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Chemical Compound Review:

Sarmesin (2S)-2-[[(2S)-1-[(2S)-2- [[(2S,3S)-2-[[(2S)...

Synonyms: AC1L3TSY, AR-1K7644, 88874-29-7, Smt-angiotensin II, 1-Sar-4-Me-tyr-angiotensin II, ...

Matsoukas, J. et al., Criscione, L. et al., Mavromoustakos, T. et al., Tchekalarova, J. et al., Scanlon, M.N. et al., et al.

Georgiev, Tchekalarova, Mavromoustakos, Kolocouris, Zervou, Roumelioti, Matsoukas, Weisemann,

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Disease relevance of Smt-angiotensin II

An effort to understand the molecular basis of hypertension through the study of conformational analysis of losartan and sarmesin using a combination of nuclear magnetic resonance spectroscopy and theoretical calculations [1].

High impact information on Smt-angiotensin II

In addition, molecular modeling of the peptide Sarmesin [Sar1Tyr(OMe)4AII], a competitive antagonist of AII, was also developed based on NMR and computational analysis data [1].
Analogues of Sarmesin ([Sar1,Tyr-(OMe)4]ANGII) with Aze and Pip at position 7 had pA2 values of 7.4 and 6.5, respectively [2].
Substitution of the Arg2 residue of sarmesin with Nle or Sar abolished antagonist activity [3].
Analogues of the competitive angiotensin antagonist [Sar1,Tyr(ME)4]angiotensin II (sarmesin) with modifications at the N-terminus have been prepared by the solid-phase method and purified by reversed-phase HPLC [3].
Substitution of the Sar1 residue of sarmesin with N,N-dimethyl-Gly, N-ethyl-Gly, aminoisobutyric, (methylamino)isobutyric, aminocaproic, and oxamic acids gave analogues that had the following respective antagonist activities (pA2) in the rat isolated uterus assay: less than 6, 6.9, 5.5, 6.0, less than 6, and 5 [3].

Biological context of Smt-angiotensin II

Sarmesin, [Sar1, Tyr(Me)4]angiotensinII], has been reported to be a competitive angiotensin II (AII) receptor antagonist in rat smooth muscle preparations (Scanlon et al., (1984), Life Science 34, 317-321) [4].
In the present study, sarmesin displaced AII from its binding sites in rat aortic smooth muscle cells and in a rabbit aorta membrane preparation (IC50 5 and 6 nM resp.; Ki 4.1 and 5.3 resp.) In rabbit aortic rings, sarmesin (0.003-3 microM) produced concentration-dependent contractions (ED50 89 nM) and this effect was inhibited by saralasin [4].

Associations of Smt-angiotensin II with other chemical compounds

The relationships of adenosine A1 receptor agonists and antagonists in combination with angiotensin II (AT II) and its analogue sarmesin in PTZ (pentylenetetrazol) kindling in ICR mice were studied [5].
The selective AT1 receptor antagonist losartan blocked the anticonvulsant effect of ANG II, sarmesin and CPA [6].

Gene context of Smt-angiotensin II

The effects of sarmesin, an Angiotensin II analogue on seizure susceptibility, memory retention and nociception [7].

Analytical, diagnostic and therapeutic context of Smt-angiotensin II

Taken together, these results reveal sarmesin as a behaviorally active peptide in the studied experimental animal models [7].
2. Binding constants for angiotensins II and III at uterine smooth muscle receptors have been compared in bioassays and binding assays, using the competitive antagonist Sarmesin to verify the binding assay/bioassay interrelationship [8].

References

An effort to understand the molecular basis of hypertension through the study of conformational analysis of losartan and sarmesin using a combination of nuclear magnetic resonance spectroscopy and theoretical calculations. Mavromoustakos, T., Kolocouris, A., Zervou, M., Roumelioti, P., Matsoukas, J., Weisemann, R. J. Med. Chem. (1999) [Pubmed]
Synthesis and biological activities of angiotensin II, Sarilesin, and Sarmesin analogues containing Aze or Pip at position 7. Matsoukas, J.M., Agelis, G., Hondrelis, J., Yamdagni, R., Wu, Q., Ganter, R., Smith, J.R., Moore, D., Moore, G.J. J. Med. Chem. (1993) [Pubmed]
Importance of the N-terminal domain of the type II angiotensin antagonist sarmesin for receptor blockade. Matsoukas, J., Cordopatis, P., Belte, U., Goghari, M.H., Ganter, R.C., Franklin, K.J., Moore, G.J. J. Med. Chem. (1988) [Pubmed]
Sarmesin is a partial agonist of angiotensin-II receptors in rabbit, but not in rat, aortic rings. Criscione, L., Thomann, H., Whitebread, S., de Gasparo, M., Kamber, B. Biochem. Biophys. Res. Commun. (1990) [Pubmed]
Interaction of angiotensin II and adenosine receptors in pentylenetetrazol-induced kindling in mice. Georgiev, V.P., Tchekalarova, J.D. Brain Res. (1998) [Pubmed]
Adenosine-angiotensin II interactions in pentylenetetrazol seizure threshold in mice. Tchekalarova, J., Georgiev, V. J. Physiol. Paris (1999) [Pubmed]
The effects of sarmesin, an Angiotensin II analogue on seizure susceptibility, memory retention and nociception. Tchekalarova, J., Pechlivanova, D., Kambourova, T., Matsoukas, J., Georgiev, V. Regul. Pept. (2003) [Pubmed]
The relationship between homotropic and heterotropic cooperativity for angiotensin receptors in smooth muscle. Scanlon, M.N., Koziarz, P., Moore, G.J. Gen. Pharmacol. (1990) [Pubmed]

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