Synthesis and cellular uptake of carbamoylated mannose derivatives

Hidde Elferink; Kim Geurts; Stijn Jue; Somhairle MacCormick; Gerrit Veeneman; Thomas J Boltje

doi:10.1016/j.carres.2019.06.008

Synthesis and cellular uptake of carbamoylated mannose derivatives

Carbohydr Res. 2019 Jul 15:481:67-71. doi: 10.1016/j.carres.2019.06.008. Epub 2019 Jun 15.

Authors

Hidde Elferink¹, Kim Geurts¹, Stijn Jue¹, Somhairle MacCormick², Gerrit Veeneman², Thomas J Boltje³

Affiliations

¹ Radboud University, Institute for Molecules and Materials, Heyendaalseweg 135, 6525, AJ, Nijmegen, the Netherlands.
² PharmaCytics B.V. Noviotech Campus, Transistorweg 7-N, 6534, AT, Nijmegen, the Netherlands.
³ Radboud University, Institute for Molecules and Materials, Heyendaalseweg 135, 6525, AJ, Nijmegen, the Netherlands. Electronic address: [email protected].

PMID: 31252337
DOI: 10.1016/j.carres.2019.06.008

Abstract

A series of 3-carbamoyl- and 2,3-dicarbamoyl-mannose derivatives were synthesized, conjugated to a fluorescent dye (Cy5^GE, AF 647 or NBD) and their cellular uptake in A549 and THP-1 cell lines was studied by FACS. In contrast to earlier studies on carbamoyl mannosides, the observed uptake was not related to carbamoyl group on the mannose residue but rather to the cyanine dye attached, a trend previously observed for Cy5-fructose conjugates. The NBD-conjugates however, showed a temperature and concentration dependent uptake in case of mannose conjugates. These results suggest a profound impact of the dye which should be taken into consideration when studying the uptake of small molecules by dye conjugation.

Keywords: Bleomycin; Cancer targeting; Fluorescence activated cell sorting; Glycoconjugates.

MeSH terms

A549 Cells
Biological Transport
Chemistry Techniques, Synthetic
Flow Cytometry
Humans
Mannose / chemical synthesis
Mannose / chemistry*
Mannose / metabolism*
Temperature

Substances

Mannose