Sincalide

Sincalide is an octapeptide fragment of cholestocystokinin (CCK) that activates the CCK receptor on immune cell surfaces. Sincalide is more potent when sulfated. Sincalide exhibits neuroprotective, immunosuppressive, and anorexigenic activities.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.
Sincalide(CAS 25126-32-3)

CAT No: R1676

CAS No:25126-32-3

Synonyms/Alias:Sincalide;25126-32-3;CCK-8;Sincalida;Kinevac;Sincalidum;Syncalide;CCK C-terminal octapeptide;SQ 19844;Human CCK-8;cholecystokinin C-terminal octapeptide;Cholecystokinin octapeptide;UNII-M03GIQ7Z6P;3-10-Caerulein, 5-L-methionine-;M03GIQ7Z6P;DTXSID7048617;SQ-19844;Sincalidum [INN-Latin];EINECS 246-639-0;Sincalida [INN-Spanish];MFCD00079849;Cholecystokinin-pancreozymin;H-Asp-Tyr(SO3H)-Met-Gly-Trp-Met-Asp-Phe-NH2;Caerulein, 1-de(5-oxo-L-proline)-2-de-L-glutamine-5-L-methionine-;CHEMBL1121;DTXCID4028543;Sincalide [USAN:USP:INN:BAN];L-Aspartyl-L-tyrosyl-L-methionylglycyl-L-tryptophyl-L-methionyl-L-aspartylphenyl-L-alaninamide hydrogen sulfate (ester);Sincalidum (INN-Latin);1-De(5-oxo-L-proline)-2-de-L-glutamine-5-L-methioninecaerulein;Sincalida (INN-Spanish);SINCALIDE (MART.);SINCALIDE [MART.];cholecystokinin 8;L-alpha-Aspartyl-O-sulfo-L-tyrosyl-L-methionylglycyl-L-tryptophyl-L-methionyl-L-alpha-aspartyl-L-phenylalaninamide;SINCALIDE (USP IMPURITY);SINCALIDE [USP IMPURITY];Sincalide (USAN:USP:INN:BAN);(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;(3S,6S,9S,15S,18S,21S)-9-((1H-indol-3-yl)methyl)-21-amino-3-(((S)-1-amino-1-oxo-3-phenylpropan-2-yl)carbamoyl)-6,15-bis(2-(methylthio)ethyl)-5,8,11,14,17,20-hexaoxo-18-(4-(sulfooxy)benzyl)-4,7,10,13,16,19-hexaazatricosanedioic acid;CAS-25126-32-3;CCK-8 (sulphated);CCK-OP;OP-CCK;CCK-8S;NCGC00183278-01;NCGC00183363-01;Kinevac (TN);SINCALIDE [INN];SINCALIDE [MI];CCK Octapeptide sulfated;Sincalide (USAN/INN);SINCALIDE [USAN];SINCALIDE [VANDF];SINCALIDE [WHO-DD];GTPL864;Cholecystokinin Pancreozymin C Terminal Octapeptide;Cholecystokinin Pancreozymin C-Terminal Octapeptide;SCHEMBL122365;CCK-8(SO3);SINCALIDE [ORANGE BOOK];BDBM21147;EX-A8006C;V04CC03;CHEBI:135946;Pancreozymin C-terminal octapeptide;[125I]CCK-8;HY-P0093;Tox21_112955;Tox21_113481;AKOS016340423;CS-5963;DB09142;FS41124;HS-2026;NCGC00167273-01;Cholecystokinin, CCK Octapeptide (26-33);NS00050642;D05845;E78048;Asp26-Tyr(SO3H)-Met-Gly-Trp-Met-Asp-PheNH2;CHOLECYSTOKININ C-TERMINAL OCTAPEPTIDE [MI];EN300-19650945;Q7521885;(3S)-3-[(2S)-2-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-carboxypropanamido]-3-[4-(sulfooxy)phenyl]propanamido]-4-(methylsulfanyl)butanamido]acetamido}-3-(1H-indol-3-yl)propanamido]-4-(methylsulfanyl)butanamido]-3-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}propanoic acid;(3S)-3-[(2S)-2-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(3S)-3-amino-3-formamidopropanoic acid]-3-[4-(sulfooxy)phenyl]propanamido]-4-(methylsulfanyl)butanamido]acetamido}-3-(1H-indol-3-yl)propanamido]-4-(methylsulfanyl)butanamido]-3-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}propanoic acid;(3S)-3-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-4-hydroxy-4-oxobutanoyl]amino]-3-(4-sulfooxyphenyl)propanoyl]amino]-4-methylsulfanylbutanoyl]amino]acetyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-4-methylsulfanylbutanoyl]amino]-4-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-4-oxobutanoic acid;(3S,6S,9S,15S,18S,21S)-9-((1H-indol-3-yl)methyl)-21-amino-3-(((S)-1-amino-1-oxo-3-phenylpropan-2-yl)carbamoyl)-6,15-bis(2-(methylthio)ethyl)-5,8,11,14,17,20-hexaoxo-18-(4-(sulfooxy)benzyl)-4,7,10,13,16,19-hexaazatricosane-1,23-dioic acid;(3S,6S,9S,15S,18S,21S)-9-((1H-indol-3-yl)methyl)-21-amino-3-((S)-1-amino-1-oxo-3-phenylpropan-2-ylcarbamoyl)-6,15-bis(2-(methylthio)ethyl)-5,8,11,14,17,20-hexaoxo-18-(4-(sulfooxy)benzyl)-4,7,10,13,16,19-hexaazatricosane-1,23-dioic acid;246-639-0;L-.ALPHA.-ASPARTYL-O-SULFO-L-TYROSYL-L-METHIONYLGLYCYL-L-TRYPTOPHYL-L-METHIONYL-L-.ALPHA.-ASPARTYL-L-PHENYLALANINAMIDE;L-Aspartyl-L-tyrosyl-L-methionylglycyl-L-tryptophyl-L-methionyl-L-aspartylphenyl-L-alaninamide Hydrogen Sulfate(ester);

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M.F/Formula
C49H62N10O16S3
M.W/Mr.
1143.3
Sequence
One Letter Code:DXMGWMDF
Three Letter Code:H-Asp-Tyr(SO3H)-Met-Gly-Trp-Met-Asp-Phe-NH2
Biological Activity
Sincalide (Cholecystokinin octapeptide) is a rapid-acting amino acid polypeptide hormone analogue of cholecystokinin (CCK) for intravenous use in postevacuation cholecystography. Sincalide ammonium is an agent that promotes gallbladder contraction by injection and helps diagnose gallbladder and pancreas disorders. The hepatobiliary physiologic effect of Sincalide ammonium is to increase bile secretion, cause the gallbladder to contract and relax the sphincter of Oddi, resulting in bile drainage into the duodenum.

Sincalide is a synthetic peptide analog of the endogenous hormone cholecystokinin (CCK), specifically corresponding to the C-terminal octapeptide sequence of CCK-8. As a peptide compound, it is structurally designed to mimic the physiological actions of natural CCK in stimulating the gallbladder, pancreas, and gastrointestinal tract. Sincalide's biochemical activity centers on its capacity to bind and activate CCK receptors, making it a valuable tool in research focused on gastrointestinal physiology, peptide hormone signaling, and receptor-ligand interactions. Its defined sequence and receptor specificity have established it as an important reagent for studying the regulatory mechanisms governing digestive enzyme secretion, gallbladder motility, and neuroendocrine signaling pathways.

Receptor binding studies: Sincalide serves as a reference ligand in investigations of cholecystokinin receptor (CCKR) pharmacology. By utilizing this peptide in competitive binding assays, researchers can characterize the affinity and selectivity of novel agonists or antagonists for CCK1 and CCK2 receptors. Its well-defined interaction profile supports structure-activity relationship (SAR) analyses and facilitates the elucidation of critical residues involved in peptide-receptor recognition. These studies are essential for advancing the understanding of CCK receptor function and for the rational design of new modulators targeting gastrointestinal and neuroendocrine systems.

Gastrointestinal physiology research: Due to its potent stimulatory effects on gallbladder contraction and pancreatic enzyme secretion, sincalide is widely employed in experimental models to probe digestive processes. By administering the peptide in vitro or in vivo, investigators can induce and monitor physiological responses, enabling detailed analysis of biliary kinetics, sphincter of Oddi function, and exocrine pancreatic activity. Such applications are instrumental in dissecting the complex regulatory networks that control nutrient digestion and absorption, and in validating the roles of CCK signaling pathways in gastrointestinal homeostasis.

Peptide signaling pathway analysis: As a synthetic analog of a key gut-brain peptide, sincalide is utilized to activate CCK-dependent signaling cascades in cellular and tissue models. Researchers employ it to trigger downstream events such as intracellular calcium mobilization, kinase activation, and gene expression changes, thereby enabling mechanistic studies of signal transduction. These experiments contribute to a broader understanding of how peptide hormones orchestrate physiological responses at the molecular level, supporting the identification of novel regulatory nodes within neuroendocrine and digestive systems.

Pharmacological screening: Sincalide is frequently incorporated into high-throughput screening platforms to evaluate candidate compounds for modulatory effects on CCK-mediated pathways. Its consistent activity profile allows for the benchmarking of test molecules, whether as potential agonists, antagonists, or allosteric modulators of CCK receptors. This application supports drug discovery efforts aimed at identifying new agents that influence gastrointestinal motility, satiety regulation, or pancreatic function, providing a robust and reproducible standard for comparative analyses.

Peptide stability and metabolism studies: The defined structure of sincalide makes it an ideal substrate for research into peptide degradation, enzymatic processing, and metabolic stability in biological systems. By tracking the fate of the peptide in various tissue extracts, plasma, or cellular environments, scientists can assess the roles of proteases and peptidases in modulating peptide bioavailability and function. These studies are pivotal for optimizing peptide-based research tools and for developing strategies to enhance the stability of therapeutic or diagnostic peptides in complex biological matrices.

Shipping Condition
Room temperature in continental US; may vary elsewhere.
InChI
InChI=1S/C49H62N10O16S3/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)/t32-,34-,35-,36-,37-,38-,39-/m0/s1
InChI Key
IZTQOLKUZKXIRV-YRVFCXMDSA-N

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