C9026

Caerulein

≥95% (HPLC), suitable for immunohistochemistry

• 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
• NACRES: NA.26
• PubChem Substance ID: 24893129
• UNSPSC Code: 12352209
• MDL number: MFCD00076478
• Beilstein/REAXYS Number: 5422487

Properties

• Product Name: Caerulein, ≥95% (HPLC)
• Quality Segment: 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

Application

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

Biochem/physiol Actions

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.

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.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)