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Synthesis and biological study of a flavone acetic acid analogue containing an azido reporting group designed as a multifunctional binding site probe.

Authors
  • Malolanarasimhan, Krishnan
  • Lai, Christopher C
  • Kelley, James A
  • Iaccarino, Lynn
  • Reynolds, Della
  • Young, Howard A
  • Marquez, Victor E
Type
Published Article
Journal
Bioorganic & Medicinal Chemistry
Publisher
Elsevier
Publication Date
Apr 15, 2005
Volume
13
Issue
8
Pages
2717–2722
Identifiers
PMID: 15781383
Source
Medline
License
Unknown

Abstract

Flavone-8-acetic acid (FAA) is a potent immunomodulatory small molecule that is uniquely characterized as being active on mouse but not human cells. Although FAA is a potent inducer of murine cytokine, chemokine and interferon gene expression, its mode of action remains unknown. In this report, we describe the synthesis of a new flavone acetic acid (FAA) analogue, (2-[2-(4-azidophenyl)-4-oxochromen-8-yl-]acetic acid (compound 2). We demonstrate that compound 2 is equally active as the parent FAA in inducing chemokine gene expression and that the azide functional group is capable of reacting with a reporter molecule, such as the FLAG peptide-phosphine, under mild conditions. This reaction will be useful for detecting the drug-bound protein active complex utilizing an anti-FLAG antibody.

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