cibinetide   Click here for help

GtoPdb Ligand ID: 9677

Synonyms: ARA 290 | ARA-290 | PH-BSP | PHBSP
Immunopharmacology Ligand
Compound class: Peptide or derivative
Comment: Cibinetide (ARA 290) is an engineered peptide that mimics the 3 dimensional structure of the helix B surface domain of erythropoietin (EPO). It is designed to bind selectively to the non-hematopoietic EPO receptor (sometimes referred to as the innate repair receptor or IRR), that is believed to be a heterodimer of EPOR and the cytokine family beta common receptor (βCR, CD131) [1-2]. Non-hematopoietic EPO ligands have potential tissue protective and anti-inflammatory actions [4-6,8-10]. The IRR is suggested to be a point of integration between the immune system and pain signalling (via nociception) [11].
Cibinetide is SEQ ID NO. 282 (and peptide ID) as claimed in patent WO2009094172 [3].
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES OCC(C(=O)NC(C(=O)O)CO)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C1CCC(=O)N1)CCC(=O)O)CCC(=O)N)CC(C)C)CCC(=O)O)CCCN=C(N)N)C)CC(C)C)CC(=O)N
Isomeric SMILES OC[C@@H](C(=O)N[C@H](C(=O)O)CO)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]1CCC(=O)N1)CCC(=O)O)CCC(=O)N)CC(C)C)CCC(=O)O)CCCN=C(N)N)C)CC(C)C)CC(=O)N
InChI InChI=1S/C51H84N16O21/c1-22(2)17-30(47(84)65-32(19-36(53)71)48(85)66-33(20-68)49(86)67-34(21-69)50(87)88)63-40(77)24(5)57-41(78)25(7-6-16-56-51(54)55)59-43(80)29(11-15-39(75)76)62-46(83)31(18-23(3)4)64-45(82)27(8-12-35(52)70)60-44(81)28(10-14-38(73)74)61-42(79)26-9-13-37(72)58-26/h22-34,68-69H,6-21H2,1-5H3,(H2,52,70)(H2,53,71)(H,57,78)(H,58,72)(H,59,80)(H,60,81)(H,61,79)(H,62,83)(H,63,77)(H,64,82)(H,65,84)(H,66,85)(H,67,86)(H,73,74)(H,75,76)(H,87,88)(H4,54,55,56)/t24-,25-,26-,27-,28-,29-,30-,31-,32-,33-,34-/m0/s1
InChI Key WZTIQQBMSJTRBR-WYKNNRPVSA-N
References
1. Brines M, Cerami A. (2012)
The receptor that tames the innate immune response.
Mol Med, 18: 486-96. [PMID:22183892]
2. Brines M, Cerami A. (2013)
Erythropoietin and engineered innate repair activators.
Methods Mol Biol, 982: 1-11. [PMID:23456859]
3. Cerami A, Brines M. (2009)
Tissue protective peptides and peptide analogs for preventing and treating diseases and disorders associated with tissue damage.
Patent number: WO2009094172. Assignee: Araim Pharmaceuticals, Inc.. Priority date: 18/10/2017. Publication date: 22/01/2009.
4. Collino M, Thiemermann C, Cerami A, Brines M. (2015)
Flipping the molecular switch for innate protection and repair of tissues: Long-lasting effects of a non-erythropoietic small peptide engineered from erythropoietin.
Pharmacol Ther, 151: 32-40. [PMID:25728128]
5. Joshi D, Abraham D, Shiwen X, Baker D, Tsui J. (2014)
Potential role of erythropoietin receptors and ligands in attenuating apoptosis and inflammation in critical limb ischemia.
J Vasc Surg, 60 (1): 191-201, 201.e1-2. [PMID:24055514]
6. Liu Y, Luo B, Han F, Li X, Xiong J, Jiang M, Yang X, Wu Y, Zhang Z. (2014)
Erythropoietin-derived nonerythropoietic peptide ameliorates experimental autoimmune neuritis by inflammation suppression and tissue protection.
PLoS ONE, 9 (3): e90942. [PMID:24603865]
7. Nairz M, Haschka D, Dichtl S, Sonnweber T, Schroll A, Aßhoff M, Mindur JE, Moser PL, Wolf D, Swirski FK et al.. (2017)
Cibinetide dampens innate immune cell functions thus ameliorating the course of experimental colitis.
Sci Rep, 7 (1): 13012. [PMID:29026145]
8. Sanchis-Gomar F, Perez-Quilis C, Lippi G. (2013)
Erythropoietin receptor (EpoR) agonism is used to treat a wide range of disease.
Mol Med, 19: 62-4. [PMID:23615965]
9. Swartjes M, van Velzen M, Niesters M, Aarts L, Brines M, Dunne A, Cerami A, Dahan A. (2014)
ARA 290, a peptide derived from the tertiary structure of erythropoietin, produces long-term relief of neuropathic pain coupled with suppression of the spinal microglia response.
Mol Pain, 10: 13. [PMID:24529189]
10. Watanabe M, Lundgren T, Saito Y, Cerami A, Brines M, Östenson CG, Kumagai-Braesch M. (2016)
A Nonhematopoietic Erythropoietin Analogue, ARA 290, Inhibits Macrophage Activation and Prevents Damage to Transplanted Islets.
Transplantation, 100 (3): 554-62. [PMID:26683514]
11. Zhang W, Yu G, Zhang M. (2016)
ARA 290 relieves pathophysiological pain by targeting TRPV1 channel: Integration between immune system and nociception.
Peptides, 76: 73-9. [PMID:26774587]