Syntheses of 1,2,3-triazole-BODIPYs bearing up to three carbohydrate unitsElectronic supplementary information (ESI) available: It contains 1H, 11B and 13C NMR spectra for all BODIPYs. CCDC 1580552 and 1580553. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8nj00041g

• Main Authors: Nguyen, Alex L, Griffin, Kaitlin E, Zhou, Zehua, Fronczek, Frank R, Smith, Kevin M, Vicente, M. Graça H
• Format: Journal Article
• Language: English
• Published: 14.05.2018
• ISSN: 1144-0546; 1369-9261
• DOI: 10.1039/c8nj00041g

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 1 H, 13 C and 11 B 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 (IC 50 > 100 μM). The time-dependent cellular uptake increased with the increase number of glucose units. BODIPYs bearing up to three glucose units were synthesized and their cytotoxicity and uptake investigated in human HEp2 cells.