Synthesis and photophysicochemical studies of poly(ethylene glycol) conjugated symmetrical and asymmetrical zinc phthalocyanines

被引:20
作者
Dincer, Hatice [1 ]
Mert, Humeyra [2 ]
Caliskan, Emel [2 ]
Atmaca, Goknur Yasa [3 ]
Erdogmus, Ali [3 ]
机构
[1] Istanbul Tech Univ, Fac Sci & Letters, Dept Chem, TR-34469 Istanbul, Turkey
[2] Hitit Univ, Fac Engn, Dept Chem Engn, TR-19030 Corum, Turkey
[3] Yildiz Tech Univ, Fac Arts & Sci, Dept Chem, TR-34210 Istanbul, Turkey
关键词
Symmetrical zinc phthalocyanine; Asymmetrical zinc phthalocyanine; Click; Star polymer; Photodynamic therapy; HALOGENATED SILICON(IV) PHTHALOCYANINES; WATER-SOLUBLE PHTHALOCYANINES; PHOTODYNAMIC THERAPY; STAR POLYMERS; PHOTOSENSITIZER; PORPHYRINS; PEGYLATION; CHLORO; CHAINS;
D O I
10.1016/j.molstruc.2015.08.067
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Synthesis and characterization of poly(ethylene glycol) conjugated symmetrical and asymmetrical zinc phthalocyanines (ZnPcs) is described. Copper (I) catalyzed azide-alkyne cycloaddition (CuAAC) click reaction between azide functional methoxypoly(ethylene glycol) (mPEG-N-3) and tetra terminal alkynyl substituted ZnPc yields star polymer with ZnPc core. Furthermore, CuAAC click reaction between asymmetrically terminal alkynyl substituted zinc phthalocyanine (aZnPc) and mPEG-N-3 yields aZnPc end functionalized PEG. Spectral, photophysical (fluorescence quantum yield), photochemical (singlet oxygen (Phi(Delta)), and photodegradation quantum yield (Phi(d)) properties of the symmetrically, and asymmetrically PEGylated ZnPcs are investigated to be used as sensitizers in photodynamic therapy (PDT). The quantum yield values of fluorescence (Phi(F)) and singlet oxygen generation (Phi(Delta)) for water soluble symmetrically PEGylated ZnPc in aqueous solution are calculated as 0.01 and 0.14 respectively, suggesting its potential as photosensitizer in PDT treatment. (C) 2015 Elsevier B.V. All rights reserved.
引用
收藏
页码:190 / 196
页数:7
相关论文
共 46 条
  • [1] Current status of phthalocyanines in the photodynamic therapy of cancer
    Allen, CM
    Sharman, WM
    Van Lier, JE
    [J]. JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, 2001, 5 (02) : 161 - 169
  • [2] Novel axially carborane-cage substituted silicon phthalocyanine photosensitizer; synthesis, characterization and photophysicochemical properties
    Atmaca, Goknur Yasa
    Dizman, Cemil
    Eren, Tarik
    Erdogmus, Ali
    [J]. SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2015, 137 : 244 - 249
  • [3] PEG-Modified Carbon Nanotubes in Biomedicine: Current Status and Challenges Ahead
    Bottini, Massimo
    Rosato, Nicola
    Bottini, Nunzio
    [J]. BIOMACROMOLECULES, 2011, 12 (10) : 3381 - 3393
  • [4] Thermotropic and lyotropic mesophase behavior of some novel phthalocyanine-centered poly(oxyethylene)s
    Clarkson, GJ
    Hassan, BM
    Maloney, DR
    McKeown, NB
    [J]. MACROMOLECULES, 1996, 29 (05) : 1854 - 1856
  • [5] Din D., 2003, PORPHYRIN HDB, P1
  • [6] Synthesis and characterization of novel tetra terminal alkynyl-substituted phthalocyanines and their star polymers via click reaction
    Dincer, Hatice
    Mert, Humeyra
    Sen, Betul Nur
    Dag, Aydan
    Bayraktar, Sinem
    [J]. DYES AND PIGMENTS, 2013, 98 (02) : 246 - 254
  • [7] Synthetic pathways to water-soluble phthalocyanines and close analogs
    Dumoulin, Fabienne
    Durmus, Mahmut
    Ahsen, Vefa
    Nyokong, Tebello
    [J]. COORDINATION CHEMISTRY REVIEWS, 2010, 254 (23-24) : 2792 - 2847
  • [8] The synthesis and photophysicochemical behaviour of novel water-soluble cationic indium(III) phthalocyanine
    Durmus, Mahmut
    Erdogmus, Ali
    Ogunsipe, Abimbola
    Nyokong, Tebello
    [J]. DYES AND PIGMENTS, 2009, 82 (02) : 244 - 250
  • [9] Synthesis of zinc phthalocyanine derivatives with improved photophysicochemical properties in aqueous media
    Erdogmus, Ali
    Nyokong, Tebello
    [J]. JOURNAL OF MOLECULAR STRUCTURE, 2010, 977 (1-3) : 26 - 38
  • [10] Gregory P, 2000, J PORPHYR PHTHALOCYA, V4, P432, DOI 10.1002/(SICI)1099-1409(200006/07)4:4<432::AID-JPP254>3.3.CO