Polyethylene glycol-functionalized benzylidene cyclopentanone dyes for two-photon excited photodynamic therapy

Yuxia Zhao; Weijia Wang; Feipeng Wu; Yang Zhou; Naiyan Huang; Ying Gu; Qianli Zou; Wei Yang

doi:10.1039/C0OB01278E

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Organic & Biomolecular Chemistry

Issue 11, 2011

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Polyethylene glycol-functionalized benzylidene cyclopentanone dyes for two-photon excited photodynamic therapy

Yuxia Zhao , Weijia Wang , Feipeng Wu , Yang Zhou , Naiyan Huang , Ying Gu , Qianli Zou and Wei Yang

Org. Biomol. Chem., 2011,9, 4168-4175

DOI: 10.1039/C0OB01278E
Received 31 Dec 2010, Accepted 10 Mar 2011
First published on the web 11 Mar 2011

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A series of polyethylene glycol-functionalized benzylidene cyclopentanone dyes with varying lipid/water partition coefficients were synthesized in high yields by a simple process. Detailed characterization and systematic studies of these molecules, including linear and nonlinear photophysical properties, reactive oxygen yields, and in vitro photodynamic therapy (PDT) activities, were conducted. Four of these dyes exhibited good solubility in PBS (>2 mg ml⁻¹, which is sufficient for clinical venous injection), high reactive oxygen yields, large two-photon absorption and low dark toxicity, under the therapy dosage. Among them, two dyes could be absorbed efficiently by human rectal cancer 1116 cells, and presented strong two-photon excited PDT activity in in vitro cell experiments.