Imidazole metalloporphyrins as photosensitizers for photodynamic therapy: Role of molecular charge, central metal and hydroxyl radical production

Mroz, 2007, Photodynamic therapy with fullerenes, Photochem. Photobiol. Sci., 6, 1139, 10.1039/b711141j Castano, 2004, Mechanisms in photodynamic therapy: part one – photosensitizers photochemistry and cellular localization, Photodiagn. Photodyn. Ther., 1, 279, 10.1016/S1572-1000(05)00007-4 Detty, 2004, Current clinical and preclinical photosensitizers for use in photodynamic therapy, J. Med. Chem., 47, 3897, 10.1021/jm040074b Boyle, 1996, Structure and biodistribution relationships of photodynamic sensitizers, Photochem. Photobiol., 64, 469, 10.1111/j.1751-1097.1996.tb03093.x Mroz, 2007, Functionalized fullerenes mediate photodynamic killing of cancer cells: Type I versus Type II photochemical mechanism, Free Radic. Biol. Med., 43, 711, 10.1016/j.freeradbiomed.2007.05.005 Gomer, 1988, What makes a good photosensitizer for photodynamic therapy?, J. Photochem. Photobiol. B, 1, 376, 10.1016/1011-1344(88)85027-9 Peng, 2005, Mitochondrion-targeted photosensitizer enhances the photodynamic effect-induced mitochondrial dysfunction and apoptosis, Ann. NY Acad. Sci., 1042, 419, 10.1196/annals.1338.035 Ball, 1999, A comparative study of the cellular uptake and photodynamic efficacy of three novel zinc phthalocyanines of differing charge, Photochem. Photobiol., 69, 390, 10.1562/0031-8655(1999)069<0390:ACSOTC>2.3.CO;2 Hamblin, 2004, Photodynamic therapy: a new antimicrobial approach to infectious disease?, Photochem. Photobiol. Sci., 3, 436, 10.1039/b311900a Rodal, 1998, Liposome-bound Zn(II)-phthalocyanine. Mechanisms for cellular uptake and photosensitization, J. Photochem. Photobiol. B, 45, 150, 10.1016/S1011-1344(98)00175-4 van Leengoed, 1993, In vivo fluorescence kinetics of phthalocyanines in a skin-fold observation chamber model: role of central metal ion and degree of sulfonation, Photochem. Photobiol., 58, 233, 10.1111/j.1751-1097.1993.tb09554.x He, 1997, The synthesis photophysical and photobiological properties and in vitro structure-activity relationships of a set of silicon phthalocyanine PDT photosensitizers, Photochem. Photobiol., 65, 581, 10.1111/j.1751-1097.1997.tb08609.x Mang, 1998, A phase II/III clinical study of tin ethyl etiopurpurin (Purlytin)-induced photodynamic therapy for the treatment of recurrent cutaneous metastatic breast cancer, Cancer J. Sci. Am., 4, 378 Ciulla, 2005, Photodynamic therapy with PhotoPoint photosensitiser MV6401 indium chloride methyl pyropheophorbide achieves selective closure of rat corneal neovascularisation and rabbit choriocapillaris, Brit. J. Ophthalmol., 89, 113, 10.1136/bjo.2004.043075 Verigos, 2006, Updated results of a phase I trial of motexafin lutetium-mediated interstitial photodynamic therapy in patients with locally recurrent prostate cancer, J. Environ. Pathol. Toxicol. Oncol., 25, 373, 10.1615/JEnvironPatholToxicolOncol.v25.i1-2.230 Koudinova, 2003, Photodynamic therapy with Pd-bacteriopheophorbide (TOOKAD): successful in vivo treatment of human prostatic small cell carcinoma xenografts, Int. J. Cancer, 104, 782, 10.1002/ijc.11002 Berdugo, 2008, Evaluation of the new photosensitizer Stakel (WST-11) for photodynamic choroidal vessel occlusion in rabbit and rat eyes, Invest. Ophthalmol. Vis. Sci., 49, 1633, 10.1167/iovs.07-0767 Bhaumik, 2006, Masked imidazolyl-dipyrromethanes in the synthesis of imidazole-substituted porphyrins, J. Org. Chem., 71, 8807, 10.1021/jo061461r Srinivasan, 1999, Investigation of MALDI-TOF mass spectrometry of diverse synthetic metalloporphyrins phthalocyanines and multiporphyrin arrays, J. Porphyr. Phthalocyan., 3, 283, 10.1002/(SICI)1099-1409(199904)3:4<283::AID-JPP132>3.0.CO;2-F Whitten, 1986, 2-(Trimethylsilyl)ethoxy]methyl (SEM) as a novel and effective imidazole and fused aromatic imidazole protecting group, J. Org. Chem., 51, 1891, 10.1021/jo00360a044 Perry, 1955, Cultivation of large cultures of HeLa cells in horse serum, Science, 121, 805, 10.1126/science.121.3153.805 Brattain, 1980, Establishment of mouse colonic carcinoma cell lines with different metastatic properties, Cancer Res., 40, 2142 He, 2009, Enhanced apoptotic effect of combined modality of 9-hydroxypheophorbide alpha-mediated photodynamic therapy and carboplatin on AMC-HN-3 human head and neck cancer cells, Oncol. Rep., 21, 329 Lobner, 2000, Comparison of the LDH and MTT assays for quantifying cell death: validity for neuronal apoptosis?, J. Neurosci. Methods, 96, 147, 10.1016/S0165-0270(99)00193-4 Merlin, 1992, MTT assays allow quick and reliable measurement of the response of human tumour cells to photodynamic therapy, Eur. J. Cancer, 28A, 1452, 10.1016/0959-8049(92)90542-A Hamblin, 2000, Scavenger-receptor targeted photodynamic therapy, Photochem. Photobiol., 72, 533, 10.1562/0031-8655(2000)072<0533:SRTPT>2.0.CO;2 Sapan, 1999, Colorimetric protein assay techniques, Biotechnol. Appl. Biochem., 29, 99 Gronda, 2005, Assessment of the downstream portion of the mitochondrial pathway of caspase activation in patients with acute myeloid leukemia, Apoptosis, 10, 1285, 10.1007/s10495-005-2764-4 Sane, 1998, Distinct steps in DNA fragmentation pathway during camptothecin-induced apoptosis involved caspase- benzyloxycarbonyl- and N-tosyl-L-phenylalanylchloromethyl ketone-sensitive activities, Cancer Res., 58, 3066 Kessel, 1997, The role of subcellular localization in initiation of apoptosis by photodynamic therapy, Photochem. Photobiol., 65, 422, 10.1111/j.1751-1097.1997.tb08581.x Marchesi, 1999, Photoreduction of the fluorescent dye 2′-7′-dichlorofluorescein: a spin trapping and direct electron spin resonance study with implications for oxidative stress measurements, Free Radic. Biol. Med., 26, 148, 10.1016/S0891-5849(98)00174-9 Kee, 2008, Photophysical characterization of imidazolium-substituted Pd(II), In(III), and Zn(II) porphyrins as photosensitizers for photodynamic therapy, J. Photochem. Photobiol. A, 200, 346, 10.1016/j.jphotochem.2008.08.006 Redmond, 1999, A compilation of singlet oxygen yields from biologically relevant molecules, Photochem. Photobiol., 70, 391, 10.1562/0031-8655(1999)070<0391:ACOSOY>2.3.CO;2 Luo, 1997, Initiation of apoptosis versus necrosis by photodynamic therapy with chloroaluminum phthalocyanine, Photochem. Photobiol., 66, 479, 10.1111/j.1751-1097.1997.tb03176.x Antunes, 2001, Apoptosis induced by exposure to a low steady-state concentration of H2O2 is a consequence of lysosomal rupture, Biochem. J., 356, 549, 10.1042/0264-6021:3560549 Setsukinai, 2003, Development of novel fluorescence probes that can reliably detect reactive oxygen species and distinguish specific species, J. Biol. Chem., 278, 3170, 10.1074/jbc.M209264200 Athar, 1988, Differential role of reactive oxygen intermediates in photofrin-I- and photofrin-II-mediated photoenhancement of lipid peroxidation in epidermal microsomal membranes, J. Invest. Dermatol., 90, 652, 10.1111/1523-1747.ep12560814 Ding, 2004, Hematoporphyrin monomethyl ether photodynamic damage on HeLa cells by means of reactive oxygen species production and cytosolic free calcium concentration elevation, Cancer Lett., 216, 43, 10.1016/j.canlet.2004.07.005 Milanesio, 2003, Photodynamic activity of monocationic and non-charged methoxyphenylporphyrin derivatives in homogeneous and biological media, Photochem. Photobiol. Sci., 2, 926, 10.1039/B212890J Kolarova, 2007, Comparison of sensitizers by detecting reactive oxygen species after photodynamic reaction in vitro, Toxicol. In Vitro, 21, 1287, 10.1016/j.tiv.2007.04.017 Rosenfeld, 2006, Photosensitizers derived from 13(2)-oxo-methyl pyropheophorbide-a: enhanced effect of indium(III) as a central metal in in vitro and in vivo photosensitizing efficacy, Photochem. Photobiol., 82, 626, 10.1562/2005-09-29-RA-704 Gijsens, 2002, Targeting of the photocytotoxic compound AlPcS4 to Hela cells by transferrin conjugated PEG-liposomes, Int. J. Cancer, 101, 78, 10.1002/ijc.10548 van Nostrum, 2004, Delivery of photosensitizers in photodynamic therapy, Adv. Drug Deliver. Rev., 56, 5, 10.1016/j.addr.2003.10.003 Margaron, 1996, Structure-photodynamic activity relationships of a series of 4-substituted zinc phthalocyanines, Photochem. Photobiol., 63, 217, 10.1111/j.1751-1097.1996.tb03017.x Dummin, 1997, Selective photosensitization of mitochondria in HeLa cells by cationic Zn(II) phthalocyanines with lipophilic side-chains, J. Photochem. Photobiol. B, 37, 219, 10.1016/S1011-1344(96)07416-7 MacDonald, 1999, Subcellular localization patterns and their relationship to photodynamic activity of pyropheophorbide-a derivatives, Photochem. Photobiol., 70, 789, 10.1111/j.1751-1097.1999.tb08284.x Kee, 2008, Photophysical characterization of imidazolium-substituted Pd(II), In(III), and Zn(II) porphyrins as photosensitizers for photodynamic therapy, J. Photochem. Photobiol. A, 200, 346, 10.1016/j.jphotochem.2008.08.006 Kohanski, 2007, A common mechanism of cellular death induced by bactericidal antibiotics, Cell, 130, 797, 10.1016/j.cell.2007.06.049 Chatterjee, 1999, Photodynamic effects induced by meso-tetrakis[4-(carboxymethyleneoxy)phenyl] porphyrin on isolated Sarcoma 180 ascites mitochondria, J. Photochem. Photobiol. B, 50, 79, 10.1016/S1011-1344(99)00073-1 Hadjur, 1997, Production of the free radicals O2- and OH by irradiation of the photosensitizer zinc(II) phthalocyanine, J. Photochem. Photobiol. B, 38, 196, 10.1016/S1011-1344(96)07440-4 Hoebeke, 1997, Electron spin resonance evidence of the generation of superoxide anion, hydroxyl radical and singlet oxygen during the photohemolysis of human erythrocytes with bacteriochlorin a, Photochem. Photobiol., 66, 502, 10.1111/j.1751-1097.1997.tb03180.x An, 2003, Photogeneration of free radicals (OH and HB-) and singlet oxygen (1O2) by hypocrellin B in TX-100 micelles microsurroundings, Free Radic. Res., 37, 1107, 10.1080/10715760310001601056 Weishaupt, 1976, Identification of singlet oxygen as the cytotoxic agent in photoinactivation of a murine tumor, Cancer Res., 36, 2326 Clo, 2007, Control and selectivity of photosensitized singlet oxygen production: challenges in complex biological systems, Chembiochem, 8, 475, 10.1002/cbic.200600454 Jarvi, 2006, Singlet oxygen luminescence dosimetry (SOLD) for photodynamic therapy: current status challenges and future prospects, Photochem. Photobiol., 82, 1198, 10.1562/2006-05-03-IR-891 Moan, 2006, Singlet oxygen in photosensitization, J. Environ. Pathol. Toxicol. Oncol., 25, 29, 10.1615/JEnvironPatholToxicolOncol.v25.i1-2.30 Koppenol, 2001, The Haber–Weiss cycle – 70 years later, Redox Rep., 6, 229, 10.1179/135100001101536373 Beckman, 1990, Apparent hydroxyl radical production by peroxynitrite: implications for endothelial injury from nitric oxide and superoxide, Proc. Natl. Acad. Sci. USA, 87, 1620, 10.1073/pnas.87.4.1620 Felton, 1978, vol. V, 5 Kalyanasundaram, 1982, Photophysical and redox properties of water-soluble porphyrins in aqueous media, J. Phys. Chem., 86, 5169, 10.1021/j100223a022 Hanson, 1987, Electrochromic effects of charge separation in bacterial photosynthesis: theoretical models, J. Am. Chem. Soc., 109, 4728, 10.1021/ja00249a050 Vakrat-Haglili, 2005, The microenvironment effect on the generation of reactive oxygen species by Pd-bacteriopheophorbide, J. Am. Chem. Soc., 127, 6487, 10.1021/ja046210j