Propargylated Purine Deoxynucleosides: New Tools for Fluorescence Imaging Strategies

Molecules. 2019 Jan 28;24(3):468. doi: 10.3390/molecules24030468.

Abstract

In vivo imaging of biological processes is an important asset of modern cell biology. Selectively reacting fluorophores herein are an important tool and click chemistry reactions take a large share in these events. 5-Ethynyl-2'-deoxyuridine (EdU) is well known for visualizing DNA replication, but does not show any selectivity for incorporation into DNA. Striving for specific visualization of virus replication, in particular HIV replication, a series of propargylated purine deoxynucleosides were prepared aiming for selective incorporation by HIV reverse transcriptase (RT). We here report on the synthesis and preliminary biological effects (cellular toxicity, HIV inhibitory effects, and feasibility of the click reaction) of these nucleoside analogues.

Keywords: DNA visualization; HIV toxicity; Mitsunobu reaction; click reaction; ethynyl-2′-deoxyuridine (EdU); fluorophores; imaging; propargylated nucleosides.

MeSH terms

  • Cell Line
  • Cell Survival
  • Click Chemistry
  • Fluorescent Dyes* / chemistry
  • Gene Expression
  • Genes, Reporter
  • HIV-1 / drug effects
  • HIV-1 / physiology
  • Humans
  • Molecular Structure
  • Optical Imaging* / methods
  • Purine Nucleosides* / chemistry
  • Virus Replication / drug effects

Substances

  • Fluorescent Dyes
  • Purine Nucleosides