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Molecules 2017, 22(5), 845; doi:10.3390/molecules22050845

Preparation and In Vitro Photodynamic Activity of Glucosylated Zinc(II) Phthalocyanines as Underlying Targeting Photosensitizers

1
State Key Laboratory of Photocatalysis on Energy and Environment & National & Local Joint Biomedical Engineering Research Center on Photodynamic Technologies, College of Chemistry, Fuzhou University, Fuzhou 350108, China
2
Fuzhou General Hospital of Nanjing Military Command, Fuzhou 350005, China
*
Authors to whom correspondence should be addressed.
Academic Editors: Michel Hanack, João Paulo C. Tomé and Augusto C. Tomé
Received: 17 April 2017 / Revised: 9 May 2017 / Accepted: 15 May 2017 / Published: 19 May 2017
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Abstract

Two novel glucosylated zinc(ІІ) phthalocyanines 7a–7b, as well as the acetyl-protected counterparts 6a–6b, have been synthesized by the Cu(I)-catalyzed 1,3-dipolar cycloaddition between the propargylated phthalocyanine and azide-substituted glucoses. All of these phthalocyanines were characterized with various spectroscopic methods and studied for their photo-physical, photo-chemical, and photo-biological properties. With glucose as the targeting unit, phthalocyanines 7a–7b exhibit a specific affinity to MCF-7 breast cancer cells over human embryonic lung fibroblast (HELF) cells, showing higher cellular uptake. Upon illumination, both photosensitizers show high cytotoxicity with IC50 as low as 0.032 µM toward MCF-7 cells, which are attributed to their high cellular uptake and low aggregation tendency in the biological media, promoting the generation of intracellular reactive oxygen species (ROS). Confocal laser fluorescence microscopic studies have also revealed that they have high and selective affinities to the lysosomes, but not the mitochondria, of MCF-7 cells. The results show that these two glucosylated zinc(II) phthalocyanines are potential anticancer agents for targeting photodynamic therapy. View Full-Text
Keywords: glucosylated phthalocyanine; photodynamic therapy; targeting photosensitizer; click chemistry glucosylated phthalocyanine; photodynamic therapy; targeting photosensitizer; click chemistry
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Liu, J.-Y.; Wang, C.; Zhu, C.-H.; Zhang, Z.-H.; Xue, J.-P. Preparation and In Vitro Photodynamic Activity of Glucosylated Zinc(II) Phthalocyanines as Underlying Targeting Photosensitizers. Molecules 2017, 22, 845.

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