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 Janv. 2018
Accepted
28 Febr. 2018
First published
01 Marts 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements