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Identification of the principal circulating metabolite of a synthetic 5,4 '-diaminoflavone (NSC 686288), an antitumor agent, in the rat

  1. Author:
    Phillips, L. R.
    Bramhall, C.
    Buckley, J.
    Wolfe, T.
    House, T. L.
    Stinson, S. F.

  2. Author Address

    Phillips LR NCI, Lab Drug Discovery Res & Dev, Dev Therapeut Program, Div Canc Treatment Diag & Ctr Frederick, MD 21701 USA NCI, Lab Drug Discovery Res & Dev, Dev Therapeut Program, Div Canc Treatment Diag & Ctr Frederick, MD 21701 USA SAIC Frederick, Frederick Canc Res & Dev Ctr Frederick, MD 21701 USA
    1. Year: 2000
  2. Journal: Journal of Chromatography B
    1. 741
    2. 2
    3. Pages: 205-211
  4. Type of Article: Article
  1. Abstract:

    During the course of our study to develop analytical methodology for quantitating the investigative antitumor agent 5-amino-2-(4-amino-3-fluorophenyl)-6,8-difluoro-7-methyl-4H-1-benzop yran-4-one (DAF; NSC 686288) in plasma, a significant concentration of a metabolite was observed in a post-dosed rat. The results of electron-ionization (EI) mass spectrometric analysis of the metabolite suggested that N-acetylation had occurred, brit, interestingly, that only one of the compound's two primary amino groups had been transformed. Comparing the mass spectra and gas chromatographic retention times of a mono-acetylated sample of DAF and that of the metabolite showed both to be the same. A retro-Diels-Alder (RDA) fragmentation of the B ring of DAF results in formation of two abundant product ions, each retaining one of the amino groups. The EI mass spectrum of mono-N-acetamido-d(3) DAF shows loss of ketene-d(2), leading to formation of an -NHD group. The ensuing RDA fragmentation easily identifies which of the two product ions contains the deuterium, thereby allowing us to assign the site of N-acetylation as the amino group on ring C (the 4' position) of DAF. (C) 2000 Elsevier Science B.V. All rights reserved. [References: 10]

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