Synonym
Cholecystokinin pentapeptide; CCK-5; Gly-trp-met-asp-phe-NH2;
IUPAC/Chemical Name
(S)-4-(((S)-1-amino-1-oxo-3-phenylpropan-2-yl)amino)-3-((S)-2-((S)-2-(2-aminoacetamido)-3-(1H-indol-3-yl)propanamido)-4-(methylthio)butanamido)-4-oxobutanoic acid
InChi Key
AGNHQKAXUWFRGP-QORCZRPOSA-N
InChi Code
InChI=1S/C31H39N7O7S/c1-46-12-11-22(36-30(44)24(35-26(39)16-32)14-19-17-34-21-10-6-5-9-20(19)21)29(43)38-25(15-27(40)41)31(45)37-23(28(33)42)13-18-7-3-2-4-8-18/h2-10,17,22-25,34H,11-16,32H2,1H3,(H2,33,42)(H,35,39)(H,36,44)(H,37,45)(H,38,43)(H,40,41)/t22-,23-,24-,25-/m0/s1
SMILES Code
O=C(N)[C@H](CC1=CC=CC=C1)NC([C@H](CC(O)=O)NC([C@H](CCSC)NC([C@H](CC2=CNC3=C2C=CC=C3)NC(CN)=O)=O)=O)=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
653.75
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Bernardini F, Warburton MJ. Lysosomal degradation of cholecystokinin-(29-33)-amide in mouse brain is dependent on tripeptidyl peptidase-I: implications for the degradation and storage of peptides in classical late-infantile neuronal ceroid lipofuscinosis. Biochem J. 2002 Sep 1;366(Pt 2):521-9. PubMed PMID: 12038963; PubMed Central PMCID: PMC1222804.
2: Löfberg C, Harro J, Gottfries CG, Oreland L. Cholecystokinin peptides and receptor binding in Alzheimer's disease. J Neural Transm (Vienna). 1996;103(7):851-60. PubMed PMID: 8872869.
3: Fournie-Zaluski MC, Durieux C, Lux B, Belleney J, Pham P, Gerard D, Roques BP. Conformational analysis of cholecystokinin fragments CCK4, CCK5, and CCK6 by 1H-NMR spectroscopy and fluorescence-transfer measurements. Biopolymers. 1985 Sep;24(9):1663-81. PubMed PMID: 4052579.
4: Rose C, Camus A, Schwartz JC. A serine peptidase responsible for the inactivation of endogenous cholecystokinin in brain. Proc Natl Acad Sci U S A. 1988 Nov;85(21):8326-30. PubMed PMID: 3186727; PubMed Central PMCID: PMC282422.
5: Shively J, Reeve JR Jr, Eysselein VE, Ben-Avram C, Vigna SR, Walsh JH. CCK-5: sequence analysis of a small cholecystokinin from canine brain and intestine. Am J Physiol. 1987 Feb;252(2 Pt 1):G272-5. PubMed PMID: 3826354.
6: Crespi F. The role of cholecystokinin (CCK), CCK-A or CCK-B receptor antagonists in the spontaneous preference for drugs of abuse (alcohol or cocaine) in naive rats. Methods Find Exp Clin Pharmacol. 1998 Oct;20(8):679-97. PubMed PMID: 9922984.
7: Xiang H, Xiang GY, Lu ZM, Guo L, Eckstein H. Total enzymatic synthesis of cholecystokinin CCK-5. Amino Acids. 2004 Aug;27(1):101-5. Epub 2004 Mar 16. PubMed PMID: 15309578.
8: Yoshida H, Tsunoda Y, Owyang C. Cholecystokinin peptides stimulate pancreatic secretion by multiple signal transduction pathways. Am J Physiol. 1997 Sep;273(3 Pt 1):G735-47. PubMed PMID: 9316479.
9: Lara N, Chrapko WE, Archer SL, Bellavance F, Mayers I, Le Mellédo JM. Pulmonary and systemic nitric oxide measurements during CCK-5-induced panic attacks. Neuropsychopharmacology. 2003 Oct;28(10):1840-5. PubMed PMID: 12865901.
