Syntheses of 1,2,3-triazole-BODIPYs bearing up to three carbohydrate units
© 2018 The Royal Society of Chemistry and the Centre National de la Recherche Scientifique. A series of BODIPYs bearing one (4b,c), two (6a) or three (3b) glucose units attached to the meso(8) and the boron atom positions were synthesized using a Cu(i)-catalyzed Huisgen cycloaddition reaction. The resulting 1,2,3-triazole-BODIPYs were characterized by 1H, 13C and 11B NMR, HRMS, and in the case of 4a and 4b by X-ray crystallography. Triazole-BODIPYs 3b, 4b and 6a were highly permeable in cells and non-toxic to human HEp2 cells, both in the dark and upon light irradiation (IC50 > 100 μM). The time-dependent cellular uptake increased with the increase number of glucose units.
Publication Source (Journal or Book title)
New Journal of Chemistry
Nguyen, A., Griffin, K., Zhou, Z., Fronczek, F., Smith, K., & Vicente, M. (2018). Syntheses of 1,2,3-triazole-BODIPYs bearing up to three carbohydrate units. New Journal of Chemistry, 42 (10), 8241-8246. https://doi.org/10.1039/c8nj00041g