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

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Porphyrins
Sulfhydryl Compounds
Water
Derivatives
Optical properties
Infrared radiation
Amino Acids

All Science Journal Classification (ASJC) codes

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

Cite this

Colorimetric/fluorogenic detection of thiols by N-fused porphyrin in water. / Ikawa, Yoshiya; Touden, Satoshi; Katsumata, Sho; Furuta, Hiroyuki.

In: Bioorganic and Medicinal Chemistry, Vol. 21, No. 21, 01.11.2013, p. 6501-6505.

Research output: Contribution to journalArticle

Ikawa, Yoshiya ; Touden, Satoshi ; Katsumata, Sho ; Furuta, Hiroyuki. / Colorimetric/fluorogenic detection of thiols by N-fused porphyrin in water. In: Bioorganic and Medicinal Chemistry. 2013 ; Vol. 21, No. 21. pp. 6501-6505.
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