Issue 10, 2018

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
03 ጃንዩ 2018
Accepted
28 ፌብሩ 2018
First published
01 ማርች 2018

New J. Chem., 2018,42, 8241-8246

Author version available

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

A. L. Nguyen, K. E. Griffin, Z. Zhou, F. R. Fronczek, K. M. Smith and M. G. H. Vicente, New J. Chem., 2018, 42, 8241 DOI: 10.1039/C8NJ00041G

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