Discovery Structure Gene, mRNA, and precursor Synthesis and release Biological functions Clinical implications
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CAERULEIN

Discovery Structure Gene, mRNA, and precursor Synthesis and release Biological functions Clinical implications
CAERULEIN Structure
CAERULEIN
  • CAS No.17650-98-5
  • Chemical Name:CAERULEIN
  • CBNumber:CB2384634
  • Molecular Formula:C58H73N13O21S2
  • Formula Weight:1352.4
  • MOL File:17650-98-5.mol
CAERULEIN Property
  • 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
  • WGK Germany  :3
  • F  :10-21
  • HS Code  :2935909099
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal word
  • Hazard statements
  • Precautionary statements
CAERULEIN Price More Price(1)
  • Brand: Sigma-Aldrich(India)
  • Product number: C9026
  • Product name : Caerulein
  • Purity: ≥95% (HPLC)
  • Packaging: 0.1MG
  • Price: ₹8313.6
  • Updated: 2022/06/14
  • Buy: Buy

CAERULEIN Chemical Properties,Usage,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
Preparation Products
CAERULEIN Suppliers
Global(152)Suppliers
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    BOC Sciences
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CAERULEIN Spectrum
17650-98-5, CAERULEINRelated Search:
  • peptide
  • 目录多肽
  • 抑制剂
  • 化学试剂
  • 生化试剂
  • 原料药
  • 药物肽
  • 优势产品
  • 药物多肽
  • 定制
  • 生化试剂-蛋白质
  • 多肽
  • Other Peptides
  • Peptides
  • Biochemicals and Reagents
  • BioChemical
  • Amino Acids and Peptides
  • C58H73N13O21S2
  • CERULETIDE 铵盐
  • CAERULEIN 雨蛙素 | CAS 17650-98-5
  • CAERULEIN (FI-6934) 雨蛙素
  • CAERULEIN (雨蛙素,雨蛙肽)
  • CERULETIDE 铵盐,CCK激动剂
  • 化合物CERULETIDE AMMONIUM SALT
  • 雨蛙素 ≥95.0%
  • (3S,6S,9S,15S,18S,21S)-9-((1H-吲哚-3-基)甲基)-3-(((S)-1-氨基-1-氧代-3-苯丙烷-2-基)氨甲酰基)-21-((S)-5-氨基-5-氧代-2-((S)-5-氧代吡咯烷-2-甲酰胺)戊酰胺基)-15-((R)-1-羟乙基)-6-(2-(甲硫基)乙基)-5,8,11,14,17,20-六氧代-18-(4-(亚砜基)苄基)-4,7,10,13,16,19-六氮杂二十三烷二酸
  • CAERULEIN雨蛙素
  • CERULETIDE游离态
  • 雨蛙素,雨蛙肽,硫酸化蓝肽
  • 雨蛙素 雨蛙肽 蓝肽
  • 雨蛙肽
  • 硫酸化蓝肽
  • 蓝肽
  • 雨蛙素
  • 17650-98-5
  • Caerulein triammonium
  • Caerulein, Ceruletide - 1 mg
  • Ceruletide ammonium salt
  • (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
  • CERULEIN
  • Caerulein (Caerulein
  • CAERULEIN USP/EP/BP
  • Ceruletide, >99%
  • Caerulein ammonium salt
  • CAERULEIN
  • CAERULEIN 500 UG
  • Caerulein (~90%)
  • Caerulein, Ceruletide
  • Ceruletide, Cerulein
  • Caerulein Ceruletide, Cerulein
  • Caerulein,Caerulein Sulfated, Cerulein, Ceruletide, [Tyr(SO3H)4]Caerulein, pGlu-Gln-Asp-Tyr(SO3H)-Thr-Gly-Trp-Met-Asp-Phe-NH2
  • FI-6934
  • Ceosunin
  • 5-Oxo-L-Pro-L-Gln-L-αAsp-O-sulfo-L-Tyr-L-Thr-Gly-L-Trp-L-Met-L-αAsp-L-Phe-NH2
  • [Tyr(SO3H)4]Caerulein, Caerulein Sulfated, Cerulein, Ceruletide, pGlu-Gln-Asp-Tyr(SO3H)-Thr-Gly-Trp-Met-Asp-Phe-NH2
  • CAERULEIN SULFATED
  • GLP-GLN-ASP-TYR(SO3H)-THR-GLY-TRP-MET-ASP-PHE-NH2

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