A novel 10B-enriched carboranyl-containing phthalocyanine as a radio- and photo-sensitising agent for boron neutron capture therapy and photodynamic therapy of tumours: In vitro and in vivo studies

Photochemical and Photobiological Sciences

Volumn 5, Issue 1, 2006, Pages 39-50

  Friso, Elisabetta ^a   Roncucci, Gabrio ^b   Dei, Donata ^b   Soncin, Marina ^b   Fabris, Clara ^b   Chiti, Giacomo ^b   Colautti, Paolo ^c   Esposito, Juan ^c   De Nardo, Laura ^a,c   Riccardo Rossi, Carlo ^a   Nitti, Donato ^a   Giuntini, Francesca ^a   Borsetto, Lara ^a   Jori, Giulio ^a  

^a UNIVERSITY OF PADOVA   (Italy)

^b Molteni Farmaceutici   (Italy)

^c INFN SEZIONE DI ROMA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BORON 10; BORON DERIVATIVE; DIOLEOYLPHOSPHATIDYLCHOLINE; MACROCYCLIC COMPOUND; PHOTOSENSITIZING AGENT; PHTHALOCYANINE ZINC; PORPHYRIN DERIVATIVE; RADIOSENSITIZING AGENT; SINGLET OXYGEN; BORON; INDOLE DERIVATIVE; ISOTOPE; LIPOSOME; ORGANOMETALLIC COMPOUND; PHTHALOCYANINE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CANCER GROWTH; CANCER INHIBITION; CANCER RADIOTHERAPY; CANCER THERAPY; CANCER TRANSPLANTATION; CELL DEATH; CELL ORGANELLE; CONTROLLED STUDY; DRUG ACCUMULATION; DRUG ACTIVITY; DRUG BLOOD LEVEL; DRUG SYNTHESIS; FEMALE; IN VITRO STUDY; IN VIVO STUDY; IRRADIATION; MELANOMA; MELANOMA CELL; MOUSE; NEUTRON CAPTURE THERAPY; NEUTRON RADIATION; NONHUMAN; PHOTOCHEMISTRY; PHOTODYNAMIC THERAPY; PHOTOSENSITIZATION; PHYSICS; PIGMENTATION; PRIORITY JOURNAL; QUANTUM YIELD; RADIOSENSITIZATION; RED LIGHT; TREATMENT RESPONSE; ANIMAL; C57BL MOUSE; CELL PROLIFERATION; CHEMICAL STRUCTURE; CHEMISTRY; COMPARATIVE STUDY; DISEASE MODEL; DRUG EFFECT; EXPERIMENTAL MELANOMA; METHODOLOGY; MULTIMODALITY CANCER THERAPY; PHOTOCHEMOTHERAPY; RADIATION EXPOSURE; SKIN TUMOR; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TIME; TUMOR CELL LINE;

ANIMALIA;

ANIMALS; BORON; BORON NEUTRON CAPTURE THERAPY; CELL DEATH; CELL LINE, TUMOR; CELL PROLIFERATION; COMBINED MODALITY THERAPY; DISEASE MODELS, ANIMAL; FEMALE; INDOLES; ISOTOPES; LIPOSOMES; MELANOMA, EXPERIMENTAL; MICE; MICE, INBRED C57BL; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PHOTOCHEMOTHERAPY; PHOTOSENSITIZING AGENTS; SKIN NEOPLASMS; STRUCTURE-ACTIVITY RELATIONSHIP; TIME FACTORS;

EID: 33645505981     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/b506364g     Document Type: Article

References (44)

1. A. Z. Diaz J. A. Coderre A. D. Chanana R. Ma Boron neutron capture therapy for malignant gliomas Ann. Med. 2000 32 81-85.
2. R. Ackroyd C. Kelty N. Brown M. Reed The history of photodetection and photodynamic therapy Photochem. Photobiol. 2001 74 656-659.
3. R. F. Barth A. H. Soloway J. H. Goldman R. A. Gadbauer N. Gupta T. E. Blue W. Yang W. Tjarks Boron neutron capture therapy of brain tumours: an emerging therapeutic modality Neurosurgery 1999 44 433-451.
4. B. W. Henderson T. J. Dougherty How does photodynamic therapy work? Photochem. Photobiol. 1999 55 145-147.
5. M. Ochsner Photophysical and photobiological processes in photodynamic therapy of tumours J. Photochem. Photobiol., B 1997 39 1-18.
6. R. F. Barth W. Yang J. D. Rotaru M. L. Moeschberger C. P. Boesel A. H. Soloway D. D. Joel M. M. Nawrocky K. Ono J. H. Goodman Boron neutron capture therapy of brain tumours: enhanced survival and cure following blood-brain barrier disruption and intracarotid injection of sodium borocaptate and boronphenylalanine Int. J. Radiat. Oncol. Biol., Phys. 2000 47 209-218.
7. R. Bonnett, Chemical Aspects of Photodynamic Therapy, Gordon and Breach Science Publishers, Amsterdam, 2000.
8. M. Miura P. L. Micca C. D. Fisher C. R. Gordon J. C. Heinrichs D. N. Slatkin Evaluation of carborane-containing porphyrins as tumour targeting agents for boron neutron capture therapy Br. J. Radiol. 1998 71 773-781.
9. S. B. Kahl J. Li Synthesis and characterization of a boronated metallo–phthalocyanine for boron neutron capture therapy Inorg. Chem. 1996 35 3878-3880.
10. G. Jori, Photodynamic therapy: basic and preclinical aspects, in CRC Handbook of Organic Photochemistry and Photobiology, ed. W. Horspool and F. Lenci, CRC Press, Baton Rouge, 2nd edn, 2004, pp. 146-1–146-10.
11. C. Fabris G. Jori F. Giuntini G. Roncucci Photosensitising properties of a boronated phthalocyanine: studies at the molecular and cellular level J. Photochem. Photobiol., B 2001 64 1-7.
12. W. L. F. Armarego and D. D. Perrin, Purification of Laboratory Chemicals, Butterworth-Heinemann, Oxford, 4th edn, 1996.
13. F. Giuntini Y. Raoul D. Dei M. Municchi G. Chiti C. Fabris P. Colautti G. Jori G. Roncucci Synthesis of tetrasubstituted Zn(II)–phthalocyanines carrying four carboranyl-units as potential BNCT and PDT agents Tetrahedron Lett. 2005 46 2979-2982.
14. G. Valduga S. Nonell E. Reddi G. Jori S. Braslavsky The production of singlet molecular oxygen by Zinc(II)–phthalocyanine in ethanol and in unilamellar vesicles. Chemical quenching and phosphorescence studies Photochem. Photobiol. 1988 48 1-5.
15. E. Gross B. Ehrenberg F. Johnson Singlet oxygen generation by porphyrins and the kinetics of 9,10-dimethyl-anthracene photosensitisation in liposomes Photochem. Photobiol. 1993 57 808-813.
16. J. E. van Lier and J. D. Spikes, The chemistry, photophysics and photosensitising properties of phthalocyanines, in Photosensitising Compounds: their Chemistry, Biology and Clinical Use, ed. G. Bock and S. Harnett, Ciba Foundation Symposium 146, London, 1989, pp. 17–26.
17. G. Valduga E. Reddi G. Jori Spectroscopic studies on Zn(II)–phthalocyanine in homogeneous and microheterogeneous systems J. Inorg. Chem. 1987 29 59-65.
18. P. K. Smith R. I. Krohn G. T. Hermanson A. K. Mallia F. H. Gartner M. D. Provenzano Measurement of protein using bicinchoninic acid Anal. Biochem. 1985 150 76-85.
19. S. Rockwell In vivo-in vitro tumour cell lines: characteristics and model for human cancer Br. J. Cancer 1980 41 118-126.
20. C. Fabris G. Valduga G. Miotto G. Jori S. Garbisa E. Reddi Photosensitisation with Zn(II)–phthalocyanine as a switch in the decision between apoptosis and necrosis Cancer Res. 2001 61 7495-7500.
21. K. W. Burn L. Casalini S. Martini M. Mazzini E. Nava C. Petrovich G. Rosi M. Sarotto R. Tinti An epithermal facility for treating brain gliomas at the TAPIRO reactor Appl. Radiat. Isot. 2004 61 987-991.
22. G. Rosi G. Gambarini V. Colli S. Gay L. Scolari O. Fiorani A. Perrone E. Nava E. Fasola L. Visca A. Zanini Characterisation of TAPIRO BNCT thermal facility Radiat. Prot. Dosim. 2004 110 651-654.
23. J. A. Coderre D. N. Slatkin P. L. Micca J. R. Cialella Boron Neutron Capture therapy of a Murine Melanoma with p-Boronophenylanine: Dose-Response Analysis using a Morbidity Index Radiat. Res. 1991 128 177-185.
24. ICRU Report 46: Photon, Proton, Electron and Neutron Interaction data for body tissues, International Commission on Radiation Units and Measurements, 1992.
25. J. S. Hendricks, MCNPX (Version 2.5e), Los Alamos National Laboratory Report, LA-UR-04-0569, February 2004.
26. ICRU 63 Report: Nuclear Data for Neutron and Proton Radiotherapy and for Radiation Protection, International Commission on Radiation Units and Measurements, 2000.
27. L. De Nardo E. Seravalli G. Rosi J. Esposito P. Colautti V. Conte G. Tornielli BNCT microdosimetry at the Tapiro reactor thermal column Radiat. Prot. Dosim. 2004 110 579-586.
28. J. L. Maurer F. Berchier A. J. Serino C. B. Knobler M. F. Hawthorne Preparation and properties of metallo–phthalocyanines J. Org. Chem. 1990 55 838-843.
29. C. C. Leznoff, Synthetic strategies for peripherally substituted phthalocyanines, in Phthalocyanines, Properties and Applications, ed. C. C. Leznoff and A. B. P. Lever, VCH Publishers Inc., New York, 1989, vol. 1, pp. 159–169.
30. N. Oleinick R. L. Morris I. Belichenko The role of apoptosis in response to photodynamic therapy: what, where, why and how Photochem. Photobiol. Sci. 2002 1 1-21.
31. G. Jori, Low-density lipoproteins-liposome delivery systems for tumour photosensitisers in vivo, in Photodynamic Therapy, ed. B. W. Henderson and T. J. Dougherty, Marcel Dekker Inc., New York, 1992, pp. 173–176.
32. G. Jori, In vivo transport and pharmacokinetic behaviour of tumour photosensitisers, in Photosensitising Compounds: their Chemistry, Biology and Clinical Use, ed. G. Bock and S. Harnett, Ciba Foundation Symposium 146, London, 1989, pp. 173–186.
33. V. Gottumukkala R. Luguya F. R. Fronczek M. G. H. Vicente Synthesis and cellular studies of an octa-anionic 5,10,15,20-tetra[3,5-(nido-carboranylmethyl)phenyl]porphyrin (H2OCP) for application in BNCT Biorg. Med. Chem. 2005 13 1633-1640.
34. R. Luguya F. R. Fronczek K. M. Smith M. G. H. Vicente Synthesis of novel carboranylchlorins with dual application in boron neutron capture therapy (BNCT) and photodynamic therapy (PDT) Appl. Radiat. Isot. 2004 61 1117-1123.
35. M. G. H. Vicente Porphyrin-based sensitisers in the detection and treatment of cancer: recent progress Curr. Med. Chem.:Anti-Cancer Agents 2001 1 175-194.
36. K. Berg, Mechanisms of cell damage in photodynamic therapy, in The Fundamental Basis of Phototherapy, ed. H. Hönigsmann, G. Jori and A. R. Young, OEMF, Milano, 1996, pp. 181–207.
37. A. C. E. Moor, B. Ortel and T. Hasan, Mechanisms of photodynamic therapy, in Photodynamic Therapy, ed. T. Patrice, Royal Society of Chemistry, Cambridge, 2003, pp. 19–57.
38. T. J. Dougherty C. J. Gomer B. W. Henderson G. Jori D. Kessel M. Korbelik J. Moan Q. Peng Photodynamic therapy J. Natl. Cancer Inst. 1998 90 889-905.
39. G. Jori E. Reddi The role of lipoproteins in the delivery of tumour-targeting photosensitisers Int. J. Biochem. 1993 25 1369-1375.
40. C. Fitsch G. Goerz T. Ruzicka Photodynamic therapy in dermatology: a review Arch. Dermatol. 1998 134 207-214.
41. P. G. Calzavara-Pinton, R. M. Szeimies and B. Ortel, Photodynamic Therapy and Fluorescence Diagnosis in Dermatology, ed. D. P. Häder and G. Jori, Elsevier Publishing Co., Amsterdam, 2001.
42. 10B boron neutron capture therapy: enhancement of the tumour dose via beam filtration and dose rate, and the effects of these parameters on minimum boron content; a theoretical evaluation Int. J. Radiat. Oncol. Biol., Phys. 1985 11 831-840.
43. M. Miura G. M. Morris P. L. Micca D. T. Lombardo K. M. Youngs J. A. Kalef-Ezra D. A. Hoch D. N. Slatkin R. Ma J. A. Coderre Boron neutron capture therapy of a murine mammary carcinoma using a lipophilic carboranyltetraphenylporphyrin Radiat. Res. 2001 155 603-610.
44. M. A. Rosenthal B. Kavar J. S. Hill D. J. Morgan R. L. Nation S. S. Stylli R. L. Basser S. Uren H. Geldard M. D. Green S. B. Kahl A. K. Kaye Phase I and pharmacokinetic study of photodynamic therapy for high-grade gliomas using a novel boronated porphyrin J. Clin. Oncol. 2001 19 519-524.