Description
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.
Chemical properties
| Chemical formula | Net charge | Average mass |
|---|---|---|
| C21H27N7O | 0 | 393.48540 |
Nomenclature
| IUPAC | SMILES | InChI | InChIKey | Synonyms |
|---|---|---|---|---|
| N(6)-cyclohexyl-N(2)-[4-(morpholin-4-yl)phenyl]-9H-purine-2,6-diamine | C1CCC(CC1)Nc1nc(Nc2ccc(cc2)N2CCOCC2)nc2[nH]cnc12 | 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) | ZFLJHSQHILSNCM-UHFFFAOYSA-N |
|
Citations
- Chen, S, et al. 2004. Dedifferentiation of lineage-committed cells by a small molecule. Journal of the American Chemical Society. 126(2).
- Chen, S, et al. 2007. Reversine increases the plasticity of lineage-committed mammalian cells. Proceedings of the National Academy of Sciences of the United States of America. 104(25).
- Conforti, E, et al. 2011. Reversine increases multipotent human mesenchymal cells differentiation potential. Journal of Biological Regulators and Homeostatic Agents. 25(2 Suppl).
- D'Alise, AM, et al. 2008. Reversine, a novel Aurora kinases inhibitor, inhibits colony formation of human acute myeloid leukemia cells. Molecular Cancer Therapeutics. 7(5).
- Hsieh, TC, et al. 2007. The 2,6-disubstituted purine reversine induces growth arrest and polyploidy in human cancer cells. International Journal of Oncology. 31(6).
- Hua, SC, et al. 2012. Reversine, a 2,6-disubstituted purine, as an anti-cancer agent in differentiated and undifferentiated thyroid cancer cells. Pharmaceutical Research. 29(7).
- Jemaà, M, et al. 2012. Preferential killing of p53-deficient cancer cells by reversine. Cell Cycle (Georgetown, Tex.). 11(11).
- Kim, YK, et al. 2007. Reversine stimulates adipocyte differentiation and downregulates Akt and p70(s6k) signaling pathways in 3T3-L1 cells. Biochemical and Biophysical Research Communications. 358(2).
- Kuo, CH, et al. 2012. Reversine induces cell cycle arrest, polyploidy, and apoptosis in human breast cancer cells. Breast Cancer (Tokyo, Japan). 21(3).
- Lee, YR, et al. 2012. Reversine suppresses oral squamous cell carcinoma via cell cycle arrest and concomitantly apoptosis and autophagy. Journal of Biomedical Science. 19.
- Li, R, et al. 2007. Reversine inhibits spontaneous synaptic transmission in cultured rat hippocampal neurons. Cell Biology International. 31(6).
- Lv, X, et al. 2012. Reversine promotes porcine muscle derived stem cells (PMDSCs) differentiation into female germ-like cells. Journal of Cellular Biochemistry. 113(12).
- Miyoshi, K, et al. 2010. Beneficial effects of reversine on in vitro development of miniature pig somatic cell nuclear transfer embryos. The Journal of Reproduction and Development. 56(2).
- Perreira, M, et al. 2005. "Reversine" and its 2-substituted adenine derivatives as potent and selective A3 adenosine receptor antagonists. Journal of Medicinal Chemistry. 48(15).
- Piccoli, M, et al. 2012. The synthetic purine reversine selectively induces cell death of cancer cells. Journal of Cellular Biochemistry. 113(10).
- Santaguida, S, et al. 2010. Dissecting the role of MPS1 in chromosome biorientation and the spindle checkpoint through the small molecule inhibitor reversine. The Journal of Cell Biology. 190(1).
- Saraiya, M, et al. 2009. Reversine enhances generation of progenitor-like cells by dedifferentiation of annulus fibrosus cells. Tissue Engineering. Part A. 16(4).
- Shan, SW, et al. 2007. Induction of growth arrest and polycomb gene expression by reversine allows C2C12 cells to be reprogrammed to various differentiated cell types. Proteomics. 7(23).