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=1725GM) 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.
Original language | English |
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Pages (from-to) | 2357-2364 |
Number of pages | 8 |
Journal | ChemBioChem |
Volume | 16 |
Issue number | 16 |
DOIs | |
Publication status | Published - 1 Nov 2015 |
Scopus Subject Areas
- Biochemistry
- Molecular Medicine
- Molecular Biology
- Organic Chemistry
User-Defined Keywords
- amphiphiles
- BODIPY
- photodynamic therapy
- porphyrinoids
- two-photon absorption