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Issue 10, 2018
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Syntheses of 1,2,3-triazole-BODIPYs bearing up to three carbohydrate units

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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

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Publication details

The article was received on 03 Jan 2018, accepted on 28 Feb 2018 and first published on 01 Mar 2018


Article type: Paper
DOI: 10.1039/C8NJ00041G
Citation: New J. Chem., 2018,42, 8241-8246
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    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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