Accumulation and Photocytotoxicity of Hypericin and Analogs in Two- and Three-Dimensional Cultures of Transitional Cell Carcinoma Cells

Photochemistry and Photobiology

Volumn 78, Issue 6, 2003, Pages 607-614

  Huygens, Ann ^a   Huyghe, Dieter ^a   Bormans, Guy ^a   Verbruggen, Alfons ^a   Kamuhabwa, Appolinary R ^a   Roskams, Tania ^a   De Witte, Peter A M ^a  

^a UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

DIIODOHYPERICIN; HYPERICIN; IODINE DERIVATIVE; IODOHYPERICIN; PHOTOSENSITIZING AGENT; UNCLASSIFIED DRUG;

ARTICLE; BIOACCUMULATION; BLADDER CARCINOMA; CELL PROLIFERATION; CONTROLLED STUDY; CYTOTOXICITY; FLUORESCENCE; HUMAN; HUMAN CELL; HYDROPHILICITY; IN VITRO STUDY; LIPOPHILICITY; PHOTODYNAMIC THERAPY; PHOTOTOXICITY; SPHEROID CELL; TRANSITIONAL CELL CARCINOMA;

ANTINEOPLASTIC AGENTS; CARCINOMA, TRANSITIONAL CELL; CELL CULTURE TECHNIQUES; CELL DEATH; HUMANS; PERYLENE; PHOTOCHEMOTHERAPY; RADIATION-SENSITIZING AGENTS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0347761644     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1562/0031-8655(2003)078<0607:AAPOHA>2.0.CO;2     Document Type: Article

References (41)

1. Dougherty, J. T., J. C. C. Gomer, B. W. Henderson, G. Jori, D. Kessel, M. Korbelik, J. Moan and Q. Peng (1998) Photodynamic therapy. J. Natl. Cancer Inst. 90, 889-905.
2. Ochsner, M. (1997) Photophysical and photobiological processes in the photodynamic therapy of tumours. J. Photochem. Photobiol. B: Biol. 39, 1-18.
3. Fabris, C., G. Valduga, G. Miotto, L. Borsetto, G. Jori, S. Garbisa and E. Reddi (2001) Photosensitization with zinc(II) phthalocyanine as a switch in the decision between apoptosis and necrosis. Cancer Res. 61(20), 7498-7500.
4. Zimmermann, A., M. Ritsch-Marte and H. Kostron (2001) mTHPC-mediated photodynamic diagnosis of malignant brain tumors. Photochem. Photobiol. 74(4), 611-616.
5. Battah, S. H., C. E. Cheen, H. Nakanishi, S. Gerscher, A. J. MacRobert and C. Edward (2001) Synthesis and biological studies of 5-aminolevulinic acid-containing dendrimers for photodynamic therapy. Bioconjug. Chem. 12(6), 980-988.
6. Matroule, J. Y., C. M. Carthy, D. J. Granville, O. Jolois, D. W. Hunt and J. Piette (2001) Mechanism of colon cancer cell apoptosis mediated by pyropheophorbide-a methylester photosensitization. Oncogene 20(30), 4070-4084.
7. Fox, F. E., Z. Niu, A. Tobia and A. H. Rook (1998) Photoactivated hypericin is an anti-proliferative agent that induces a high rate of apoptotic death of normal, transformed and malignant T lymphocytes: implications for the treatment of cutaneous lymphoproliferative and inflammatory disorders. J. Investig. Dermatol. 111, 327-332.
8. Johnson, S. A., A. E. Dalton and R. S. Pardini (1998) Time-course of hypericin phototoxicity and effect on mitochondrial energies in EMT6 mouse mammary carcinoma cells. Free Radic. Biol. Med. 25, 144-152.
9. Vandenbogaerde, A. L., E. M. Delaey, A. M. Vanthiegem, B. E. Himpens, W. J. Merlevede and P. A. de Witte (1998) Cytotoxicity and anti-proliferative effect of hypericin and derivatives after photosensitization. Photochem. Photobiol. 67, 119-125.
10. Vandenbogaerde, A. L., K. R. Geboes, J. F. Cuveele, P. M. Agostinis, W. J. Merlevede and P. A. de Witte (1996) Antitumour activity of photosensitized hypericin on A431 cell xenografts. Anticancer Res. 16, 1619-1625.
11. Chen, B. and P. A. de Witte (2000) Photodynamic therapy efficacy and tissue distribution of hypericin in a mouse P388 lymphoma tumor model. Cancer Lett. 150, 111-117.
12. Lavie, G., Y. Mazur, D. Lavie and D. Meruelo (1995) The chemical and biological properties of hypericin: a compound with a broad spectrum of biological activities. Med. Res. Rev. 15, 111-119.
13. Jardon, P., N. Lazorchak and R. Gautron (1986) Propriétés du premier état triplet de l'hypericine étude par spectroscopie laser. J. Chim. Phys. 83, 311-315.
14. Racinet, H., P. Jardon and R. Gautron (1988) Formation d'oxygène singulet photosensibilisée par l'hypericine étude cinétique en milieu micellaire non ionique. J. Chim. Phys. 85, 971-977.
15. Duran, N. and P. S. Song (1986) Hypericin and its photodynamic action. Photochem. Photobiol. 43, 677-680.
16. Kraus, G. A., W. J. Zhang, M. J. Fehr, K. W. Petrich, Y. Wannemuehler, and S. Carpenter (1996) Research at the interface between chemistry and virology: development of a molecular flashlight. Chem. Rev. 1, 523-535.
17. Diwu, Z. and J. W. Lown (1993) Photosensitization with anticancer agents. 17. EPR studies of photodynamic action of hypericin: formation of semiquinone radical and activated oxygen species on illumination. Free Radic. Biol. Med. 14, 209-215.
18. D'Hallewin, M. A., P. A. de Witte, E. Waelkens, W. Merlevede and L. Baert (2000) Fluorescence detection of flat bladder carcinoma in situ after intravesical instillation of hypericin. J. Urol. 164, 349-351.
19. D'Hallewin, M. A., A. R. Kamuhabwa, T. Roskams, P. A. M. de Witte and L. Baert (2002) Hypericin-based fluorescence diagnosis of bladder carcinoma. BJU Int. 89, 760-763.
20. Kunz-Schughart, L. A., M. Kreutz and R. Knuechel (1998) Current status review: multicellular spheroids: a three-dimensional in vitro culture system to study tumour biology. Int. J. Exp. Pathol. 79, 1-23.
21. Mueller-Klieser, W. (1987) Guest editorial: multicellular spheroids: a review on cellular aggregates in cancer research. J. Cancer Res. Clin. Oncol. 113, 101-122.
22. Hamilton, G. (1998) Multicellular spheroids as an in vitro tumor model. Cancer Lett. 131, 29-34.
23. Obermüller, R. A., K. Hohenthanner, and H. Falk (2001) Toward hypericin-derived potential photodynamic therapy agents. Photochem. Photobiol. 74, 211-215.
24. Delaey, E., I. Zupko, B. Chen, A. Derycke, F. Van Laar D. De Vos and P. A. de Witte (2003) Comparison of hexamethylhypericin and tetrabromohypericin to hypericin for their in vivo efficacy as PDT tools. Int. J. Oncol. 23, 519-524.
25. Falk, H. and W. Schmitzberger (1993) On the bromination of hypericin: the gymnochrome chromophores. Monatsh. Chem. 124, 77-81.
26. Falk, H. and M. Oberreiter (1993) A convenient semisynthetic route to hypericin. Monatsh. Chem. 124, 339-341.
27. Lin, C. W., J. R. Shulok, Y. K. Wong, C. F. Schanbacher, L. Cincotta and J. W. Foley (1991) Photosensitization, uptake and retention of phenoxazine Nile blue derivatives in human bladder carcinoma cells. Cancer Res. 51, 1109-1116.
28. Siboni, G., H. Weitman, D. Freeman, Y. Mazur, Z. Malik and B. Ehrenberg (2002) The correlation between hydrophilicity of hypericins and helianthrone: internalization mechanisms, subcellular distribution and photodynamic action in colon carcinoma cells. Photochem. Photobiol. Sci. 1, 483-491.
29. Atkins, P. W. (1994) Spectroscopy 2: electronic transitions. In Physical Chemistry, (J. Crowe, ed.) p. 599. Oxford University Press Oxford, U.K.
30. Delaey, E. M., F. van Laar, D. de Vos, A. Kamuhabwa, P. Jacobs and P. A. M. de Witte (2000) A comparative study of the photosensitizing characteristics of some cyanine dyes. J. Photochem. Photobiol. 55B, 27-36.
31. Agostinis, P., A. Vanthiegem, W. Merlevede and P. A. M. de Witte (2002) Review: hypericin in cancer treatment: more light on the way. Int. J. Biochem. Cell Biol. 34, 221-241.
32. Oleinick, N. L. and H. H. Evans (1998) The photobiology of photodynamic therapy: cellular targets and mechanisms. Radiat. Res. 150, S146-S156.
33. Dubessy, C., J. L. Merlin, C. Marchal and F. Guillemin (2000) Spheroids in radiobiology and photodynamic therapy. Crit. Rev. Oncol. Hematol. 36, 179-192.
34. Oleinick, N. L., R. L. Morris and I. Belichenko (2002) The role of apoptosis in response to photodynamic therapy: what, where, why, and how. Photochem. Photobiol. Sci. 1, 1-21.
35. Coutier, S., S. Mitra, L. N. Bezdetnaya, R. M. Parache, I. Georgakoudi, T. H. Foster and F. Guillemin (2001) Effects of fluence rate on cell survival and photobleaching in meta-tetra-(hydroxyphenyl)chlorin-photosensitized Colo 26 multicell tumor spheroids. Photochem. Photobiol. 73(3), 297-303.
36. West, C. M. L. (1989) Size-dependent resistance of human tumour spheroids to photodynamic treatment. Br. J. Cancer 59, 510-514.
37. Wilson, C. B., J. Leopard, D. A. Cheresh and R. M. Nakamura (1996) Extracellular matrix and integrin composition of the normal bladder wall. World J. Urol. 14, S30-S37.
38. De Klerk, D. P. (1985) The glycosaminoglycans of human bladder cancers of varying grade and stage. J. Urol. 134, 978-981.
39. Glimelius, B., B. Norling, T. Nederman and J. Carlsson (1988) Extracellular matrices in multicellular spheroids of human glioma origin: increased incorporation of proteoglycans and fibronectin as compared to monolayer cultures. Acta Pathol. Microbiol. Scand. 96, 433-444.
40. Foster, T. H., D. F. Hartley, M. G. Nichols and R. Hilf (1993) Fluence rate effects in photodynamic therapy of multicell tumor spheroids. Cancer Res. 53, 1249-1254.
41. Wood, S. R., J. A. Holroyd and S. B. Brown (1997) The subcellular localization of Zn(II) phthalocyanines and their redistribution on exposure to light. Photochem. Photobiol. 65, 397-402.