ed., 251. John Wiley & Sons, Inc., New York.
16. Lide, D. R. (1997) CRC Handbook of Chemistry and Physics, 77th ed., pp. 8-43 to 8-45. CRC Press, Boca Raton, FL.
17. Kortüm, G., W. Vogel and K. Andrussow (1961) Dissociation Constants of Organic Acids in Aqueous Solution. Butterworths, London.
18. Taft, R. W., M. H. Abraham, G. R. Famini, R. M. Doherty, J.-L. M. Abboud and M. J. Kamlet (1985) Solubility properties in polymers and biological media 5: an analysis of the physicochemical properties which influence octanol-water partition coefficients of aliphatic and aromatic solutes. J. Pharm. Sci. 74, 807-814.
19. Abraham, M. H., H. S. Chadha, G. S. Whiting and R. C. Mitchell (1994) Hydrogen bonding. 32. An analysis of water-octanol and wateralkane partitioning and the Δlog P parameter of Seiler. J. Pharm. Sci. 83, 1085-1100.
20. Bonnett, R., B. D. Djelal and A. Nguyen (2001) Physical and chemical studies related to the development of m-THPC (FOSCAN) for the photodynamic therapy (PDT) of tumors. J. Porphyrins Phthalocyanines 5, 652-661.
21. Pottier, R. H., J. P. Laplante, Y. F. A. Chow and J. Kennedy (1985) Photofrins: a spectral study. Can. J. Chem. 63, 1463-1467.
22. Desroches, M.-C., S. Layac, P. Prognon, P. Maillard, D. S. Grierson, E. Cutis, I. Nicolis and A. Kasselouri (2003) Speciation of new triand tetra-glucoconjugated tetrapyrrolic macrocycles (porphyrins and chlorins): an electronic molecular spectroscopy study. Appl. Spectrosc. 57, 950-959.
23. Gouterman, M. (1978) Optical spectra and electronic structure of porphyrins and related rings. In The Porphyrins, Vol. 3 (Edited by D. Dolphin), pp. 1. Academic Press, New York.
24. Akins, D. L., H.-R. Zhu and C. Guo (1994) Absorption and Raman scattering by aggregated meso-tetrakis(p-sulfonatophenyl)porphine. J. Phys. Chem. 98, 3612-3618.
25. Pasternack, R. F., K. F. Schaefer and P. Hambright (1994) Resonance light-scattering studies of porphyrin diacid aggregates. Inorg. Chem. 33, 2062-2065.
26. Ribó, J. M., J. Crusats, J.-A. Farrera and M. L. Valero (1994) Aggregation in water solutions of tetrasodium diprotonated meso-tetrakis(4-sulfonatophenyl)porphyrin. J. Chem. Soc. Chem. Commun. 681-682.
27. Venkatesh, B., R. Jayakumar, R. P. Pandian and P. T. Manoharan (1996) Surface active peptide-mediated porphyrin aggregation. Biochem. Biophys. Res. Commun. 223, 390-396.
28. Asokan, A. and M. J. Cho (2002) Exploitation of intracellular pH gradients in the cellular delivery of macromolecules. J. Pharm. Sci. 91, 903-913.
29. Altan, N., Y. Chen, M. Schindler and S. M. Simon (1998) Defective acidification in human breast tumor cells and implications for chemotherapy. J. Exp. Med. 187, 1583-1598.
30. Ma, L., J. Moan and K. Berg (1994) Evaluation of a new photosensitizer, meso-tetra-hydroxyphenyl-chlorin, for use in photodynamic therapy: a comparison of its photobiological properties with those of two other photosensitizers. Int. J. Cancer 57, 883-888.
31. Teiten, M.-H., L. Bezdetnaya, J.-L. Merlin, C. Bour-Dill, M. E. Pauly, M. Dicato and F. Guillemin (2001) Effect of meta-tetra(hydroxyphenyl)chlorine (mTHPC)-mediated photodynamic therapy on sensitive and multi-drug-resistant human breast cancer cells. J. Photochem. Photobiol. B: Biol. 62, 146-152.