Cholecystokinin (CCK) octapeptide is a peptide hormone found in the intestine and brain, which stimulates digestion, mediates satiety, and participates in anxiety disorders. It is a cleavage product of intact CCK prohormones. The activity of CCK octapeptide (unsulfated) is 1/300 of that of sulfated CCK octapeptide.
CAT No: 10-101-247
CAS No:25679-24-7
Synonyms/Alias:25679-24-7;H-ASP-TYR-MET-GLY-TRP-MET-ASP-PHE-NH2;Cholecystokinin Octapeptide (desulfated);CCK(26-33) Desulfated;Cholecystokinin Octapeptide, desulfated;Asp-Tyr-Met-Gly-Trp-Met-Asp-Phe-NH2;CHEMBL216166;Desulfated CCK-8;(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]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-4-oxobutanoic acid;CCK Octapeptide, desulfated;Desulfated CCK8;OIXQINQYMGNCII-YRVFCXMDSA-N;MFCD00076488;DYMGWMDF-NH2;CHEBI:138169;HY-P0196;BDBM50007921;AKOS015994633;FC108598;MS-31915;Asp-Tyr-Met-Gly-Trp-Met-Asp-Phe-NH(2);CS-0021290;L-Asp-L-Tyr-L-Met-Gly-L-Trp-L-Met-L-Asp-L-Phe-NH2;(3S,6S,9S,15S,18S,21S)-9-((1H-indol-3-yl)methyl)-21-amino-3-((S)-1-amino-1-oxo-3-phenylpropan-2-ylcarbamoyl)-18-(4-hydroxybenzyl)-6,15-bis(2-(methylthio)ethyl)-5,8,11,14,17,20-hexaoxo-4,7,10,13,16,19-hexaazatricosane-1,23-dioic acid;3-{2-[2-(2-{2-[2-(2-Amino-3-carboxy-propionylamino)-3-(4-hydroxy-phenyl)-propionylamino]-4-methylsulfanyl-butyrylamino}-acetylamino)-3-(1H-indol-3-yl)-propionylamino]-4-methylsulfanyl-butyrylamino}-N-(1-carbamoyl-2-phenyl-ethyl)-succinamic acid;L-alpha-aspartyl-L-tyrosyl-L-methionylglycyl-L-tryptophyl-L-methionyl-L-alpha-aspartyl-L-phenylalaninamide;
Chemical Name:(3R,6S,9S,15R,18R,21R)-9-((1H-indol-3-yl)methyl)-21-amino-3-((R)-2-hydrazinyl-3-phenylpropanamido)-18-(4-hydroxybenzyl)-6,15-bis(2-(methylthio)ethyl)-4,7,10,13,16,19,20-heptaoxo-5,8,11,14,17-pentaazatricosane-1,23-dioic acid
Cholecystokinin Octapeptide (desulfated) is a synthetic peptide analogue derived from the naturally occurring gastrointestinal hormone cholecystokinin (CCK), but lacking the sulfation typically present at the tyrosine residue. As an important biochemical tool, this peptide variant is widely utilized in the study of peptide-receptor interactions, signal transduction mechanisms, and the physiological roles of CCK in both central and peripheral tissues. Its desulfated form offers a unique perspective on the structural and functional importance of post-translational modifications, making it a valuable resource for researchers investigating the molecular basis of peptide hormone activity and receptor specificity.
Receptor Binding Studies: The desulfated CCK-8 peptide is frequently employed in receptor binding assays to elucidate the structural determinants required for high-affinity interaction with CCK receptors, particularly CCK1 and CCK2 subtypes. By contrasting the binding affinities and biological responses of the desulfated and sulfated forms, researchers gain critical insights into the contribution of tyrosine sulfation to receptor recognition and activation. This comparative approach is instrumental in mapping ligand-receptor interactions and characterizing the pharmacological profiles of novel CCK analogues or antagonists.
Signal Transduction Research: In cellular and molecular pharmacology, the desulfated octapeptide serves as a tool to dissect downstream signaling pathways initiated by CCK receptor activation. Its altered receptor affinity and efficacy enable precise delineation of G protein-coupled receptor (GPCR) signaling events, such as intracellular calcium mobilization, cAMP production, and kinase activation. Such studies are essential for understanding the mechanistic nuances of peptide hormone signaling and for identifying receptor subtype-specific functional responses.
Structure-Activity Relationship (SAR) Analysis: The structural modification inherent in the desulfated form makes it an indispensable reference compound in SAR studies. By systematically comparing biological activities of sulfated and desulfated analogues, scientists can define the role of specific functional groups in modulating peptide potency, selectivity, and stability. These investigations inform the rational design of peptide-based ligands with tailored pharmacological properties for basic research or drug discovery applications.
Peptide-Receptor Interaction Modeling: Desulfated CCK-8 is often incorporated into computational and biophysical studies aimed at modeling peptide-receptor complexes. Its use facilitates the validation of docking algorithms, molecular dynamics simulations, and NMR-based conformational analyses. Through these approaches, researchers can visualize the impact of tyrosine sulfation on peptide conformation, receptor binding orientation, and dynamic behavior, thereby advancing the understanding of peptide-membrane protein recognition at the atomic level.
Neuroscience and Behavioral Studies: The distinct pharmacological profile of the desulfated octapeptide allows neuroscientists to explore the role of endogenous CCK signaling in brain function and behavior. By comparing the effects of sulfated and desulfated peptides on neuronal activity, neurotransmitter release, and behavioral endpoints, investigators can clarify the functional significance of peptide modifications in neuropeptide signaling. Such studies contribute to a deeper understanding of the molecular mechanisms underlying appetite regulation, anxiety, and other CCK-mediated central nervous system processes.
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