An Amphiphilic BODIPY-Porphyrin Conjugate: Intense Two-Photon Absorption and Rapid Cellular Uptake for Two-Photon-Induced Imaging and Photodynamic Therapy.
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.
MOE Key Laboratory of Laser Life Science, Institute of Laser Life Science, College of Biophotonics, South China Normal University, Guangzhou, 510631, China.
Tao
T
Zhang
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, Waterloo Road, Hong Kong, China.
Rongfeng
R
Lan
MOE Key Laboratory of Laser Life Science, Institute of Laser Life Science, College of Biophotonics, South China Normal University, Guangzhou, 510631, China.
Longlong
L
Gong
MOE Key Laboratory of Laser Life Science, Institute of Laser Life Science, College of Biophotonics, South China Normal University, Guangzhou, 510631, China.
Baoyan
B
Wu
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, Waterloo Road, Hong Kong, China.
Yuzhi
Y
Wang
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, Waterloo Road, Hong Kong, China. dkwong@hkbu.edu.hk.
Daniel W J
DW
Kwong
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, Waterloo Road, Hong Kong, China. wkwong@hkbu.edu.hk.
Wai-Kwok
WK
Wong
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, Waterloo Road, Hong Kong, China. klwong@hkbu.edu.hk.
Ka-Leung
KL
Wong
MOE Key Laboratory of Laser Life Science, Institute of Laser Life Science, College of Biophotonics, South China Normal University, Guangzhou, 510631, China. xingda@scnu.edu.cn.
Da
D
Xing
D001896:Boron Compounds / Q000737:chemistry*; D002470:Cell Survival / Q000187:drug effects; D006801:Humans; D061986:MCF-7 Cells; D018613:Microscopy, Confocal; D009369:Neoplasms / Q000188:drug therapy; D010778:Photochemotherapy; D017785:Photons; D017319:Photosensitizing Agents / Q000737:chemistry* / Q000627:therapeutic use / Q000633:toxicity; D011166:Porphyrins / Q000737:chemistry*; D011789:Quantum Theory; D026082:Singlet Oxygen / Q000737:chemistry / Q000378:metabolism
C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001896:Boron Compounds; D017319:Photosensitizing Agents; D011166:Porphyrins; D026082:Singlet Oxygen
BODIPY; amphiphiles; photodynamic therapy; porphyrinoids; two-photon absorption