Red fluorescent scaffold for highly sensitive protease activity probes

Yu Kushida, Kenjiro Hanaoka, Toru Komatsu, Takuya Terai, Tasuku Ueno, Kengo Yoshida, Masanobu Uchiyama, Tetsuo Nagano

Research output: Contribution to journalArticlepeer-review

33 Citations (Scopus)

Abstract

We have developed a novel red fluorescent dye, 2Me SiR600 (λem = 613 nm), in which the O atom of Rhodamine Green at the 10 position of the xanthene moiety is replaced with a Si atom, as a scaffold for probes to detect protease activity with extremely high S/N ratio. As proof of concept, we designed and synthesized probes for caspase-3 activity (Z-DEVD-SiR600) and leucine aminopeptidase activity (Leu-SiR600). Caspase-3-mediated cleavage of Z-DEVD-SiR600 resulted in a large bathochromic shift (93 nm) of the absorption maximum and a 432-fold fluorescence enhancement.

Original languageEnglish
Pages (from-to)3908-3911
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume22
Issue number12
DOIs
Publication statusPublished - 2012 Jun 15
Externally publishedYes

Keywords

  • Enzymes
  • Fluorescent probes
  • Proteases

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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