Analogues of cholecystokinin methylated in the side chain of carboxyterminal phenylalanine

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Title:Analogues of cholecystokinin methylated in the side chain of carboxyterminal phenylalanine
Creators:
Hlaváček, Jan
Pírková, Jana
Majer, Pavel
Žertová, Miroslava
Maletínská, Lenka
Slaninová, Jiřina
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 56, 12, pp. 2991-2998

Abstract

In the course of our study on cholecystokinin (CCK) a series of Boc-CCK-7 was synthesized. Their carboxyterminal part was modified by phenylalanine derivatives containing 2 or 4 and 2,6 or 2,4,6 methylated aromatic side-chain. During the synthesis, the racemic phenylalanine derivatives were used and peptides containing either L- or D- methylated phenylalanine were separated using a preparative HPLC. Gall bladder contraction, anorectic, sedative and analgetic bioassays of these analogues revealed that all of them behaved as CCK-8 agonists. While the analogues containing L-form of the methylated phenylalanines had almost the same potency (80% - 130%) in comparison to CCK-8, the presence of the D-form decreased the biological activity of corresponding analogues to 8 – 62% of the CCK-8 potency. These results are in agreement with the suggestion that phenylalanine residue in C-terminus takes part in biological activity transduction only.

Title:Analogues of cholecystokinin methylated in the side chain of carboxyterminal phenylalanine
Creators:
Hlaváček, Jan
Pírková, Jana
Majer, Pavel
Žertová, Miroslava
Maletínská, Lenka
Slaninová, Jiřina
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:56
Number:12
Page Range:pp. 2991-2998
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19912991UNSPECIFIED
ID Code:5205
Item Type:Article
Deposited On:22 Feb 2010 11:32
Last Modified:22 Feb 2010 10:33

Citation

Hlaváček, Jan; Pírková, Jana; Majer, Pavel; Žertová, Miroslava; Maletínská, Lenka; Slaninová, Jiřina (1991) Analogues of cholecystokinin methylated in the side chain of carboxyterminal phenylalanine. Collection of Czechoslovak Chemical Communications, 56 (12). pp. 2991-2998. ISSN 0010-0765

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