FC131

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

Please kindly note that our products and services can only be used to support research purposes (Not for clinical use).

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]

Quick InquiryCustom Peptide Synthesis

Peptide Library Construction and Screening

Powerful screening tools in biological and chemical research

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

1. Multifunctional peptide-oligonucleotide conjugate promoted sensitive electrochemical biosensing of cardiac troponin I

2. The effect of sex on immune responses to a homocitrullinated peptide in the DR4-transgenic mouse model of Rheumatoid Arthritis

3. A possible role of tachykinin-related peptide on an immune system activity of mealworm beetle, Tenebrio molitor L

4. Immune-awakening Saccharomyces-inspired nanocarrier for oral target delivery to lymph and tumors

5. Myotropic activity and immunolocalization of selected neuropeptides of the burying beetle Nicrophorus vespilloides (Coleoptera: Silphidae)

Write a review Ask a question
My Review for FC131

Required fields are marked with *

  • Basic Information
×
Ask a Question for FC131

Required fields are marked with *

  • Basic Information
×
Featured Recommendations
Related Screening Libraries:
Peptide Drug Gene Construction and Expression Platform Peptide Screening Services High-throughput Screening Peptide Tools AI-based Peptide Drug Discovery and Structure Analysis Platform
Related Small Molecules:
PentagastrinEptifibatide AcetateTriptorelin PamoateZiconotideRomidepsinEptifibatide Impurity 1Zonisamide
Useful Tools

Peptide Calculator

Abbreviation List

Peptide Glossary

If you have any peptide synthesis requirement in mind, please do not hesitate to contact us at info@creative-peptides.com. We will endeavor to provide highly satisfying products and services.

Featured Services
Hot Products

  • Teriparatide Acetate

    Teriparatide(recombinant human parathyroid hormone) /PTH (1-34) (human) corresponds to the N-terminal part of human parathyroid hormone, a peptide consisting of 84 amino acids.

    Inquiry

  • Elcatonin Acetate

    Elcatonin acetate inhibits the absorption and autolysis of bones, thus leads to blood calcium descending. In addition, it inhibits the bone salts dissolving and transferring and promotes the excretion of calcium and phosphorus in urine.

    Inquiry

  • Deslorelin

    Deslorelin is a gonadotropin releasing hormone super-agonist (GnRH agonist) also known as an LHRH agonist. It stops the production of sex hormones (testosterone and oestrogen). It is currently approved for use in veterinary medicine and is used to induce ovulation in mares as part of the artificial insemination process. It is also used to stabilize high-risk pregnancies, mainly of livestock. Unlike other GnRH agonists, which are mainly used to inhibit luteinizing hormone and follicle-stimulating hormone by their ultimate downregulation of the pituitary gland.

    Inquiry

  • Glucagon

    Glucagon (Porcine glucagon) is a peptide hormone, produced by pancreatic α-cells. Glucagon stimulates gluconeogenesis. Glucagon decreases the activity of HNF-4. Glucagon increases HNF4α phosphorylation.

    Inquiry

  • Fertirelin Acetate

    Fertirelin acetate is a potent LHRH agonist. After a transient increase, continuous administration results in downregulation of LH and FSH levels followed by a suppression of ovarian and testicular steroid biosynthesis.

    Inquiry

  • Somatostatin

    Somatostatin is a tetradecapeptide which can suppress the growth hormone (GH) secretion and control the pituitary hormone secretion in human CNS.

    Inquiry

  • Atosiban

    Atosiban is a nonapeptide, desamino-oxytocin analogue, and a competitive vasopressin/oxytocin receptor antagonist (VOTra). Atosiban is indicated to delay imminent pre-term birth in pregnant adult women. Atosiban is useful in improving the pregnancy outcome of in vitro fertilization-embryo transfer (IVF-ET) in patients with repeated implantation failure (RIF). The pregnancy rate improved from zero to 43.7%.

    Inquiry

  • Terlipressin

    Terlipressin is a synthetic triglycyllysine derivative of vasopressin with vasoconstrictive, antihemorrhagic, and antidiuretic properties. Upon intravenous administration, terlipressin, an inactive prodrug, is biotransformed to its active moiety, lysine vasopressin (LVP), a nonselective vasopressin analogue with affinity for vasopressin receptors V1 (V1a), V2 and V3 (V1b). As a V1 agonist, terlipressin increases systemic vascular resistance, particularly in the splanchnic area, resulting in a decrease of portal pressure. V1 binding also promotes platelet aggregation and glycogenolysis, while V3 binding induces adrenocorticotropic hormone (ACTH) secretion. Compared to vasopressin, terlipressin has a minimal effect on V2 receptors, which are responsible for promotion of water reabsorption in the collecting ducts of the kidney via stimulation of cyclic AMP production.

    Inquiry

  • Gonadorelin Acetate

    Gonadorelin is a trophic peptide hormone responsible for the release of follicle-stimulating hormone (FSH) and luteinizing hormone (LH) from the anterior pituitary. GnRH is synthesized and released from GnRH neurons within the hypothalamus. The peptide belongs to gonadotropin-releasing hormone family. It constitutes the initial step in the hypothalamic–pituitary–gonadal axis.

    Inquiry

  • Carbetocin

    Carbetocin is a long-acting synthetic agonist analogue of human oxytocin, with antihemorrhagic and uterotonic activities. Upon administration, carbetocin targets, binds to and activates peripheral oxytocin receptors that are present on the smooth musculature of the uterus. This causes uterus contractions and prevents excessive bleeding after childbirth, particularly following Cesarean section, and may be used to decrease blood loss during hysteroscopic myomectomy.

    Inquiry

  • Teriparatide Acetate

    Teriparatide(recombinant human parathyroid hormone) /PTH (1-34) (human) corresponds to the N-terminal part of human parathyroid hormone, a peptide consisting of 84 amino acids.

    Inquiry

  • Elcatonin Acetate

    Elcatonin acetate inhibits the absorption and autolysis of bones, thus leads to blood calcium descending. In addition, it inhibits the bone salts dissolving and transferring and promotes the excretion of calcium and phosphorus in urine.

    Inquiry

  • Deslorelin

    Deslorelin is a gonadotropin releasing hormone super-agonist (GnRH agonist) also known as an LHRH agonist. It stops the production of sex hormones (testosterone and oestrogen). It is currently approved for use in veterinary medicine and is used to induce ovulation in mares as part of the artificial insemination process. It is also used to stabilize high-risk pregnancies, mainly of livestock. Unlike other GnRH agonists, which are mainly used to inhibit luteinizing hormone and follicle-stimulating hormone by their ultimate downregulation of the pituitary gland.

    Inquiry

  • Glucagon

    Glucagon (Porcine glucagon) is a peptide hormone, produced by pancreatic α-cells. Glucagon stimulates gluconeogenesis. Glucagon decreases the activity of HNF-4. Glucagon increases HNF4α phosphorylation.

    Inquiry

  • Fertirelin Acetate

    Fertirelin acetate is a potent LHRH agonist. After a transient increase, continuous administration results in downregulation of LH and FSH levels followed by a suppression of ovarian and testicular steroid biosynthesis.

    Inquiry
Get in touch with us

Copyright © 2025 Creative Peptides. All rights reserved.

We use cookies to understand how you use our site and to improve the overall user experience. This includes personalizing content and advertising. Read our Privacy Policy

Accept Cookies
x