239825

AMD3100

≥98% (HPLC), CXCR4 receptor antagonist, liquid

• Synonym(s): InSolution CXCR4 Antagonist I, AMD3100, 1,1ʹ(1,4-Phenylenebis(methylene))-bis-1,4,8,11-tetraazacyclotetradecane, 8HCl, 4H₂O, 1,4-bis((1,4,8,11-Tetraazacyclotetradecan-1-yl)methyl)benzene, 8HCl, 4H₂O
• Empirical Formula (Hill Notation): C₂₈H₅₄N₈ · 8HCl · 4H₂O
• CAS Number: 155148-31-5
• Molecular Weight: 866.53
• MDL number: MFCD04974488
• UNSPSC Code: 51111800
• NACRES: NA.77
• Assay: ≥98% (HPLC)
• Form: liquid
• Storage condition: OK to freeze, avoid repeated freeze/thaw cycles, protect from light

Properties

• Product Name: AMD3100, InSolution, ≥98%, 50 mM aqueous solution, CXCR4 antagonist I
• Quality Segment: 100
• assay: ≥98% (HPLC)
• form: liquid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze, avoid repeated freeze/thaw cycles, protect from light
• shipped in: dry ice
• storage temp.: −70°C
• SMILES string: Cl.Cl.Cl.Cl.Cl.Cl.Cl.Cl.N3(CCNCCCNCCNCCC3)Cc1ccc(cc1)CN2CCNCCCNCCNCCC2
• InChI: 1S/C28H54N8.8ClH/c1-9-29-15-17-31-13-3-21-35(23-19-33-11-1)25-27-5-7-28(8-6-27)26-36-22-4-14-32-18-16-30-10-2-12-34-20-24-36;;;;;;;;/h5-8,29-34H,1-4,9-26H2;8*1H
• InChI key: UEUPDYPUTTUXLJ-UHFFFAOYSA-N

Description

General description

A symmetrical bicyclam compound that antagonizes CXCL12 (SDF1) binding to CXCR4 (IC₅₀ = 108 and 245 nM using rat and human CXCR4, respectively) and inhibits SDF1-induced Ca²⁺ flux (by 100% at 100 ng/ml in SUP-T1 and THP-1 cultures) as well as CXCR4-, but not CCR5-, mediated HIV infection (IC₅₀ = 200 nM), while enhancing the binding of SDF1 to CXCR7 (by ~60% at 1 mM with CXCR7-expressing HEK293T cells) and SDF1-induced β-arrestin recruitment to CXCR7 (EC₅₀ = 6.48 and 11.8 nM, in the presence and absence of 10 µM AMD3100, respectively). Administration AMD3100 via intravenous infusion is also reported to result in hematopoietic stem cell mobilization in humans, dogs, and mice in vivo. Exhibits no inhibitory effects against chemokine-induced signaling via CXCR1/2/3 or CCR1/2/3/4/5/6/7/8/9.

Biochem/physiol Actions

Cell permeable: yes

Primary Target
CXCR4

Reversible: yes

Packaging

Packaged under inert gas

Physical form

A 50 mM (15 mg/308 µL) solution of CXCR4 Antagonist I, AMD3100 (Cat. No. 239820) in H₂O.

Preparation Note

Following initial thaw, aliquot and freeze (-70°C). Aliquots are stable for up to 1 year at -70°C.

Other Notes

Kalatskaya, I., et al. 2009. Mol. Pharmacol.77, 1240.
Pitchford, S.C., et al. 2009. Cell Stem Cell4, 62.
De Clercq, E. 2009. Biochem. Pharmacol.77, 1655.
Thoma, G., et al. 2008. J. Med. Chem.51, 7915.
De Clercq, E. 2000. Mol. Pharmacol.57, 833.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

Safety Information

• Storage Class: 10 - Combustible liquids
• WGK: WGK 3