Solid phase synthesis and some pharmacological properties of 8-D-homoarginine-vasopressin and 1-deamino-8-D-homoarginine-vasopressin.
Fully protected 8-D-lysine-vasopresin and 1-deamino-8-D-lysine-vasopressin were synthesized by the solid phase method. Selective removal of the lysine protection and reaction with 1-guanyl-3,5-dimethylpyrazole converted D-lysine into D-homoarginine. The title compounds were then obtained by treatment with sodium in liquid ammonia and oxidation in dilute aqueous solution. Although the antidiuretic activities are lower than for the corresponding D-argining derivatives, the even lower pressor effects make the new analogues highly specific antidiuretic agents. The A/P ratios for 8-D-homoarginine-vasopressin and its 1-deamino derivative are 100 and 3,300, respectively.
D000818:Animals; D001120:Arginine / Q000031:analogs & derivatives*; D001127:Arginine Vasopressin / Q000138:chemical synthesis* / Q000494:pharmacology; D001794:Blood Pressure / Q000187:drug effects*; D003894:Deamino Arginine Vasopressin / Q000138:chemical synthesis* / Q000494:pharmacology; D004231:Diuresis / Q000187:drug effects*; D006709:Homoarginine / Q000138:chemical synthesis* / Q000494:pharmacology; D008297:Male; D051381:Rats; D014667:Vasopressins / Q000031:analogs & derivatives*
D014667:Vasopressins; D001127:Arginine Vasopressin; D006709:Homoarginine; D001120:Arginine; D003894:Deamino Arginine Vasopressin