R3904

Reversine

≥98% (HPLC), A₃ adenosine receptor antagonist, solid

• Synonyme(s) : 2-(4-Morpholinoanilino)-6-cyclohexylaminopurine
• Formule empirique (notation de Hill) : C₂₁H₂₇N₇O
• Numéro CAS: 656820-32-5
• Poids moléculaire : 393.49
• UNSPSC Code: 12352200
• PubChem Substance ID: 24724590
• NACRES: NA.77
• MDL number: MFCD07784513
• Assay: ≥98% (HPLC)
• Form: solid

Propriétés

• Nom du produit: Reversine, ≥98% (HPLC), solid
• Quality Segment: 200
• assay: ≥98% (HPLC)
• form: solid
• solubility: DMSO: soluble 7 mg/mL, H₂O: insoluble
• storage temp.: 2-8°C
• SMILES string: C1CCC(CC1)Nc2nc(Nc3ccc(cc3)N4CCOCC4)nc5nc[nH]c25
• InChI: 1S/C21H27N7O/c1-2-4-15(5-3-1)24-20-18-19(23-14-22-18)26-21(27-20)25-16-6-8-17(9-7-16)28-10-12-29-13-11-28/h6-9,14-15H,1-5,10-13H2,(H3,22,23,24,25,26,27)
• InChI key: ZFLJHSQHILSNCM-UHFFFAOYSA-N
• Gene Information: human ... ADORA1(134), ADORA2A(135), ADORA2B(136), ADORA3(140) ; rat ... Adora3(25370)

Description

Application

Reversine has been used as a monopolar spindle 1 (Mps1) kinase inhibitor or mitotic spindle assembly checkpoint (SAC) inhibitor:

• to study the need of mitotic arrest for combretastatin A4 (CA4)-mediated cytotoxicity
• to study the contribution of SAC activation to epstein-barr virus (EBV) replication
• to induce chromosome mis-segregation

Biochem/physiol Actions

Reversine is an A₃ adenosine receptor antagonist, Aurora kinase inhibitor, and Mps1 kinase inhibitor.

Reversine was first described as a synthetic substituted purine with activity as a dedifferentiation agent; it was shown to induces differentiated lineage-committed cells to become multipotent mesenchymal stem cells (MSCs). Reversine has also been show to have activity as a potent, selective human A₃ adenosine receptor antagonist (K_i value of 0.66 μM), as an ATP-competitive Aurora kinase inhibitor, and as a Mps1 kinase inhibitor. Additionally, studies have shown reversine to be an anti-cancer agent, inhibiting growth and inducing cell death in various cancer cell types.

Preparation Note

According to other sources, stock solutions of Reversine in DMSO are stable refrigerated for short term only. For long term storage aliquotes should be stable at -20°C for up to 2 years. Solution storage at ambient temperature is not recommended.

Informations sur la sécurité

• Classe de stockage: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves