Ceruletide

Ceruletide is 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 gastrointestinal 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. It has a role as a diagnostic agent and a gastrointestinal drug.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.
Ceruletide(CAS 17650-98-5)

CAT No: C03003

CAS No:17650-98-5

Synonyms/Alias:Caerulein;Ceruletide;17650-98-5;Cerulein;Ceruletida;Ceruletidum;Ceruletidum [INN-Latin];Ceruletida [INN-Spanish];Ceruletide [USAN:INN:BAN];CCRIS 3063;5-Oxo-L-prolyl-L-glutaminyl-L-alpha-aspartyl-O-sulfo-L-tyrosyl-L-threonylglycyl-L-tryptophyl-L-methionyl-L-alpha-aspartyl-L-phenylalaninamide;CHEBI:59219;CERULETIDE [MI];CERULETIDE [INN];CERULETIDE [USAN];5-Oxo-L-prolyl-L-glutaminyl-L-aspartyl-L-tyrosyl-L-threonylglycyl-L-tryptophyl-L-methionyl-L-aspartylphenyl-L-alaninamide 4-(hydrogen sulfate) (ester);CERULETIDE [MART.];CERULETIDE [WHO-DD];888Y08971B;DTXSID8040434;Caerulein (~85%);Ceruletidum (INN-Latin);Ceruletida (INN-Spanish);CERULETIDE (MART.);(3S)-3-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}-3-[(2S)-2-[(2S)-2-{2-[(2S,3R)-2-[(2S)-2-[(2S)-2-[(2S)-4-carbamoyl-2-{[(2S)-5-oxopyrrolidin-2-yl]formamido}butanamido]-3-carboxypropanamido]-3-[4-(sulfooxy)phenyl]propanamido]-3-hydroxybutanamido]acetamido}-3-(1H-indol-3-yl)propanamido]-4-(methylsulfanyl)butanamido]propanoic acid;pGlu-Gln-Asp-Tyr(SO3H)-Thr-Gly-Trp-Met-Asp-Phe-NH2;Ceruletid;5-OXO-L-PROLYL-L-GLUTAMINYL-L-A-ASPARTYL-O-SULFO-L-TYROSYL-L-THREONYLGLYCYL-L-TRYPTOPHYL-L-METHIONYL-L-.ALPHA.-ASPARTYL-L-PHENYLALANINAMIDE;5-oxo-L-prolyl-L-glutaminyl-L-a-aspartyl-O-sulfo-L-tyrosyl-L-threonylglycyl-L-tryptophyl-L-methionyl-L-a-aspartyl-L-phenylalaninamide;Ceruletide (USAN/INN);UNII-888Y08971B;(3S)-3-(((1S)-1-carbamoyl-2-phenylethyl)carbamoyl)-3-((2S)-2-((2S)-2-(2-((2S,3R)-2-((2S)-2-((2S)-2-((2S)-4-carbamoyl-2-(((2S)-5-oxopyrrolidin-2-yl)formamido)butanamido)-3-carboxypropanamido)-3-(4-(sulfooxy)phenyl)propanamido)-3-hydroxybutanamido)acetamido)-3-(1H-indol-3-yl)propanamido)-4-(methylsulfanyl)butanamido)propanoic acid;Caerulein, sulfated;Caerulein triammonium;MFCD00076478;ceruletide diethylamide;Ceruletide (Standard);SCHEMBL29520;GTPL7589;CHEMBL1201355;DTXCID6020434;HY-A0190R;V04CC04;YRALAIOMGQZKOW-HYAOXDFASA-N;HY-A0190;AKOS030529560;CS-5876;DB00403;AS-56061;FC108931;NS00004791;C73362;D03442;EN300-23248418;Q5065299;(3S)-3-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}-3-[(2S)-2-[(2S)-2-{2-[(2S,3R)-2-[(2S)-2-[(2S)-2-[(2S)-4-carbamoyl-2-{[(2S)-5-oxopyrrolidin-2-yl]formamido}butanamido]-3-carboxypropanamido]-3-[4-(sulfooxy)phenyl]propanamido]-3-hydroxybutanamido]acetamido}-3-(indol-3-yl)propanamido]-4-(methylsulfanyl)butanamido]propanoic acid;5-OXO-L-PROLYL-L-GLUTAMINYL-L-A-ASPARTYL-O-SULFO-L-TYROSYL-L-THREONYLGLYCYL-L-TRYPTOPHYL-L-METHIONYL-L-ALPHA-ASPARTYL-L-PHENYLALANINAMIDE;

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

Custom Peptide Synthesis
cGMP Peptide
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  • IND and NDA support
  • Drug master files (DMF) filing
M.F/Formula
C58H73N13O21S2
M.W/Mr.
1352.4
Sequence
One Letter Code:XQDXTGWMDF
Three Letter Code:H-Pyr-Gln-Asp-Tyr(SO3H)-Thr-Gly-Trp-Met-Asp-Phe-NH2
Activity
Agonist
Biological Activity
CCK agonist. Stimulates biosynthesis of pancreatic enzymes in AR4-2J pancreatic cells in vitro. Induces acute pancreatitis in mice. Also enhances proteasome activity in Gdeg mice.
Target
CCK receptor

Ceruletide, also known as caerulein, is a decapeptide originally isolated from the skin of certain amphibians and is structurally related to the gastrointestinal hormone cholecystokinin. Distinguished by its ability to mimic the physiological effects of endogenous peptides, ceruletide is widely utilized in diverse research applications, particularly those investigating digestive system functions and peptide receptor interactions. Its robust activity in stimulating smooth muscle contraction and exocrine secretion has made it a valuable tool in both basic and applied scientific studies. The compound's stability and bioactivity in experimental models allow for precise modulation and observation of physiological responses, enabling researchers to elucidate complex biological pathways with a high degree of specificity and reproducibility.

Gastrointestinal Physiology Research: Ceruletide serves as a pivotal agent in the study of gastrointestinal motility and secretion. By binding to cholecystokinin receptors, it induces contraction of the gallbladder and smooth muscle within the digestive tract, facilitating the investigation of mechanisms underlying bile flow, pancreatic enzyme secretion, and intestinal peristalsis. Scientists leverage its potent stimulatory effects to model physiological and pathophysiological states in animal and cell-based systems, thereby advancing the understanding of digestive processes and related disorders.

Pancreatic Function Analysis: In experimental settings, caerulein is frequently employed to stimulate the pancreas, prompting the release of digestive enzymes such as amylase and lipase. This property enables researchers to dissect the regulatory pathways governing pancreatic exocrine function, as well as to develop and refine models of pancreatic inflammation and injury. The reproducible induction of enzyme secretion and tissue responses makes it an indispensable tool for probing the molecular and cellular events associated with pancreatic physiology.

Neurobiology and Peptide Receptor Studies: As a cholecystokinin analog, ceruletide provides unique opportunities to investigate neural pathways and receptor pharmacology. Its interaction with central and peripheral receptors facilitates the study of neurotransmitter release, neuronal signaling, and the modulation of pain perception. By utilizing this peptide in neurobiological assays, researchers can explore the roles of CCK receptors in the brain and peripheral nervous system, shedding light on mechanisms of neuropeptide action and receptor-mediated signaling.

Pharmacological Screening and Drug Development: Ceruletide's well-characterized receptor interactions and biological effects make it an effective reference compound in pharmacological assays. It is commonly used to evaluate the efficacy and specificity of novel cholecystokinin receptor antagonists or agonists, supporting the development of new therapeutic agents targeting gastrointestinal and neurological pathways. Its application in high-throughput screening and receptor binding studies accelerates the identification and optimization of candidate molecules with desired pharmacodynamic profiles.

Inflammation and Disease Modeling: The ability of caerulein to induce acute and chronic responses in various tissues has established it as a standard agent in the creation of experimental models of inflammation, particularly in the pancreas and gastrointestinal tract. Researchers utilize these models to investigate the cellular and molecular events involved in inflammatory processes, test anti-inflammatory compounds, and unravel the pathophysiology of diseases such as pancreatitis. The reproducibility and reliability of these models enhance their value for translational research and the exploration of new therapeutic strategies.

In summary, ceruletide continues to be a cornerstone in biochemical, physiological, and pharmacological research due to its multifaceted bioactivity and relevance to key regulatory systems. Its application spans from fundamental studies of digestive and neural function to advanced drug discovery and disease modeling, supporting the advancement of scientific knowledge and the development of innovative research tools.

Long-term Storage Conditions
Soluble to 1 mg/ml in water
Shipping Condition
Evaluation sample solution : ship with blue ice
All other available size: ship with RT , or blue ice upon request
InChI
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-HYAOXDFASA-N
Canonical SMILES
CC(C(C(=O)NCC(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)NC(CCSC)C(=O)NC(CC(=O)O)C(=O)NC(CC3=CC=CC=C3)C(=O)N)NC(=O)C(CC4=CC=C(C=C4)OS(=O)(=O)O)NC(=O)C(CC(=O)O)NC(=O)C(CCC(=O)N)NC(=O)C5CCC(=O)N5)O
Isomeric SMILES
C[C@H]([C@@H](C(=O)NCC(=O)N[C@@H](CC1=CNC2=CC=CC=C21)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CC3=CC=CC=C3)C(=O)N)NC(=O)[C@H](CC4=CC=C(C=C4)OS(=O)(=O)O)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@@H]5CCC(=O)N5)O

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