Synthesis, antidiuretic and pressor activities of [arginine4]arginine-vasopressin and two related analogues.
Using well-established solid-phase techniques, three new analogues of arginine-vasopressin (AVP) were synthesized. In these the glutamine residue in position 4 was replaced with an additional arginine. The new analogues were: [Arginine4]arginine-vasopressin ([Arg4]AVP), [2-thiopropionic acid1,arginine4]arginine-vasopressin (d[Arg4]AVP) and [1-thiocyclohexaneacetic acid1,arginine4]arginine-vasopressin (d(CH2)5[Arg4]AVP). [Arg4]AVP showed about the same antidiuretic activity as AVP but had only about 40% of its pressor activity. Unexpectedly, deamination caused a drop in the antidiuretic activity to about 50%. d(CH2)5[Arg4]AVP had practically negligible antidiuretic and low pressor effects.
D000595:Amino Acid Sequence; D000818:Animals; D001127:Arginine Vasopressin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D001681:Biological Assay; D004231:Diuresis / Q000187:drug effects; D007202:Indicators and Reagents; D051381:Rats; D013329:Structure-Activity Relationship
D007202:Indicators and Reagents; D001127:Arginine Vasopressin