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

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 H-1, C-13 and B-11 NMR, HRMS, and in...

Full description

Saved in:
Bibliographic Details
Published inNew journal of chemistry Vol. 42; no. 10; pp. 8241 - 8246
Main Authors Nguyen, Alex L., Griffin, Kaitlin E., Zhou, Zehua, Fronczek, Frank R., Smith, Kevin M., Vicente, M. Graca H.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 2018
Royal Society of Chemistry
Subjects
Boron
Carbohydrates
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Crystallography
Cycloaddition
Glucose
Light irradiation
NMR
Nuclear magnetic resonance
Physical Sciences
Science & Technology
BODIPY DYES
CELLS
FLUORESCENT
PHOTODYNAMIC THERAPY
Online AccessGet full text

Cover

More Information
Summary: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 H-1, C-13 and B-11 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 mu M). The time-dependent cellular uptake increased with the increase number of glucose units.
ISSN:1144-0546
1369-9261
DOI:10.1039/c8nj00041g