Design, synthesis and evaluation of novel P450 fluorescent probes bearing α-cyanoether

Rong Zhang, Kyung Don Kang, Guomin Shan, Bruce D. Hammock

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Four α-cyano-containing ethers based on 2-alkoxy-2-naphthylacetonitriles have been designed as a novel structural class of cytochrome P450 fluorescent probes. Their syntheses, fluorescence properties and evaluation in the fluorogenic assay of cytochrome P450 monooxygenase are reported. After P450 enzymatic O-dealkylation, the cyanohydrin metabolite of the four new substrates rearranges to a fluorescent aromatic aldehyde with a larger Stokes shift, and the new substrates exhibit higher specific activities than that of the commercial substrate 7-ethoxyresorufin (ER).

Original languageEnglish (US)
Pages (from-to)4331-4334
Number of pages4
JournalTetrahedron Letters
Volume44
Issue number23
DOIs
StatePublished - Jun 2 2003

Fingerprint

Bearings (structural)
Fluorescent Dyes
Cytochrome P-450 Enzyme System
Dealkylation
Ethers
Substrates
Mixed Function Oxygenases
Aldehydes
Fluorescence
Metabolites
Assays

Keywords

  • α-cyanoether
  • 2-alkoxy-2-naphthylacetonitriles
  • Cytochrome P450
  • Fluorescent probes

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Design, synthesis and evaluation of novel P450 fluorescent probes bearing α-cyanoether. / Zhang, Rong; Kang, Kyung Don; Shan, Guomin; Hammock, Bruce D.

In: Tetrahedron Letters, Vol. 44, No. 23, 02.06.2003, p. 4331-4334.

Research output: Contribution to journalArticle

Zhang, Rong ; Kang, Kyung Don ; Shan, Guomin ; Hammock, Bruce D. / Design, synthesis and evaluation of novel P450 fluorescent probes bearing α-cyanoether. In: Tetrahedron Letters. 2003 ; Vol. 44, No. 23. pp. 4331-4334.
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