| Identification | Back Directory | [Name]
REVERSINE | [CAS]
656820-32-5 | [Synonyms]
CS-870
REVERSINE
Reversine, >96%
Reversine, >=98%
REVERSINE USP/EP/BP
Picropodophyllin (PPP)
2-(4-MORPHOLINOANILINO)-6-CYCLOHEXYLAMINOPURINE
N6-CYCLOHEXYL-N2-(4-MORPHOLINOPHENYL)-9H-PURINE-2,6-DIAMINE
N6-Cyclohexyl-N2-(4-morpholinophenyl)-7H-purine-2,6-diamine
N6-CYCLOHEXYL-N2-[4-(4-MORPHOLINYL)PHENYL]-1H-PURINE-2,6-DIAMINE
9H-Purine-2,6-diamine,N6-cyclohexyl-N2-[4-(4-morpholinyl)phenyl]-
Reversine
N6-Cyclohexyl-N2-[4-(4-morpholinyl)phenyl]-1H-purine-2,6-diamine
N6-Cyclohexyl-N2-[4-(4-morpholinyl)phenyl]-1H-purine-2,6-diamine Reversine | [Molecular Formula]
C21H27N7O | [MDL Number]
MFCD07784513 | [MOL File]
656820-32-5.mol | [Molecular Weight]
393.49 |
| Chemical Properties | Back Directory | [Melting point ]
305℃ (decomposition) | [Boiling point ]
736.4±70.0 °C(Predicted) | [density ]
1.343±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C
| [solubility ]
DMSO: 7 mg/mL, soluble
| [form ]
solid
| [pka]
10.51±0.10(Predicted) | [color ]
Off-white | [Stability:]
Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months | [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) | [InChIKey]
ZFLJHSQHILSNCM-UHFFFAOYSA-N | [SMILES]
C1CCC(CC1)Nc2nc(Nc3ccc(cc3)N4CCOCC4)nc5nc[nH]c25 |
| Hazard Information | Back Directory | [Description]
Reversine is a 2,6-disubstituted purine derivative that was originally found to induce dedifferentiation of C2C12 culture myoblast cells into stem cell progenitors when used at a concentration of 5 μM for four days.1 Depending on cell type, reversine promotes either differentiation or dedifferentiation. For example, in NT2 neuronal and HL-60 human promyelocytic leukemia cells, it induces differentiation.2 It inhibits the Aurora A, B, and C kinases with IC50 values of 98-876 nM and acts as an antagonist at the adenosine A3 receptor with a Ki value of 0.66 μM.2,3,4 Reversine is also used for studies of chromosome segregation. It inhibits the mitotic spindle checkpoint enzyme MPS1 with IC50 values of 6 and 2.8 nM for its kinase domain and full-length version, respectively).4 Reversine induces autophagy in WRO human follicular thyroid cancer cells and decreases Akt/mTOR signaling.5 | [Uses]
Induces dedifferentiation in murine C2C12 myoblasts. The cells were also shown to regain multipluripotency following removal of the compound. Potent and selective A3 adenosine receptor antagonist (Ki = 0.66μM) and a novel aurora kinase inhibitor (IC50's of 30-550nM for blast colony formation assay). | [Definition]
ChEBI: A member of the class of purines that is 9H-purine in which the hydrogens at positions 2 and 6 are replaced by a [4-(morpholin-4-yl)phenyl]nitrilo group and a cyclohexylamino group, respectively. | [Biochem/physiol Actions]
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 (Ki 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. | [in vitro]
reversine could be used to induce dedifferentiation of murine myoblasts. previous reports also showed that reversine had a role in regeneration. moreover, a recent report indicated reversine had anti-tumor capabilities for a myeloma cell line, as demonstrated by that reversine could suppress the expression of cell cycle related proteins aurora kinase a and aurora kinase b [1]. | [in vivo]
the effects of reversine on tumor weight and volume were assessed using a murine model of cervical cancer with u14 cells, separately or combined with aspirin. the inhibition rate of cells in the combination group significantly increased; moreover, such combination could synergistically inhibit the proliferation of five cervical cancer cell lines. in the mouse model, tumor weight and volume of cervical cancer bearing mice were more reduced [1]. | [IC 50]
150, 500 and 400 nm for aurora kinase a, b and c respectively | [References]
1) Chen et al. (2004), Dedifferentiation of lineage-committed cells by a small molecule; J. Am. Chem. Soc., 126 410
2) Chen et al. (2007), Reversine increases the plasticity of lineage-committed mammalian cells; Proc. Natl. Acad. Sci. USA, 104 10482
3) Perreira et al. (2005), Reversine and its 2-substituted adenine derivatives as potent and selective A3 adenosine receptor antagonists; J. Med. Chem., 48 4910 |
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