- Plerixafor (AMD3100)
- AMD-070 hydrochloride
- Reparixin
- Reparixin L-lysine salt
- SCH 527123
| AMD-070CXCR4 antagonist,potent and selective |
Sample solution is provided at 25 µL, 10mM.
Nature.2017 Jan 19;541(7637):417-420.
Nature.2018 Nov;563(7731):407-411.Nature.2018 Jun 13.Nature.2018 Jun 27.Nature.2018 Mar 29;555(7698):673-677.Nature.2017 Sep 7;549(7670):96-100.Nature.2016 Apr 21;532(7599):398-401.
Science.2016 Aug 5;353(6299)594-8Nat Nanotechnol.2017 Dec;12(12):1190-1198.Nature Biotechnology.2017 Jun;35(6):569-576Nat Med.2018 Sep 17.Cell.2018 Dec 21. pii: S0092-8674(18)31561-7.Cell.Available online 25 October 2018.Cell.2018 Sep 27. pii: S0092-8674(18)31183-8.Cell.2018 Jun 28;174(1):172-186.e21.Cell.2018 Feb 22;172(5):1007-1021.e17.Cell.2017 Nov 30;171(6):1284-1300.e21.Cell.2017 Aug 17. pii: S0092-8674(17)30869-3.Cell.2017 Jul 13;170(2):312-323Nat Med.2018 Jan 29.Nat Med.2017 Nov;23(11):1342-1351.Cell.2017 Apr 6;169(2):286-300.Cell.2015 Aug 27;162(5):987-1002.Cell.2015 Feb 12;160(4):729-44.Nature Medicine.2017 Apr;23(4):493-500.Cancer Cell.2018 May 14;33(5):905-921.e5.Cancer Cell.2018 Apr 9;33(4):752-769.e8.Cancer Cell.2018 Mar 12;33(3):401-416.e8.Cancer Cell.2017 Aug 14;32(2):253-267.e5.Nat Methods.2018 Jul;15(7):523-526.Cell Stem Cell.2018 May 3;22(5):769-778.e4.Cell Stem Cell.2017 Nov 20. pii: S1934-5909(17)30375-2.Quality Control & MSDS
- View current batch:
- Purity = 98.00%
- COA (Certificate Of Analysis)
- NMR (Nuclear Magnetic Resonance)
- MSDS (Material Safety Data Sheet)
- Datasheet
Chemical structure
| Cell experiment [1,2]: | |
Cell lines | Melanoma cells CHL-1 and A375, HOS cells |
Preparation method | The solubility of this compound in DMSO is >17.5mg/mL. General tips for obtaining a higher concentration: Please warm the tube at 37℃ for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below -20℃ for several months. |
Reacting condition | 6.6 μM, 24h |
Applications | In melanoma cells CHL-1 and A375, treatment of AMD-070 significantly inhibited the migration of cells. Besides that, the void sizes of cells were also increased by the inhibitor treatment. In HOS cells expressing human CXCR4, AMD-070 inhibited HIV-1 infection with IC50 value of 10 nM. |
Other notes | Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal. |
References: [1] O"boyle G, Swidenbank I, Marshall H, et al. Inhibition of CXCR4–CXCL12 chemotaxis in melanoma by AMD11070[J]. British journal of cancer, 2013, 108(8): 1634. [2] Gudmundsson K S, Sebahar P R, Richardson L D A, et al. Amine substituted N-(1H-benzimidazol-2ylmethyl)-5, 6, 7, 8-tetrahydro-8-quinolinamines as CXCR4 antagonists with potent activity against HIV-1[J]. Bioorganic & medicinal chemistry letters, 2009, 19(17): 5048-5052. | |
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| Cas No. | 558447-26-0 | SDF | Download SDF |
| Synonyms | AMD 070; AMD070 | ||
| Chemical Name | N"-(1H-benzimidazol-2-ylmethyl)-N"-[(8S)-5,6,7,8-tetrahydroquinolin-8-yl]butane-1,4-diamine | ||
| Canonical SMILES | C1CC(C2=C(C1)C=CC=N2)N(CCCCN)CC3=NC4=CC=CC=C4N3 | ||
| Formula | C21H27N5 | M.Wt | 349.48 |
| Solubility | ≥17.45 mg/mL in DMSO, ≥44.5 mg/mL in EtOH, ≥7.47 mg/mL in H2O with gentle warming | Storage | Store at -20°C |
| Physical Appearance | A brown oil | Shipping Condition | Evaluation sample solution : ship with blue ice.All other available size:ship with RT , or blue ice upon request |
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. | ||
AMD-070 is a selective and oral bioavailable antagonist of chemokine receptor CXCR4 with IC50 value of 13 nM [1].CXCR4 is a G-protein-coupled receptor that plays important roles in tumor development. It affects the migration, proliferation and survival of cancer cells through the CXCL12-mediated MAPK signaling. AMD-070 is an orally bioavailable antagonist of CXCR4 and is found to be an inhibitor of tumor cell migration. CXCR4 is also one of the two chemokine receptors that are used by virus for infecting human cells. As a CXCR4 inhibitor, AMD-070 can repress the replication of X4 (T-tropic) HIV-1 and the interaction of gp120/CXCR4 potently. The mechanistic studies demonstrate that AMD-070 is an allosteric inhibitor. It was found that a hydrogen bond was formed between the benzimidazole of AMD-070 and the Tyr45 residue of CXCR4 whereas the residues Asp262, Asp171 and Glu288 were not involved in the direct interactions with AMD-070 [1, 2 and 3].AMD-070 is selective against CXCR4 over other related G-protein-coupled chemokine receptors including CXCR1, CXCR2, CCR1, CCR2b, CCR4 and CCR5. The IC50 values of AMD-070 against these GPCRs were all above 10 μM. In HOS cells expressing human CXCR4, AMD-070 inhibited HIV-1 infection with IC50 value of 10 nM. In CD4+CXCR4+T cells, AMD-070 showed anti-HIV-1 activity (IC50 value of 2 nM) through inhibiting the SDF-1 induced calcium flux with IC50 value of 12 nM. In addition, AMD-070 inhibited the competitive binding of 125I-SDF-1with IC50 value of 13 nM. In melanoma cells CHL-1 and A375, treatment of AMD-070 significantly inhibited the migration of cells. Besides that, the void sizes of cells were also increased by the inhibitor treatment [1, 2 and 4]. References:[1] Skerlj RT, Bridger GJ, Kaller A, McEachern EJ, Crawford JB, Zhou Y, Atsma B, Langille J, Nan S, Veale D, Wilson T, Harwig C, Hatse S, Princen K, De Clercq E, Schols D. Discovery of novel small molecule orally bioavailable C-X-C chemokine receptor 4 antagonists that are potent inhibitors of T-tropic (X4) HIV-1 replication. J Med Chem. 2010 Apr 22;53(8):3376-88. [2] O"Boyle G, Swidenbank I, Marshall H, Barker CE, Armstrong J, White SA, Fricker SP, Plummer R, Wright M, Lovat PE. Inhibition of CXCR4-CXCL12 chemotaxis in melanoma by AMD11070. Br J Cancer. 2013 Apr 30;108(8):1634-40. [3] Wong RS, Bodart V, Metz M, Labrecque J, Bridger G, Fricker SP. Comparison of the potential multiple binding modes of bicyclam, monocylam, and noncyclam small-molecule CXC chemokine receptor 4 inhibitors. Mol Pharmacol. 2008 Dec;74(6):1485-95. [4] Gudmundsson KS, Sebahar PR, Richardson LD, Miller JF, Turner EM, Catalano JG, Spaltenstein A, Lawrence W, Thomson M, Jenkinson S. Amine substituted N-(1H-benzimidazol-2ylmethyl)-5,6,7,8-tetrahydro-8-quinolinamines as CXCR4 antagonists with potent activity against HIV-1. Bioorg Med Chem Lett. 2009 Sep 1;19(17):5048-52.
