Acetylene functionalized BODIPY dyes and their application in the synthesis of activity based proteasome probes

Martijn Verdoes; Ulrik Hillaert; Bogdan I Florea; Myra Sae-Heng; Martijn D P Risseeuw; Dmitri V Filippov; Gijsbert A van der Marel; Herman S Overkleeft

doi:10.1016/j.bmcl.2007.09.025

Acetylene functionalized BODIPY dyes and their application in the synthesis of activity based proteasome probes

Bioorg Med Chem Lett. 2007 Nov 15;17(22):6169-71. doi: 10.1016/j.bmcl.2007.09.025. Epub 2007 Sep 8.

Authors

Martijn Verdoes¹, Ulrik Hillaert, Bogdan I Florea, Myra Sae-Heng, Martijn D P Risseeuw, Dmitri V Filippov, Gijsbert A van der Marel, Herman S Overkleeft

Affiliation

¹ Leiden Institute of Chemistry, Leiden University, Leiden, The Netherlands.

PMID: 17888658
DOI: 10.1016/j.bmcl.2007.09.025

Abstract

The synthesis of three acetylene functionalized BODIPY dyes is described. These dyes are used to fluorescently modify an azido functionalized epoxomicin analogue employing the Huisgen 1,3-dipolar cycloaddition, resulting in a panel of fluorescent epoxomicin derived proteasome probes.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkynes / chemistry*
Boron Compounds / chemical synthesis*
Boron Compounds / chemistry
Cell Line
Fluorescent Dyes / chemical synthesis*
Fluorescent Dyes / chemistry
Fluorescent Dyes / pharmacokinetics
Molecular Structure
Oligopeptides / chemistry
Proteasome Endopeptidase Complex / analysis*
Proteasome Endopeptidase Complex / chemistry

Substances

4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
Alkynes
Boron Compounds
Fluorescent Dyes
Oligopeptides
Proteasome Endopeptidase Complex
epoxomicin