Sincalide ammonium

• CAT Number: I046034
• CAS Number: 70706-98-8
• Molecular Formula: C49H65N11O16S3
• Molecular Weight: 1160.30
• Purity: ≥95%
• Synonyms: (3S)-3-amino-4-[[(2S)-1-[[(2S)-1-[[2-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]amino]-1-oxo-3-(4-sulfooxyphenyl)propan-2-yl]amino]-4-oxobutanoic acid;azane
• InChI: InChI=1S/C49H62N10O16S3.H3N/c1-76-18-16-34(55-47(69)37(58-44(66)32(50)23-41(61)62)21-28-12-14-30(15-13-28)75-78(72,73)74)45(67)53-26-40(60)54-38(22-29-25-52-33-11-7-6-10-31(29)33)48(70)56-35(17-19-77-2)46(68)59-39(24-42(63)64)49(71)57-36(43(51)65)20-27-8-4-3-5-9-27;/h3-15,25,32,34-39,52H,16-24,26,50H2,1-2H3,(H2,51,65)(H,53,67)(H,54,60)(H,55,69)(H,56,70)(H,57,71)(H,58,66)(H,59,68)(H,61,62)(H,63,64)(H,72,73,74);1H3/t32-,34-,35-,36-,37-,38-,39-;/m0./s1
• InChIKey: SKHSHPLUIPFDPM-ITZXPNBCSA-N
• SMILES: CSCCC(C(=O)NCC(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)NC(CCSC)C(=O)NC(CC(=O)O)C(=O)NC(CC3=CC=CC=C3)C(=O)N)NC(=O)C(CC4=CC=C(C=C4)OS(=O)(=O)O)NC(=O)C(CC(=O)O)N.N

Sincalide ammonium (Cholecystokinin octapeptide ammonium, CCK-8 ammonium) is a rapid-acting amino acid polypeptide hormone analogue of cholecystokinin (CCK) for intravenous use in postevacuation cholecystography. Sincalide ammonium is a major bioactive segment of CCK that retains most of the biological activities of CCK. CCK‐8 can promote gallbladder contraction by injection and helps diagnose gallbladder and pancreas disorders. Sincalide ammonium can increase bile secretion, cause the gallbladder to contract and relax the sphincter of Oddi, resulting in bile drainage into the duodenum. Sincalide ammonium is a major bioactive segment of CCK that retains most of the biological activities of CCK[1][2][3].
Sincalide ammonium (Cholecystokinin octapeptide ammonium, CCK-8 ammonium), as a novel cardiovascular hormone, has a significant inhibitory effect on myocardial fibrosis in noninfarcted areas. Sincalide ammonium also plays a positive role in fighting inflammation, apoptosis and collagen deposition. CCK‐8 (ammonium) protects H9c2 cardiomyoblasts from Ang II‐induced apoptosis partly via activation of the CCK1 receptor and the phosphatidyqinositol‐3 kinase/protein kinase B (PI3K/Akt) signaling pathway[3].
Sincalide ammonium (Cholecystokinin octapeptide ammonium, CCK-8 ammonium) alleviates fibrosis in the noninfarcted regions and delay the left ventricular remodeling and the progress of heart failure in a MI rat model[4].

Reference

[1]. Maher KA. Kinevac (sincalide for injection)/Squibb Diagnostics. Gastroenterol Nurs. 1991 Oct;14(2):98-100.
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[2]. Ziessman HA. Sincalide: A Review of Clinical Utility, Proper Infusion Methodology, and Alternative Cholecystogogues. J Nucl Med Technol. 2019 Sep;47(3):210-212.
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[3]. Can Wang, et al. Protective effect of cholecystokinin octapeptide on angiotensin II-induced apoptosis in H9c2 cardiomyoblast cells. J Cell Biochem. 2020 Jul;121(7):3560-3569.
 [Content Brief]

[4]. Can Wang, et al. Cholecystokinin octapeptide reduces myocardial fibrosis and improves cardiac remodeling in post myocardial infarction rats. Int J Biochem Cell Biol. 2020 Aug;125:105793.
 [Content Brief]