For research use only. Not for therapeutic Use.
Alamandine, a member of the renin-angiotensin system (RAS), a vasoactive peptide, is an endogenous ligand of the G protein-coupled receptor MrgD. Alamandine targets to protect the kidney and heart through anti-hypertensive actions[1][2].
Alamandine is generated by catalysis of Ang A via ACE2 or directly from Angiotensin 1-7 (Ang-(1-7)). Derived from angiotensin II (Ang II) by Ang II-converting enzyme 2 (ACE2), it shows vasodilating (thus protective) properties. Ang (1-7) can be decarboxylated to a peptide called Alamandine. Alamandine is also an endogenous peptide identified in human blood[1].
Alamandine elevates cAMP concentration in primary endothelial and mesangial cells, also suggesting Gs coupling[2].
Alamandine decreases secretion, expression, and blood levels of leptin. Alamandine induced expression of iNOS and plasminogen activator inhibitor-1 (PAI-1) in adipose tissue and isolated adipocytes[2].
Alamandine (0.15 μL/h; administered by mini-osmotic pumps; for 6 weeks) treatment ameliorates hypertension and impaires left ventricle (LV) function in SHRs. Also decreases the mass gains of heart and lung in SHRs, suppresses cardiomyocyte cross-sectional area expansion, and inhibits the mRNA levels of atrial natriuretic peptide and brain natriuretic peptide[3].
| Catalog Number | I044238 |
| CAS Number | 1176306-10-7 |
| Synonyms | (2S)-1-[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-aminopropanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-methylpentanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]pyrrolidine-2-carboxylic acid |
| Molecular Formula | C40H62N12O9 |
| Purity | ≥95% |
| InChI | InChI=1S/C40H62N12O9/c1-6-22(4)32(37(58)49-29(18-25-19-44-20-46-25)38(59)52-16-8-10-30(52)39(60)61)51-35(56)28(17-24-11-13-26(53)14-12-24)48-36(57)31(21(2)3)50-34(55)27(47-33(54)23(5)41)9-7-15-45-40(42)43/h11-14,19-23,27-32,53H,6-10,15-18,41H2,1-5H3,(H,44,46)(H,47,54)(H,48,57)(H,49,58)(H,50,55)(H,51,56)(H,60,61)(H4,42,43,45)/t22-,23-,27-,28-,29-,30-,31-,32-/m0/s1 |
| InChIKey | QVMYBFKDLPBYSO-GIGALADGSA-N |
| SMILES | CCC(C)C(C(=O)NC(CC1=CN=CN1)C(=O)N2CCCC2C(=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)C(C)N |
| Reference | [1]. Daniel C Villela, et al. Alamandine: a new member of the angiotensin family. Curr Opin Nephrol Hypertens. 2014 Mar;23(2):130-4. [2]. Johanna Schleifenbaum. Alamandine and Its Receptor MrgD Pair Up to Join the Protective Arm of the Renin-Angiotensin System. Front Med (Lausanne). 2019 Jun 11;6:107. [3]. Chi Liu, et al. Alamandine attenuates hypertension and cardiac hypertrophy in hypertensive rats. Amino Acids. 2018 Aug;50(8):1071-1081. |
