C9026

Caerulein

≥95% (HPLC)

• Synonym(s): Caerulein Sulfated, Cerulein, Ceruletide, [Tyr(SO₃H)⁴]Caerulein, pGlu-Gln-Asp-Tyr(SO₃H)-Thr-Gly-Trp-Met-Asp-Phe-NH₂
• Empirical Formula (Hill Notation): C₅₈H₇₃N₁₃O₂₁S₂
• CAS Number: 17650-98-5
• Molecular Weight: 1352.40
• Beilstein: 5422487
• MDL number: MFCD00076478
• PubChem Substance ID: 24893129
• NACRES: NA.26

Properties

• Quality Level: 200
• Assay: ≥95% (HPLC)
• form: powder
• technique(s): immunohistochemistry: suitable
• color: white
• storage temp.: −20°C
• SMILES string: CSCC[C@H](NC(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)CNC(=O)C(NC(=O)[C@H](Cc3ccc(OS(O)(=O)=O)cc3)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H]4CCC(=O)N4)[C@@H](C)O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](Cc5ccccc5)C(N)=O
• InChI: 1S/C58H73N13O21S2/c1-29(72)49(71-57(87)40(23-31-12-14-33(15-13-31)92-94(89,90)91)68-56(86)43(26-48(78)79)69-52(82)37(16-18-44(59)73)65-51(81)36-17-19-45(74)63-36)58(88)62-28-46(75)64-41(24-32-27-61-35-11-7-6-10-34(32)35)54(84)66-38(20-21-93-2)53(83)70-42(25-47(76)77)55(85)67-39(50(60)80)22-30-8-4-3-5-9-30/h3-15,27,29,36-43,49,61,72H,16-26,28H2,1-2H3,(H2,59,73)(H2,60,80)(H,62,88)(H,63,74)(H,64,75)(H,65,81)(H,66,84)(H,67,85)(H,68,86)(H,69,82)(H,70,83)(H,71,87)(H,76,77)(H,78,79)(H,89,90,91)/t29-,36+,37+,38+,39+,40+,41+,42+,43+,49?/m1/s1
• InChI key: YRALAIOMGQZKOW-HJMGKOKZSA-N

Description

Amino Acid Sequence

Glp-Gln-Asp-Tyr(SO3H)-Thr-Gly-Trp-Met-Asp-Phe-NH2

Application

Caerulein has been used to induce pancreatitis in Sprague-Dawley rats, mice and other experimental animals.

Biochem/physiol Actions

Caerulein is a gastro regulatory molecule with actions similar to cholecystokinin. It possesses a tyrosine sulfate residue and induces smooth muscle contraction. It has gastrin-like activity. Caerulein is used to study cell signaling mediated by NF-κB upregulation of proteins such as intercellular adhesion molecule-1(ICAM-1) and inflammation related molecules, such as NADPH oxidase and Janus kinase signal transducer. Caerulein also regulates thermoregulation, sedation and satiety.

Effects on perception of pain are conflicting. It prevents gall bladder pain, renal colic, and the pain of intermittent claudication; however, in general, it is seen as an antagonist of endogenous opioids.

Safety Information

• Storage Class Code: 13 - Non Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves