An irreversible blocker for the β-adrenergic receptor

New reversible blockers for the β-adrenergic receptor have been synthesized. All the compunds possess free amine(s) residues which have been bromoacetylated. The N-bromoacetyl derivatives were also found to be potent β-blockers. One of these bromoacetyl derivatives: N-(2-hydroxy-3-naphthoxypropyl)-N′-bromoacetyl-ethylenediamine is shown to inhibit irreversibly 1-epinephrine-dependent adenylate cyclase from turkey erythrocytes, whereas it has no effect on the fluoride-dependent activity of the enzyme. This compound also eliminates the specific [³H]-propranolol binding to the β-receptors. These findings suggest that the compound N-(2-hydroxy-3-naphthoxypropyl)-N′-bromoacetyl-ethylenediamine is a potent β-receptor-directed affinity label.