PeptideDB

Alamandine 1176306-10-7

Alamandine 1176306-10-7

CAS No.: 1176306-10-7

Alamandine is a vasoactive peptide, a member of the renin-angiotensin system (RAS), and an endogenous ligand of the G pr
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Alamandine is a vasoactive peptide, a member of the renin-angiotensin system (RAS), and an endogenous ligand of the G protein-coupled receptor MrgD. Alamandine protects the kidneys and heart through antihypertensive effects.

Physicochemical Properties


Molecular Formula C40H62N12O9
Molecular Weight 855.00
Exact Mass 854.476
CAS # 1176306-10-7
PubChem CID 44192273
Appearance White to off-white solid powder
Density 1.4±0.1 g/cm3
Index of Refraction 1.657
LogP 0.12
Hydrogen Bond Donor Count 11
Hydrogen Bond Acceptor Count 12
Rotatable Bond Count 23
Heavy Atom Count 61
Complexity 1540
Defined Atom Stereocenter Count 8
SMILES

CC[C@H](C)[C@@H](C(=O)N[C@@H](CC1=CN=CN1)C(=O)N2CCC[C@H]2C(=O)O)NC(=O)[C@H](CC3=CC=C(C=C3)O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](C)N

InChi Key QVMYBFKDLPBYSO-GIGALADGSA-N
InChi Code

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
Chemical Name

(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
HS Tariff Code 2934.99.9001
Storage

Powder-20°C 3 years

4°C 2 years

In solvent -80°C 6 months

-20°C 1 month

Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.
Shipping Condition Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity


ln Vitro Alamandine is made either directly from angiotensin 1-7 (Ang-(1-7)) or via ACE2 catalyzing Ang A. It is produced from angiotensin II (Ang II) by the Ang II converting enzyme 2 (ACE2), and because of this, it has protective (vasodilatory) qualities. It is possible to decarboxylate Ang (1–7) to produce the peptide alamandine. Another endogenous peptide that can be found in human blood is alamandine [1]. In primary endothelial and mesangial cells, alamandine raises the concentration of cAMP, which also suggests Gs coupling [2]. Leptin secretion, expression, and blood levels are all reduced by amandine. In both isolated adipocytes and adipose tissue, alamandine stimulates the expression of plasminogen activator inhibitor-1 (PAI-1) and iNOS [2].
ln Vivo After six weeks of treatment with alamandine (0.15 μL/h; given by mini-osmotic pump), hypertension was improved and left ventricular (LV) function was compromised in patients with SHR. Additionally, it slowed the growth of the cross-sectional area of myocardial cells, decreased the mass increase of the heart and lungs in SHR, and decreased the levels of brain and atrial natriuretic peptide mRNA[3].
Animal Protocol Animal/Disease Models: Male spontaneously hypertensive rats (SHRs, 50weeks old)[3]
Doses: 0.15 μL/h (~50 μg/kg/day)
Route of Administration: Administered by mini-osmotic pumps; for 6 weeks
Experimental Results: Attenuated hypertension , alleviated cardiac hypertrophy, and improved LV function.
References

[1]. 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]. Alamandine attenuates hypertension and cardiac hypertrophy in hypertensive rats. Amino Acids. 2018 Aug;50(8):1071-1081.

Additional Infomation Alamandine is a peptide.

Solubility Data


Solubility (In Vitro) H2O: 25 mg/mL (29.24 mM)
Solubility (In Vivo) Solubility in Formulation 1: 25 mg/mL (29.24 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with heating and sonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.1696 mL 5.8480 mL 11.6959 mL
5 mM 0.2339 mL 1.1696 mL 2.3392 mL
10 mM 0.1170 mL 0.5848 mL 1.1696 mL
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.