Targeted Singlet Oxygen Generation Using Different DNA-Interacting Perylene Diimide Type Photosensitizers

被引:21
作者
Dincalp, Haluk [1 ]
Kizilok, Sevki [1 ]
Icli, Siddik [2 ]
机构
[1] Celal Bayar Univ, Dept Chem, Fac Arts & Sci, TR-45030 Muradiye, Manisa, Turkey
[2] Ege Univ, Solar Energy Inst, TR-35100 Izmir, Turkey
关键词
Perylene diimide; Pyrene; Charge transfer; G-quadruplex DNA; Singlet oxygen; DPBF method; G-QUADRUPLEX; PHOTODYNAMIC THERAPY; MOLECULAR-OXYGEN; ELECTROCHEMICAL PROPERTIES; ELECTRON-TRANSFER; EXCITED SINGLET; TRIPLET-STATES; DERIVATIVES; BINDING; PYRENE;
D O I
10.1007/s10895-014-1372-5
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
Singlet oxygen quantum yields (I broken vertical bar (Delta)) of different perylene diimides (PDIs) containing phenyl (PDI-Ph), pyrene (PDI-Pyr), and indole (PDI-In) units in bay positions of the ring were determined using 1,3-diphenylisobenzofuran (DPBF) method in toluene/methanol (99:1) system. Pyrene-substituted PDI were the most efficient singlet oxygen generator among the investigated photosensitizers with a quantum yield of I broken vertical bar (Delta) = 0.93 in toluene/methanol. Additionally, their binding affinities to G-quadruplex DNA structure were investigated by steady-state measurements. There were marked red shifts of absorbance bands for PDI-Pyr/DNA strand complexes with respect to the absorption maxima of DNA-free solution of PDI-Pyr in phosphate buffer at pH 6.
引用
收藏
页码:917 / 924
页数:8
相关论文
共 63 条
[1]   Singlet oxygen formation efficiencies following quenching of excited singlet and triplet states of aromatic hydrocarbons by molecular oxygen [J].
Abdel-Shafi, AA ;
Worrall, DR ;
Wilkinson, F .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2001, 142 (2-3) :133-143
[2]   Mechanism of the excited singlet and triplet states quenching by molecular oxygen in acetonitrile [J].
Abdel-Shafi, AA ;
Worrall, DR .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2005, 172 (02) :170-179
[3]   Porphyrin binding to quadruplexed T4G4 [J].
Anantha, NV ;
Azam, M ;
Sheardy, RD .
BIOCHEMISTRY, 1998, 37 (09) :2709-2714
[4]  
[Anonymous], 1999, PRINCIPLES FLUORESCE, DOI DOI 10.1007/978-1-4757-3061-6
[5]   Targeted photodynamic therapy - a promising strategy of tumor treatment [J].
Bugaj, Andrzej M. .
PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, 2011, 10 (07) :1097-1109
[6]   Study of binding affinity and selectivity of perylene and coronene derivatives towards duplex and quadruplex DNA by ESI-MS [J].
Casagrande, Valentina ;
Alvino, Antonello ;
Bianco, Armandodoriano ;
Ortaggi, Giancarlo ;
Franceschin, Marco .
JOURNAL OF MASS SPECTROMETRY, 2009, 44 (04) :530-540
[7]   Photophysical and electrochemical properties of 1,7-diaryl-substituted perylene diimides [J].
Chao, CC ;
Leung, MK ;
Su, YO ;
Chiu, KY ;
Lin, TH ;
Shieh, SJ ;
Lin, SC .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (11) :4323-4331
[8]   Foreword [J].
Chen, Chih-Ming ;
Flandorfer, Hans ;
Chen, Sinn-Wen ;
Lee, Jae-Ho ;
Yen, Yee-Wen ;
Schmetterer, Clemens ;
Ohnuma, Ikuo ;
Wang, Chao-Hong .
JOURNAL OF ELECTRONIC MATERIALS, 2012, 41 (01) :1-1
[9]   Low reflection and photo-sensitive organic light-emitting device with perylene diimide and double-metal structure [J].
Chiu, Tien-Lung ;
Chuang, Kai-Hsiang ;
Lin, Chi-Feng ;
Ho, Yu-Hsuan ;
Lee, Jiun-Haw ;
Chao, Chun-Chieh ;
Leung, Man-Kit ;
Wan, De-Hui ;
Li, Cheng-Yu ;
Chen, Hsuen-Li .
THIN SOLID FILMS, 2009, 517 (13) :3712-3716
[10]   Photodynamic therapy in the treatment of multiple primary tumours in the head and neck, located to the oral cavity and oropharynx [J].
Copper, M. P. ;
M, Triesscheijn ;
Tan, I. B. ;
Ruevekamp, M. C. ;
Stewart, F. A. .
CLINICAL OTOLARYNGOLOGY, 2007, 32 (03) :185-189