Design and synthesis of dye-conjugated hepsin inhibitors

Kyul Kim, Hongmok Kwon, Doyoung Choi, Taehyeong Lim, Il Minn, Sang Hyun Son, Youngjoo Byun

Research output: Contribution to journalArticlepeer-review

3 Scopus citations


Hepsin is a type II serine protease that is highly expressed in neoplastic prostate. It is an attractive biomarker for imaging metastatic prostate cancer because of its overexpression in advanced prostate cancer and the location of its active site on the cell surface. We designed and synthesized novel hepsin-targeted imaging probes by conjugating the hepsin-binding ligand with near-infrared (NIR) optical dyes. The Leu-Arg dipeptides, attached to BODIPY or SulfoCy7, exhibited strong hepsin-inhibitory activities with Ki values of 21 and 22 nM, respectively. Compound 2 showed selective uptake and retention in hepsin-overexpressing cells. This is the first report of hepsin-targeted optical probes with strong binding affinities and high selectivity over matriptase. Compound 2 has the potential to be used for developing hepsin-based imaging probes and be as a prototype molecule in the design of new hepsin inhibitors.

Original languageEnglish (US)
Article number102990
JournalBioorganic Chemistry
StatePublished - Aug 2019


  • Hepsin
  • Optical dye
  • SulfoCy7

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Drug Discovery
  • Organic Chemistry


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