Colorimetric/fluorogenic detection of thiols by N-fused porphyrin in water

Yoshiya Ikawa, Satoshi Touden, Sho Katsumata, Hiroyuki Furuta

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

A water-soluble derivative of N-fused porphyrin (NFP) possessing four cationic side-arms (pPyNFP) serves as a unique class of colorimetric/fluorogenic reporters that selectively react with biothiols in aquaous media to afford N-confused porphyrin (NCP) derivatives, while other nucleophilic amino acids were inert under a wide range of pH conditions. Owing to the large difference of the optical properties between NCP and NFP, the transformation enabled selective detection of biothiols in colorimetric/fluorogenic manner, especially in the near-infrared region. To the best our knowledge, this is the first example of porphyrin-based thiol detection systems that use the direct attack of thiol group on the optical reporter.

Original languageEnglish
Pages (from-to)6501-6505
Number of pages5
JournalBioorganic and Medicinal Chemistry
Volume21
Issue number21
DOIs
Publication statusPublished - Nov 1 2013

All Science Journal Classification (ASJC) codes

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

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