Synthesis of 5-nitro-2-(N-3-(4-azidophenyl)-propylamino)-benzoic acid: Photoaffinity labeling of human red blood cell ghosts with a 5-nitro-2-(3-phenylpropylamino)-benzoic acid analog

Journal Article · Mon Apr 15 00:00:00 EDT 1991 · Biochemical and Biophysical Research Communications; (USA)

DOI:https://doi.org/10.1016/0006-291X(91)90946-5· OSTI ID:5574307

Branchini, B R; Murtiashaw, M H; Egan, L A ^[1]

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1. Connecticut Coll., New London (USA)

A photoaffinity analog of the potent epithelial chloride channel blocker 5-nitro-2-(3-phenylpropylamino)-benzoic acid has been synthesized and characterized. In the dark, this reagent, 5-nitro-2-(N-3-(4-azidophenyl)-propylamino)-benzoic acid, and the parent compound reversibly inhibited chloride efflux in human red blood cell ghosts. Irradiation of ghost membranes with 350 microM arylazide analog reduced the rate of chloride efflux to 33% of the control value. The photoinactivation process was not reversed by exhaustive washing of ghost membranes. Covalent incorporation of the photoaffinity reagent was supported by difference ultraviolet spectroscopy, which indicated the attachment of the substituted 2-amino-5-nitrobenzoic acid chromophore to ghost membranes. The novel photolabeling agent described here should be a useful structural probe for chloride channels in erythrocyte membranes and epithelial cells.

• OSTI ID: 5574307
• Journal Information: Biochemical and Biophysical Research Communications; (USA), Vol. 176:1; ISSN 0006-291X
• Country of Publication: United States
• Language: English

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