Highly Potent Antidiuretic Antagonists: Conformational Studies of Vasopressin Analogues Modified with 1-Naphthylalanine Enantiomers at Position 2

Synthesis of four vasopressin analogues which do not contain the glycinamine residue in position 9 and have a basic non-coded amino acid in position 8 is described. All the analogues exhibit very low endocrine activities and are effective in the passive avoidance test.

Download Full-text

Polarographic study of hydrolysis of [8-lysine]vasopressin and its derivatives with blood serum of pregnant women

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19801099 ◽

1980 ◽

Vol 45 (4) ◽

pp. 1099-1108 ◽

Cited By ~ 1

Author(s):

Mikuláš Chavko ◽

Michal Bartík ◽

Evžen Kasafírek

Keyword(s):

Blood Serum ◽

Pregnant Women ◽

Degree Of Hydrolysis ◽

Polarographic Study ◽

Ph Optimum ◽

Lysine Vasopressin ◽

Rate Of Hydrolysis ◽

Hydrolysis Of ◽

Vasopressin Analogues

A polarographic study of the hydrolysis of [8-lysine]vasopressin and some hormonogens of the vasopressin series with the blood serum of women in the last week of pregnancy was studied. The dependence of hydrolysis on pH (pH optimum: 7.4-7.50, substrate concentration (Km 1.2 . 10-5M), pH stability and thermal stability were determined. The rate of hydrolysis of individual vasopressin analogues decreases in the order: [8-lysine]vasopressin > Nα-glycyl-prolyl[8-lysine]-vasopressin > Nα-leucyl-[8-lysine]vasopressin > Nα-alanyl-[8-lysine]vasopressin > Nα-phenyl alanyl-[8-lysine]vasopressin > Nα-diglycyl-[8-lysine]vasopressin > Nα-prolyl-[8-lysine]vasopressin > Nα-triglycyl-[8-lysine]vasopressin > Nα-sarcosyl-glycyl-[8-lysine]vasopressin. The degree of hydrolysis gradually increases to a multiple with the length of the pregnancy in consequence of the presence of oxytocine. However, vasopressin is also hydrolysed to a small extent with the enzymes from the blood sera of non-pregnant women. Under similar analytical conditions oxytocin was not hydrolysed with the sera of non-pregnant women and therefore oxytocin is a more suitable substrate than vasopressin for polarographic determination of serum oxytocinase.

Download Full-text

Vasopressin analogues modified in positions 2, 3 and 8. Synthesis and biological effects

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19831341 ◽

1983 ◽

Vol 48 (5) ◽

pp. 1341-1351 ◽

Cited By ~ 2

Author(s):

Ivo Bláha ◽

Danuta Konopinska ◽

Milan Zaoral

Keyword(s):

Amino Acid ◽

Solid Phase ◽

Biological Effects ◽

Solution Synthesis ◽

Antidiuretic Activity ◽

Pressor Activity ◽

Vasopressin Analogues

Four vasopressin analogues, modified in positions 2, 3 and 8 were prepared by solid phase as well as solution synthesis. Analogues, containing a D-amino acid in position 3, exhibit a low but markedly specific antidiuretic activity. Analogues with a D-substituent in position 2 show a more specific pressor activity.

Download Full-text