PMID: 3761315Oct 1, 1986Paper

Role of the C-terminal carboxylate in angiotensin II activity: alcohol, ketone, and ester analogues of angiotensin II

Journal of Medicinal Chemistry
K H Hsieh, G R Marshall

Abstract

[Ac-Asn1, Val5]angiotensin II analogues containing a C-terminal alcohol (Phe-ol), methyl ketone (Pmk), methyl ester (Phe-OMe), or alpha-methyl methyl ester (Phe(alpha Me)-OMe) were prepared in order to examine the relative importance of COOH-mediated ionic vs. hydrogen bonding interactions in angiotensin activities. Based on the observation that only [Ac-Asn1,Phe-OMe8]AII (AII, angiotensin II) had significant activities (20% oxytocic and 13% pressor) in the rat, with all other analogues having negligible agonistic and antagonistic effects, it is concluded that ionic interaction of the C-terminal carboxylate with the receptor is necessary for angiotensin binding and that hydrogen bonding has little effect. Thus, the different potencies observed for the AII methyl ester and for various C-terminal analogues previously reported may simply reflect their relative abilities to generate the active carboxylate species in situ.

Citations

Mar 1, 1992·Medicinal Research Reviews·J V DunciaP B Timmermans
Nov 10, 1995·Regulatory Peptides·J W Wright, J W Harding
May 7, 1998·European Journal of Pharmacology·R BouleyE Escher
Nov 25, 1997·Brain Research. Brain Research Reviews·J W Wright, J W Harding
Apr 1, 1993·Journal of Biomolecular Structure & Dynamics·F FormaggioJ Kamphuis
Sep 1, 1996·Clinical and Experimental Pharmacology & Physiology·S S KarnikR M Graham
Jan 26, 2007·Organic & Biomolecular Chemistry·Henning Vogt, Stefan Bräse
Apr 13, 2007·Physiological Reviews·Laerte OliveiraAntonio C M Paiva
Dec 1, 1995·International Journal of Peptide and Protein Research·M P JosephH A Scheraga
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Oct 2, 2003·Journal of the American Chemical Society·Claude SpinoCédrickx Gobdout

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