An inhibitor of CXCR4 activation
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FC 131

Item No. 11960

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
cyclo[3-(2-naphthalenyl)-L-alanylglycyl-D-tyrosyl-L-arginyl-L-arginyl]
CAS Number
606968-52-9
Molecular Formula
C36H47N11O6
Formula Weight
729.8
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 1 mg/ml
λmax
226, 277 nm
SMILES
O=C(NCC(N[C@@H]1CC2=CC=C(O)C=C2)=O)[C@@H](NC([C@@H](NC([C@@H](NC1=O)CCCNC(N)=N)=O)CCCNC(N)=N)=O)CC3=CC(C=CC=C4)=C4C=C3
InChi Code
InChI=1S/C36H47N11O6/c37-35(38)41-15-3-7-26-32(51)45-27(8-4-16-42-36(39)40)33(52)47-28(19-22-9-12-23-5-1-2-6-24(23)17-22)31(50)43-20-30(49)44-29(34(53)46-26)18-21-10-13-25(48)14-11-21/h1-2,5-6,9-14,17,26-29,48H,3-4,7-8,15-16,18-20H2,(H,43,50)(H,44,49
InChi Key
MBXBICVKLVYNKD-XFTNXAEASA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Cayman Chemical
    Neutrophil Biology Wall Poster

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    Product 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.1,2,3 FC 131 is an inhibitor of CXCR4 activation by SDF-1 (IC50 = 4.5 nM) and also blocks HIV-induced cytopathogenicity (EC50 = 73 nM).3 FC 131 derivatives can be used for imaging CXCR4 and elucidating its function.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Broxmeyer, H.E., Orschell, C.M., Clapp, D.W., et al. Rapid mobilization of murine and human hematopoietic stem and progenitor cells with AMD3100, a CXCR4 antagonist. J. Exp. Med. 201(8), 1307-1318 (2005).

    2. Dorsam, R.T., and Gutkind, J.S. G-protein-coupled receptors and cancer. Nat. Rev. Cancer 7(2), 79-94 (2007).

    3. Tamamura, H., Hiramatsu, K., Ueda, S., et al. 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. Med. Chem. 48(2), 380-391 (2005).

    4. Kuil, J., Buckle, T., and van Leeuwen, F.W.B. Imaging agents for the chemokine receptor 4 (CXCR4). Chem. Soc. Rev. 41(15), 5239-5261 (2012).