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Comparing a thioglycosylated chlorin and phthalocyanine as potential theranostic agents
Affiliation:1. Department of Natural Sciences, LaGuardia Community College of the City University of New York, 31-10 Thompson Avenue, Long Island City, NY 11101, United States;2. Department of Chemistry, Hunter College of the City University of New York, 695 Park Avenue, New York, NY 10065, United States;3. Department of Chemistry, New York City College of Technology, 285 Jay Street, Brooklyn, NY, 11201, United States;4. Department of Chemistry and Physics, SUNY College at Old Westbury, Old Westbury, Long Island, NY 11568, United States;1. Department of Biochemistry and Biotechnology, University of Thessaly, Biopolis, 41500 Larissa, Greece;2. Department of Organic Chemistry, University of Debrecen, H-4002 POB 400 Debrecen, Hungary;3. Institute of Chemical Biology, National Hellenic Research Foundation, 48 Vassileos Constantinou Avenue, 11635 Athens, Greece;1. Karadeniz Technical University, Faculty of Pharmacy, Department of Biochemistry, Trabzon, Turkey;2. Karadeniz Technical University, Faculty of Pharmacy, Department of Pharmaceutical Toxicology, Trabzon, Turkey;3. Karadeniz Technical University, Drug and Pharmaceutical Technology Application and Research Center, Trabzon, Turkey;4. Karadeniz Technical University, Faculty of Science, Department of Chemistry, Trabzon, Turkey;5. Recep Tayyip Erdoğan University, Faculty of Arts and Sciences, Department of Chemistry, Rize, Turkey;1. Marmara University, Faculty of Art and Science, Department of Chemistry, 34722 Kadikoy, Istanbul, Turkey;2. Gebze Technical University, Department of Chemistry, Gebze 41400, Kocaeli, Turkey;1. Karadeniz Technical University, Faculty of Pharmacy, Department of Biochemistry, Trabzon, Turkey;2. Karadeniz Technical University, Drug and Pharmaceutical Technology Application and Research Center, Trabzon, Turkey;3. Karadeniz Technical University, Faculty of Science, Department of Chemistry, Trabzon, Turkey
Abstract:Herein we describe the design, efficient synthesis, and photophysical properties of two macrocycle dyes for cancer theranostics. This study compares a glycosylated chlorin with a glycosylated phthalocyanine designed to specifically target cancer, wherein the photophysical properties enable both fluorescence imaging and the sensitization of the formation of reactive oxygen species (ROS) for photodynamic therapy. Both the compounds show low darktoxicity (IC50 > 100 μM). The glycosylated phthalocyanine showed low phototoxicity (IC50 > 100 μM) while glycosylated chlorin showed high phototoxicity (IC50 = 1–2 μM). ZnPcGlc8 has low solubility and also form aggregates in aqueous media, thus resulting in minimal uptake in two different human breast cancer cell lines: MDA-MB-231 and MCF-7. The glycosylated chlorin however was efficiently taken up by these two cell lines, thus allows fluorescence imaging in cells and in xenograft tumor model in mice. In this study, we find that the chlorin conjugate is the more promising theranostic agent.
Keywords:Chlorins  Phthalocyanines  Theranostics  Photodynamic therapy  Fluorescence imaging  Glycosylation
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