Gallium phthalocyanine photosensitizers: Carboxylation enhances the cellular uptake and improves the photodynamic therapy of cancers

Anti-Cancer Agents in Medicinal Chemistry

Volumn 12, Issue 6, 2012, Pages 604-610

  Zhao, Jin F ^a   Wang, Jing ^a   Chen, Ji Yao ^a   Chidawanykia, Wadzanai ^b   Nyokong, Tebello ^b   Ishii, Kazuyuki ^c   Kobayashi, Nagao ^d  

^a FUDAN UNIVERSITY   (China)

^b RHODES UNIVERSITY   (South Africa)

^c INSTITUTE OF INDUSTRIAL SCIENCE   (Japan)

^d TOHOKU UNIVERSITY   (Japan)

Author keywords

Cellular uptake; Photodynamic therapy; Phthalocyanine; Singlet oxygen

Indexed keywords

PHOTOSENSITIZING AGENT; PHTHALOCYANINE ALUMINUM; PHTHALOCYANINE GALLIUM; SINGLET OXYGEN; UNCLASSIFIED DRUG;

ARTICLE; CANCER CELL; CANCER THERAPY; CARBOXYLATION; CARCINOMA CELL; CELL KILLING; CELL TRANSPORT; CONTROLLED STUDY; HUMAN; HUMAN CELL; PHOTODYNAMIC THERAPY; PHOTOTOXICITY; SULFONATION;

EID: 84861694002     PISSN: 18715206     EISSN: 18755992     Source Type: Journal    
DOI: 10.2174/187152012800617740     Document Type: Article

References (26)

1. Carcenac, M.; Dorvillius, M.; Garambois, V.; Glaussel, F.; Larroque, Ch.; Langlois, R.; Hynes, N.E.; van Lier, J.E.; Pèlegrin, A. Internalisation enhances photo-induced cytotoxicity of monoclonal antibody-phthalocyanine conjugates. Br. J. Cancer, 2001, 85(1), 1787-1793.
2. Sibrian-Vazquez, M.; Ortiz, J.; Nesterova, I.V.; Fernández-Lázaro, F.; Sastre-Santos, A.; Soper, S.A. and Vicente, M.G.H. Synthesis and Properties of Cell-Targeted Zn(II)-Phthalocyanine-Peptide Conjugates. Bioconjugate Chem., 2007, 18(2), 410-420.
3. Brasseur, N.; Ouellet, R.; La Madeleine, C.; van Lier, J.E. Watersoluble aluminium phthalocyanine-polymer conjugates for PDT: photodynamic activities and pharmacokinetics in tumour-bearing mice. Br. J. Cancer, 1999, 80(10), 1533-1541.
4. Moore, C.M.; Pendse, D. and Emberton, M. Photodynamic therapy for prostate cancer-a review of current status and future promise. Nat. clin. practice urology Rev., 2009, 6(1), 18-30.
5. Garcia, M.A.; Campero, A. Aggregation Properties of Metallic Tetrasulphophthalocyanines Encapsulated in Sol-Gel Materials. Sol-Gel Sci. Technol., 1998, 13, 651-655.
6. Chan, W.S.; Brasseur, N.; La Madeleine, C.; Ouellet, R. and van Lier, J.E. Efficacy and Mechanism of Aluminium Phthalocyanine and its Sulphonated Derivatives Mediated Photodynamic Therapy on Murine Tumours. Eur. Cancer, 1997, 33(11), 1855-1859.
7. Masilela, N.; Idowu, M.; Nyokong, T. Photophysical. Photochemical and electrochemical properties of water soluble silicon, titanium and zinc phthalocyanines. Photochem. Photobiol. A: Chem., 2009, 201, 91-97.
8. Idowu, M.; Nyokong, T. Photophysical and photochemical properties of zinc and aluminum phthalocyanines in the presence of magnetic fluid. Photochem. Photobiol. A: Chem., 2007, 188, 200-206.
9. Idowu, M.; Chen, J.Y.; Nyokong, T. Photoinduced energy transfer between water-soluble CdTe quantum dots and aluminium tetrasulfonated phthalocyanine. New J. Chem., 2008, 32, 290-296.
10. Dulog, L.; Gittinger, A. Octaalkyl Esters of 2,3,9,10,16,17,23,24-(29H,31H)-Phthalocyanineoctacarboxylic Acid: A New Homologous Series of Discotic Liquid Crystals. Mol. Cryst. Liq. Cryst., 1992, 213(1), 31-42.
11. Sergeyev, S.; Debever, O.; Pouzet, E.; Geerts, Y.H. Transition temperature engineering of octaalkoxycarbonyl phthalocyanines. J. Mater. Chem., 2007, 17(29), 3002-3007.
12. Masilela, N.; Nyokong, T. The synthesis and photophysical properties of water soluble tetrasulfonated, octacarboxylated and quaternised 2,(3)-tetra-(2pyridiloxy)Ga phthalocyanines. Dyes and Pigments., 2010, 84(1), 242-248.
13. Wohrle, D.; Wahl, B. Octa-substituted phthalocyanine from 1,2,4,5-tetracyanobenzene. Tet. Lett. 1979; 20 (3), 227-228.
14. Ambroz, M.; Beeby, A.; McRobert, A.J.; Simpson, M.S.C.; Svensen, R.K.; Phillips, D. Preparative, analytical and fluorescence spectroscopic studies of sulfonated aluminium phthalocyanine photosensitizers. J. Photochem. Photobiol. B: Biol., 1991, 9(1), 87-95.
15. Ogunsipe, A.; Nyokong, T. Photophysicochemical consequences of bovine serum albumin binding to non-transition metal phthalocyanine sulfonates. Photochem. Photobio. Sci., 2005, 4 (7), 510-516.
16. Demas, J.N.; Crosby, G.A. Measurement of Photoluminescence Quantum Yields. J. Phys. Chem. Rev., 1971, 75, 991-1024.
17. Carloni, P.; Damiani, E.; Greci, L.; Stipa, P.; Tanfani, F.; Tartaglini, E.; Wozniak, M. On the use of 1,3-diphenylisobenzofuran (DPBF). Reactions with carbon and oxygen centered radicals in model and natural systems. Res. Chem. Intermed., 1993, 19(5), 395-405.
18. Hadjur, C.; Lange, N.; Rebstein, J.; Monnier, P.; van den Bergh, H.; Wagnieres, G. Spectroscopic studies of photobleaching and photoproduct formation of meta(tetrahydroxyphenyl) chlorin (m-THPC) used in photodynamic therapy. J. Photochem. Photobiol. B: Biol., 1998, 45,170-178.
19. Detty, M.R.; Gibson, S.L.; Wagner, S.J. Current clinical and preclinical photosensitizers for use in photodynamic therapy. J. Med. Chem., 2004, 47, 3897-3915.
20. Anholt, H.; Peng, Q.; Moan, J. Uptake, localization and effect of laser treatment on CaD2 tumours sensitized with aluminium phthalocyanine tetrasulfonate (AIPcS4). Lasers Med. Sci., 1994, 9, 111-118.
21. Ma, J.; Chen, J.Y.; Idowu, M.; Nyokong, T. Generation of Singlet Oxygen via the Composites of Water-Soluble Thiol-Capped CdTe Quantum Dots-Sulfonated Aluminum Phthalocyanines. J. Phys. Chem. B, 2008, 112, 4465-4469.
22. Niedre, M.J.; Yu, C.S.; Patterson, M.S.; Wilson, B.C. Singlet oxygen luminescence as an in vivo photodynamic therapy dose metric: validation in normal mouse skin with topical aminolevulinic acid. Br. J. Cancer, 2005, 92, 298-304.
23. Gomes, E.R.; Cruz, T.; Lopes, C.F.; Carvalho, A.P.; Duarte, C.B. Photosensitization of lymphoblastoid cells with phthalocyanines at different saturating incubation times. Cell Biol. Toxicol., 2004, 15(4), 249-260.
24. Moore, C.M.; Pendse, D.; Emberton, M. Photodynamic therapy for prostate cancer-a review of current status and future promise. Nat. Clin. Practice Urology Rev., 2009, 6(1), 18-30.
25. Chan, W.S.; Brasseur, N.; La Madeleine, C.; Ouellet, R. and van Lier, J.E. Efficacy and Mechanism of Aluminium Phthalocyanine and its Sulphonated Derivatives Mediated Photodynamic Therapy on Murine Tumours. Eur. Cancer, 1997, 33(11), 1855-1859.
26. Zhao, J.F.; Chen, J.Y.; Mi, L.; Wang, P.N.; Peng, Q. Enhancement of Intracellular Delivery of Anti-cancer Drugs by the Tat Peptide. Ultrastruct Pathol., 2011, 35(3), 119-123.