FC131

Name: FC131
Brand: Creative Peptides
SKU: 10-101-256
Availability: MadeToOrder

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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M.F/Formula	C36H47N11O6
M.W/Mr.	729.8
Sequence	Three Letter Code:cyclo[2Nal-Gly-D-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)(H,45,51)(H,46,53)(H,47,52)(H4,37,38,41)(H4,39,40,42)/t26-,27-,28-,29+/m0/s1
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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