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MedKoo Cat#: 333200 | Name: Caerulein
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Caerulein is a specific decapeptide obtained from the skin of Hila caerulea, an Australian amphibian. Caerulein 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.

Chemical Structure

Caerulein
Caerulein
CAS#17650-98-5

Theoretical Analysis

MedKoo Cat#: 333200

Name: Caerulein

CAS#: 17650-98-5

Chemical Formula: C58H73N13O21S2

Exact Mass: 1351.4485

Molecular Weight: 1352.41

Elemental Analysis: C, 51.51; H, 5.44; N, 13.46; O, 24.84; S, 4.74

Price and Availability

Size Price Availability Quantity
1mg USD 350.00 2 Weeks
5mg USD 950.00 2 Weeks
100mg USD 6,950.00 2 Weeks
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Related CAS #
No Data
Synonym
Caerulein; Ceruletide; Cerulein; Ceruletida
IUPAC/Chemical Name
(3S)-3-[[(2S)-5-amino-5-oxo-2-[[(2S)-5-oxopyrrolidine-2-carbonyl]amino]pentanoyl]amino]-4-[[(2S)-1-[[(2S,3R)-1-[[2-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1-oxo-3-(4-sulfooxyphenyl)propan-2-yl]amino]-4-oxobutanoic acid
InChi Key
YRALAIOMGQZKOW-HYAOXDFASA-N
InChi Code
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 Code
O=C(O)C[C@@H](C(N[C@@H](CC1=CC=CC=C1)C(N)=O)=O)NC([C@H](CCSC)NC([C@H](CC2=CNC3=C2C=CC=C3)NC(CNC([C@H]([C@H](O)C)NC([C@H](CC4=CC=C(OS(=O)(O)=O)C=C4)NC([C@@H](NC([C@@H](NC([C@H](CC5)NC5=O)=O)CCC(N)=O)=O)CC(O)=O)=O)=O)=O)=O)=O)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 1,352.41 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Huang C, Chen S, Zhang T, Li D, Huang Z, Huang J, Qin Y, Chen B, Cheng G, Ma F, Zhou M. TLR3 Ligand PolyI:C Prevents Acute Pancreatitis Through the Interferon-β/Interferon-α/β Receptor Signaling Pathway in a Caerulein-Induced Pancreatitis Mouse Model. Front Immunol. 2019 May 3;10:980. doi: 10.3389/fimmu.2019.00980. eCollection 2019. PubMed PMID: 31130960; PubMed Central PMCID: PMC6509240. 2: Yuan J, Hasdemir B, Tan T, Chheda C, Rivier J, Pandol SJ, Bhargava A. Protective effects of urocortin 2 against caerulein-induced acute pancreatitis. PLoS One. 2019 May 17;14(5):e0217065. doi: 10.1371/journal.pone.0217065. eCollection 2019. PubMed PMID: 31100090; PubMed Central PMCID: PMC6524941. 3: Amiti, Tamizhselvi R, Manickam V. Menadione (vitamin K3) inhibits hydrogen sulfide and substance P via NF-кB pathway in caerulein-induced acute pancreatitis and associated lung injury in mice. Pancreatology. 2019 Mar;19(2):266-273. doi: 10.1016/j.pan.2019.01.012. Epub 2019 Jan 18. PubMed PMID: 30685119. 4: Vojdani Z, Bagheri J, Talaei-Khozani T, Azarpira N, Salmannjad M, Farrokhi A. Fetal microchimerism in mouse caerulein-induced pancreatitis model. Iran J Basic Med Sci. 2018 Sep;21(9):889-895. doi: 10.22038/IJBMS.2018.26976.6595. PubMed PMID: 30524688; PubMed Central PMCID: PMC6272076. 5: Ozer Cakir O, Findik S. Diclofenac Sodium Treatment Ameliorates Extrapancreatic Organ Injuries in a Murine Model of Acute Pancreatitis Induced by Caerulein. Gastroenterol Res Pract. 2018 Oct 31;2018:9829208. doi: 10.1155/2018/9829208. eCollection 2018. PubMed PMID: 30515205; PubMed Central PMCID: PMC6234455. 6: Zhao D, Ge H, Ma B, Xue D, Zhang W, Li Z, Sun H. The interaction between ANXA2 and lncRNA Fendrr promotes cell apoptosis in caerulein-induced acute pancreatitis. J Cell Biochem. 2018 Nov 26. doi: 10.1002/jcb.28097. [Epub ahead of print] PubMed PMID: 30474876. 7: Ren Z, Li H, Zhang M, Zhao Y, Fang X, Li X, Chen W, Zhang H, Wang Y, Pan LL, Sun J. A Novel Derivative of the Natural Product Danshensu Suppresses Inflammatory Responses to Alleviate Caerulein-Induced Acute Pancreatitis. Front Immunol. 2018 Oct 30;9:2513. doi: 10.3389/fimmu.2018.02513. eCollection 2018. PubMed PMID: 30425719; PubMed Central PMCID: PMC6218618. 8: Quan S, Principe DR, Dean AE, Park SH, Grippo PJ, Gius D, Horikoshi N. Loss of Sirt2 increases and prolongs a caerulein-induced pancreatitis permissive phenotype and induces spontaneous oncogenic Kras mutations in mice. Sci Rep. 2018 Nov 7;8(1):16501. doi: 10.1038/s41598-018-34792-y. PubMed PMID: 30405152; PubMed Central PMCID: PMC6220268. 9: Huang HL, Tang GD, Liang ZH, Qin MB, Wang XM, Chang RJ, Qin HP. Role of Wnt/β-catenin pathway agonist SKL2001 in Caerulein-induced acute pancreatitis. Can J Physiol Pharmacol. 2019 Jan;97(1):15-22. doi: 10.1139/cjpp-2018-0226. Epub 2018 Oct 16. PubMed PMID: 30326193. 10: da Silva-Leite KES, Girão DKFB, de Freitas Pires A, Assreuy AMS, de Moraes PAF, Cunha AP, Ricardo NMPS, Criddle DN, de Souza MHLP, Pereira MG, Soares PMG. Ximenia americana heteropolysaccharides ameliorate inflammation and visceral hypernociception in murine caerulein-induced acute pancreatitis: Involvement of CB2 receptors. Biomed Pharmacother. 2018 Oct;106:1317-1324. doi: 10.1016/j.biopha.2018.07.067. Epub 2018 Jul 21. PubMed PMID: 30119202. 11: Velusamy RK, Tamizhselvi R. Protective effect of methylsulfonylmethane in caerulein-induced acute pancreatitis and associated lung injury in mice. J Pharm Pharmacol. 2018 Sep;70(9):1188-1199. doi: 10.1111/jphp.12946. Epub 2018 Jul 3. PubMed PMID: 29971769. 12: Wang Y, Wang G, Cui L, Liu R, Xiao H, Yin C. Angiotensin 1-7 ameliorates caerulein-induced inflammation in pancreatic acinar cells by downregulating Toll-like receptor 4/nuclear factor-κB expression. Mol Med Rep. 2018 Mar;17(3):3511-3518. doi: 10.3892/mmr.2017.8354. Epub 2017 Dec 27. PubMed PMID: 29286117; PubMed Central PMCID: PMC5802148. 13: Dolai S, Liang T, Orabi AI, Xie L, Holmyard D, Javed TA, Fernandez NA, Xie H, Cattral MS, Thurmond DC, Thorn P, Gaisano HY. Depletion of the membrane-fusion regulator Munc18c attenuates caerulein hyperstimulation-induced pancreatitis. J Biol Chem. 2018 Feb 16;293(7):2510-2522. doi: 10.1074/jbc.RA117.000792. Epub 2017 Dec 28. PubMed PMID: 29284677; PubMed Central PMCID: PMC5818203. 14: Huang W, Haynes AC, Mukherjee R, Wen L, Latawiec D, Tepikin AV, Criddle DN, Prinjha RK, Smithers N, Sutton R. Selective inhibition of BET proteins reduces pancreatic damage and systemic inflammation in bile acid- and fatty acid ethyl ester- but not caerulein-induced acute pancreatitis. Pancreatology. 2017 Sep - Oct;17(5):689-697. doi: 10.1016/j.pan.2017.06.005. Epub 2017 Jun 10. PubMed PMID: 28648518. 15: Komar HM, Serpa G, Kerscher C, Schwoegl E, Mace TA, Jin M, Yang MC, Chen CS, Bloomston M, Ostrowski MC, Hart PA, Conwell DL, Lesinski GB. Inhibition of Jak/STAT signaling reduces the activation of pancreatic stellate cells in vitro and limits caerulein-induced chronic pancreatitis in vivo. Sci Rep. 2017 May 11;7(1):1787. doi: 10.1038/s41598-017-01973-0. PubMed PMID: 28496202; PubMed Central PMCID: PMC5431930. 16: Bonior J, Ceranowicz P, Gajdosz R, Kuśnierz-Cabala B, Pierzchalski P, Warzecha Z, Dembiński A, Pędziwiatr M, Kot M, Leja-Szpak A, Nawrot-Porąbka K, Link-Lenczowski P, Olszanecki R, Bartuś K, Jaworek J. Molecular Ghrelin System in the Pancreatic Acinar Cells: The Role of the Polypeptide, Caerulein and Sensory Nerves. Int J Mol Sci. 2017 May 2;18(5). pii: E929. doi: 10.3390/ijms18050929. PubMed PMID: 28468316; PubMed Central PMCID: PMC5454842. 17: Shapiro JP, Komar HM, Hancioglu B, Yu L, Jin M, Ogata Y, Hart PA, Cruz-Monserrate Z, Lesinski GB, Conwell DL. Laser Capture Microdissection of Pancreatic Acinar Cells to Identify Proteomic Alterations in a Murine Model of Caerulein-Induced Pancreatitis. Clin Transl Gastroenterol. 2017 Apr 13;8(4):e89. doi: 10.1038/ctg.2017.15. PubMed PMID: 28406494; PubMed Central PMCID: PMC5415897. 18: Yin T, Peeters R, Liu Y, Feng Y, Zhang X, Jiang Y, Yu J, Dymarkowski S, Himmelreich U, Oyen R, Ni Y. Visualization, Quantification and Characterization of Caerulein-Induced Acute Pancreatitis in Rats by 3.0T Clinical MRI, Biochemistry and Histomorphology. Theranostics. 2017 Jan 1;7(2):285-294. doi: 10.7150/thno.16282. eCollection 2017. PubMed PMID: 28042334; PubMed Central PMCID: PMC5197064. 19: Sun Y, He Y, Wang F, Zhang H, de Vos P, Sun J. Low-methoxyl lemon pectin attenuates inflammatory responses and improves intestinal barrier integrity in caerulein-induced experimental acute pancreatitis. Mol Nutr Food Res. 2017 Apr;61(4). doi: 10.1002/mnfr.201600885. Epub 2017 Jan 30. PubMed PMID: 27921358. 20: Song R, Yu D, Park J. Changes in gene expression of tumor necrosis factor alpha and interleukin 6 in a canine model of caerulein-induced pancreatitis. Can J Vet Res. 2016 Jul;80(3):236-41. PubMed PMID: 27408338; PubMed Central PMCID: PMC4924559.

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