Synthesis and photophysical properties of symmetrical tetraaryltetranaphtho[2,3]porphyrin derivatives

被引:1
作者
Wang, Jia-Li [1 ,2 ]
Xu, Tao [2 ]
Mi, Le [2 ]
Wang, Ming-Jie [2 ]
Yan, Yi-Jia [1 ,3 ]
Chen, Zhi-Long [1 ,2 ]
机构
[1] Fudan Univ, Huadong Hosp, Dept Pharm, Shanghai 200040, Peoples R China
[2] Donghua Univ, Dept Pharmaceut Sci & Technol, Shanghai 201620, Peoples R China
[3] Shanghai Xianhui Pharmaceut Co Ltd, Shanghai 201620, Peoples R China
基金
中国国家自然科学基金;
关键词
Photosensitizer; Photodynamic therapy; Naphthoporphyrin; Fluorescence; Optical material; UP-CONVERSION;
D O I
10.1016/j.dyepig.2024.112362
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The discovery of new photosensitizers with strong absorption near-infrared region, obvious fluorescence emission, and high reactive oxygen generation ability has attracted great attention as optical agents in life science and material industry. Herein a series of meso-tetraaryltetranaphtho[2,3]porphyrins (Ar 4TNPs) with different substitutions were designed and synthesized. They had strong absorptions at similar to 730 nm and fluorescence emission at 760 nm after excitation with similar to 503 nm light. All compounds possessed excellent reactive oxygen species (ROS) generation ability. The singlet oxygen generation rate of compound 10m (meso-5,10,15,20-tetra[2-(2-hydroxyethoxy)ethylbenzoate]tetrana-phthoporphyrin) is 0.1898 s(-1) with a Phi(Delta) value of 0.73, which is significantly higher than that of verteporfin. Therefore, Ar(4)TNPs have great potential as an effective optical material, biotracker, and photodynamic drug candidate.
引用
收藏
页数:7
相关论文
共 20 条
[1]   Tuning Photosensitized Singlet Oxygen Generation Efficiency of Novel Aza-BODIPY Dyes [J].
Adarsh, Nagappanpillai ;
Avirah, Rekha R. ;
Ramaiah, Danaboyina .
ORGANIC LETTERS, 2010, 12 (24) :5720-5723
[2]   Oncologic photodynamic therapy photosensitizers: A clinical review [J].
Allison, Ron R. ;
Sibata, Claudio H. .
PHOTODIAGNOSIS AND PHOTODYNAMIC THERAPY, 2010, 7 (02) :61-75
[3]   Blue-green up-conversion:: Noncoherent excitation by NIR light [J].
Baluschev, Stanislav ;
Yakutkin, Vladimir ;
Miteva, Tzenka ;
Avlasevich, Yuri ;
Chernov, Sergei ;
Aleshchenkov, Sergei ;
Nelles, Gabriele ;
Cheprakov, Andrei ;
Yasuda, Akio ;
Muellen, Klaus ;
Wegner, Gerhard .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (40) :7693-7696
[4]   New NIR-emitting complexes of platinum(II) and palladium(II) with fluorinated benzoporphyrins [J].
Borisov, S. M. ;
Nuss, G. ;
Haas, W. ;
Saf, R. ;
Schmuck, M. ;
Klimant, I. .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2009, 201 (2-3) :128-135
[5]   Photodynamic therapy (PDT) of cancer: from local to systemic treatment [J].
Dabrowski, Janusz M. ;
Arnaut, Luis G. .
PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, 2015, 14 (10) :1765-1780
[6]   The synthesis of new tetrabenzo- and tetranaphthoporphyrins via the addition reactions of 4,7-dihydroisoindole [J].
Filatov, Mikhail A. ;
Cheprakov, Andrei V. .
TETRAHEDRON, 2011, 67 (19) :3559-3566
[7]   Synthesis and luminescence of soluble meso-unsubstituted tetrabenzo- and tetranaphtho[2,3]porphyrins [J].
Finikova, OS ;
Cheprakov, AV ;
Vinogradov, SA .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (23) :9562-9572
[8]   Synthesis of symmetrical tetraaryltetranaphtho[2,3]porphyrins [J].
Finikova, OS ;
Aleshchenkov, SE ;
Briñas, RP ;
Cheprakov, AV ;
Carroll, PJ ;
Vinogradov, SA .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (12) :4617-4628
[9]   Novel route to functionalized tetraaryltetra[2,3]naphthaloporphyrins via oxidative aromatization [J].
Finikova, OS ;
Cheprakov, AV ;
Carroll, PJ ;
Vinogradov, SA .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (19) :7517-7520
[10]   Synthesis of [2,3]naphthoporphyrins using 4,9-dihydro-4,9-ethano-2H-benz[f]isoindole as a benz[f]isoindole equivalent [J].
Ishii, Yutaro ;
Ito, Satoshi ;
Saito, Yuki ;
Uno, Daiki ;
Oba, Toru .
TETRAHEDRON, 2015, 71 (47) :8892-8898