CAERULEIN | 17650-98-5

CAERULEIN Properties

Melting point	224-226° (dec)
alpha	D20 -26° (c = 1 in DMF)
Density	1.464±0.06 g/cm3(Predicted)
storage temp.	Sealed in dry,Store in freezer, under -20°C
solubility	0.05 M ammonium hydroxide: 1 mg/mL, clear, colorless
pka	-4.17±0.18(Predicted)
form	Solid
color	White to Off-White
Water Solubility	Soluble to 1 mg/ml in water
Merck	13,2015
BRN	5422487
InChIKey	YRALAIOMGQZKOW-HYAOXDFASA-N
EWG's Food Scores	1
FDA UNII	888Y08971B
ATC code	V04CC04

SAFETY

Risk and Safety Statements

WGK Germany	3
F	10-21
HS Code	2935909099

CAERULEIN price More Price(21)

Manufacturer	Product number	Product description	CAS number	Packaging	Price	Updated	Buy
Sigma-Aldrich	C9026	Caerulein ≥95% (HPLC)	17650-98-5	0.1mg	$118	2024-03-01	Buy
Sigma-Aldrich	C9026	Caerulein ≥95% (HPLC)	17650-98-5	0.5MG	$346	2024-03-01	Buy
Sigma-Aldrich	C9026	Caerulein ≥95% (HPLC)	17650-98-5	1MG	$515	2024-03-01	Buy
Alfa Aesar	J64320	Caerulein, sulfated	17650-98-5	1mg	$190	2023-06-20	Buy
Alfa Aesar	J64320	Caerulein, sulfated	17650-98-5	0.5mg	$96.4	2021-12-16	Buy

Product number	Packaging	Price	Buy
C9026	0.1mg	$118	Buy
C9026	0.5MG	$346	Buy
C9026	1MG	$515	Buy
J64320	1mg	$190	Buy
J64320	0.5mg	$96.4	Buy

CAERULEIN Chemical Properties,Uses,Production

Discovery

Caerulein is a peptide secreted from the skin of frogs. Caerulein shares the conserved C-terminal sequence that is responsible for receptor activation with vertebrate gastrin and cholecystokinin (CCK), and functions as their agonist. Caerulein was first described in a number of Australian amphibians as a polypeptide that stimulates pancreatic external secretion and elicits a decrease in blood pressure and extravascular smooth muscle contraction in mammals. Caerulein was first purified from the Australian tree frog Hyla caerulea in 1967.

Structure

Caerulein is a decapeptide that contains the C-terminal four aa sequence (Trp-Met-Asp-Phe-NH2) that is conserved in the vertebrate gastrin and CCK. A pyroglutamate residue is present in the N-terminus, and a C-terminal phenylalanine residue is amidated. Caerulein possesses a sulfated tyrosine at the seventh residue from the C-terminus. Two caerulein precursors, preproCPF-St6 and preproCPF-St7, have been reported in the western clawed frog Silurana tropicalis. The precursor contains a signal peptide, an antimicrobial peptide called a caerulein precursor fragment (CPF), and mature caerulein. Caerulein has been identified in various frog species, including Xenopus laevis, Litoria splendida, and Hylambates maculatus. Sauvage’s leaf frog, Phyllomedusa sauvagei, possesses a caerulein-like nonapeptide called phyllocaerulein. These peptides share the C-terminal four aa sequence. Caerulein 1.2 of the magnificent tree frog, Litoria splendida, does not have the consensus 4-aa sequence (Trp-Phe-Asn-Phe-NH2). Mr: H. caerulea caerulein, 1352. Caerulein is soluble in DMSO, but insoluble in acetone and diethyl ether.
Structure of Caerulein

Gene, mRNA, and precursor

In S. tropicalis, two caerulein precursor genes have been identified, and they have a four-exon structure. Two caerulein mRNAs are 428 and 418 bases in length and encode precursors of 98 and 91 aa residues, respectively.

Synthesis and release

In X. laevis, a caerulein-like substance is released in response to adrenaline treatment. This substance stimulates the contraction of the guinea pig gall bladder and pancreatic secretions in rats. Amino acid analysis of the secreted substance shows a similar aa composition to that of caerulein. Seasonal changes in caerulein synthesis have been reported. For example, L. splendida synthesizes caerulein during the reproductive season in summer. In winter, the synthesis of caerulein is less active. Also, the desulfated form of caerulein increases and caerulein 1.2, which has relatively low biological activity, is released.

Biological functions

Treatment of the outside of frog skin with caerulein results in an influx of sodium ions while treatment of the inside of frog skin represses sodium ion influx. These results suggest that caerulein is associated with the maintenance of sodium ion levels in the dermal cells. In addition, preprocaerulein contains antimicrobial CRF, and caerulein can affect gastrin and CCK signaling in other animals. These suggest that CRF and caerulein may function as defensive peptides against microbes and predators in the frog.

Clinical implications

Caerulein is used to generate rodent models of pancreatitis. Caerulein acts as an agonist of CCK1R and CCK2R because of its structural similarity to gastrin and CCK. Treatment with a high dose of caerulein induces the secretion of pancreatic juice and results in acute pancreatitis in rodents.

Originator

Ceosunin,Kyowa Hakko,Japan,1976

Uses

Stimulant (gastric secretory).

Uses

Caerulein is a ten amino acid oligopeptide that stimulates smooth muscle and increases digestive secretions. It is similar in action and composition to cholecystokinin. It stimulates gastric, biliary, and pancreatic secretion; and certain smooth muscle. It is used in paralytic ileus and as diagnostic aid in pancreatic malfunction. It is used to induce pancreatitis in experimental animal models.

Definition

ChEBI: A decapeptide comprising 5-oxoprolyl, glutamyl, aspartyl, O-sulfotyrosyl, threonyl, glycyl, tryptopyl, methionyl, aspartyl and phenylalaninamide residues in sequence. Found in the skins of certain Australian amphibians, it is an analogue of the gastrointes inal peptide hormone cholecystokinin and stimulates gastric, biliary, and pancreatic secretion. It is used in cases of paralysis of the intestine (paralytic ileus) and as a diagnostic aid in pancreatic malfunction.

Manufacturing Process

The tetrapeptide, L-pyroglutamyl-L-glutaminyl-L-aspartyl-L-tyrosine-azide (I), is condensed with the hexapeptide, L-threonyl-glycyl-L-tryptophanyl-L-methionyl-L-aspartyl-L-phenylalaninamide (II), having the hydroxyl of the threonyl radical blocked by an acyl radical in a suitable solvent, such as dimethylformamide, to obtain the decapeptide, L-pyroglutamyl-L-glutaminyl-L-aspartyl-L-tyrosyl-L-threonylglycyl-L-tryptophanyl-L-methionyl-L-aspartyl-Lphenylaninamide (III) having the hydroxy group of the threonyl radical blocked by an acyl radical. The decapeptide (III) is treated, at low temperature, with the complex anhydrous pyridine sulfuric anhydride finally to obtain the decapeptide, L-pyroglutamyl-L-glutaminyl-L-aspartyl-L-tyrosyl-L-threonyl-glycyl-L-tryptophanyl-L-methionyl-L-aspartyl-L-phenylalaninamide (IV) having the phenolic group of the tyrosyl radical protected by a sulfate radical and the hydroxyl of the threonyl radical protected by an acyl radical.
Finally, by mild alkaline hydrolysis of the decapeptide (IV) one obtains the decapeptide product.

Therapeutic Function

Stimulant (gastric secretory)

Hazard

A poison.

Safety Profile

A poison by subcutaneous route. When heated to decomposition it emits toxic vapors of NOx and SOx

storage

Store at -20°C

CAERULEIN Preparation Products And Raw materials

Raw materials

Sodium carbonate

Preparation Products

CAERULEIN Suppliers

Global( 136)Suppliers

Supplier	Tel	Email	Country	ProdList	Advantage
Cellmano Biotech Limited	0551-65326643 18156095617	info@cellmano.com	China	999	58
Hebei Mojin Biotechnology Co., Ltd	+8613288715578	sales@hbmojin.com	China	12452	58
Shanghai Daken Advanced Materials Co.,Ltd	+86-371-66670886	info@dakenam.com	China	15371	58
ATK CHEMICAL COMPANY LIMITED	+undefined-21-51877795	ivan@atkchemical.com	China	32480	60
Shanghai Zheyan Biotech Co., Ltd.	18017610038	zheyansh@163.com	CHINA	3620	58
career henan chemical co	+86-0371-86658258	sales@coreychem.com	China	29914	58
Hubei Jusheng Technology Co.,Ltd.	18871490254	linda@hubeijusheng.com	CHINA	28180	58
BOC Sciences	+1-631-485-4226	inquiry@bocsci.com	United States	19553	58
Shanghai Longyu Biotechnology Co., Ltd.	+8615821988213	info@longyupharma.com	China	2531	58
Chongqing Chemdad Co., Ltd	+86-023-61398051 +8613650506873	sales@chemdad.com	China	39916	58

Supplier	Advantage
Cellmano Biotech Limited	58
Hebei Mojin Biotechnology Co., Ltd	58
Shanghai Daken Advanced Materials Co.,Ltd	58
ATK CHEMICAL COMPANY LIMITED	60
Shanghai Zheyan Biotech Co., Ltd.	58
career henan chemical co	58
Hubei Jusheng Technology Co.,Ltd.	58
BOC Sciences	58
Shanghai Longyu Biotechnology Co., Ltd.	58
Chongqing Chemdad Co., Ltd	58

View Lastest Price from CAERULEIN manufacturers

Update time	Product	Price	Min. Order	Purity	Supply Ability	Manufacturer
2023-09-28	CAERULEIN 17650-98-5	US $0.00 / KG	1KG	99%	50000KG/month	Hebei Mojin Biotechnology Co., Ltd
2019-12-17	Caerulein, 17650-98-5	US $500.00 / mg	10mg	95% HPLC	10g	Cellmano Biotech Limited
2019-07-06	CAERULEIN 17650-98-5	US $8.80 / KG	1KG	97%-99%	100kg	Career Henan Chemical Co

CAERULEIN
17650-98-5
US $0.00 / KG
99%
Hebei Mojin Biotechnology Co., Ltd

Caerulein,
17650-98-5
US $500.00 / mg
95% HPLC
Cellmano Biotech Limited

CAERULEIN
17650-98-5
US $8.80 / KG
97%-99%
Career Henan Chemical Co

CAERULEIN Spectrum

CAERULEIN(17650-98-5)MS

17650-98-5(CAERULEIN)Related Search:

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1of4

[TYR(SO3H)4]CAERULEIN PGLU-GLN-ASP-TYR[SO3H]-THR-GLY-TRP-MET-ASP-PHE-NH2 PYROGLU-GLN-ASP-TYR[SO3H]-THR-GLY-TRP-MET-ASP-PHE-NH2 PYROGLU-GLN-ASP-TYR(SO3H)-THR-GLY-TRP-MET-ASP-PHE-NH2.2NH3 PYR-QD-Y(SO3H)-TGWMDF-NH2 PYR-GLN-ASP-TYR(SO3H)-THR-GLY-TRP-MET-ASP-PHE-NH2 GLP-GLN-ASP-TYR(SO3H)-THR-GLY-TRP-MET-ASP-PHE-NH2 CAERULEIN SULFATED [Tyr(SO3H)4]Caerulein, Caerulein Sulfated, Cerulein, Ceruletide, pGlu-Gln-Asp-Tyr(SO3H)-Thr-Gly-Trp-Met-Asp-Phe-NH2 5-Oxo-L-Pro-L-Gln-L-αAsp-O-sulfo-L-Tyr-L-Thr-Gly-L-Trp-L-Met-L-αAsp-L-Phe-NH2 Ceosunin FI-6934 Caerulein,Caerulein Sulfated, Cerulein, Ceruletide, [Tyr(SO3H)4]Caerulein, pGlu-Gln-Asp-Tyr(SO3H)-Thr-Gly-Trp-Met-Asp-Phe-NH2 Caerulein Ceruletide, Cerulein Ceruletide, Cerulein Caerulein, Ceruletide Caerulein (~90%) CAERULEIN 500 UG CAERULEIN Caerulein ammonium salt Ceruletide, >99% CAERULEIN USP/EP/BP Caerulein (Caerulein CERULEIN CERULETIDE (3S,6S,9S,15S,18S,21S)-9-((1H-Indol-3-yl)methyl)-3-(((S)-1-amino-1-oxo-3-phenylpropan-2-yl)carbamoyl)-21-((S)-5-amino-5-oxo-2-((S)-5-oxopyrrolidine-2-carboxamido)pentanamido)-15-((R)-1-hydroxyethyl)-6-(2-(methylthio)ethyl)-5,8,11,14,17,20-hexaoxo-18-(4-(sulfooxy)benzyl)-4,7,10,13,16,19-hexaazatricosanedioic acid Ceruletide ammonium salt 17650-98-5 C58H73N13O21S2 Amino Acids and Peptides BioChemical Biochemicals and Reagents Peptides Other Peptides peptide