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AMD 3465 hexahydrobromide

Potent and selective CXCR4 antagonist CAS# 185991-07-5

AMD 3465 hexahydrobromide

Catalog No. BCC5182----Order now to get a substantial discount!

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Chemical structure

AMD 3465 hexahydrobromide

3D structure

Chemical Properties of AMD 3465 hexahydrobromide

Cas No. 185991-07-5 SDF Download SDF
PubChem ID 9897616 Appearance Powder
Formula C24H44Br6N6 M.Wt 896.07
Type of Compound N/A Storage Desiccate at -20°C
Synonyms GENZ-644494 hexahydrobromide
Solubility H2O : ≥ 38 mg/mL (42.41 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name N-(pyridin-2-ylmethyl)-1-[4-(1,4,8,11-tetrazacyclotetradec-1-ylmethyl)phenyl]methanamine;hexahydrobromide
SMILES C1CNCCNCCCN(CCNC1)CC2=CC=C(C=C2)CNCC3=CC=CC=N3.Br.Br.Br.Br.Br.Br
Standard InChIKey ARHBIBDGWDRBJH-UHFFFAOYSA-N
Standard InChI InChI=1S/C24H38N6.6BrH/c1-2-13-29-24(5-1)20-28-19-22-6-8-23(9-7-22)21-30-17-4-12-26-15-14-25-10-3-11-27-16-18-30;;;;;;/h1-2,5-9,13,25-28H,3-4,10-12,14-21H2;6*1H
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.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of AMD 3465 hexahydrobromide

DescriptionPotent, selective CXCR4 antagonist; exhibits 8-fold higher affinity than AMD 3100. Inhibits SDF-1α-ligand binding (Ki = 41.7 nM). Potently inhibits HIV cell entry in vitro; causes leukocytosis and mobilizes haematopoietic stem cells in vivo.

AMD 3465 hexahydrobromide Dilution Calculator

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AMD 3465 hexahydrobromide Molarity Calculator

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Preparing Stock Solutions of AMD 3465 hexahydrobromide

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.116 mL 5.5799 mL 11.1598 mL 22.3197 mL 27.8996 mL
5 mM 0.2232 mL 1.116 mL 2.232 mL 4.4639 mL 5.5799 mL
10 mM 0.1116 mL 0.558 mL 1.116 mL 2.232 mL 2.79 mL
50 mM 0.0223 mL 0.1116 mL 0.2232 mL 0.4464 mL 0.558 mL
100 mM 0.0112 mL 0.0558 mL 0.1116 mL 0.2232 mL 0.279 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on AMD 3465 hexahydrobromide

AMD 3465 6HBr(GENZ-644494) is a potent, selective CXCR4 antagonist; exhibits 8-fold higher affinity than AMD 3100; inhibits SDF-1α-ligand binding (Ki = 41.7 nM).

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References on AMD 3465 hexahydrobromide

Pharmacology of AMD3465: a small molecule antagonist of the chemokine receptor CXCR4.[Pubmed:19540208]

Biochem Pharmacol. 2009 Oct 15;78(8):993-1000.

CXCR4 is widely expressed in multiple cell types, and is involved in neonatal development, hematopoiesis, and lymphocyte trafficking and homing. Disruption of the CXCL12/CXCR4 interaction has been implicated in stem cell mobilization. Additionally CXCR4 is a co-receptor for HIV. Selective small molecule antagonists of CXCR4 therefore have therapeutic potential. AMD3465 is an N-pyridinylmethylene monocyclam CXCR4 antagonist which can block infection of T-tropic, CXCR4-using HIV. Using the CCRF-CEM T-cell line which expresses CXCR4 we have demonstrated that AMD3465 is an antagonist of SDF-1 ligand binding (K(i) of 41.7+/-1.2nM), and inhibits SDF-1 mediated signaling as shown by inhibition of GTP binding, calcium flux, and inhibition of chemotaxis. AMD3465 is selective for CXCR4 and does not inhibit chemokine-stimulated calcium flux in cells expressing CXCR3, CCR1, CCR2b, CCR4, CCR5 or CCR7, nor does it inhibit binding of LTB(4) to its receptor, BLT1. The pharmacokinetics of AMD3465 was investigated in mice and dogs. Absorption was rapid following subcutaneous administration. AMD3465 was cleared from dog plasma in a biphasic manner with a terminal half-life of 1.56-4.63h. Comparison of exposure to the intravenous and subcutaneous doses indicated 100% bioavailability following subcutaneous administration. AMD3465 caused leukocytosis when administered subcutaneously in mice and dogs, with peak mobilization occurring between 0.5 and 1.5h following subcutaneous dosing in mice and with maximum peak plasma concentration of compound preceding peak mobilization in dogs, indicating that AMD3465 has the potential to mobilize hematopoietic stem cells. These data demonstrate the therapeutic potential for the CXCR4 antagonist AMD3465.

Molecular mechanism of action of monocyclam versus bicyclam non-peptide antagonists in the CXCR4 chemokine receptor.[Pubmed:17599916]

J Biol Chem. 2007 Sep 14;282(37):27354-65.

AMD3465 is a novel, nonpeptide CXCR4 antagonist and a potent inhibitor of HIV cell entry in that one of the four-nitrogen cyclam rings of the symmetrical, prototype bicyclam antagonist AMD3100 has been replaced by a two-nitrogen N-pyridinylmethylene moiety. This substitution induced an 8-fold higher affinity as determined against (125)I-12G5 monoclonal CXCR4 antibody binding, and a 22-fold higher potency in inhibition of CXCL12-induced signaling through phosphatidylinositol accumulation. Mutational mapping of AMD3465 and a series of analogs of this in a library of 23 mutants covering the main ligand binding pocket of the CXCR4 receptor demonstrated that the single cyclam ring of AMD3465 binds in the pocket around AspIV:20 (Asp(171)), in analogy with AMD3100, whereas the N-pyridinylmethylene moiety mimics the other cyclam ring through interactions with the two acidic anchor-point residues in transmembrane (TM)-VI (AspVI:23/Asp(262)) and TM-VII (GluVII:06/Glu(288)). Importantly, AMD3465 has picked up novel interaction sites, for example, His(281) located at the interface of extracellular loop 3 and TM-VII and HisIII:05 (His(113)) in the middle of the binding pocket. It is concluded that the simple N-pyridinylmethylene moiety of AMD3465 substitutes for one of the complex cyclam moieties of AMD3100 through an improved and in fact expanded interaction pattern mainly with residues located in the extracellular segments of TM-VI and -VII of the CXCR4 receptor. It is suggested that the remaining cyclam ring of AMD3465, which ensures the efficacious blocking of the receptor, in a similar manner can be replaced by chemical moieties allowing for, for example, oral bioavailability.

Description

AMD 3465 hexahydrobromide (GENZ-644494 hexahydrobromide) is a potent antagonist of CXCR4, inhibits binding of 12G5 mAb and CXCL12AF647 to CXCR4, with IC50s of 0.75 nM and 18 nM in SupT1 cells; AMD 3465 also potently inhibits the replication of X4 HIV strains (IC50: 1-10 nM), but has no effect on CCR5-using (R5) viruses.

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