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MedKoo Cat#: 526872 | Name: FC-131

Description:

WARNING: This product is for research use only, not for human or veterinary use.

FC-131 is a CXCR4 antagonist (IC50 = 126 nM). FC-131 displays anti-HIV activity. FC 131 derivatives can be used for imaging CXCR4 and elucidating its function.

Chemical Structure

FC-131
FC-131
CAS#606968-52-9

Theoretical Analysis

MedKoo Cat#: 526872

Name: FC-131

CAS#: 606968-52-9

Chemical Formula: C36H47N11O6

Exact Mass: 729.3711

Molecular Weight: 729.84

Elemental Analysis: C, 59.25; H, 6.49; N, 21.11; O, 13.15

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
FC 131; FC-131; FC131; d-Tyr-Arg-Arg-2-Nal-Gly; Cyclo[2-Nal-Gly-D-Tyr-Arg-Arg]; cyclo(tyrosyl-arginyl-arginyl-3-(2-naphthyl)alanyl-glycyl).
IUPAC/Chemical Name
1,1'-(((2S,5S,8S,14R)-14-(4-hydroxybenzyl)-8-(naphthalen-2-ylmethyl)-3,6,9,12,15-pentaoxo-1,4,7,10,13-pentaazacyclopentadecane-2,5-diyl)bis(propane-3,1-diyl))diguanidine
InChi Key
MBXBICVKLVYNKD-XFTNXAEASA-N
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)(H,45,51)(H,46,53)(H,47,52)(H4,37,38,41)(H4,39,40,42)/t26-,27-,28-,29+/m0/s1
SMILES Code
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
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 729.84 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Oishi S, Kuroyanagi T, Kubo T, Montpas N, Yoshikawa Y, Misu R, Kobayashi Y, Ohno H, Heveker N, Furuya T, Fujii N. Development of novel CXC chemokine receptor 7 (CXCR7) ligands: selectivity switch from CXCR4 antagonists with a cyclic pentapeptide scaffold. J Med Chem. 2015 Jul 9;58(13):5218-25. doi: 10.1021/acs.jmedchem.5b00216. Epub 2015 Jun 18. PubMed PMID: 26042340. 2: George GP, Pisaneschi F, Stevens E, Nguyen QD, Åberg O, Spivey AC, Aboagye EO. Scavenging strategy for specific activity improvement: application to a new CXCR4-specific cyclopentapeptide positron emission tomography tracer. J Labelled Comp Radiopharm. 2013 Nov;56(13):679-85. doi: 10.1002/jlcr.3095. Epub 2013 Jul 16. PubMed PMID: 25196030. 3: Thiele S, Mungalpara J, Steen A, Rosenkilde MM, Våbenø J. Determination of the binding mode for the cyclopentapeptide CXCR4 antagonist FC131 using a dual approach of ligand modifications and receptor mutagenesis. Br J Pharmacol. 2014 Dec;171(23):5313-29. doi: 10.1111/bph.12842. PubMed PMID: 25039237; PubMed Central PMCID: PMC4294042. 4: Li X, Qian H, Miyamoto F, Naito T, Kawaji K, Kajiwara K, Hattori T, Matsuoka M, Watanabe K, Oishi S, Fujii N, Kodama EN. A simple, rapid, and sensitive system for the evaluation of anti-viral drugs in rats. Biochem Biophys Res Commun. 2012 Jul 27;424(2):257-61. doi: 10.1016/j.bbrc.2012.06.097. Epub 2012 Jun 23. PubMed PMID: 22735265. 5: Yoshikawa Y, Kobayashi K, Oishi S, Fujii N, Furuya T. Molecular modeling study of cyclic pentapeptide CXCR4 antagonists: new insight into CXCR4-FC131 interactions. Bioorg Med Chem Lett. 2012 Mar 15;22(6):2146-50. doi: 10.1016/j.bmcl.2012.01.134. Epub 2012 Feb 8. PubMed PMID: 22365757. 6: Kobayashi K, Oishi S, Hayashi R, Tomita K, Kubo T, Tanahara N, Ohno H, Yoshikawa Y, Furuya T, Hoshino M, Fujii N. Structure-activity relationship study of a CXC chemokine receptor type 4 antagonist, FC131, using a series of alkene dipeptide isosteres. J Med Chem. 2012 Mar 22;55(6):2746-57. doi: 10.1021/jm2016914. Epub 2012 Mar 6. PubMed PMID: 22352868. 7: Mandawat A, Fiskus W, Buckley KM, Robbins K, Rao R, Balusu R, Navenot JM, Wang ZX, Ustun C, Chong DG, Atadja P, Fujii N, Peiper SC, Bhalla K. Pan-histone deacetylase inhibitor panobinostat depletes CXCR4 levels and signaling and exerts synergistic antimyeloid activity in combination with CXCR4 antagonists. Blood. 2010 Dec 9;116(24):5306-15. doi: 10.1182/blood-2010-05-284414. Epub 2010 Sep 1. PubMed PMID: 20810927. 8: Evans BJ, Wang Z, Broach JR, Oishi S, Fujii N, Peiper SC. Expression of CXCR4, a G-protein-coupled receptor for CXCL12 in yeast identification of new-generation inverse agonists. Methods Enzymol. 2009;460:399-412. doi: 10.1016/S0076-6879(09)05220-3. PubMed PMID: 19446737. 9: Cluzeau J, Oishi S, Ohno H, Wang Z, Evans B, Peiper SC, Fujii N. Design and synthesis of all diastereomers of cyclic pseudo-dipeptides as mimics of cyclic CXCR4 pentapeptide antagonists. Org Biomol Chem. 2007 Jun 21;5(12):1915-23. Epub 2007 May 14. PubMed PMID: 17551641. 10: Tamamura H, Esaka A, Ogawa T, Araki T, Ueda S, Wang Z, Trent JO, Tsutsumi H, Masuno H, Nakashima H, Yamamoto N, Peiper SC, Otaka A, Fujii N. Structure-activity relationship studies on CXCR4 antagonists having cyclic pentapeptide scaffolds. Org Biomol Chem. 2005 Dec 21;3(24):4392-4. Epub 2005 Nov 15. PubMed PMID: 16327900. 11: Tamamura H, Hiramatsu K, Ueda S, Wang Z, Kusano S, Terakubo S, Trent JO, Peiper SC, Yamamoto N, Nakashima H, Otaka A, Fujii N. 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. 2005 Jan 27;48(2):380-91. PubMed PMID: 15658852.