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| | REVERSINE Basic information |
| Product Name: | REVERSINE | | Synonyms: | 9H-Purine-2,6-diamine,N6-cyclohexyl-N2-[4-(4-morpholinyl)phenyl]-;N6-Cyclohexyl-N2-(4-morpholinophenyl)-7H-purine-2,6-diamine;2-(4-MORPHOLINOANILINO)-6-CYCLOHEXYLAMINOPURINE;N6-CYCLOHEXYL-N2-(4-MORPHOLINOPHENYL)-9H-PURINE-2,6-DIAMINE;Picropodophyllin (PPP);N6-Cyclohexyl-N2-[4-(4-morpholinyl)phenyl]-1H-purine-2,6-diamine Reversine;Reversine
N6-Cyclohexyl-N2-[4-(4-morpholinyl)phenyl]-1H-purine-2,6-diamine;REVERSINE | | CAS: | 656820-32-5 | | MF: | C21H27N7O | | MW: | 393.49 | | EINECS: | | | Product Categories: | Inhibitors | | Mol File: | 656820-32-5.mol |  |
| | REVERSINE Chemical Properties |
| 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 |
| Hazard Codes | Xn | | Risk Statements | 22 | | WGK Germany | 3 |
| | REVERSINE Usage And Synthesis |
| 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. 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. 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. 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). Reversine induces autophagy in WRO human follicular thyroid cancer cells and decreases Akt/mTOR signaling. | | Uses | Reversine acts as a potent human A3 adenosine receptor antagonist and pan-aurora A/B/C kinase inhibitor. Used for stem cell differentiation. | | 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 |
| | REVERSINE Preparation Products And Raw materials |
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