Probes for vasopressin receptors. Attachment of affinity and fluorescent groups in vasopressin

Fluorescent, photoreactive, and biotinylated analogs of vasopressin have been prepared in which one of these three groups has been attached to a reactive amino group in either position 4 or position 7. Using solid phase methodology, we have synthesized two active parent compounds, [1-desamino,4-lysine,7-hydroxyproline]arginine vasopressin and [1-desamino,7-aminoproline]arginine vasopressin, and acylated them to obtain biotinyl, azidobenzoyl, and fluoresceinyl derivatives. We have also prepared analogs in which a "spacer arm" was inserted between lysine in position 4 and the marker group. Some of these derivatives have good antidiuretic activity and could be valuable probes in studying hormone-receptor interaction and in receptor visualization and purification.