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Volumn 58, Issue 4, 2015, Pages 1736-1749

Far-red-absorbing cationic phthalocyanine photosensitizers: Synthesis and evaluation of the photodynamic anticancer activity and the mode of cell death induction

Author keywords

[No Author keywords available]

Indexed keywords

CASPASE; PHOTOSENSITIZING AGENT; PHTHALOCYANINE; ZINC COMPLEX; ANTINEOPLASTIC AGENT; INDOLE DERIVATIVE; MAGNESIUM; ORGANOMETALLIC COMPOUND; ZINC;

EID: 84923914198     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm5014852     Document Type: Article
Times cited : (98)

References (50)
  • 2
    • 73649095641 scopus 로고    scopus 로고
    • Photodynamic therapy
    • Lang, A. R. Nova Science Publishers, Inc. New York
    • Zimcik, P.; Miletin, M. Photodynamic therapy. In Dyes and Pigments: New Research; Lang, A. R., Ed.; Nova Science Publishers, Inc.: New York, 2009; pp 1-62.
    • (2009) Dyes and Pigments: New Research , pp. 1-62
    • Zimcik, P.1    Miletin, M.2
  • 4
    • 34548247761 scopus 로고    scopus 로고
    • Molecular effectors of multiple cell death pathways initiated by photodynamic therapy
    • Buytaert, E.; Dewaele, M.; Agostinis, P. Molecular effectors of multiple cell death pathways initiated by photodynamic therapy Biochim. Biophys. Acta, Rev. Cancer 2007, 1776, 86-107
    • (2007) Biochim. Biophys. Acta, Rev. Cancer , vol.1776 , pp. 86-107
    • Buytaert, E.1    Dewaele, M.2    Agostinis, P.3
  • 5
    • 79951672119 scopus 로고    scopus 로고
    • Photochemical and photophysical properties of metallophthalocyanines
    • Kadish, K. M. Smith, K. M. Guilard, R. World Scientific Publishing: Singapore
    • Nyokong, T.; Antunes, E. Photochemical and photophysical properties of metallophthalocyanines. In Handbook of Porphyrin Science; Kadish, K. M.; Smith, K. M.; Guilard, R., Eds.; World Scientific Publishing: Singapore, 2010; Vol. 7; pp 247-358.
    • (2010) Handbook of Porphyrin Science , vol.7 , pp. 247-358
    • Nyokong, T.1    Antunes, E.2
  • 6
    • 84892763430 scopus 로고    scopus 로고
    • Design, synthesis, and properties of phthalocyanine complexes with main-group elements showing main absorption and fluorescence beyond 1000 nm
    • Furuyama, T.; Satoh, K.; Kushiya, T.; Kobayashi, N. Design, synthesis, and properties of phthalocyanine complexes with main-group elements showing main absorption and fluorescence beyond 1000 nm J. Am. Chem. Soc. 2014, 136, 765-776
    • (2014) J. Am. Chem. Soc. , vol.136 , pp. 765-776
    • Furuyama, T.1    Satoh, K.2    Kushiya, T.3    Kobayashi, N.4
  • 9
    • 84901253881 scopus 로고    scopus 로고
    • A dual activatable photosensitizer toward targeted photodynamic therapy
    • Lau, J. T. F.; Lo, P.-C.; Jiang, X.-J.; Wang, Q.; Ng, D. K. P. A dual activatable photosensitizer toward targeted photodynamic therapy J. Med. Chem. 2014, 57, 4088-4097
    • (2014) J. Med. Chem. , vol.57 , pp. 4088-4097
    • Lau, J.T.F.1    Lo, P.-C.2    Jiang, X.-J.3    Wang, Q.4    Ng, D.K.P.5
  • 10
    • 84880889746 scopus 로고    scopus 로고
    • Synthesis and in vitro photodynamic activity of oligomeric ethylene glycol-quinoline substituted zinc(II) phthalocyanine derivatives
    • Jia, X.; Yang, F.-F.; Li, J.; Liu, J.-Y.; Xue, J.-P. Synthesis and in vitro photodynamic activity of oligomeric ethylene glycol-quinoline substituted zinc(II) phthalocyanine derivatives J. Med. Chem. 2013, 56, 5797-5805
    • (2013) J. Med. Chem. , vol.56 , pp. 5797-5805
    • Jia, X.1    Yang, F.-F.2    Li, J.3    Liu, J.-Y.4    Xue, J.-P.5
  • 11
    • 84899638423 scopus 로고    scopus 로고
    • An effective zinc phthalocyanine derivative for photodynamic antimicrobial chemotherapy
    • Chen, Z.; Zhou, S.; Chen, J.; Li, L.; Hu, P.; Chen, S.; Huang, M. An effective zinc phthalocyanine derivative for photodynamic antimicrobial chemotherapy J. Lumin. 2014, 152, 103-107
    • (2014) J. Lumin. , vol.152 , pp. 103-107
    • Chen, Z.1    Zhou, S.2    Chen, J.3    Li, L.4    Hu, P.5    Chen, S.6    Huang, M.7
  • 12
    • 84900796916 scopus 로고    scopus 로고
    • A glutathione-activated phthalocyanine-based photosensitizer for photodynamic therapy
    • He, H.; Lo, P.-C.; Ng, D. K. P. A glutathione-activated phthalocyanine-based photosensitizer for photodynamic therapy Chem.-Eur. J. 2014, 20, 6241-6245
    • (2014) Chem.-Eur. J. , vol.20 , pp. 6241-6245
    • He, H.1    Lo, P.-C.2    Ng, D.K.P.3
  • 13
    • 84874627421 scopus 로고    scopus 로고
    • Phthalocyanine-peptide conjugates: Receptor-targeting bifunctional agents for imaging and photodynamic therapy
    • Ranyuk, E.; Cauchon, N.; Klarskov, K.; Guérin, B.; van Lier, J. E. Phthalocyanine-peptide conjugates: receptor-targeting bifunctional agents for imaging and photodynamic therapy J. Med. Chem. 2013, 56, 1520-1534
    • (2013) J. Med. Chem. , vol.56 , pp. 1520-1534
    • Ranyuk, E.1    Cauchon, N.2    Klarskov, K.3    Guérin, B.4    Van Lier, J.E.5
  • 14
    • 84872108661 scopus 로고    scopus 로고
    • Pyrazinoporphyrazines with externally appended pyridine rings. 13. Structure, UV-visible spectral features, and noncovalent interaction with DNA of a positively charged binuclear (Zn-II/Pt-II) macrocycle with multimodal anticancer potentialities
    • Manet, I.; Manoli, F.; Donzello, M. P.; Viola, E.; Masi, A.; Andreano, G.; Ricciardi, G.; Rosa, A.; Cellai, L.; Ercolani, C.; Monti, S. Pyrazinoporphyrazines with externally appended pyridine rings. 13. Structure, UV-visible spectral features, and noncovalent interaction with DNA of a positively charged binuclear (Zn-II/Pt-II) macrocycle with multimodal anticancer potentialities Inorg. Chem. 2013, 52, 321-328
    • (2013) Inorg. Chem. , vol.52 , pp. 321-328
    • Manet, I.1    Manoli, F.2    Donzello, M.P.3    Viola, E.4    Masi, A.5    Andreano, G.6    Ricciardi, G.7    Rosa, A.8    Cellai, L.9    Ercolani, C.10    Monti, S.11
  • 15
    • 77957960110 scopus 로고    scopus 로고
    • Synthetic pathways to water-soluble phthalocyanines and close analogs
    • Dumoulin, F.; Durmus, M.; Ahsen, V.; Nyokong, T. Synthetic pathways to water-soluble phthalocyanines and close analogs Coord. Chem. Rev. 2010, 254, 2792-2847
    • (2010) Coord. Chem. Rev. , vol.254 , pp. 2792-2847
    • Dumoulin, F.1    Durmus, M.2    Ahsen, V.3    Nyokong, T.4
  • 17
    • 39149104356 scopus 로고    scopus 로고
    • Syntheses and properties of a series of cationic water-soluble phthalocyanines
    • Li, H.; Jensen, T. J.; Fronczek, F. R.; Vicente, M. G. Syntheses and properties of a series of cationic water-soluble phthalocyanines J. Med. Chem. 2008, 51, 502-511
    • (2008) J. Med. Chem. , vol.51 , pp. 502-511
    • Li, H.1    Jensen, T.J.2    Fronczek, F.R.3    Vicente, M.G.4
  • 18
    • 78651109269 scopus 로고    scopus 로고
    • Phthalocyanine-polyamine conjugates as highly efficient photosensitizers for photodynamic therapy
    • Jiang, X. J.; Yeung, S. L.; Lo, P. C.; Fong, W. P.; Ng, D. K. P. Phthalocyanine-polyamine conjugates as highly efficient photosensitizers for photodynamic therapy J. Med. Chem. 2011, 54, 320-330
    • (2011) J. Med. Chem. , vol.54 , pp. 320-330
    • Jiang, X.J.1    Yeung, S.L.2    Lo, P.C.3    Fong, W.P.4    Ng, D.K.P.5
  • 19
    • 73649113454 scopus 로고    scopus 로고
    • Synthesis, properties and in vitro photodynamic activity of water-soluble azaphthalocyanines and azanaphthalocyanines
    • Zimcik, P.; Miletin, M.; Radilova, H.; Novakova, V.; Kopecky, K.; Svec, J.; Rudolf, E. Synthesis, properties and in vitro photodynamic activity of water-soluble azaphthalocyanines and azanaphthalocyanines Photochem. Photobiol. 2010, 86, 168-175
    • (2010) Photochem. Photobiol. , vol.86 , pp. 168-175
    • Zimcik, P.1    Miletin, M.2    Radilova, H.3    Novakova, V.4    Kopecky, K.5    Svec, J.6    Rudolf, E.7
  • 20
    • 31344458229 scopus 로고    scopus 로고
    • Comparison of aggregation properties and photodynamic activity of phthalocyanines and azaphthalocyanines
    • Kostka, M.; Zimcik, P.; Miletin, M.; Klemera, P.; Kopecky, K.; Musil, Z. Comparison of aggregation properties and photodynamic activity of phthalocyanines and azaphthalocyanines J. Photochem. Photobiol., A 2006, 178, 16-25
    • (2006) J. Photochem. Photobiol., A , vol.178 , pp. 16-25
    • Kostka, M.1    Zimcik, P.2    Miletin, M.3    Klemera, P.4    Kopecky, K.5    Musil, Z.6
  • 21
    • 0242383973 scopus 로고    scopus 로고
    • Effect of peripheral substitution on the electronic absorption and fluorescence spectra of metal-free and zinc phthalocyanines
    • Kobayashi, N.; Ogata, H.; Nonaka, N.; Lukyanets, E. A. Effect of peripheral substitution on the electronic absorption and fluorescence spectra of metal-free and zinc phthalocyanines Chem.-Eur. J. 2003, 9, 5123-5134
    • (2003) Chem.-Eur. J. , vol.9 , pp. 5123-5134
    • Kobayashi, N.1    Ogata, H.2    Nonaka, N.3    Lukyanets, E.A.4
  • 22
    • 77958004733 scopus 로고    scopus 로고
    • Synthesis and electrochemical characterisation of new tantalum(V) alkythio phthalocyanines
    • Chauke, V.; Nyokong, T. Synthesis and electrochemical characterisation of new tantalum(V) alkythio phthalocyanines Inorg. Chim. Acta 2010, 363, 3662-3669
    • (2010) Inorg. Chim. Acta , vol.363 , pp. 3662-3669
    • Chauke, V.1    Nyokong, T.2
  • 25
    • 84865452173 scopus 로고    scopus 로고
    • Towards near-infrared photosensitisation: A photosensitising hydrophilic non-peripherally octasulfanyl-substituted Zn phthalocyanine
    • Aydin Tekdas, D.; Kumru, U.; Gurek, A. G.; Durmus, M.; Ahsen, V.; Dumoulin, F. Towards near-infrared photosensitisation: a photosensitising hydrophilic non-peripherally octasulfanyl-substituted Zn phthalocyanine Tetrahedron Lett. 2012, 53, 5227-5230
    • (2012) Tetrahedron Lett. , vol.53 , pp. 5227-5230
    • Aydin Tekdas, D.1    Kumru, U.2    Gurek, A.G.3    Durmus, M.4    Ahsen, V.5    Dumoulin, F.6
  • 26
    • 58149336778 scopus 로고    scopus 로고
    • Synthesis, photophysical and photochemical studies of water soluble cationic zinc phthalocyanine derivatives
    • Idowu, M.; Nyokong, T. Synthesis, photophysical and photochemical studies of water soluble cationic zinc phthalocyanine derivatives Polyhedron 2009, 28, 416-424
    • (2009) Polyhedron , vol.28 , pp. 416-424
    • Idowu, M.1    Nyokong, T.2
  • 28
    • 84894415407 scopus 로고    scopus 로고
    • Structural factors influencing the intramolecular charge transfer and photoinduced electron transfer in tetrapyrazinoporphyrazines
    • Novakova, V.; Hladik, P.; Filandrova, T.; Zajicova, I.; Krepsova, V.; Miletin, M.; Lenco, J.; Zimcik, P. Structural factors influencing the intramolecular charge transfer and photoinduced electron transfer in tetrapyrazinoporphyrazines Phys. Chem. Chem. Phys. 2014, 16, 5440-5446
    • (2014) Phys. Chem. Chem. Phys. , vol.16 , pp. 5440-5446
    • Novakova, V.1    Hladik, P.2    Filandrova, T.3    Zajicova, I.4    Krepsova, V.5    Miletin, M.6    Lenco, J.7    Zimcik, P.8
  • 29
    • 33748068080 scopus 로고    scopus 로고
    • Cationic azaphthalocyanines bearing aliphatic tertiary amino substituents-synthesis, singlet oxygen production and spectroscopic studies
    • Zimcik, P.; Miletin, M.; Musil, Z.; Kopecky, K.; Kubza, L.; Brault, D. Cationic azaphthalocyanines bearing aliphatic tertiary amino substituents-synthesis, singlet oxygen production and spectroscopic studies J. Photochem. Photobiol., A 2006, 183, 59-69
    • (2006) J. Photochem. Photobiol., A , vol.183 , pp. 59-69
    • Zimcik, P.1    Miletin, M.2    Musil, Z.3    Kopecky, K.4    Kubza, L.5    Brault, D.6
  • 30
    • 77950036829 scopus 로고    scopus 로고
    • Preparation and in vitro photodynamic activity of amphiphilic zinc(II) phthalocyanines substituted with 2-(dimethylamino)ethylthio moieties and their N-alkylated derivatives
    • Duan, W. B.; Lo, P. C.; Duan, L.; Fong, W. P.; Ng, D. K. P. Preparation and in vitro photodynamic activity of amphiphilic zinc(II) phthalocyanines substituted with 2-(dimethylamino)ethylthio moieties and their N-alkylated derivatives Bioorg. Med. Chem. 2010, 18, 2672-2677
    • (2010) Bioorg. Med. Chem. , vol.18 , pp. 2672-2677
    • Duan, W.B.1    Lo, P.C.2    Duan, L.3    Fong, W.P.4    Ng, D.K.P.5
  • 32
    • 0036801288 scopus 로고    scopus 로고
    • Photosensitized oxidation of 2′,7′-dichlorofluorescin: Singlet oxygen does not contribute to the formation of fluorescent oxidation product 2′,7′-dichlorofluorescein
    • Bilski, P.; Belanger, A. G.; Chignell, C. F. Photosensitized oxidation of 2′,7′-dichlorofluorescin: singlet oxygen does not contribute to the formation of fluorescent oxidation product 2′,7′-dichlorofluorescein Free Radical Biol. Med. 2002, 33, 938-946
    • (2002) Free Radical Biol. Med. , vol.33 , pp. 938-946
    • Bilski, P.1    Belanger, A.G.2    Chignell, C.F.3
  • 33
    • 0345708223 scopus 로고    scopus 로고
    • Localization and photodynamic efficacy of two cationic porphyrins varying in charge distribution
    • Kessel, D.; Luguya, R.; Vicente, M. G. H. Localization and photodynamic efficacy of two cationic porphyrins varying in charge distribution Photochem. Photobiol. 2003, 78, 431-435
    • (2003) Photochem. Photobiol. , vol.78 , pp. 431-435
    • Kessel, D.1    Luguya, R.2    Vicente, M.G.H.3
  • 34
    • 0034745672 scopus 로고    scopus 로고
    • Relocalization of cathepsin D and cytochrome c early in apoptosis revealed by immunoelectron microscopy
    • Roberg, K. Relocalization of cathepsin D and cytochrome c early in apoptosis revealed by immunoelectron microscopy Lab. Invest. 2001, 81, 149-158
    • (2001) Lab. Invest. , vol.81 , pp. 149-158
    • Roberg, K.1
  • 35
  • 38
    • 0029043888 scopus 로고
    • A novel assay for apoptosis-flow cytometric detection of phosphatidylserine expression on early apoptotic cells using fluorescein-labeled annexin-V
    • Vermes, I.; Haanen, C.; Steffensnakken, H.; Reutelingsperger, C. A novel assay for apoptosis-flow cytometric detection of phosphatidylserine expression on early apoptotic cells using fluorescein-labeled annexin-V J. Immunol. Methods 1995, 184, 39-51
    • (1995) J. Immunol. Methods , vol.184 , pp. 39-51
    • Vermes, I.1    Haanen, C.2    Steffensnakken, H.3    Reutelingsperger, C.4
  • 39
    • 33845891045 scopus 로고    scopus 로고
    • Aspartic protease and caspase 3/7 activation are central for macrophage apoptosis following infection with Escherichia coli
    • Albee, L.; Shi, B.; Perlman, H. Aspartic protease and caspase 3/7 activation are central for macrophage apoptosis following infection with Escherichia coli J. Leukocyte Biol. 2007, 81, 229-237
    • (2007) J. Leukocyte Biol. , vol.81 , pp. 229-237
    • Albee, L.1    Shi, B.2    Perlman, H.3
  • 41
    • 0035300531 scopus 로고    scopus 로고
    • Caspase-3 activation by lysosomal enzymes in cytochrome c -independent apoptosis in myelodysplastic syndrome-derived cell line P39
    • Hishita, T.; Tada-Oikawa, S.; Tohyama, K.; Miura, Y.; Nishihara, T.; Tohyama, Y.; Yoshida, Y.; Uchiyama, T.; Kawanishi, S. Caspase-3 activation by lysosomal enzymes in cytochrome c -independent apoptosis in myelodysplastic syndrome-derived cell line P39 Cancer Res. 2001, 61, 2878-2884
    • (2001) Cancer Res. , vol.61 , pp. 2878-2884
    • Hishita, T.1    Tada-Oikawa, S.2    Tohyama, K.3    Miura, Y.4    Nishihara, T.5    Tohyama, Y.6    Yoshida, Y.7    Uchiyama, T.8    Kawanishi, S.9
  • 44
    • 72549095406 scopus 로고    scopus 로고
    • Regulation mechanisms and signaling pathways of autophagy
    • He, C. C.; Klionsky, D. J. Regulation mechanisms and signaling pathways of autophagy Annu. Rev. Genet. 2009, 43, 67-93
    • (2009) Annu. Rev. Genet. , vol.43 , pp. 67-93
    • He, C.C.1    Klionsky, D.J.2
  • 45
    • 0034948738 scopus 로고    scopus 로고
    • The autophagosomal-lysosomal compartment in programmed cell death
    • Bursch, W. The autophagosomal-lysosomal compartment in programmed cell death Cell Death Differ. 2001, 8, 569-581
    • (2001) Cell Death Differ. , vol.8 , pp. 569-581
    • Bursch, W.1
  • 47
    • 10844276286 scopus 로고    scopus 로고
    • Synthesis and characterization of novel soluble octa-cationic phthalocyanines
    • Bayir, Z. A. Synthesis and characterization of novel soluble octa-cationic phthalocyanines Dyes Pigm. 2005, 65, 235-242
    • (2005) Dyes Pigm. , vol.65 , pp. 235-242
    • Bayir, Z.A.1
  • 48
    • 38049024723 scopus 로고    scopus 로고
    • Synthesis and evaluation of cationic phthalocyanine derivatives as potential inhibitors of telomerase
    • Zhang, L.; Huang, J.; Ren, L.; Bai, M.; Wu, L.; Zhai, B.; Zhou, X. Synthesis and evaluation of cationic phthalocyanine derivatives as potential inhibitors of telomerase Bioorg. Med. Chem. 2008, 16, 303-312
    • (2008) Bioorg. Med. Chem. , vol.16 , pp. 303-312
    • Zhang, L.1    Huang, J.2    Ren, L.3    Bai, M.4    Wu, L.5    Zhai, B.6    Zhou, X.7
  • 49
    • 84896793514 scopus 로고    scopus 로고
    • Role of steric hindrance in the Newman-Kwart rearrangement and in the synthesis and photophysical properties of arylsulfanyl tetrapyrazinoporphyrazines
    • Novakova, V.; Miletin, M.; Filandrová, T.; Lenčo, J.; Růžička, A.; Zimcik, P. Role of steric hindrance in the Newman-Kwart rearrangement and in the synthesis and photophysical properties of arylsulfanyl tetrapyrazinoporphyrazines J. Org. Chem. 2014, 79, 2082-2093
    • (2014) J. Org. Chem. , vol.79 , pp. 2082-2093
    • Novakova, V.1    Miletin, M.2    Filandrová, T.3    Lenčo, J.4    Růžička, A.5    Zimcik, P.6
  • 50
    • 0030265697 scopus 로고    scopus 로고
    • Unsymmetrically substituted benzonaphthoporphyrazines: A new class of cationic photosensitizers for the photodynamic therapy of cancer
    • Michelsen, U.; Kliesch, H.; Schnurpfeil, G.; Sobbi, A. K.; Wöhrle, D. Unsymmetrically substituted benzonaphthoporphyrazines: a new class of cationic photosensitizers for the photodynamic therapy of cancer Photochem. Photobiol. 1996, 64, 694-701
    • (1996) Photochem. Photobiol. , vol.64 , pp. 694-701
    • Michelsen, U.1    Kliesch, H.2    Schnurpfeil, G.3    Sobbi, A.K.4    Wöhrle, D.5


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