Synonym
Cholecystokinin (27-32)-amide; Cholecystokinin (27-32)-NH2;
IUPAC/Chemical Name
(5S,11S,14S,17S)-11-((1H-indol-3-yl)methyl)-5-((S)-2-amino-3-(4-(sulfooxy)phenyl)propanamido)-17-carbamoyl-14-(2-(methylthio)ethyl)-6,9,12,15-tetraoxo-2-thia-7,10,13,16-tetraazanonadecan-19-oic acid
InChi Key
WUUXPYBWGKLWBA-CISYKLKFSA-N
InChi Code
InChI=1S/C36H48N8O12S3/c1-57-13-11-26(42-33(49)24(37)15-20-7-9-22(10-8-20)56-59(53,54)55)34(50)40-19-30(45)41-29(16-21-18-39-25-6-4-3-5-23(21)25)36(52)43-27(12-14-58-2)35(51)44-28(32(38)48)17-31(46)47/h3-10,18,24,26-29,39H,11-17,19,37H2,1-2H3,(H2,38,48)(H,40,50)(H,41,45)(H,42,49)(H,43,52)(H,44,51)(H,46,47)(H,53,54,55)/t24-,26-,27-,28-,29-/m0/s1
SMILES Code
O=C(O)C[C@@H](C(N)=O)NC([C@H](CCSC)NC([C@H](CC1=CNC2=C1C=CC=C2)NC(CNC([C@H](CCSC)NC([C@H](CC3=CC=C(OS(=O)(O)=O)C=C3)N)=O)=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
>2 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
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
881.00
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: Tarasova NI, Stauber RH, Choi JK, Hudson EA, Czerwinski G, Miller JL, Pavlakis GN, Michejda CJ, Wank SA. Visualization of G protein-coupled receptor trafficking with the aid of the green fluorescent protein. Endocytosis and recycling of cholecystokinin receptor type A. J Biol Chem. 1997 Jun 6;272(23):14817-24. PubMed PMID: 9169450.
2: Staley J, Jensen RT, Moody TW. CCK antagonists interact with CCK-B receptors on human small cell lung cancer cells. Peptides. 1990 Sep-Oct;11(5):1033-6. PubMed PMID: 2178246.
3: Menozzi D, Gardner JD, Jensen RT, Maton PN. Properties of receptors for gastrin and CCK on gastric smooth muscle cells. Am J Physiol. 1989 Jul;257(1 Pt 1):G73-9. PubMed PMID: 2473654.
4: Barone FC, Bondinell WE, Labosh TJ, White RF, Ormsbee HS 3rd. Cholecystokinin stimulates neuronal receptors to produce contraction of the canine colon. Life Sci. 1989;44(8):533-42. PubMed PMID: 2927258.
5: Vinayek R, Jensen RT, Gardner JD. Role of sulfate ester in influencing biologic activity of cholecystokinin-related peptides. Am J Physiol. 1987 Feb;252(2 Pt 1):G178-81. PubMed PMID: 2435164.
6: Yoder DG, Moody TW. High affinity binding of cholecystokinin to small cell lung cancer cells. Peptides. 1987 Jan-Feb;8(1):103-7. PubMed PMID: 3033616.
7: Otsuki M, Okabayashi Y, Ohki A, Oka T, Fujii M, Nakamura T, Sugiura N, Yanaihara N, Baba S. Action of cholecystokinin analogues on exocrine and endocrine rat pancreas. Am J Physiol. 1986 Apr;250(4 Pt 1):G405-11. PubMed PMID: 2421584.
8: Vigna SR, Szecòwka J, Williams JA. Do antagonists of pancreatic cholecystokinin receptors interact with central nervous system cholecystokinin receptors? Brain Res. 1985 Sep 23;343(2):394-7. PubMed PMID: 2996701.
9: Briet C, Aumelas A, Martinez J. Synthesis of Z-CCK-27-32-NH2, Z-Tyr(SO-3)-Met-Gly-Trp-Met-Asp-NH2, a cholecystokinin receptor antagonist and an inhibitor of gastrin-induced acid secretion. Int J Pept Protein Res. 1985 Sep;26(3):294-8. PubMed PMID: 2997059.
10: Martinez J, Bali JP. A new class of potent gastrin antagonists. Regul Pept. 1984 Nov;9(4):259-62. PubMed PMID: 6097950.
11: Howard JM, Knight M, Jensen RT, Gardner JD. Discovery of a cholecystokinin analogue with partial agonist activity. Am J Physiol. 1984 Sep;247(3 Pt 1):G261-4. PubMed PMID: 6206732.
12: Spanarkel M, Martinez J, Briet C, Jensen RT, Gardner JD. Cholecystokinin-27-32-amide. A member of a new class of cholecystokinin receptor antagonists. J Biol Chem. 1983 Jun 10;258(11):6746-9. PubMed PMID: 6304053.