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[Sar1,Ile8]-Angiotensin II

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

It is a specific antagonist of angiotensin receptor, and it is also a peptide that has multiple effect on vascular smooth muscle.

Category

Peptide Inhibitors

Catalog number

BAT-010415

CAS number

37827-06-8

Molecular Formula

C46H73N13O10

Molecular Weight

968.15

Specification
Reference Reading

IUPAC Name

(2S,3S)-2-[[(2S)-1-[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-(diaminomethylideneamino)-2-[[2-(methylamino)acetyl]amino]pentanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-methylpentanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]pyrrolidine-2-carbonyl]amino]-3-methylpentanoic acid

Synonyms

Sarilesin; H-Sar-Arg-Val-Tyr-Ile-His-Pro-Ile-OH; sarcosyl-L-arginyl-L-valyl-L-tyrosyl-L-isoleucyl-L-histidyl-L-prolyl-L-isoleucine

Appearance

White or Off-white Lyophilized Powder

Purity

≥95%

Density

1.37±0.1 g/cm3 (Predicted)

Sequence

SAR-RVYIHPI

Storage

Store at -20°C

InChI

InChI=1S/C46H73N13O10/c1-8-26(5)37(43(66)55-33(21-29-22-50-24-52-29)44(67)59-19-11-13-34(59)41(64)58-38(45(68)69)27(6)9-2)57-40(63)32(20-28-14-16-30(60)17-15-28)54-42(65)36(25(3)4)56-39(62)31(53-35(61)23-49-7)12-10-18-51-46(47)48/h14-17,22,24-27,31-34,36-38,49,60H,8-13,18-21,23H2,1-7H3,(H,50,52)(H,53,61)(H,54,65)(H,55,66)(H,56,62)(H,57,63)(H,58,64)(H,68,69)(H4,47,48,51)/t26-,27-,31-,32-,33-,34-,36-,37-,38-/m0/s1

InChI Key

ZVUNAQTWOGAJRE-VRZYMZKVSA-N

Canonical SMILES

CCC(C)C(C(=O)NC(CC1=CN=CN1)C(=O)N2CCCC2C(=O)NC(C(C)CC)C(=O)O)NC(=O)C(CC3=CC=C(C=C3)O)NC(=O)C(C(C)C)NC(=O)C(CCCN=C(N)N)NC(=O)CNC

1. Comparative studies on the central effects of the angiotensin II analogue (Sar1 azaVal3 Ile8) AT II

T S Kambourova, V D Petkov, R K Mutsenietse, D P Getova, V E Klusha, S V Svirskis, J E Ancans, V P Georgiev, M Zh Oppitz Acta Physiol Pharmacol Bulg . 1988;14(1):22-9.

The effects of the newly-synthesized AT II analogue (Sar1 azaVal3 Ile8) AT II were investigated in comparison with the octapeptide AT II and the analogue saralazin (Sar1 Ala8) AT II, using intracerebroventricular administration, with respect to the following parameters: the level of biogenic monoamines (DA, NA and 5-HT) and the metabolites HVA and 5-HIAA in mouse forebrain; the behaviour of the animals--cataleptogenic actions of mice, PTZ convulsive--seizure threshold in mice, apomorphine stereotypy in rats and behaviour of rats in a conflict situation. The analogue (Sar1 azaVal3 Ile8) AT II, unlike saralazin and AT II, was found to induce a rise in the NA and 5-HT levels, causing also catalepsy that is different from the catalepsy induced by saralazine, AT II and haloperidol, because of its rapid onset and decline; it increases the PTZ convulsive--seizure threshold and reduces the number of punished responses to the conflict drinking test (anxiomimetic effect) in a dose 20 times lower than the dose inducing the remaining effects. This effect was antagonized by saralazine. It is concluded that the newly-synthesized analogue (Sar1 azaVal3 Ile8) AT II induces effects similar to those caused by AT II, being at the same time different to a certain extent from the effects (quantitative and qualitative) of octapeptide AT II.

2. Two angiotensin II binding sites in rat brain revealed using [125I]Sar1, Ile8-angiotensin II and selective nonpeptide antagonists

R S Chang, K A Faust, T B Chen, V J Lotti Biochem Biophys Res Commun . 1990 Sep 14;171(2):813-7. doi: 10.1016/0006-291x(90)91218-h.

[125I]Sar1, Ile8 angiotensin II labeled two distinct binding sites in rat brain. The displacement potencies of WL-19, a selective ligand for the angiotensin II subtype 2 receptor, angiotensin II and related peptides indicated that one binding site in the rat brain is the same as the adrenal angiotensin subtype 2 receptor. The second binding site in rat brain was displaced by the selective angiotensin II subtype 1 receptor antagonist DuP-753; however, the displacement potencies of angiotensin II, angiotensin III and Ile7-angiotensin III were significantly less than at the adrenal angiotensin subtype 1 receptor. The data suggests that this binding site in rat brain may represent an angiotensin II receptor subtype which shares some characteristics with the adrenal angiotensin subtype 1 receptor.

3. Effect of three angiotensin II antagonists, [Sar1, Thr8]-, [Sar1, Ile8]- and [Sar1, Ala8]angiotensin II on blood pressure and endocrine factors in normal subjects

T Hata, S Gotoh, K Masuo, S Saeki, M Nakamaru, Y Kumahara, T Ogihara, A Kumagai Eur J Clin Pharmacol . 1982;23(1):7-10. doi: 10.1007/BF01061369.

The biological effects of 1-Sarcosine, 8-Threonine angiotensin II ([Sar1, Thr8]ANG II) on blood pressure, plasma aldosterone concentration (PAC) and plasma renin activity (PRA) were investigated in six normal subjects on an unrestricted diet, and compared with those of 1-Sarcosine, 8-Isoleucine ANG II ([Sar1, Ile8]ANG II) and 1-Sarcosine, 8-Alanine ANG II ([Sar1, Ala8]ANG II). All three ANG II analogues (AIIA) showed agonistic pressor activity, that of [Sar1, Ile8]ANG II being greater than that of [Sar1, Thr8]ANG II or [Sar1, Ala8]ANG II. The antagonistic effect of [Sar1, Thr8]ANG II on blood pressure was less than [Sar1, I1e8]ANG II or [Sar1, Ala8]ANG II. Both [Sar1, Ile8]ANG II and [Sar1, Ala8]ANG II increased PAC and blocked the steroidogenic action of ANG II, while [Sar1, Thr8]ANG II showed little effect on PAC. All three AIIA caused similar suppression of PRA and showed no inhibitory effect on the decrease in PRA produced by ANG II. These results indicate that [Sar1, Thr8]ANG II is an AIIA with weak agonistic pressor action and that it has vascular selective properties. It is also suggested that ANG II receptors in a variety of target organs are heterogeneous.