An Amphiphilic BODIPY‐Porphyrin Conjugate: Intense Two‐Photon Absorption and Rapid Cellular Uptake for Two‐Photon‐Induced Imaging and Photodynamic Therapy |
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| Authors: | Dr. Tao Zhang Dr. Rongfeng Lan Longlong Gong Dr. Baoyan Wu Yuzhi Wang Dr. Daniel W. J. Kwong Prof. Wai‐Kwok Wong Dr. Ka‐Leung Wong Prof. Da Xing |
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| Affiliation: | 1. MOE Key Laboratory of Laser Life Science, Institute of Laser Life Science, College of Biophotonics, South China Normal University, Guangzhou, China;2. Institute of Molecular Functional Materials, Areas of Excellence Scheme University Grants Committee Hong Kong) and, Department of Chemistry and Institute of Advanced Materials, Hong Kong Baptist University, Hong Kong, China |
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| Abstract: | 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. |
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| Keywords: | amphiphiles BODIPY photodynamic therapy porphyrinoids two-photon absorption |
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