Saralasin

Saralasin ([Sar1], [Ala8]-Ang II) is a partial agonist of angiotensin II receptors, though it is commonly mistaken as a competitive antagonist.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.
Saralasin(CAS 34273-10-4)

CAT No: 10-101-304

CAS No:34273-10-4

Synonyms/Alias:Saralasin;34273-10-4;Saralasina;Saralasine;Saralasinum;Sar-Arg-Val-Tyr-Val-His-Pro-Ala;Saralasinum [INN-Latin];Saralasin [INN:BAN];Saralasine [INN-French];Saralasina [INN-Spanish];DTXSID2046549;(Sar1,Val5,Ala8)-Angiotensin II;CHEMBL938;H2AFV2HE66;1-Sar-8-Ala-angiotensin II;(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-(diaminomethylideneamino)-2-[[2-(methylamino)acetyl]amino]pentanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-methylbutanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]pyrrolidine-2-carbonyl]amino]propanoic acid;DTXCID0026549;Angiotensin II, 1-(N-methylglycine)-5-L-valine-8-L-alanine-;(Sar(1),Ala(8))ANGII;(1-(N-Methylglycin) 5-L-valin, 8-L-alanin)angiotensin II;Saralasine (INN-French);Saralasinum (INN-Latin);Saralasina (INN-Spanish);N-(1-(N-(N-(N-(N-(N2-(N-methylglycly)-L-arginyl)-L-valyl)-L-tyrosyl)-L-valyl)-L-histidyl)-L-prolyl)-L-alanine;UNII-H2AFV2HE66;1 Sar 8 Ala Angiotensin II;1-Sar-8-Ala Angiotensin II;Angiotensin II, 1-Sar-8-Ala;(Sar1,Val5,Ala8)Angiotensin II;NCGC00166135-01;(2S)-2-(((2S)-1-((2S)-2-(((2S)-2-(((2S)-2-(((2S)-2-(((2S)-5-(diaminomethylideneamino)-2-((2-(methylamino)acetyl)amino)pentanoyl)amino)-3-methylbutanoyl)amino)-3-(4-hydroxyphenyl)propanoyl)amino)-3-methylbutanoyl)amino)-3-(1H-imidazol-5-yl)propanoyl)pyrrolidine-2-carbonyl)amino)propanoic acid;angiotensin II, Sar(1)-Ala(8)-;1 Sarcosine 8 Alanine Angiotensin II;1-Sarcosine-8-Alanine Angiotensin II;Angiotensin II, 1-Sarcosine-8-Alanine;angiotensin II, sarcosyl(1)-alanine(8)-;SARALASIN [INN];SARALASIN [MI];SCHEMBL23;CHEBI:135894;2-((1-(2-((2-((2-((2-((5-(diaminomethylideneamino)-2-((2-methylaminoacetyl)amino)pentanoyl)amino)-3-methylbutanoyl)amino)-3-(4-hydroxyphenyl)propanoyl)amino)-3-methylbutanoyl)amino)-3-(3H-imidazol-4-yl)propanoyl)pyrrolidine-2-carbonyl)amino)propanoic acid;2-[[1-[2-[[2-[[2-[[2-[[5-(diaminomethylideneamino)-2-[(2-methylaminoacetyl)amino]pentanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-methylbutanoyl]amino]-3-(3H-imidazol-4-yl)propanoyl]pyrrolidine-2-carbonyl]amino]propanoic acid;HY-P0205;Tox21_112332;BDBM50009338;BDBM50229504;AKOS024456428;DB06763;NCGC00167316-01;FS108389;CAS-34273-10-4;CS-0021297;NS00073478;Sar-Arg-Val-Tyr-Val-His-Pro-Ala (sarlasin);[Sar1-Arg2-Val3-Tyr4-Val5-His6-Pro7-Ala8];Q410298;(Sar 1,Val5,Ala8)-Angiotensin II trifluoroacetate salt;ANGIOTENSIN II, 1-SARCOSINE-5-L-VALINE-8-L-ALANINE-;Saralasin;Sar-Arg-Val-Tyr-Val-His-Pro-Ala-OH trifluoroacetate salt;L-ALANINE, N-METHYLGLYCYL-L-ARGINYL-L-VALYL-L-TYROSYL-L-VALYL-L-HISTIDYL-L-PROLYL-;(S)-2-((S)-1-((6S,9S,12S,15S,18S)-18-((1H-imidazol-4-yl)methyl)-6-(3-guanidinopropyl)-12-(4-hydroxybenzyl)-9,15-diisopropyl-4,7,10,13,16-pentaoxo-2,5,8,11,14,17-hexaazanonadecane)pyrrolidine-2-carboxamido)propanoic acid;(S)-2-((S)-1-((S)-2-((S)-2-((S)-2-((S)-2-((S)-5-(diaminomethyleneamino)-2-(2-(methylamino)acetamido)pentanamido)-3-methylbutanamido)-3-(4-hydroxyphenyl)propanamido)-3-methylbutanamido)-3-(1H-imidazol-5-yl)propanoyl)pyrrolidine-5-carboxamido)propanoic acid;60173-70-8;

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M.F/Formula
C42H65N13O10
M.W/Mr.
912
Sequence
One Letter Code:GRVYVHPA
Three Letter Code:H-Sar-Arg-Val-Tyr-Val-His-Pro-Ala-OH
Purity
≥97% (HPLC)
Activity
Agonist
Target
Angiotensin II Receptors

Saralasin is a synthetic peptide analogue of angiotensin II, designed to function as a competitive antagonist at angiotensin II receptor sites. Structurally modified to enhance receptor affinity while reducing agonist activity, Saralasin is a valuable molecular probe for dissecting the physiological and biochemical roles of the renin-angiotensin system. Its ability to selectively block angiotensin II-mediated effects has established it as a pivotal tool in cardiovascular, renal, and endocrine research, offering insight into receptor signaling pathways and regulatory mechanisms underpinning blood pressure, fluid balance, and electrolyte homeostasis.

Receptor Pharmacology Studies: As a potent angiotensin II receptor antagonist, Saralasin is widely employed in receptor binding assays and functional studies to map the distribution, density, and subtype specificity of angiotensin II receptors in various tissues. Researchers utilize the peptide to differentiate between AT1 and AT2 receptor-mediated responses, enabling a deeper understanding of receptor pharmacodynamics and the molecular determinants of ligand-receptor interactions. These investigations are instrumental in elucidating the mechanisms of hormone action and receptor regulation under physiological and pathophysiological conditions.

Signal Transduction Research: The compound serves as a critical tool for exploring the downstream signaling cascades activated by angiotensin II. By competitively inhibiting receptor activation, Saralasin facilitates the dissection of G protein-coupled receptor pathways, including those involving phospholipase C, intracellular calcium mobilization, and protein kinase activation. Such studies contribute to the identification of key molecular targets and secondary messengers involved in vascular tone regulation, cardiac function, and cellular growth responses.

Vascular and Renal Physiology Investigations: In experimental models, Saralasin is frequently used to assess the contribution of endogenous angiotensin II to blood pressure control, renal hemodynamics, and sodium handling. Its administration allows researchers to evaluate the physiological significance of angiotensin II signaling in both normal and altered states, such as hypertension, heart failure, or impaired renal function. These applications help clarify the interplay between hormonal regulation and organ-specific functions in cardiovascular and renal systems.

Peptide Structure-Activity Relationship (SAR) Analysis: As a modified peptide, Saralasin is a reference compound in studies examining the structure-activity relationships of angiotensin analogues. By comparing its biological activity and receptor affinity to native angiotensin II and other synthetic derivatives, scientists gain valuable insights into the structural features that govern receptor binding, agonist versus antagonist behavior, and metabolic stability. These findings inform the rational design of novel peptide-based modulators targeting the renin-angiotensin axis.

Analytical Method Development: The unique properties of Saralasin make it a useful standard or control in the development and validation of analytical techniques, such as high-performance liquid chromatography (HPLC) and mass spectrometry, for peptide quantification and purity assessment. Its well-characterized chemical structure supports assay calibration and method optimization, ensuring accurate detection and measurement of angiotensin-related peptides in complex biological matrices. Through these applications, Saralasin underpins both fundamental research and technical innovation in peptide analysis and receptor biology.

Source#
Synthetic
Long-term Storage Conditions
1 mg/ml in water
Shipping Condition
+20°C (International: -20°C)
InChI
InChI=1S/C42H65N13O10/c1-22(2)33(53-35(58)28(50-32(57)20-45-6)9-7-15-47-42(43)44)38(61)51-29(17-25-11-13-27(56)14-12-25)36(59)54-34(23(3)4)39(62)52-30(18-26-19-46-21-48-26)40(63)55-16-8-10-31(55)37(60)49-24(5)41(64)65/h11-14,19,21-24,28-31,33-34,45,56H,7-10,15-18,20H2,1-6H3,(H,46,48)(H,49,60)(H,50,57)(H,51,61)(H,52,62)(H,53,58)(H,54,59)(H,64,65)(H4,43,44,47)/t24-,28-,29-,30-,31-,33-,34-/m0/s1
InChI Key
PFGWGEPQIUAZME-NXSMLHPHSA-N
Canonical SMILES
CC(C)C(C(=O)NC(CC1=CC=C(C=C1)O)C(=O)NC(C(C)C)C(=O)NC(CC2=CN=CN2)C(=O)N3CCCC3C(=O)NC(C)C(=O)O)NC(=O)C(CCCN=C(N)N)NC(=O)CNC
Isomeric SMILES
C[C@@H](C(=O)O)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CC2=CN=CN2)NC(=O)[C@H](C(C)C)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)CNC

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