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FC131

FC 131 is an antagonist of CXCR4 with anti-HIV activity

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CAT No: 10-101-256

CAS No: 606968-52-9

Synonyms/Alias: FC131;606968-52-9;FC 131;Cyclo(-D-Tyr-Arg-Arg-Nal-Gly-);2-[3-[(2S,5S,8S,14R)-5-[3-(diaminomethylideneamino)propyl]-14-[(4-hydroxyphenyl)methyl]-8-(naphthalen-2-ylmethyl)-3,6,9,12,15-pentaoxo-1,4,7,10,13-pentazacyclopentadec-2-yl]propyl]guanidine;CHEMBL436283;CHEMBL2180076;Fc-131;Cyclo[2-Nal-Gly-D-Tyr-Arg-Arg];SCHEMBL15987252;CHEBI:183910;GLXC-04293;Cyclo(-Nal-Gly-D-Tyr-Arg-Arg-);HY-P1104;BDBM50166106;BDBM50399002;Cyclo-[2-Nal-Gly-D-Tyr-Arg-Arg];EX-A11275;AKOS040745190;DA-53131;CS-0027759;Cyclo[3-(2-naphthalenyl)-L-alanylglycyl-D-tyrosyl-L-arginyl-L-arginyl];1-[3-[(2S,5S,8S,14R)-5-(3-guanidinopropyl)-14-[(4-hydroxyphenyl)methyl]-8-(2-naphthylmethyl)-3,6,9,12,15-pentaoxo-1,4,7,10,13-pentazacyclopentadec-2-yl]propyl]guanidine;N-{3-[(2S,5S,8S,14R)-5-(3-carbamimidamidopropyl)-14-[(4-hydroxyphenyl)methyl]-8-(naphthalen-2-ylmethyl)-3,6,9,12,15-pentaoxo-1,4,7,10,13-pentaazacyclopentadecan-2-yl]propyl}guanidine;N-{3-[(2S,5S,8S,14R)-5-(3-Guanidino-propyl)-14-(4-hydroxy-benzyl)-8-naphthalen-2-ylmethyl-3,6,9,12,15-pentaoxo-1,4,7,10,13pentaaza-cyclopentadec-2-yl]-propyl}-guanidine;

Chemical Name: cyclo[3-(2-naphthalenyl)-L-alanylglycyl-D-tyrosyl-L-arginyl-L-arginyl]

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Specification Technical Data Publications Customer reviews and Q&A
M.F/FormulaC36H47N11O6
M.W/Mr.729.8
SequenceThree Letter Code:cyclo[2Nal-Gly-D-Tyr-Arg-Arg]
Labeling TargetC-X-C chemokine receptor type 4 (CXCR4)
ApplicationCXCR4 antagonist (IC50 = 126 nM). Displays anti-HIV activity in assays using NL4-3 and IIIB strains (EC50 = 21 nM for both strains).
AppearanceCrystalline solid
Purity≥95%
ActivityAntagonist
Biological ActivityFC131 (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.
TargetCXCR
Source#Synthetic
Long-term Storage ConditionsSoluble in 20% acetonitrile/water (2 mg/ml).
Shipping ConditionShipped at room temperature
Short-term Storage ConditionsDry, dark and at 0 - 4 °C
Solubility-20 °C
InChIInChI=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)(H,45,51)(H,46,53)(H,47,52)(H4,37,38,41)(H4,39,40,42)/t26-,27-,28-,29+/m0/s1
InChI KeyMBXBICVKLVYNKD-XFTNXAEASA-N
Canonical SMILESO=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 SMILESC1C(=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
BoilingPointN/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 PointN/A

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