Synthesis and in vitro photodynamic activities of an integrin-targeting cRGD-conjugated zinc(II) phthalocyanine

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journalpeer-review

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Original languageEnglish
Pages (from-to)554-561
Journal / PublicationChemistry - An Asian Journal
Issue number2
Publication statusPublished - Feb 2014
Externally publishedYes


A 1,4-disubstituted zinc(II) phthalocyanine conjugated with a cyclic Arg-Gly-Asp-D-Phe-Lys (cRGDfK) moiety through a triazole linker was prepared and characterized by UV/Vis spectroscopy and high-resolution ESI-MS. The conjugate showed a relatively weak fluorescence emission in N,N-dimethylformamide (ΦF=0.08), but it was a very efficient singlet oxygen generator (ΦΔ=0.80) as a result of the di-α-substituted structure. Owing to the presence of the cyclic peptide sequence cRGDfK, which is a well-known αvβ3-integrin antagonist, this conjugate exhibited significantly higher cellular uptake toward the αvβ3 + U87-MG cells compared with the αvβ3 - MCF-7 cells, as determined by flow cytometry and fluorescence microscopy. The photocytotoxicity of this compound against these two cell lines, however, was comparable owing to the similar efficiency of intracellular reactive oxygen species generation. Confocal microscopic studies also revealed that this conjugate localized preferentially in the lysosomes, but not in the nucleus, endoplasmic reticulum, and mitochondria of the U87-MG cells. Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Research Area(s)

  • imaging agents, peptides, photochemistry, phthalocyanines, sensitizers