Reversine

• CAT Number: I004478
• CAS Number: 656820-32-5
• Molecular Formula: C₂₁H₂₇N₇O
• Molecular Weight: 393.49
• Purity: ≥95%
• Target: Aurora Kinase
• Solubility: 10 mM in DMSO
• Storage: Store at -20°C
• IC50: 150 nM (Aurora Kinase A); 500 (Aurora Kinase B); 400 nM (Aurora Kinase C) [1]
• InChI: 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)NC2=NC(=NC3=C2NC=N3)NC4=CC=C(C=C4)N5CCOCC5

Reversine (CAT: I004478) is a small synthetic purine analogue, specifically a 2,6-disubstituted purine, known for its potent inhibitory effects on the Aurora kinase family, including Aurora A, Aurora B, and Aurora C. The Aurora kinases are key regulators of mitosis and play a crucial role in cell division and chromosome segregation. By inhibiting these kinases, Reversine interferes with mitotic progression and can induce abnormal cell division, leading to cell cycle arrest and apoptosis in certain cancer cell lines. Reversine has been studied as a potential anticancer agent, particularly in the field of targeted cancer therapy, due to its ability to disrupt cell division processes.

Reference

1:Inhibition of Suicidal Erythrocyte Death by Reversine. Jemaà M, Fezai M, Lang F.Cell Physiol Biochem. 2017 Apr 27;41(6):2363-2373. doi: 10.1159/000475654. [Epub ahead of print] PMID: 28463842 Free Article2:Effect of reversine on cell cycle, apoptosis, and activation of hepatic stellate cells. Huang Y, Huang D, Weng J, Zhang S, Zhang Q, Mai Z, Gu W.Mol Cell Biochem. 2016 Dec;423(1-2):9-20. Epub 2016 Oct 13. PMID: 27734224 3:Structural basis of reversine selectivity in inhibiting Mps1 more potently than aurora B kinase. Hiruma Y, Koch A, Dharadhar S, Joosten RP, Perrakis A.Proteins. 2016 Dec;84(12):1761-1766. doi: 10.1002/prot.25174. Epub 2016 Oct 11. PMID: 27699881 4:Reversine triggers mitotic catastrophe and apoptosis in K562 cells. Rodrigues Alves AP, Machado-Neto JA, Scheucher PS, Paiva HH, Simões BP, Rego EM, Traina F.Leuk Res. 2016 Sep;48:26-31. doi: 10.1016/j.leukres.2016.06.011. Epub 2016 Jul 1. PMID: 27447890 5:Reversine Induced Multinucleated Cells, Cell Apoptosis and Autophagy in Human Non-Small Cell Lung Cancer Cells. Lu YC, Lee YR, Liao JD, Lin CY, Chen YY, Chen PT, Tseng YS.PLoS One. 2016 Jul 6;11(7):e0158587. doi: 10.1371/journal.pone.0158587. eCollection 2016. PMID: 27385117 Free PMC Article6:Ovine fetal mesenchymal stem cell differentiation to cardiomyocytes, effects of co-culture, role of small molecules; reversine and 5-azacytidine. Soltani L, Rahmani HR, Daliri Joupari M, Ghaneialvar H, Mahdavi AH, Shamsara M.Cell Biochem Funct. 2016 Jun;34(4):250-61. doi: 10.1002/cbf.3187. Epub 2016 Apr 27. PMID: 27121349 7:Reversine Increases the Plasticity of Long-Term Cryopreserved Fibroblasts to Multipotent Progenitor Cells through Activation of Oct4. Li X, Guo Y, Yao Y, Hua J, Ma Y, Liu C, Guan W.Int J Biol Sci. 2016 Jan 1;12(1):53-62. doi: 10.7150/ijbs.12199. eCollection 2016. PMID: 26722217 Free PMC Article8:Reversine increases the plasticity of lineage-committed preadipocytes to osteogenesis by inhibiting adipogenesis through induction of TGF-β pathway in vitro. Park JG, Lee DH, Moon YS, Kim KH.Biochem Biophys Res Commun. 2014 Mar 28;446(1):30-6. doi: 10.1016/j.bbrc.2014.02.036. Epub 2014 Feb 15. PMID: 24548409 9:Reversine induces multipotency of lineage-committed cells through epigenetic silencing of miR-133a. Kim M, Yi SA, Lee H, Bang SY, Park EK, Lee MG, Nam KH, Yoo JH, Lee DH, Ryu HW, Kwon SH, Han JW.Biochem Biophys Res Commun. 2014 Feb 28;445(1):255-62. doi: 10.1016/j.bbrc.2014.02.002. Epub 2014 Feb 7. PMID: 24513286 10:Targeting focal adhesion turnover in invasive breast cancer cells by the purine derivative reversine. Bijian K, Lougheed C, Su J, Xu B, Yu H, Wu JH, Riccio K, Alaoui-Jamali MA.Br J Cancer. 2013 Nov 26;109(11):2810-8. doi: 10.1038/bjc.2013.675. Epub 2013 Oct 29. PMID: 24169345 Free PMC Article