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Volumn 46, Issue 2, 2011, Pages 712-720

Metallation of pentaphyrin with Lu(III) dramatically increases reactive-oxygen species production and cell phototoxicity

Author keywords

Cell proliferation; Lu(III); PDT; Pentaphyrin; ROS

Indexed keywords

20 [[4' ( TRIMETHYLSILYL)ETHOXYCARBONYL]PHENYL 2,13 DIMETHYL 3,12 DIETHYL [24] ISOPENTAPHYRIN; HEAVY METAL; LUTETIUM; METAL COMPLEX; PHOTOSENSITIZING AGENT; PORPHYRIN; REACTIVE OXYGEN METABOLITE; UNCLASSIFIED DRUG;

EID: 79151485517     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2010.12.007     Document Type: Article
Times cited : (23)

References (67)
  • 3
    • 20744447896 scopus 로고    scopus 로고
    • Group 10 metal complexes of meso-aryl-substituted [26]hexaphyrins with a metal-carbon bond
    • S. Mori, S. Shimizu, R. Taniguchi, and A. Osuka Group 10 metal complexes of meso-aryl-substituted [26]hexaphyrins with a metal-carbon bond Inorg. Chem. 44 2005 4127 4129
    • (2005) Inorg. Chem. , vol.44 , pp. 4127-4129
    • Mori, S.1    Shimizu, S.2    Taniguchi, R.3    Osuka, A.4
  • 4
    • 17444387995 scopus 로고    scopus 로고
    • Magnetic resonance spectroscopic investigations of the electronic ground and excited states in strongly nonplanar iron(III) dodecasubstituted porphyrins
    • L.A. Yatsunyk, N.V. Shokhirev, and F.A. Walker Magnetic resonance spectroscopic investigations of the electronic ground and excited states in strongly nonplanar iron(III) dodecasubstituted porphyrins Inorg. Chem. 44 2005 2848 2866
    • (2005) Inorg. Chem. , vol.44 , pp. 2848-2866
    • Yatsunyk, L.A.1    Shokhirev, N.V.2    Walker, F.A.3
  • 5
    • 0035543097 scopus 로고    scopus 로고
    • Sapphyrins: Versatile anion binding agents
    • J.L. Sessler, and J.M. Davis Sapphyrins: versatile anion binding agents Acc. Chem. Res. 34 2001 989 997
    • (2001) Acc. Chem. Res. , vol.34 , pp. 989-997
    • Sessler, J.L.1    Davis, J.M.2
  • 8
    • 0001612469 scopus 로고
    • Large metal ion-centered template reactions. Uranyl complex of cyclopentakis(2-iminoisoindoline)
    • V.W. Day, T.J. Marks, and W.A. Wachter Large metal ion-centered template reactions. Uranyl complex of cyclopentakis(2-iminoisoindoline) J. Am. Chem. Soc. 97 1975 4519 4527
    • (1975) J. Am. Chem. Soc. , vol.97 , pp. 4519-4527
    • Day, V.W.1    Marks, T.J.2    Wachter, W.A.3
  • 10
    • 0003624726 scopus 로고
    • Nucleophilic-attack at the meso position of a uranyl sapphyrin complex
    • A.K. Burrell, M. Cyr, V. Lynch, and J.L. Sessler Nucleophilic-attack at the meso position of a uranyl sapphyrin complex J. Chem. Soc. Chem. Commun. 24 1991 1710 1713
    • (1991) J. Chem. Soc. Chem. Commun. , vol.24 , pp. 1710-1713
    • Burrell, A.K.1    Cyr, M.2    Lynch, V.3    Sessler, J.L.4
  • 11
    • 0000032080 scopus 로고
    • Uranylpentaphyrin - An actinide complex of an expanded porphyrin
    • A.K. Burrell, G. Hemmi, V. Lynch, and J.L. Sessler Uranylpentaphyrin - an actinide complex of an expanded porphyrin J. Am. Chem. Soc. 113 1991 4690 4692
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 4690-4692
    • Burrell, A.K.1    Hemmi, G.2    Lynch, V.3    Sessler, J.L.4
  • 12
    • 33751390835 scopus 로고
    • Synthesis and X-ray characterization of a uranyl(VI) schiff-base complex derived from a 2:2 condensation product of 3,4-diethyl pyrrole-2,5- dicarbaldehyde and 1,2-diamino-4,5-dimethoxybenzene
    • J.L. Sessler, T.D. Mody, and V. Lynch Synthesis and X-ray characterization of a uranyl(VI) schiff-base complex derived from a 2:2 condensation product of 3,4-diethyl pyrrole-2,5-dicarbaldehyde and 1,2-diamino-4,5-dimethoxybenzene Inorg. Chem. 31 1992 529 531
    • (1992) Inorg. Chem. , vol.31 , pp. 529-531
    • Sessler, J.L.1    Mody, T.D.2    Lynch, V.3
  • 17
    • 0642275488 scopus 로고
    • Porphycenes as photodynamic therapy agents
    • de Gruyter Berlin
    • K. Schaffner, E. Vogel, and G. Jori Porphycenes as photodynamic therapy agents Biological Effects of Light 1994 de Gruyter Berlin 312 321 (and references therein)
    • (1994) Biological Effects of Light , pp. 312-321
    • Schaffner, K.1    Vogel, E.2    Jori, G.3
  • 18
    • 0001200926 scopus 로고
    • Site-specific hydrolysis of RNA by europium(III) texaphyrin conjugated to a synthetic oligodeoxyribonucleotide
    • D. Magda, R.A. Miller, J.L. Sessler, and B.L. Iverson Site-specific hydrolysis of RNA by europium(III) texaphyrin conjugated to a synthetic oligodeoxyribonucleotide J. Am. Chem. Soc. 116 1994 7439 7440
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 7439-7440
    • Magda, D.1    Miller, R.A.2    Sessler, J.L.3    Iverson, B.L.4
  • 19
    • 0024391508 scopus 로고
    • Photodynamic therapy in the treatment of malignancies
    • C.J. Gomer Photodynamic therapy in the treatment of malignancies Semin. Hematol. 26 1989 27 34
    • (1989) Semin. Hematol. , vol.26 , pp. 27-34
    • Gomer, C.J.1
  • 20
    • 0020828176 scopus 로고
    • Hematoporphyrin as a photosensitizer of tumors
    • T.J. Dougherty Hematoporphyrin as a photosensitizer of tumors Photochem. Photobiol. 38 1983 377 379
    • (1983) Photochem. Photobiol. , vol.38 , pp. 377-379
    • Dougherty, T.J.1
  • 21
    • 0027446986 scopus 로고
    • Photodynamic therapy in oncology - Mechanisms and clinical use
    • H.I. Pass Photodynamic therapy in oncology - mechanisms and clinical use J. Natl. Cancer Inst. 85 1993 443 456
    • (1993) J. Natl. Cancer Inst. , vol.85 , pp. 443-456
    • Pass, H.I.1
  • 22
    • 0001235517 scopus 로고
    • New light on cancer therapy
    • S.B. Brown, and T.G. Truscott New light on cancer therapy Chem. Brit. 29 1993 955 958
    • (1993) Chem. Brit. , vol.29 , pp. 955-958
    • Brown, S.B.1    Truscott, T.G.2
  • 24
    • 77953513143 scopus 로고    scopus 로고
    • Curr. Pharm. Des 16 2010 1863 1976
    • (2010) Curr. Pharm. des , vol.16 , pp. 1863-1976
  • 25
    • 77956927110 scopus 로고    scopus 로고
    • Photodynamic therapy: Illuminating the road from cell death towards anti-tumor immunity
    • A.D. Garg, D. Nowis, J. Golab, and P. Agostinis Photodynamic therapy: illuminating the road from cell death towards anti-tumor immunity Apoptosis 15 2010 1050 1071
    • (2010) Apoptosis , vol.15 , pp. 1050-1071
    • Garg, A.D.1    Nowis, D.2    Golab, J.3    Agostinis, P.4
  • 26
    • 78049321864 scopus 로고    scopus 로고
    • Photodynamic therapy: A review of the literature and image documentation
    • M.C. Almeida Issa, and M. Manela-Azulay Photodynamic therapy: a review of the literature and image documentation Bras. Dermatol. 85 2010 501 511
    • (2010) Bras. Dermatol. , vol.85 , pp. 501-511
    • Almeida Issa, M.C.1    Manela-Azulay, M.2
  • 27
    • 77949423008 scopus 로고    scopus 로고
    • Enhancement of anti-tumor immunity by photodynamic therapy
    • S.O. Gollnick, and C.M. Brackett Enhancement of anti-tumor immunity by photodynamic therapy Immunol. Res. 46 2010 216 226
    • (2010) Immunol. Res. , vol.46 , pp. 216-226
    • Gollnick, S.O.1    Brackett, C.M.2
  • 28
  • 31
    • 0036176217 scopus 로고    scopus 로고
    • An update on photodynamic therapy applications
    • T.J. Dougherty An update on photodynamic therapy applications J. Clin. Laser Med. Surg. 20 2002 3 7
    • (2002) J. Clin. Laser Med. Surg. , vol.20 , pp. 3-7
    • Dougherty, T.J.1
  • 33
    • 0000530731 scopus 로고    scopus 로고
    • Photodynamic therapy: The sensitization of cancer cells to light
    • J. Miller Photodynamic therapy: the sensitization of cancer cells to light Chem. Educ. Today 76 1999 592 594
    • (1999) Chem. Educ. Today , vol.76 , pp. 592-594
    • Miller, J.1
  • 34
    • 0035083626 scopus 로고    scopus 로고
    • Reactive oxygen-dependent production of novel photochemotherapeutic agents
    • S. Pervaiz Reactive oxygen-dependent production of novel photochemotherapeutic agents FASEB J. 15 2001 612 617
    • (2001) FASEB J. , vol.15 , pp. 612-617
    • Pervaiz, S.1
  • 35
    • 42949143713 scopus 로고    scopus 로고
    • Photodynamic therapy and the development of metal-based photosensitizers
    • L.B. Josefsen, and R.W. Boyle Photodynamic therapy and the development of metal-based photosensitizers Metal Based Drugs 2008 Article ID 276109
    • (2008) Metal Based Drugs
    • Josefsen, L.B.1    Boyle, R.W.2
  • 36
    • 4244181626 scopus 로고    scopus 로고
    • Metal complexes as photo- and radio-sensitizers
    • H. Ali, and J.E. van Lier Metal complexes as photo- and radio-sensitizers Chem. Rev. 99 1999 2379 2450
    • (1999) Chem. Rev. , vol.99 , pp. 2379-2450
    • Ali, H.1    Van Lier, J.E.2
  • 38
    • 33745685088 scopus 로고    scopus 로고
    • Spectroscopic characterization of the oxidation control of the iso-pentaphyrin/pentaphyrin system
    • C. Comuzzi, S. Cogoi, and L.E. Xodo Spectroscopic characterization of the oxidation control of the iso-pentaphyrin/pentaphyrin system Tetrahedron 62 2006 8147 8151
    • (2006) Tetrahedron , vol.62 , pp. 8147-8151
    • Comuzzi, C.1    Cogoi, S.2    Xodo, L.E.3
  • 39
    • 0032555492 scopus 로고    scopus 로고
    • The characterization of three substituted zinc phthalocyanines of differing charge for use in photodynamic therapy. A comparative study of their aggregation and photosensitising ability in relation to mTHPC and polyhaematoporphyrin
    • D.J. Ball, S.R. Wood, D.I. Vernon, J. Griffiths, T.M.A.R. Dubbelman, and S.B. Brown The characterization of three substituted zinc phthalocyanines of differing charge for use in photodynamic therapy. A comparative study of their aggregation and photosensitising ability in relation to mTHPC and polyhaematoporphyrin J. Photochem. Photobiol. B. 45 1998 28 35
    • (1998) J. Photochem. Photobiol. B. , vol.45 , pp. 28-35
    • Ball, D.J.1    Wood, S.R.2    Vernon, D.I.3    Griffiths, J.4    Dubbelman, T.M.A.R.5    Brown, S.B.6
  • 41
    • 0034734311 scopus 로고    scopus 로고
    • Influence of large metal cations on the photophysical properties of texaphyrin, a rigid aromatic chromophore
    • D.M. Guldi, T.D. Mody, N.N. Gerasimchuk, D. Magda, and J.L. Sessler Influence of large metal cations on the photophysical properties of texaphyrin, a rigid aromatic chromophore J. Am. Chem. Soc. 122 2000 8289 8298
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 8289-8298
    • Guldi, D.M.1    Mody, T.D.2    Gerasimchuk, N.N.3    Magda, D.4    Sessler, J.L.5
  • 42
    • 0347456046 scopus 로고
    • Characterization of decamethyl and ethoxycarbonyl pentaphyrins
    • R.E. Danso-Danquah, L.Y. Xie, and D. Dolphin Characterization of decamethyl and ethoxycarbonyl pentaphyrins Heterocycles 41 1995 2553 2564
    • (1995) Heterocycles , vol.41 , pp. 2553-2564
    • Danso-Danquah, R.E.1    Xie, L.Y.2    Dolphin, D.3
  • 43
    • 33746616968 scopus 로고    scopus 로고
    • Zinc(II) and copper(II) complexes of β-substituted hydroxylporphyrins as tumor photosensitizers
    • Q.M. Huang, Z.Q. Pan, P. Wang, Z.P. Chen, X.L. Zhang, and H.S. Xu Zinc(II) and copper(II) complexes of β-substituted hydroxylporphyrins as tumor photosensitizers Bioorg. Med. Chem. Lett. 16 2006 3030 3033
    • (2006) Bioorg. Med. Chem. Lett. , vol.16 , pp. 3030-3033
    • Huang, Q.M.1    Pan, Z.Q.2    Wang, P.3    Chen, Z.P.4    Zhang, X.L.5    Xu, H.S.6
  • 45
    • 77956194988 scopus 로고    scopus 로고
    • Increasing damage to tumor blood vessels during motexafin Lutetium-PDT through use of low fluence rate
    • T.M. Busch, H.W. Wang, E.P. Wileyto, G.Q. Yu, and R.M. Bunte Increasing damage to tumor blood vessels during motexafin Lutetium-PDT through use of low fluence rate Radiat. Res. 174 2010 331 340
    • (2010) Radiat. Res. , vol.174 , pp. 331-340
    • Busch, T.M.1    Wang, H.W.2    Wileyto, E.P.3    Yu, G.Q.4    Bunte, R.M.5
  • 46
    • 69649083587 scopus 로고    scopus 로고
    • Porphyrin and nonporphyrin photosensitizers in oncology: Preclinical and clinical advances in photodynamic therapy
    • A.E. O'Connor, W.M. Gallagher, and A.T. Byrne Porphyrin and nonporphyrin photosensitizers in oncology: preclinical and clinical advances in photodynamic therapy Photochem. Photobiol. 85 2009 1053 1074
    • (2009) Photochem. Photobiol. , vol.85 , pp. 1053-1074
    • O'Connor, A.E.1    Gallagher, W.M.2    Byrne, A.T.3
  • 49
    • 18744382131 scopus 로고    scopus 로고
    • Determination of the distribution of light, optical properties, drug concentration, and tissue oxygenation in-vivo in human prostate during motexafin lutetium-mediated photodynamic therapy
    • T.C. Zhu, J.C. Finlay, and S.M. Hahn Determination of the distribution of light, optical properties, drug concentration, and tissue oxygenation in-vivo in human prostate during motexafin lutetium-mediated photodynamic therapy J. Photochem. Photobiol. B. 79 2005 231 241
    • (2005) J. Photochem. Photobiol. B. , vol.79 , pp. 231-241
    • Zhu, T.C.1    Finlay, J.C.2    Hahn, S.M.3
  • 52
    • 56949093555 scopus 로고    scopus 로고
    • The synthesis, spectroscopy, electrochemistry and photophysical properties of novel, sandwich europium(III) complexes with a porphyrin ligand bearing four pyrenyl groups in meso-positions
    • N. Sheng, P.-H. Zhu, C.-Q. Ma, and J.-Z. Jiang The synthesis, spectroscopy, electrochemistry and photophysical properties of novel, sandwich europium(III) complexes with a porphyrin ligand bearing four pyrenyl groups in meso-positions Dyes Pigm. 81 2009 91 96
    • (2009) Dyes Pigm. , vol.81 , pp. 91-96
    • Sheng, N.1    Zhu, P.-H.2    Ma, C.-Q.3    Jiang, J.-Z.4
  • 53
    • 0027418625 scopus 로고
    • Mitochondria as a source of reactive oxygen species during reductive stress in rat hepatocytes
    • T.L. Dawson, G.J. Gores, A.L. Nieminen, B. Herman, and J.J. Lemasters Mitochondria as a source of reactive oxygen species during reductive stress in rat hepatocytes Am. J. Physiol. 264 1993 C961 C967
    • (1993) Am. J. Physiol. , vol.264
    • Dawson, T.L.1    Gores, G.J.2    Nieminen, A.L.3    Herman, B.4    Lemasters, J.J.5
  • 54
    • 0030963238 scopus 로고    scopus 로고
    • Mitochondrial permeability transition in hepatocytes induced by t-BuOOH: NAD(P)H and reactive oxygen species
    • A.L. Nieminen, A.M. Byrne, B. Herman, and J.J. Lemasters Mitochondrial permeability transition in hepatocytes induced by t-BuOOH: NAD(P)H and reactive oxygen species Am. J. Physiol. 272 1997 C1286 C1294
    • (1997) Am. J. Physiol. , vol.272
    • Nieminen, A.L.1    Byrne, A.M.2    Herman, B.3    Lemasters, J.J.4
  • 55
    • 0026554428 scopus 로고
    • Evaluation of the probe 2′,7′-dichlorofluorescin as an indicator of reactive oxygen species formation and oxidative stress
    • C.P. LeBel, H. Ischiropoulos, and S.C. Bondy Evaluation of the probe 2′,7′-dichlorofluorescin as an indicator of reactive oxygen species formation and oxidative stress Chem. Res. Toxicol. 5 1992 227 231
    • (1992) Chem. Res. Toxicol. , vol.5 , pp. 227-231
    • Lebel, C.P.1    Ischiropoulos, H.2    Bondy, S.C.3
  • 56
    • 0021027358 scopus 로고
    • Detection of picomole levels of hydroperoxides using a fluorescent dichlorofluorescein assay
    • R. Cathcart, E. Schwiers, and B.N. Ames Detection of picomole levels of hydroperoxides using a fluorescent dichlorofluorescein assay Anal. Biochem. 134 1983 111 116
    • (1983) Anal. Biochem. , vol.134 , pp. 111-116
    • Cathcart, R.1    Schwiers, E.2    Ames, B.N.3
  • 57
    • 0002844195 scopus 로고
    • Synthesis of diacetyldichlorofluorescein - A stable reagent for fluorometric analysis
    • R. Brandt, and A.S. Keston Synthesis of diacetyldichlorofluorescein - a stable reagent for fluorometric analysis Anal. Biochem. 11 1965 6 9
    • (1965) Anal. Biochem. , vol.11 , pp. 6-9
    • Brandt, R.1    Keston, A.S.2
  • 58
    • 67349201695 scopus 로고    scopus 로고
    • Photodynamic therapy (PDT): A short review on cellular mechanisms and cancer research applications for PDT
    • C.A. Robertson, D. Hawkins Evans, and H. Abrahamse Photodynamic therapy (PDT): a short review on cellular mechanisms and cancer research applications for PDT J. Photochem. Photobiol. B. Biol. 96 2009 1 8
    • (2009) J. Photochem. Photobiol. B. Biol. , vol.96 , pp. 1-8
    • Robertson, C.A.1    Hawkins Evans, D.2    Abrahamse, H.3
  • 59
    • 34547094848 scopus 로고    scopus 로고
    • Functionalized fullerenes mediate photodynamic killing of cancer cells: Type i versus Type II photochemical mechanism
    • P. Mroz, A. Pawlak, M. Satti, H. Lee, T. Wharton, H. Gali, T. Sarna, and M.R. Hamblin Functionalized fullerenes mediate photodynamic killing of cancer cells: type I versus Type II photochemical mechanism Free Radic. Biol. Med. 43 2007 711 719
    • (2007) Free Radic. Biol. Med. , vol.43 , pp. 711-719
    • Mroz, P.1    Pawlak, A.2    Satti, M.3    Lee, H.4    Wharton, T.5    Gali, H.6    Sarna, T.7    Hamblin, M.R.8
  • 60
    • 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
    • P. Bilski, A.G. Belanger, and C.F. Chignell Photosensitized oxidation of 2',7'-dichlorofluorescin: singlet oxygen does not contribute to the formation of fluorescent oxidation product 2',7'-dichlorofluorescein Free Radic. Biol. Med. 33 2002 938 946
    • (2002) Free Radic. Biol. Med. , vol.33 , pp. 938-946
    • Bilski, P.1    Belanger, A.G.2    Chignell, C.F.3
  • 61
    • 0027604077 scopus 로고
    • Singlet oxygen generation by porphyrins and the kinetics of 9,10-dimethylanthracene photosensitization in liposomes
    • E. Gross, B. Ehrenberg, and F.M. Johnson Singlet oxygen generation by porphyrins and the kinetics of 9,10-dimethylanthracene photosensitization in liposomes Photochem. Photobiol. 57 1993 808 813
    • (1993) Photochem. Photobiol. , vol.57 , pp. 808-813
    • Gross, E.1    Ehrenberg, B.2    Johnson, F.M.3
  • 62
    • 33845278875 scopus 로고
    • Structural and theoretical models of photosynthetic chromophores. Implications for redox, light-absorption properties and vectorial electron flow
    • K.M. Barkigia, L. Chantranupong, K.M. Smith, and J. Fajer Structural and theoretical models of photosynthetic chromophores. Implications for redox, light-absorption properties and vectorial electron flow J. Am. Chem. Soc. 110 1988 7566 7567
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 7566-7567
    • Barkigia, K.M.1    Chantranupong, L.2    Smith, K.M.3    Fajer, J.4
  • 63
    • 0034789102 scopus 로고    scopus 로고
    • On the negligible impact of ruffling on the electronic spectra of porphine, tetramethylporphyrin, and perfluoroalkylporphyrins
    • A.K. Wertsching, A.S. Koch, and S.G. DiMagno On the negligible impact of ruffling on the electronic spectra of porphine, tetramethylporphyrin, and perfluoroalkylporphyrins J. Am. Chem. Soc. 123 2001 3932 3939
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 3932-3939
    • Wertsching, A.K.1    Koch, A.S.2    Dimagno, S.G.3
  • 64
    • 0037055031 scopus 로고    scopus 로고
    • Do nonplanar distortions of porphyrins bring about strongly red-shifted electronic spectra? Controversy, consensus, new developments, and relevance to chelatases
    • H. Ryeng, and A. Ghosh Do nonplanar distortions of porphyrins bring about strongly red-shifted electronic spectra? Controversy, consensus, new developments, and relevance to chelatases J. Am. Chem. Soc. 124 2002 8099 8103
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 8099-8103
    • Ryeng, H.1    Ghosh, A.2
  • 67
    • 0037423255 scopus 로고    scopus 로고
    • Contracted and expanded meso-alkynyl porphyrinoids: From triphyrin to hexaphyrin
    • A. Krivokapic, A.R. Cowley, and H.L. Anderson Contracted and expanded meso-alkynyl porphyrinoids: from triphyrin to hexaphyrin J. Org. Chem. 68 2003 1089 1096
    • (2003) J. Org. Chem. , vol.68 , pp. 1089-1096
    • Krivokapic, A.1    Cowley, A.R.2    Anderson, H.L.3


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