Syntheses of fluorescent imidazoquinoline conjugates as probes of Toll-like receptor 7

Nikunj M. Shukla, Cole A. Mutz, Rehman Ukani, Hemamali J. Warshakoon, David S. Moore, Sunil A. David

Research output: Contribution to journalArticlepeer-review

44 Scopus citations


Toll-like receptor (TLR)-7 agonists show prominent immunostimulatory activities. The synthesis of a TLR7-active N1-(4-aminomethyl)benzyl substituted imidazoquinoline 5d served as a convenient precursor for the covalent attachment of fluorophores without significant loss of activity. Fluorescence microscopy experiments show that the fluorescent analogues are internalized and distributed in the endosomal compartment. Flow cytometry experiments using whole human blood show differential partitioning into B, T, and natural killer (NK) lymphocytic subsets, which correlate with the degree of activation in these subsets. These fluorescently-labeled imidazoquinolines will likely be useful in examining the trafficking of TLR7 in immunological synapses.

Original languageEnglish (US)
Pages (from-to)6384-6386
Number of pages3
JournalBioorganic and Medicinal Chemistry Letters
Issue number22
StatePublished - Nov 15 2010
Externally publishedYes

Bibliographical note

Funding Information:
This work was supported by NIH/NIAID contract HHSN272200900033C .


  • Flow cytometry
  • Fluorescent probe
  • Imidazoquinoline
  • TLR7
  • Toll-like receptor


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