WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H406277
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.
Hodoodo Cat#: H406277
Name: Reversine
CAS#: 656820-32-5
Chemical Formula: C21H27N7O
Exact Mass: 393.23
Molecular Weight: 393.490
Elemental Analysis: C, 64.10; H, 6.92; N, 24.92; O, 4.07
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 and DMF
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO and DMF
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
More Info:
| 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: | In senescent myoblast cells, reversine reactivated autophagy and insulin signaling pathway via upregulation of AMPK and Akt2, restoring insulin sensitivity and glucose uptake in senescent cells. Reversine restored the loss of connectivity of glycolysis to the TCA cycle, thus restoring dysfunctional mitochondria and the impaired myogenic differentiation potential of senescent myoblasts. These findings suggest that cellular senescence can be reversed by reversine treatment and without genetic reprogramming technologies. Reference: Aging Cell. 2023 Mar;22(3):e13764. https://pubmed.ncbi.nlm.nih.gov/36625257/ |
| In vivo activity: | Intraperitoneal administration of reversine in mice upregulated thermogenesis and resulted in resistance to high-fat diet-mediated weight gain as well as browning of subcutaneous and epididymal white adipose tissues. Browning of white adipocytes is a promising approach for the prevention of obesity and obesity-associated metabolic diseases. This study demonstrates that reversine promotes browning. Reference: J Cell Physiol. 2019 Apr;234(4):3800-3813. https://pubmed.ncbi.nlm.nih.gov/30132867/ |
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 11.7 | 29.66 | |
| DMF | 20.0 | 50.83 | |
| DMF:PBS (pH 7.2) (1:8) | 0.5 | 1.27 |
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.
| 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. Rajabian N, Choudhury D, Ikhapoh I, Saha S, Kalyankar AS, Mehrotra P, Shahini A, Breed K, Andreadis ST. Reversine ameliorates hallmarks of cellular senescence in human skeletal myoblasts via reactivation of autophagy. Aging Cell. 2023 Mar;22(3):e13764. doi: 10.1111/acel.13764. Epub 2023 Jan 10. PMID: 36625257; PMCID: PMC10014065. 2. Xia P, Liang J, Jin D, Jin Z. Reversine inhibits proliferation, invasion and migration and induces cell apoptosis in gastric cancer cells by downregulating TTK. Exp Ther Med. 2021 Sep;22(3):929. doi: 10.3892/etm.2021.10361. Epub 2021 Jun 30. PMID: 34306198; PMCID: PMC8281506. 3. Kim S, Park JW, Lee MG, Nam KH, Park JH, Oh H, Lee J, Han J, Yi SA, Han JW. Reversine promotes browning of white adipocytes by suppressing miR-133a. J Cell Physiol. 2019 Apr;234(4):3800-3813. doi: 10.1002/jcp.27148. Epub 2018 Aug 21. PMID: 30132867. 4. Huang D, Tang L, Li T, Li P, Huang Z, Weng J, Zhang S, Gu W, Huang Y. Reversine attenuates cholestatic ductular reaction in rats. FEBS Open Bio. 2023 May;13(5):898-911. doi: 10.1002/2211-5463.13596. Epub 2023 Apr 7. PMID: 36929584; PMCID: PMC10153338. |
| In vitro protocol: | 1. Rajabian N, Choudhury D, Ikhapoh I, Saha S, Kalyankar AS, Mehrotra P, Shahini A, Breed K, Andreadis ST. Reversine ameliorates hallmarks of cellular senescence in human skeletal myoblasts via reactivation of autophagy. Aging Cell. 2023 Mar;22(3):e13764. doi: 10.1111/acel.13764. Epub 2023 Jan 10. PMID: 36625257; PMCID: PMC10014065. 2. Xia P, Liang J, Jin D, Jin Z. Reversine inhibits proliferation, invasion and migration and induces cell apoptosis in gastric cancer cells by downregulating TTK. Exp Ther Med. 2021 Sep;22(3):929. doi: 10.3892/etm.2021.10361. Epub 2021 Jun 30. PMID: 34306198; PMCID: PMC8281506. |
| In vivo protocol: | 1. Kim S, Park JW, Lee MG, Nam KH, Park JH, Oh H, Lee J, Han J, Yi SA, Han JW. Reversine promotes browning of white adipocytes by suppressing miR-133a. J Cell Physiol. 2019 Apr;234(4):3800-3813. doi: 10.1002/jcp.27148. Epub 2018 Aug 21. PMID: 30132867. 2. Huang D, Tang L, Li T, Li P, Huang Z, Weng J, Zhang S, Gu W, Huang Y. Reversine attenuates cholestatic ductular reaction in rats. FEBS Open Bio. 2023 May;13(5):898-911. doi: 10.1002/2211-5463.13596. Epub 2023 Apr 7. PMID: 36929584; PMCID: PMC10153338. |
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.
