An Amphiphilic BODIPY-Porphyrin Conjugate: Intense Two-Photon Absorption and Rapid Cellular Uptake for Two-Photon-Induced Imaging and Photodynamic Therapy

Tao Zhang; Rongfeng Lan; Longlong Gong; Baoyan Wu; Yuzhi Wang; Daniel W J Kwong; Wai-Kwok Wong; Ka-Leung Wong; Da Xing

doi:10.1002/cbic.201500349

An Amphiphilic BODIPY-Porphyrin Conjugate: Intense Two-Photon Absorption and Rapid Cellular Uptake for Two-Photon-Induced Imaging and Photodynamic Therapy

Chembiochem. 2015 Nov 2;16(16):2357-64. doi: 10.1002/cbic.201500349. Epub 2015 Oct 7.

Authors

Tao Zhang¹, Rongfeng Lan², Longlong Gong¹, Baoyan Wu¹, Yuzhi Wang², Daniel W J Kwong³, Wai-Kwok Wong⁴, Ka-Leung Wong⁵, Da Xing⁶

Affiliations

¹ MOE Key Laboratory of Laser Life Science, Institute of Laser Life Science, College of Biophotonics, South China Normal University, Guangzhou, 510631, 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, Waterloo Road, Hong Kong, China.
³ 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.
⁴ 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.
⁵ 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.
⁶ 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.

PMID: 26345273
DOI: 10.1002/cbic.201500349

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.

Keywords: BODIPY; amphiphiles; photodynamic therapy; porphyrinoids; two-photon absorption.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Boron Compounds / chemistry*
Cell Survival / drug effects
Humans
MCF-7 Cells
Microscopy, Confocal
Neoplasms / drug therapy
Photochemotherapy
Photons
Photosensitizing Agents / chemistry*
Photosensitizing Agents / therapeutic use
Photosensitizing Agents / toxicity
Porphyrins / chemistry*
Quantum Theory
Singlet Oxygen / chemistry
Singlet Oxygen / metabolism

Substances

4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
Boron Compounds
Photosensitizing Agents
Porphyrins
Singlet Oxygen