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

• Published in: Molecules (Basel, Switzerland) Vol. 22; no. 5; p. 845
• Main Authors: Liu, Jian-Yong, Wang, Chen, Zhu, Chun-Hui, Zhang, Zhi-Hong, Xue, Jin-Ping
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 19.05.2017; MDPI
• Subjects: Acetylation; Acids; Affinity; Biological properties; Breast cancer; Carbohydrates; Cations, Divalent; Cell Line; click chemistry; Cycloaddition; Cycloaddition Reaction; Cytotoxicity; Embryo fibroblasts; Fibroblasts - cytology; Fibroblasts - drug effects; Fluorescence; Glucose; Glucose - chemistry; glucosylated phthalocyanine; Glycosylation; Humans; Illumination; In vitro methods and tests; Indoles - chemical synthesis; Indoles - pharmacology; Inhibitory Concentration 50; Lasers; Light; Lungs; Lysosomes; Lysosomes - drug effects; Lysosomes - metabolism; MCF-7 Cells; Mitochondria; Organ Specificity; Organometallic Compounds - chemical synthesis; Organometallic Compounds - pharmacology; Peptides; Photodynamic therapy; Photosensitizing Agents - chemical synthesis; Photosensitizing Agents - pharmacology; Reactive Oxygen Species - agonists; Reactive Oxygen Species - metabolism; Sodium; Spectroscopic analysis; targeting photosensitizer; Zinc; Zinc - chemistry; click chemistry; glucosylated phthalocyanine; targeting photosensitizer; photodynamic therapy
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules22050845

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 IC 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.