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An Amphiphilic BODIPY‐Porphyrin Conjugate: Intense Two‐Photon Absorption and Rapid Cellular Uptake for Two‐Photon‐Induced Imaging and Photodynamic Therapy
Author(s) -
Zhang Tao,
Lan Rongfeng,
Gong Longlong,
Wu Baoyan,
Wang Yuzhi,
Kwong Daniel W. J.,
Wong WaiKwok,
Wong KaLeung,
Xing Da
Publication year - 2015
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201500349
Subject(s) - photodynamic therapy , singlet oxygen , amphiphile , porphyrin , photochemistry , photosensitizer , conjugate , bodipy , chemistry , cytotoxicity , ethylene glycol , two photon excitation microscopy , moiety , absorption (acoustics) , cationic polymerization , materials science , fluorescence , stereochemistry , organic chemistry , in vitro , oxygen , biochemistry , copolymer , mathematical analysis , physics , mathematics , composite material , quantum mechanics , polymer
The new amphiphilic BODPY‐porphyrin conjugate BZnPP and its precursor BZnPH were synthesised, and their linear and two‐photon photophysical properties, together with their cellular uptake and photo‐cytotoxicity, were studied. This amphiphilic conjugate consists of a hydrophobic BODIPY moiety and a hydrophilic tetra(ethylene glycol) chain bridging a cationic triphenylphosphonium group to an amphiphilic porphyrin ZnP through acetylide linkers at its meso positions. A large two‐photon absorption cross‐section ( σ =1725 GM) and a high singlet oxygen quantum yield (0.52) were recorded. Intense linear‐ and two‐photon‐induced red emissions were also observed for both BZnPP and BZnPH. Further in vitro studies showed that BZnPP exhibited very efficient cellular uptake and strong photocytotoxic but weak dark cytotoxic properties towards human breast carcinoma MCF‐7 cells. In summary, the two‐photon‐induced emission and the potent photo‐cytotoxicity of BZnPP make it an efficacious dual‐purpose tumour‐imaging and photodynamic therapeutic agent in the tissue‐transparent spectral windows.