Design, synthesis and photochemical properties of the first examples of iminosugar clusters based on fluorescent cores

Beilstein J Org Chem. 2015 May 6:11:659-67. doi: 10.3762/bjoc.11.74. eCollection 2015.

Abstract

The synthesis and photophysical properties of the first examples of iminosugar clusters based on a BODIPY or a pyrene core are reported. The tri- and tetravalent systems designed as molecular probes and synthesized by way of Cu(I)-catalysed azide-alkyne cycloadditions are fluorescent analogues of potent pharmacological chaperones/correctors recently reported in the field of Gaucher disease and cystic fibrosis, two rare genetic diseases caused by protein misfolding.

Keywords: 4-methylumbelliferone; BODIPY; fluorescent probes; iminosugars; multivalency; pyrene.