Jump to main content
Jump to site search

Issue 17, 2011
Previous Article Next Article

Two-photon induced luminescence, singlet oxygen generation, cellular uptake and photocytotoxic properties of amphiphilic Ru(ii) polypyridyl–porphyrin conjugates as potential bifunctional photodynamic therapeutic agents

Author affiliations

Abstract

Two Ru(II) polypyridyl-porphyrin and Zn(II) porphyrin conjugates (Ru-L and Ru-Zn-L) have been synthesized and their photophysical properties studied. The two conjugates, which contained a hydrophobic tetraphenylporphyrin L conjugated via an acetylide linker at its β-position with a hydrophilic Ru(II) polypyridyl complex, showed high singlet oxygen quantum yields (>70%) and substantial two-photon absorption cross-sections (∼500 GM). Ru-L gave strong emissions at ∼660 and ∼733 nm through linear or two-photon excitation. Solvatochromism was observed in the fluorescence spectra of Ru-L and Ru-Zn-L, where in less polar solvents (i.e., toluene and dichloromethane) their fluorescence emissions became slightly blue-shifted with a 3-fold reduction in intensity relative to those observed in polar solvents (i.e., acetonitrile and methanol). Cell-based studies of these complex conjugates were conducted using human nasopharyngeal carcinoma HK-1 and cervical carcinoma HeLa cells on which Ru-L showed rapid cellular uptake, low dark-cytotoxicity, and high photo-cytotoxicity. Furthermore, Ru-L can be excited and emits in the “biological window” in vitro, making it a potential potent new generation photodynamic therapeutic agent capable of singlet oxygen generation and in vitro near-infrared emission.

Graphical abstract: Two-photon induced luminescence, singlet oxygen generation, cellular uptake and photocytotoxic properties of amphiphilic Ru(ii) polypyridyl–porphyrin conjugates as potential bifunctional photodynamic therapeutic agents

Back to tab navigation

Supplementary files

Article information


Submitted
16 Mar 2011
Accepted
17 May 2011
First published
12 Jul 2011

Org. Biomol. Chem., 2011,9, 6004-6010
Article type
Paper

Two-photon induced luminescence, singlet oxygen generation, cellular uptake and photocytotoxic properties of amphiphilic Ru(II) polypyridyl–porphyrin conjugates as potential bifunctional photodynamic therapeutic agents

J. Zhang, K. Wong, W. Wong, N. Mak, D. W. J. Kwong and H. Tam, Org. Biomol. Chem., 2011, 9, 6004
DOI: 10.1039/C1OB05415E

Social activity

Search articles by author

Spotlight

Advertisements