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Volumn 113, Issue , 2016, Pages 187-197

Squaraines bearing halogenated moieties as anticancer photosensitizers: Synthesis, characterization and biological evaluation

Author keywords

Cancer; Photodynamic therapy; Photosensitizers; Singlet oxygen; Squaraines

Indexed keywords

ANTINEOPLASTIC AGENT; CARBON; CYTOCHROME C; DYE; GLUTATHIONE PEROXIDASE 1; MANGANESE SUPEROXIDE DISMUTASE; MESSENGER RNA; PHOTOSENSITIZING AGENT; PROTEIN; PROTEIN NQO1; REACTIVE OXYGEN METABOLITE; SINGLET OXYGEN; SQUARAINE DERIVATIVE; UNCLASSIFIED DRUG; CYCLOBUTANE DERIVATIVE; HALOGEN; PHENOL DERIVATIVE; SQUARAINE;

EID: 84964240822     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2016.02.035     Document Type: Article
Times cited : (55)

References (28)
  • 1
    • 84901601275 scopus 로고    scopus 로고
    • Photodynamic therapy
    • A.M. Rkein, D.M. Ozog, Photodynamic therapy, Dermatol. Clin. 32 (2014) 415-425, http://dx.doi.org/10.1016/j.det.2014.03.009.
    • (2014) Dermatol. Clin. , vol.32 , pp. 415-425
    • Rkein, A.M.1    Ozog, D.M.2
  • 2
    • 0033231402 scopus 로고    scopus 로고
    • Photodynamic therapeutics: Basic principles and clinical applications
    • W.M. Sharman, C.M. Allen, J.E. van Lier, Photodynamic therapeutics: basic principles and clinical applications, Drug Discov. Today 4 (1999) 507-517, http://dx.doi.org/10.1016/S1359-6446(99)01412-9.
    • (1999) Drug Discov. Today , vol.4 , pp. 507-517
    • Sharman, W.M.1    Allen, C.M.2    Van Lier, J.E.3
  • 3
    • 0017118879 scopus 로고
    • Identification of singlet oxygen as the cytotoxic agent in photoinactivation of a murine tumor
    • K.R. Weishaupt, C.J. Gomer, T.J. Dougherty, Identification of singlet oxygen as the cytotoxic agent in photoinactivation of a murine tumor, Cancer Res. 36 (1976) 2326-2329.
    • (1976) Cancer Res. , vol.36 , pp. 2326-2329
    • Weishaupt, K.R.1    Gomer, C.J.2    Dougherty, T.J.3
  • 4
    • 77952519831 scopus 로고    scopus 로고
    • Imaging and photodynamic therapy: Mechanisms, monitoring, and optimization
    • J.P. Celli, B.Q. Spring, I. Rizvi, C.L. Evans, K.S. Samkoe, S. Verma, et al., Imaging and photodynamic therapy: mechanisms, monitoring, and optimization, Chem. Rev. 110 (2010) 2795-2838, http://dx.doi.org/10.1021/cr900300p.
    • (2010) Chem. Rev. , vol.110 , pp. 2795-2838
    • Celli, J.P.1    Spring, B.Q.2    Rizvi, I.3    Evans, C.L.4    Samkoe, K.S.5    Verma, S.6
  • 5
    • 84875837340 scopus 로고    scopus 로고
    • Dye sensitizers for photodynamic therapy
    • A.B. Ormond, H.S. Freeman, Dye sensitizers for photodynamic therapy, Materials 6 (2013) 817-840, http://dx.doi.org/10.3390/ma6030817.
    • (2013) Materials , vol.6 , pp. 817-840
    • Ormond, A.B.1    Freeman, H.S.2
  • 6
    • 3242772115 scopus 로고    scopus 로고
    • Current clinical and preclinical photosensitizers for use in photodynamic therapy
    • M.R. Detty, S.L. Gibson, S.J. Wagner, Current clinical and preclinical photosensitizers for use in photodynamic therapy, J. Med. Chem. 47 (2004) 3897-3915, http://dx.doi.org/10.1021/jm040074b.
    • (2004) J. Med. Chem. , vol.47 , pp. 3897-3915
    • Detty, M.R.1    Gibson, S.L.2    Wagner, S.J.3
  • 7
    • 77952551346 scopus 로고    scopus 로고
    • Oncologic photodynamic therapy photosensitizers: A clinical review
    • R.R. Allison, C.H. Sibata, Oncologic photodynamic therapy photosensitizers: a clinical review, Photodiagn. Photodyn. Ther. 7 (2010) 61-75, http://dx.doi.org/10.1016/j.pdpdt.2010.02.001.
    • (2010) Photodiagn. Photodyn. Ther. , vol.7 , pp. 61-75
    • Allison, R.R.1    Sibata, C.H.2
  • 8
    • 84876473048 scopus 로고    scopus 로고
    • Near-infrared sensitization in dyesensitized solar cells
    • J. Park, G. Viscardi, C. Barolo, N. Barbero, Near-infrared sensitization in dyesensitized solar cells, Chimia 67 (2013) 129-135.
    • (2013) Chimia , vol.67 , pp. 129-135
    • Park, J.1    Viscardi, G.2    Barolo, C.3    Barbero, N.4
  • 9
    • 84908205429 scopus 로고    scopus 로고
    • Panchromatic symmetrical squaraines: A step forward in the molecular engineering of low cost blue-greenish sensitizers for dye-sensitized solar cells
    • J. Park, N. Barbero, J. Yoon, E. Dell'Orto, S. Galliano, R. Borrelli, et al., Panchromatic symmetrical squaraines: a step forward in the molecular engineering of low cost blue-greenish sensitizers for dye-sensitized solar cells, Phys. Chem. Chem. Phys. 16 (2014) 24173-24177, http://dx.doi.org/10.1039/C4CP04345F.
    • (2014) Phys. Chem. Chem. Phys. , vol.16 , pp. 24173-24177
    • Park, J.1    Barbero, N.2    Yoon, J.3    Dell'Orto, E.4    Galliano, S.5    Borrelli, R.6
  • 10
    • 84910645247 scopus 로고    scopus 로고
    • The different kinetic behavior of two potential photosensitizers for PDT
    • N. Barbero, S. Visentin, G. Viscardi, The different kinetic behavior of two potential photosensitizers for PDT, J. Photochem. Photobiol. A Chem. 299 (2015) 38-43, http://dx.doi.org/10.1016/j.jphotochem.2014.11.002.
    • (2015) J. Photochem. Photobiol. A Chem. , vol.299 , pp. 38-43
    • Barbero, N.1    Visentin, S.2    Viscardi, G.3
  • 11
    • 84856747406 scopus 로고    scopus 로고
    • Squaraine dyes in PDT: From basic design to in vivo demonstration
    • R.R. Avirah, D.T. Jayaram, N. Adarsh, D. Ramaiah, Squaraine dyes in PDT: from basic design to in vivo demonstration, Org. Biomol. Chem. 10 (2012) 911, http://dx.doi.org/10.1039/c1ob06588b.
    • (2012) Org. Biomol. Chem. , vol.10 , pp. 911
    • Avirah, R.R.1    Jayaram, D.T.2    Adarsh, N.3    Ramaiah, D.4
  • 12
    • 0030926425 scopus 로고    scopus 로고
    • Halogenated squaraine dyes as potential photochemotherapeutic agents. Synthesis and study of photophysical properties and quantum efficiencies of singlet oxygen generation
    • D. Ramaiah, A. Joy, N. Chandrasekhar, N. V Eldho, S. Das, M. V George, Halogenated squaraine dyes as potential photochemotherapeutic agents. synthesis and study of photophysical properties and quantum efficiencies of singlet oxygen generation, Synthesis (Stuttg) 65 (1997) 783-790, http://dx.doi.org/10.1111/j.1751-1097.1997.tb01925.x.
    • (1997) Synthesis (Stuttg) , vol.65 , pp. 783-790
    • Ramaiah, D.1    Joy, A.2    Chandrasekhar, N.3    Eldho, N.V.4    Das, S.5    George, M.V.6
  • 14
    • 84896728654 scopus 로고    scopus 로고
    • Twists and turns around a square: The many faces of Squaraine chemistry
    • L. Beverina, M. Sassi, Twists and turns around a square: the many faces of Squaraine chemistry, Synlett 25 (2014) 477-490, http://dx.doi.org/10.1055/s-0033-1340482.
    • (2014) Synlett , vol.25 , pp. 477-490
    • Beverina, L.1    Sassi, M.2
  • 15
    • 84935101922 scopus 로고    scopus 로고
    • Microwave-assisted synthesis of near-infrared fluorescent indole-based squaraines
    • N. Barbero, C. Magistris, J. Park, D. Saccone, P. Quagliotto, R. Buscaino, et al., Microwave-assisted synthesis of near-infrared fluorescent indole-based squaraines, Org. Lett. 17 (2015) 3306-3309.
    • (2015) Org. Lett. , vol.17 , pp. 3306-3309
    • Barbero, N.1    Magistris, C.2    Park, J.3    Saccone, D.4    Quagliotto, P.5    Buscaino, R.6
  • 16
    • 80053191773 scopus 로고    scopus 로고
    • One-pot three-component mild synthesis of 2-aryl-3-(9-alkylcarbazol-3-yl)thiazolin-4-ones
    • E. Cuevas Creencia, M. Tsukamoto, T. Horaguchi, One-pot three-component mild synthesis of 2-aryl-3-(9-alkylcarbazol-3-yl)thiazolin-4-ones, J. Heterocycl. Chem. 48 (2011) 1095-1102, http://dx.doi.org/10.1002/jhet.
    • (2011) J. Heterocycl. Chem. , vol.48 , pp. 1095-1102
    • Cuevas Creencia, E.1    Tsukamoto, M.2    Horaguchi, T.3
  • 17
    • 84906691672 scopus 로고    scopus 로고
    • A microwave-assisted and environmentally benign approach to the synthesis of near-infrared fluorescent pentamethine cyanine dyes
    • E.A. Owens, N. Bruschi, J.G. Tawney, M. Henary, A microwave-assisted and environmentally benign approach to the synthesis of near-infrared fluorescent pentamethine cyanine dyes, Dyes Pigment 113 (2015) 27-37, http://dx.doi.org/10.1016/j.dyepig.2014.07.035.
    • (2015) Dyes Pigment , vol.113 , pp. 27-37
    • Owens, E.A.1    Bruschi, N.2    Tawney, J.G.3    Henary, M.4
  • 18
    • 84865045761 scopus 로고    scopus 로고
    • Studies on a vinyl ruthenium-modified squaraine dye: Multiple visible/near-infrared absorbance switching through dye- and substituent-based redox processes
    • J. Chen, R.F. Winter, Studies on a vinyl ruthenium-modified squaraine dye: multiple visible/near-infrared absorbance switching through dye- and substituent-based redox processes, Chem. Eur. J. 18 (2012) 10733-10741, http://dx.doi.org/10.1002/chem.201200800.
    • (2012) Chem. Eur. J. , vol.18 , pp. 10733-10741
    • Chen, J.1    Winter, R.F.2
  • 19
    • 84896757044 scopus 로고    scopus 로고
    • Synthesis and effect of heterocycle modification on the spectroscopic properties of a series of unsymmetrical trimethine cyanine dyes
    • A. Levitz, S.T. Ladani, D. Hamelberg, M. Henary, Synthesis and effect of heterocycle modification on the spectroscopic properties of a series of unsymmetrical trimethine cyanine dyes, Dyes Pigment 105 (2014) 238-249, http://dx.doi.org/10.1016/j.dyepig.2014.02.009.
    • (2014) Dyes Pigment , vol.105 , pp. 238-249
    • Levitz, A.1    Ladani, S.T.2    Hamelberg, D.3    Henary, M.4
  • 20
    • 84855293879 scopus 로고    scopus 로고
    • Bright near-infrared fluorophores based on squaraines by unexpected halogen effects
    • U. Mayerhöffer, B. Fimmel, F. Würthner, Bright near-infrared fluorophores based on squaraines by unexpected halogen effects, Angew. Chem. Int. Ed. Engl. 51 (2012) 164-167, http://dx.doi.org/10.1002/anie.201107176.
    • (2012) Angew. Chem. Int. Ed. Engl. , vol.51 , pp. 164-167
    • Mayerhöffer, U.1    Fimmel, B.2    Würthner, F.3
  • 21
    • 84868651442 scopus 로고    scopus 로고
    • New unsymmetrical squaraine dyes derived from imidazo[1,5-A]pyridine
    • Y. Prostota, O.D. Kachkovsky, L.V. Reis, P.F. Santos, New unsymmetrical squaraine dyes derived from imidazo[1,5-A]pyridine, Dyes Pigment 96 (2013) 554-562, http://dx.doi.org/10.1016/j.dyepig.2012.10.006.
    • (2013) Dyes Pigment , vol.96 , pp. 554-562
    • Prostota, Y.1    Kachkovsky, O.D.2    Reis, L.V.3    Santos, P.F.4
  • 22
    • 39049127163 scopus 로고    scopus 로고
    • Assessment of water-soluble π-extended squaraines as one- and two-photon singlet oxygen photosensitizers: Design, synthesis, and characterization
    • L. Beverina, M. Crippa, M. Landenna, R. Ruffo, P. Salice, F. Silvestri, et al., Assessment of water-soluble π-extended squaraines as one- and two-photon singlet oxygen photosensitizers: design, synthesis, and characterization, J. Am. Chem. Soc. 130 (2008) 1894-1902, http://dx.doi.org/10.1021/ja075933a.
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 1894-1902
    • Beverina, L.1    Crippa, M.2    Landenna, M.3    Ruffo, R.4    Salice, P.5    Silvestri, F.6
  • 23
    • 79959724644 scopus 로고    scopus 로고
    • Cell death pathways in photodynamic therapy of cancer
    • P. Mroz, A. Yaroslavsky, G.B. Kharkwal, M.R. Hamblin, Cell death pathways in photodynamic therapy of cancer, Cancers (Basel) 3 (2011) 2516-2539, http://dx.doi.org/10.3390/cancers3022516.
    • (2011) Cancers (Basel) , vol.3 , pp. 2516-2539
    • Mroz, P.1    Yaroslavsky, A.2    Kharkwal, G.B.3    Hamblin, M.R.4
  • 24
    • 84908388219 scopus 로고    scopus 로고
    • Symmetrical diiodinated squaraine as an efficient photosensitizer for PDT applications: Evidence from photodynamic and toxicological aspects
    • M.S. Soumya, K.M. Shafeekh, S. Das, A. Abraham, Symmetrical diiodinated squaraine as an efficient photosensitizer for PDT applications: evidence from photodynamic and toxicological aspects, Chem. Biol. Interact. 222 (2014) 44-49, http://dx.doi.org/10.1016/j.cbi.2014.08.006.
    • (2014) Chem. Biol. Interact. , vol.222 , pp. 44-49
    • Soumya, M.S.1    Shafeekh, K.M.2    Das, S.3    Abraham, A.4
  • 25
    • 0842291515 scopus 로고    scopus 로고
    • Squaraine dyes for photodynamic therapy: Mechanism of cytotoxicity and DNA damage induced by halogenated squaraine dyes plus light (>600 nm)
    • D. Ramaiah, I. Eckert, K.T. Arun, L. Weidenfeller, B. Epe, Squaraine dyes for photodynamic therapy: mechanism of cytotoxicity and DNA damage induced by halogenated squaraine dyes plus light (>600 nm), Photochem. Photobiol. 79 (2004) 99-104 doi:10.1562/0031-8655(2004)79<99:SDFPTM>2.0.CO;2.
    • (2004) Photochem. Photobiol. , vol.79 , pp. 99-104
    • Ramaiah, D.1    Eckert, I.2    Arun, K.T.3    Weidenfeller, L.4    Epe, B.5
  • 26
    • 0032538407 scopus 로고    scopus 로고
    • Rapid cytochrome c release, activation of caspases 3, 6, 7 and 8 followed by Bap31 cleavage in HeLa cells treated with photodynamic therapy
    • D.J. Granville, C.M. Carthy, H. Jiang, G.C. Shore, B.M. McManus, D.W.C. Hunt, Rapid cytochrome c release, activation of caspases 3, 6, 7 and 8 followed by Bap31 cleavage in HeLa cells treated with photodynamic therapy, FEBS Lett. 437 (1998) 5-10, http://dx.doi.org/10.1016/S0014-5793(98)01193-4.
    • (1998) FEBS Lett. , vol.437 , pp. 5-10
    • Granville, D.J.1    Carthy, C.M.2    Jiang, H.3    Shore, G.C.4    McManus, B.M.5    Hunt, D.W.C.6
  • 27
    • 84892565984 scopus 로고    scopus 로고
    • Theoretical and experimental determination of the absorption and emission spectra of a prototypical indolenine-based squaraine dye
    • R. Borrelli, S. Ellena, C. Barolo, Theoretical and experimental determination of the absorption and emission spectra of a prototypical indolenine-based squaraine dye, Phys. Chem. Chem. Phys. 16 (2014) 2390-2398, http://dx.doi.org/10.1039/c3cp54298j.
    • (2014) Phys. Chem. Chem. Phys. , vol.16 , pp. 2390-2398
    • Borrelli, R.1    Ellena, S.2    Barolo, C.3
  • 28
    • 84877272959 scopus 로고    scopus 로고
    • 2-[(3,3-Dimethylindolin-2-ylidene)methyl]-4-[(3,3-dimethyl-3 H-indol-1-ium-2-yl)methylidene]-3-oxocyclobut-1-en-1-olate chloroform disolvate
    • Reports Online
    • G. Smith, D.E. Lynch, 2-[(3,3-Dimethylindolin-2-ylidene)methyl]-4-[(3,3-dimethyl-3 H-indol-1-ium-2-yl)methylidene]-3-oxocyclobut-1-en-1-olate chloroform disolvate, Acta Crystallogr. Sect. E Struct. 69 (2013) o786-o787, http://dx.doi.org/10.1107/S1600536813010386. Reports Online.
    • (2013) Acta Crystallogr. Sect. E Struct. , vol.69 , pp. o786-o787
    • Smith, G.1    Lynch, D.E.2


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