FC 131 is an antagonist of CXCR4 with anti-HIV activity
CAT No:10-101-256
CAS No:606968-52-9
Synonyms/Alias:Cyclo[2-Nal-Gly-D-Tyr-Arg-Arg]
Chemical Name:cyclo[3-(2-naphthalenyl)-L-alanylglycyl-D-tyrosyl-L-arginyl-L-arginyl]
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M.F/Formula | C36H47N11O6 |
M.W/Mr. | 729.8 |
Sequence | One Letter Code: XGYRR (Modifications: Cyclic peptide, X = 2-Nal, Tyr-3 = D-Tyr] Three Letter Code: Nal-Gly-Tyr-Arg-Arg |
Labeling Target | C-X-C chemokine receptor type 4 (CXCR4) |
Application | CXCR4 antagonist (IC50 = 126 nM). Displays anti-HIV activity in assays using NL4-3 and IIIB strains (EC50 = 21 nM for both strains). |
Appearance | Crystalline solid |
Purity | ≥95% |
Activity | Antagonist |
Biological Activity | FC131 (cyclo (-D-Tyr-Arg-Arg-Nal-Gly-)) is a selective, cyclopentapeptide CXCR4 antagonist with IC50 of 126nM, exhibits anti-HIV activity in assays using NL4-3 and IIIB strains with EC50 of 21nM. |
Target | CXCR |
Source# | Synthetic |
Long-term Storage Conditions | Soluble in 20% acetonitrile/water (2 mg/ml). |
Shipping Condition | Shipped at room temperature |
Short-term Storage Conditions | Dry, dark and at 0 - 4 °C |
Solubility | -20 °C |
InChI | 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 |
Canonical 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 |
Isomeric SMILES | C1C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)CC2=CC3=CC=CC=C3C=C2)CCCN=C(N)N)CCCN=C(N)N)CC4=CC=C(C=C4)O |
BoilingPoint | N/A |
ShelfLife | >2 years if stored properly |
References | The Arg2 and 2‐Nal3 side chains of FC131 interact with residues in TM‐3 (His113, Asp171) and TM‐5 (hydrophobic pocket) respectively. Arg1 forms charge‐charge interactions with Asp187 in ECL‐2, while D‐Tyr5 points to the extracellular side of CXCR4. Furthermore, the backbone of FC131 interacts with the chemokine receptor‐conserved Glu288 via two water molecules. Intriguingly, Tyr116 and Glu288 form a H‐bond in CXCR4 crystal structures and mutation of either residue to Ala abolishes CXCR4 activity. Determination of the binding mode for the cyclopentapeptide CXCR4 antagonist FC131 using a dual approach of ligand modifications and receptor mutagenesis Previously, we developed a highly potent CXC chemokine receptor type 4 (CXCR4) antagonist, FC131 [cyclo(-d-Tyr1-Arg2-Arg3-Nal4-Gly5-)], from a library of cyclic pentapeptides consisting of pharmacophore residues of the polyphemusin-II-derived anti-human immunodeficiency virus (HIV) peptide T140. Since this novel scaffold for CXCR4 antagonists was identified, a series of cyclic peptides and peptidomimetics have been designed for potential anti-HIV and antimetastatic agents. Structure–Activity Relationship Study of a CXC Chemokine Receptor Type 4 Antagonist, FC131, Using a Series of Alkene Dipeptide Isosteres |
Melting Point | N/A |
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