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Merck

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

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About This Item

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

Key Documents

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Product Name

Caerulein, ≥95% (HPLC)

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

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 key

YRALAIOMGQZKOW-HJMGKOKZSA-N

assay

≥95% (HPLC)

form

powder

technique(s)

immunohistochemistry: suitable

color

white

storage temp.

−20°C

Quality Level

200

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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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

C9026-VAR: + C9026-1MG-PW: + C9026-.1MG-PW: + C9026-PPG: + C9026-.5MG: + C9026-PH: + C9026-BULK-N: + C9026-.5MG-PW: + C9026-.1MG: + C9026PROC: + C9026-BULK: + C9026-1MG:

jan

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Certificates of Analysis (COA)

Lot/Batch Number
0000525240
0000525240
0000479957
0000479957
0000464828

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Shan-Ming Chen et al.
Scientific reports, 10(1), 20319-20319 (2020-11-25)
Pancreatic cancer is one of the most lethal and chemo-resistant cancers worldwide. Growing evidence supports the theory that the gut microbiota plays an essential role in modulating the host response to anti-cancer therapy. The present study aimed to explore the
Inflammation-Induced Expression and Secretion of MicroRNA 122 Leads to Reduced Blood Levels of Kidney-Derived Erythropoietin and Anemia
Gastroenterology, 999-1010 (2016)
Membrane Proteome Analysis of Cerulein-Stimulated Pancreatic Acinar Cells: Implication for Early Event of Acute Pancreatitis
Jangwon Lee
Gut and Liver, 4(1) (2010)
Abba Kastin, Abba J. Kastin
Handbook of Biologically Active Peptides (2011)
Acinar cell apoptosis and the origin of tubular complexes in caerulein-induced pancreatitis
Lynne E Reid
International Journal of Experimental Pathology (1999)
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