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

Jingxiang Zhang, Ka-Leung WONG, Rick W K WONG*, Nai Ki MAK, Daniel W J KWONG, Hoi Lam TAM

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

43 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)6004-6010
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume9
Issue number17
DOIs
Publication statusPublished - 7 Sep 2011

Scopus Subject Areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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