balixafortide   Click here for help

GtoPdb Ligand ID: 11587

Synonyms: POL-6326 | POL6326
Compound class: Peptide or derivative
Comment: Balixafortide (POL6326) is an orally bioavailable cyclic peptide antagonist of the CXC chemokine receptor 4 (CXCR4). The CXCR4/SDF-1 axis regulates function and trafficking of immune cells. Balixafortid blocks interaction of the receptor with its ligand CXCL12 (SDF-1) [1]. Disrupting the SDF-1/CXCR4 interaction is ubeing exploited for mobilisation and harvesting of peripheral blood HSCs for transplant procedures, and in cancer therapy for antimetastatic activity (by dislodging stem cells from the bone marrow).

The peptide structure is cyclo[L-alanyl-L-cysteinyl-L-seryl-L-alanyl-D-prolyl-(2S)-2,4-diaminobutanoyl-L-arginyl-L-tyrosyl-L-cysteinyl-L-tyrosyl-L-glutaminyl-L-lysyl-D-prolyl-L-prolyl-L-tyrosyl-L-histidyl](2-9)-disulfide (from the INN record for balixafortide).
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 NCCCC[C@@H]1NC(=O)[C@H]2CCCN2C(=O)[C@@H]2CCCN2C(=O)[C@H](Cc2ccc(cc2)O)NC(=O)[C@@H](NN[C@@H](C)C(=O)N[C@H]2CSSC[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC1=O)CCC(=O)N)Cc1ccc(cc1)O)C(=O)N[C@@H](Cc1ccc(cc1)O)C(=O)C(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCN)NC(=O)[C@@H]1N(C(=O)[C@@H](NC(=O)[C@@H](NC2=O)CO)C)CCC1)Cc1[nH]cnc1
Isomeric SMILES NCCCC[C@@H]1NC(=O)[C@H]2CCCN2C(=O)[C@@H]2CCCN2C(=O)[C@H](Cc2ccc(cc2)O)NC(=O)[C@@H](NN[C@@H](C)C(=O)N[C@H]2CSSC[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC1=O)CCC(=O)N)Cc1ccc(cc1)O)C(=O)N[C@@H](Cc1ccc(cc1)O)C(=O)C(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCN)NC(=O)[C@@H]1N(C(=O)[C@@H](NC(=O)[C@@H](NC2=O)CO)C)CCC1)Cc1[nH]cnc1
InChI InChI=1S/C84H118N24O21S2/c1-44-70(116)102-62-41-130-131-42-63(77(123)98-57(35-46-14-20-50(110)21-15-46)69(115)68(114)53(10-5-31-91-84(88)89)94-73(119)56(28-30-86)97-79(125)64-11-6-32-106(64)81(127)45(2)93-76(122)61(40-109)101-78(62)124)103-74(120)58(36-47-16-22-51(111)23-17-47)99-72(118)55(26-27-67(87)113)95-71(117)54(9-3-4-29-85)96-80(126)65-12-7-33-107(65)83(129)66-13-8-34-108(66)82(128)60(37-48-18-24-52(112)25-19-48)100-75(121)59(105-104-44)38-49-39-90-43-92-49/h14-25,39,43-45,53-66,104-105,109-112H,3-13,26-38,40-42,85-86H2,1-2H3,(H2,87,113)(H,90,92)(H,93,122)(H,94,119)(H,95,117)(H,96,126)(H,97,125)(H,98,123)(H,99,118)(H,100,121)(H,101,124)(H,102,116)(H,103,120)(H4,88,89,91)/t44-,45-,53-,54-,55-,56-,57-,58-,59-,60-,61-,62-,63-,64+,65+,66-/m0/s1
InChI Key OYWQJZAVFWOOBF-WBMPNIIXSA-N
Bioactivity Comments
Balixafortide achieves peak mobilisation of ~38 CD34 positive cells per μL in healthy male volunteers [1]. We have been unable to find a potency value for balixafortide vs. CXCR4. A close analogue, POL5551, has an IC50 of 1.7 nM in cells exogenously expressing human CXCR4 [2].
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
CXCR4 Hs Antagonist Antagonist - - - 1
⤷ [1]