Syntheses of 1,2,3-triazole-BODIPYs bearing up to three carbohydrate units

Abstract

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.