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AMD 3465 hexahydrobromide
- Parent CAS: 185991-24-6
- Soluble in water and DMSO
- MF: C24H38N6.6HBr
- MW: 896.07
Description
AMD 3465 hexahydrobromide is a potent and selective CXCR4 chemokine receptor antagonist that blocks CXCR4-dependent ligand and viral-entry interactions.
CXCR4 binds CXCL12/SDF-1 and regulates immune-cell trafficking, stem-cell homing, tumor migration and HIV entry. AMD 3465 is reported to block HIV gp120 interaction with CXCR4 and to show stronger CXCR4 antagonist activity than AMD3100 in comparative assays.
Key Features
- Potent CXCR4 antagonist
- Blocks CXCR4-dependent HIV gp120 interaction
- Inhibits CXCL12/SDF-1 chemokine receptor signaling
- Useful for immune trafficking and viral-entry research
Applications
- CXCR4 receptor pharmacology
- HIV entry and antiviral mechanism studies
- CXCL12-mediated chemotaxis assays
- Stem-cell trafficking and tumor migration research
More Information
| Parent CAS No. | 185991-24-6 |
|---|---|
| Chemical Name | N-(4-((1,4,8,11-tetraazacyclotetradecan-1-yl)methyl)benzyl)-1-(pyridin-2-yl)methanamine hexahydrobromide |
| SMILES | C1(CNCC2=CC=C(CN3CCCNCCNCCCNCC3)C=C2)=NC=CC=C1.Br.Br.Br.Br.Br.Br |
| MFCD | N.A. |
| InChi | InChI=1S/C24H38N6.6BrH/c1-2-13-29-24(5-1)20-28-19-22-6-8-23(9-7-22)21-30-17-4-12-26-15-14-25-10-3-11-27-16-18-30;;;;;;/h1-2,5-9,13,25-28H,3-4,10-12,14-21H2;6*1H |
| InChiKey | ARHBIBDGWDRBJH-UHFFFAOYSA-N |
| CID | 9897616 |
| Short Description | CXCR4 antgonist |
References
- S Hatse et al. AMD3465, a monomacrocyclic CXCR4 antagonist and potent HIV entry inhibitor. Biochem. Pharmacol. 2005, 70(5), 752-761.
- MM Rosenkilde et al. Molecular mechanism of action of monocyclam versus bicyclam non-peptide antagonists of the CXCR4 chemokine receptor. J. Biol. Chem. 2007, 282, 27354.
- V Bodart et al. Pharmacology of AMD3465: a small molecule antagonist of the chemokine receptor CXCR4. Biochem. Pharmacol. 2009, 78(8), 993-1000.
- GJ Bridger et al. Synthesis and structure-activity relationships of azamacrocyclic C-X-C chemokine receptor 4 antagonists: analogues containing a single azamacrocyclic ring are potent inhibitors of (...). J. Med. Chem. 2010, 53(3), 1250-1260.
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