CAS 17650-98-5|Caerulein ammonium salt
| Common Name | Caerulein ammonium salt | ||
|---|---|---|---|
| CAS Number | 17650-98-5 | Molecular Weight | 980.051 |
| Density | 1.4±0.1 g/cm3 | Boiling Point | / |
| Molecular Formula | C58H73N13O21S2 | Melting Point | 224-226° (dec) |
| MSDS | ChineseUSA | Flash Point | / |
Names
| Name | ceruletide |
|---|---|
| Synonym | More Synonyms |
Caerulein ammonium salt BiologicalActivity
| Description | Ceruletide, a biologically active decapeptide isolated from the skin of the Australian frog Hyla caerulea, is a potent cholecystokinetic agent, and acts as a cholecystokinin receptor agonist. Sequence: {pGlu}-Gln-Asp-Tyr(SO3H)-Thr-Gly-Trp-Met-Asp-Phe-NH2;{pGlu}-QD-Y(SO3H)-TGWMDF-NH2. |
|---|---|
| Related Catalog | Signaling Pathways >>GPCR/G Protein >>Cholecystokinin ReceptorPeptidesResearch Areas >>Cardiovascular DiseaseResearch Areas >>Metabolic DiseaseNatural Products >>OthersPeptides |
| Target | Cholecystokinin receptor[4] |
| In Vitro | Ceruletide is similar chemically and biologically to the human gastrointestinal hormones cholecystokinin-pancreozymin (CCK) and gastrin II. Ceruletide stimulates gallbladder contraction, pancreatic exocrine secretion, gastric secretion, and motility in the distal duodenum, jejunum, ileum and colon, while delaying gastric emptying and inhibiting motility in the proximal duodenum[1]. Ceruletide in supramaximal but not in physiological doses activates NF-kappaB/Rel in vitro. This activation may induce a self-defending genetic program before the onset of cellular injury, which may prevent higher degrees of damage of pancreatic acinar cells after secretagogue hyperstimulation[2]. |
| In Vivo | Ceruletide (0.4-0.5 mcg/kg, i.v.; 3-4 mcg/kg, s.c.) results in emesis and evacuation of the bowel in the intact conscious dog, and recovery is complete 15-30 min after i. v. administration and 2-4 hr after s.c. administration. Ceruletide (5-15 ng/kg, i.v.) shows a marked spasmogenic effect on the pylorus of rats. Ceruletide also reduces blood pressure in anesthetized dogs[1]. Ceruletide serum bile acid (SBA) stimulation circumvents exogenous and endogenous influences associated with postprandial (PP) SBA stimulation. Ceruletide SBA stimulation may perform as well as PP SBA stimulation in dogs with portosystemic shunt (PSS) and be more sensitive for the detection of hepatic dysfunction in dogs with upper respiratory disease (URD)[3]. |
| Animal Admin | Dogs[3] All dogs undergo serum bile acid (SBA) stimulation with food (<5 kg/body weight [BW] 2 teaspoons, >5 kg BW 2 tablespoons) or 0.3 μg/kg BW Ceruletide IM, respectively, on consecutive days. A diet of moderate protein content and with an increased concentration of fiber is chosen to minimize metabolic complications such as hepatic encephalopathy. Before each test, the dogs are fasted for 12 hours. Blood samples are drawn at baseline, 60 and 120 minutes after feeding, and 20, 30, and 40 minutes postinjection, respectively. The blood samples are collected in plain tubes and left to clot; they are then centrifuged at 6,500 ×g for 1 minute, and the serum is used to measure SBA by a colorimetric test with endpoint determination[3]. |
| References | [1]. Vincent ME, et al. Pharmacology, clinical uses, and adverse effects of ceruletide, a cholecystokinetic agent. Pharmacotherapy. 1982 Jul-Aug;2(4):223-34. [2]. Steinle AU, et al. NF-kappaB/Rel activation in cerulein pancreatitis. Gastroenterology. 1999 Feb;116(2):420-30. [3]. Bridger N, et al. Comparison of postprandial and ceruletide serum bile acid stimulation in dogs. J Vet Intern Med. 2008 Jul-Aug;22(4):873-8. [4]. Zarrindast MR, et al. Effects of cholecystokinin receptor agonist and antagonists on morphine dependence in mice. Pharmacol Toxicol. 1995 Dec;77(6):360-4. |
Chemical & Physical Properties
| Density | 1.4±0.1 g/cm3 |
|---|---|
| Melting Point | 224-226° (dec) |
| Molecular Formula | C58H73N13O21S2 |
| Molecular Weight | 980.051 |
| Exact Mass | 979.374573 |
| PSA | 585.08000 |
| LogP | 2.46 |
| Index of Refraction | 1.632 |
| InChIKey | YRALAIOMGQZKOW-HYAOXDFASA-N |
| SMILES | CSCCC(NC(=O)C(Cc1c[nH]c2ccccc12)NC(=O)CNC(=O)C(NC(=O)C(Cc1ccc(OS(=O)(=O)O)cc1)NC(=O)C(CC(=O)O)NC(=O)C(CCC(N)=O)NC(=O)C1CCC(=O)N1)C(C)O)C(=O)NC(CC(=O)O)C(=O)NC(Cc1ccccc1)C(N)=O |
| Storage condition | -20°C |
Safety Information
| Personal Protective Equipment | Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter |
|---|---|
| RIDADR | NONH for all modes of transport |
| WGK Germany | 3 |
Articles58
More Articles| p21(WAF1) (/Cip1) limits senescence and acinar-to-ductal metaplasia formation during pancreatitis. J. Pathol. 235(3) , 502-14, (2015) Trans-differentiation of pancreatic acinar cells into ductal-like lesions, a process defined as acinar-to-ductal metaplasia (ADM), is observed in the course of organ regeneration following pancreatiti... | |
| Overexpression of Fas and FasL is associated with infectious complications and severity of experimental severe acute pancreatitis by promoting apoptosis of lymphocytes. Inflammation 37(4) , 1202-12, (2014) This study investigated the relationship of Fas and Fas ligand (FasL) expression and apoptosis of lymphocytes in relation to the pathogenic immune response and infectious complications observed in exp... | |
| A novel 2-step culture model for long-term in vitro maintenance of human pancreatic acinar cells. Pancreas 43(5) , 762-7, (2014) Because of rapid loss of functional differentiation that regularly occurs in vitro, culture systems permitting long-term studies on pancreatic acinar cells pose a major technical challenge. We recentl... |
Synonyms
| L-Phenylalaninamide, O-sulfo-L-tyrosyl-L-threonylglycyl-L-tryptophyl-D-norleucyl-L-α-aspartyl- |
| caerulein 1.1 |
| CERULETIDE |
| FI-6934 |
| CERULEIN |
| EINECS 17650-98-5 |
| Caerulein |
| MFCD00076478 |
| sulfated caerulein |
| O-Sulfo-L-tyrosyl-L-threonylglycyl-L-tryptophyl-D-norleucyl-L-α-aspartyl-L-phenylalaninamide |
| Ceosunin |
| Ceruletide,Cerulein |
