Reversine
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MedKoo CAT#: 406277

CAS#: 656820-32-5

Description: Reversine is a small molecule developed by the group of Peter G. Schultz, used for stem cell dedifferentiation. Reversine is also a novel Aurora kinases inhibitor that inhibits colony formation of human acute myeloid leukemia cells. Reversine inhibits the phosphorylation of histone H3, a direct downstream target of Aurora kinases. Similarly to the Aurora kinase inhibitor VX-680, reversine inhibited colony formation of leukemic cells from patients with acute myeloid leukemia but was significantly less toxic than VX-680 on cells from healthy donors.


Chemical Structure

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Reversine
CAS# 656820-32-5

Theoretical Analysis

MedKoo Cat#: 406277
Name: Reversine
CAS#: 656820-32-5
Chemical Formula: C21H27N7O
Exact Mass: 393.22771
Molecular Weight: 393.49
Elemental Analysis: C, 64.10; H, 6.92; N, 24.92; O, 4.07

Price and Availability

Size Price Availability Quantity
10.0mg USD 90.0 Ready to ship
25.0mg USD 150.0 Ready to ship
50.0mg USD 250.0 Ready to ship
100.0mg USD 450.0 Ready to ship
200.0mg USD 650.0 Ready to ship
500.0mg USD 950.0 Ready to ship
1.0g USD 1650.0 Ready to ship
2.0g USD 2450.0 Ready to ship
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Synonym: Reversine.

IUPAC/Chemical Name: N6-cyclohexyl-N2-(4-morpholinophenyl)-7H-purine-2,6-diamine

InChi Key: ZFLJHSQHILSNCM-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: C12=NC(NC3=CC=C(N4CCOCC4)C=C3)=NC(NC5CCCCC5)=C1NC=N2

Appearance: white solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Biological target: Reversine is an ATP-competitive Aurora kinase inhibitor with IC50s of 400, 500 and 400 nM for Aurora A, Aurora B and Aurora C, respectively.
In vitro activity: A significant increase in LC3-II and Beclin 1 coupled with a decrease in p62 were shown in reversine treatment compared to vehicle controls (P < 0.05) (Figs. 3C–3D). These results suggested that reversine induced autophagy activation and autophagic flux occurred. To determine whether autophagic cell death induced by reversine treatment altered glucose metabolism, the glucose uptake and ATP production in reversine-treated CCA cells were examined. KKU213A and KKU213B CCA (cholangiocarcinoma) cells were treated with 4 µM reversine at 12 and 24 h. The cultured media were collected to measure the glucose uptake while the cell lysates were used to measure the ATP production. Reversine treatment significantly reduced glucose uptake at 24 h and reduced ATP production at 12 and 24 h as shown in Figs. 3E–3F. The protein expression of Hypoxia-inducible factor 1-alpha (HIF-1α) and glucose transporter 1 (GLUT1) by Western blot assay were further analyzed. The results showed markedly decreased protein expression of HIF-1α and GLUT1 in reversine treated cells compared with vehicle control (Figs. 3B–3D). Collectively, these results indicated that reversine treatment induced autophagic cell death and interfered with glucose uptake and ATP production via reduction of HIF-1α and GLUT1 protein expression levels. Reference: PeerJ. 2021 Jan 7;9:e10637. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7797171/
In vivo activity: To determine the effects of reversine treatment on chromosome segregation and the length of mitoses, embryos expressing Histone H2B-GFP15 were treated with 0.5 μM reversine and their development visualized by live imaging during the 8- to 16-cell division. Major chromosome segregation errors, such as lagging chromosomes and the formation of micronuclei, were found to occur during mitosis in 48% of reversine-treated blastomeres (n=81), compared with only 9.7% of control blastomeres (n=72, P<0.001, χ2-test; Fig. 1b). The length of metaphase was also significantly shorter in reversine-treated blastomeres (32.2 min) compared with controls (44.4 min, P<0.001, Mann–Whitney U-test; Fig. 1c). As expected, these effects were reversible. Following washout of reversine from the medium, the chromosome missegregation rate (3.1%) and length of metaphase (47.2 min) both returned to normal levels (n=32; Fig. 1b,c). These results demonstrate that reversine is an effective and reversible inhibitor of the SAC (spindle assembly checkpoint) in pre-implantation embryos. Reference: Nat Commun. 2016; 7: 11165. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4820631/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 11.67 29.66
DMF 20.0 50.83
DMF:PBS (pH 7.2) (1:8) 0.5 1.27

Preparing Stock Solutions

The following data is based on the product molecular weight 393.49 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Prajumwongs P, Waenphimai O, Vaeteewoottacharn K, Wongkham S, Sawanyawisuth K. Reversine, a selective MPS1 inhibitor, induced autophagic cell death via diminished glucose uptake and ATP production in cholangiocarcinoma cells. PeerJ. 2021 Jan 7;9:e10637. doi: 10.7717/peerj.10637. PMID: 33505802; PMCID: PMC7797171. 2. Soltani L, Rahmani HR, Daliri Joupari M, Ghaneialvar H, Mahdavi AH, Shamsara M. Effects of Different Concentrations of Reversine on Plasticity of Mesenchymal Stem Cells. Indian J Clin Biochem. 2020 Apr;35(2):188-196. doi: 10.1007/s12291-018-0800-8. Epub 2018 Dec 10. PMID: 32226250; PMCID: PMC7093655. 3. Guo Y, Zhu H, Li X, Ma C, Sun T, Wang Y, Wang C, Guan W, Liu C. Multiple functions of reversine on the biological characteristics of sheep fibroblasts. Sci Rep. 2021 Jun 11;11(1):12365. doi: 10.1038/s41598-021-91468-w. PMID: 34117304; PMCID: PMC8196188. 4. He Q, Au B, Kulkarni M, Shen Y, Lim KJ, Maimaiti J, Wong CK, Luijten MNH, Chong HC, Lim EH, Rancati G, Sinha I, Fu Z, Wang X, Connolly JE, Crasta KC. Chromosomal instability-induced senescence potentiates cell non-autonomous tumourigenic effects. Oncogenesis. 2018 Aug 15;7(8):62. doi: 10.1038/s41389-018-0072-4. PMID: 30108207; PMCID: PMC6092349.
In vitro protocol: 1. Prajumwongs P, Waenphimai O, Vaeteewoottacharn K, Wongkham S, Sawanyawisuth K. Reversine, a selective MPS1 inhibitor, induced autophagic cell death via diminished glucose uptake and ATP production in cholangiocarcinoma cells. PeerJ. 2021 Jan 7;9:e10637. doi: 10.7717/peerj.10637. PMID: 33505802; PMCID: PMC7797171. 2. Soltani L, Rahmani HR, Daliri Joupari M, Ghaneialvar H, Mahdavi AH, Shamsara M. Effects of Different Concentrations of Reversine on Plasticity of Mesenchymal Stem Cells. Indian J Clin Biochem. 2020 Apr;35(2):188-196. doi: 10.1007/s12291-018-0800-8. Epub 2018 Dec 10. PMID: 32226250; PMCID: PMC7093655.
In vivo protocol: 1. Guo Y, Zhu H, Li X, Ma C, Sun T, Wang Y, Wang C, Guan W, Liu C. Multiple functions of reversine on the biological characteristics of sheep fibroblasts. Sci Rep. 2021 Jun 11;11(1):12365. doi: 10.1038/s41598-021-91468-w. PMID: 34117304; PMCID: PMC8196188. 2. He Q, Au B, Kulkarni M, Shen Y, Lim KJ, Maimaiti J, Wong CK, Luijten MNH, Chong HC, Lim EH, Rancati G, Sinha I, Fu Z, Wang X, Connolly JE, Crasta KC. Chromosomal instability-induced senescence potentiates cell non-autonomous tumourigenic effects. Oncogenesis. 2018 Aug 15;7(8):62. doi: 10.1038/s41389-018-0072-4. PMID: 30108207; PMCID: PMC6092349.

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1: Qin HX, Yang J, Cui HK, Li SP, Zhang W, Ding XL, Xia YH. Synergistic antitumor activity of reversine combined with aspirin in cervical carcinoma in vitro and in vivo. Cytotechnology. 2013 Aug;65(4):643-53. doi: 10.1007/s10616-012-9520-8. Epub 2013 Mar 10. PubMed PMID: 23475158; PubMed Central PMCID: PMC3720971.

2: Lu CH, Liu YW, Hua SC, Yu HI, Chang YP, Lee YR. Autophagy induction of reversine on human follicular thyroid cancer cells. Biomed Pharmacother. 2012 Dec;66(8):642-7. doi: 10.1016/j.biopha.2012.08.001. Epub 2012 Sep 15. PubMed PMID: 23089471.

3: Hu X, Zhang X, Zhou Y, Yu Y, Xu H. [Research progress of cell dedifferentiation induced by reversine]. Zhongguo Xiu Fu Chong Jian Wai Ke Za Zhi. 2012 Sep;26(9):1126-9. Review. Chinese. PubMed PMID: 23057363.

4: Kuo CH, Lu YC, Tseng YS, Shi CS, Chen SH, Chen PT, Wu FL, Chang YP, Lee YR. Reversine induces cell cycle arrest, polyploidy, and apoptosis in human breast cancer cells. Breast Cancer. 2012 Aug 28. [Epub ahead of print] PubMed PMID: 22926505.

5: Lv X, Zhu H, Bai Y, Chu Z, Hu Y, Cao H, Liu C, He X, Peng S, Gao Z, Yang C, Hua J. Reversine promotes porcine muscle derived stem cells (PMDSCs) differentiation into female germ-like cells. J Cell Biochem. 2012 Dec;113(12):3629-42. doi: 10.1002/jcb.24296. PubMed PMID: 22821411.

6: Piccoli M, Palazzolo G, Conforti E, Lamorte G, Papini N, Creo P, Fania C, Scaringi R, Bergante S, Tringali C, Roncoroni L, Mazzoleni S, Doneda L, Galli R, Venerando B, Tettamanti G, Gelfi C, Anastasia L. The synthetic purine reversine selectively induces cell death of cancer cells. J Cell Biochem. 2012 Oct;113(10):3207-17. doi: 10.1002/jcb.24197. PubMed PMID: 22615034.

7: Jemaà M, Galluzzi L, Kepp O, Boilève A, Lissa D, Senovilla L, Harper F, Pierron G, Berardinelli F, Antoccia A, Castedo M, Vitale I, Kroemer G. Preferential killing of p53-deficient cancer cells by reversine. Cell Cycle. 2012 Jun 1;11(11):2149-58. doi: 10.4161/cc.20621. Epub 2012 Jun 1. PubMed PMID: 22592527.

8: Hua SC, Chang TC, Chen HR, Lu CH, Liu YW, Chen SH, Yu HI, Chang YP, Lee YR. Reversine, a 2,6-disubstituted purine, as an anti-cancer agent in differentiated and undifferentiated thyroid cancer cells. Pharm Res. 2012 Jul;29(7):1990-2005. doi: 10.1007/s11095-012-0727-3. Epub 2012 Apr 4. PubMed PMID: 22477067.

9: Lee YR, Wu WC, Ji WT, Chen JY, Cheng YP, Chiang MK, Chen HR. Reversine suppresses oral squamous cell carcinoma via cell cycle arrest and concomitantly apoptosis and autophagy. J Biomed Sci. 2012 Jan 27;19:9. doi: 10.1186/1423-0127-19-9. PubMed PMID: 22283874; PubMed Central PMCID: PMC3299600.

10: Conforti E, Arrigoni E, Piccoli M, Lopa S, de Girolamo L, Ibatici A, Di Matteo A, Tettamanti G, Brini AT, Anastasia L. Reversine increases multipotent human mesenchymal cells differentiation potential. J Biol Regul Homeost Agents. 2011 Apr-Jun;25(2 Suppl):S25-33. PubMed PMID: 22051168.



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