| Identification | Back Directory | [Name]
FC 131 | [CAS]
606968-52-9 | [Synonyms]
FC131,FC-131
cyclo(2Nal-Gly-D-Tyr-Arg-Arg)
Cyclo[3-(2-naphthalenyl)-L-alanylglycyl-D-tyrosyl-L-arginyl-L-arginyl] | [Molecular Formula]
C36H47N11O6 | [MDL Number]
MFCD28160535 | [MOL File]
606968-52-9.mol | [Molecular Weight]
729.83 |
| Chemical Properties | Back Directory | [density ]
1.45±0.1 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
DMF: 30 mg/ml; DMSO: 30 mg/ml; Ethanol: 1 mg/ml | [form ]
Powder | [pka]
9.89±0.15(Predicted) | [Water Solubility ]
Soluble to 2 mg/ml in water |
| Hazard Information | Back Directory | [Description]
C-X-C chemokine receptor 4 (CXCR4) is a receptor for the stromal cell-derived factor-1 (SDF-1) which is designated as chemokine ligand 12 (CXCL12). It is involved in cell progression, hematopoiesis, cancer, HIV entry, and rheumatoid arthritis. FC 131 is an inhibitor of CXCR4 activation by SDF-1 (IC50 = 4.5 nM) and also blocks HIV-induced cytopathogenicity (EC50 = 73 nM). FC 131 derivatives can be used for imaging CXCR4 and elucidating its function. | [Uses]
Cyclo[3-?(2-?naphthalenyl)?-?L-?alanylglycyl-?D-?tyrosyl-?L-?arginyl-?L-?arginyl] is a CXCR4 antagonist with anti-HIV properties. | [Definition]
ChEBI: Cyclo[3-(2-naphthalenyl)-l-alanylglycyl-d-tyrosyl-l-arginyl-l-arginyl] is an oligopeptide. | [IC 50]
125I-SDF-CXCR4: 4.5 nM (IC50); HIV | [References]
[1] HAL E BROXMEYER. Rapid mobilization of murine and human hematopoietic stem and progenitor cells with AMD3100, a CXCR4 antagonist.[J]. Journal of Experimental Medicine, 2005, 201 8: 1307-1318. DOI: 10.1084/jem.20041385
[2] BAKKER R, SMIT M. G Protein-Coupled Receptors and Cancer[C]. 2005: 0. DOI: 10.1201/9781420028218.ch5
[3] HIROKAZU TAMAMURA. Stereoselective Synthesis of [l-Arg-l/d-3-(2-naphthyl)alanine]-Type (E)-Alkene Dipeptide Isosteres and Its Application to the Synthesis and Biological Evaluation of Pseudopeptide Analogues of the CXCR4 Antagonist FC131[J]. Journal of Medicinal Chemistry, 2004, 48 2: 380-391. DOI: 10.1021/jm049429h
[4] KUIL J, BUCKLE T, VAN LEEUWEN F W B. Imaging agents for the chemokine receptor 4 (CXCR4)[J]. Chemical Society Reviews, 2012, 15: 5239-5261. DOI: 10.1039/c2cs35085h |
|
|