R3904
Reversine
≥98% (HPLC), A3 adenosine receptor antagonist, solid
Synonym(s):
2-(4-Morpholinoanilino)-6-cyclohexylaminopurine
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About This Item
Empirical Formula (Hill Notation):
C21H27N7O
CAS Number:
Molecular Weight:
393.49
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Product Name
Reversine, ≥98% (HPLC), solid
Quality Level
assay
≥98% (HPLC)
form
solid
solubility
DMSO: soluble 7 mg/mL, H2O: insoluble
storage temp.
2-8°C
SMILES string
C1CCC(CC1)Nc2nc(Nc3ccc(cc3)N4CCOCC4)nc5nc[nH]c25
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)
InChI key
ZFLJHSQHILSNCM-UHFFFAOYSA-N
Gene Information
human ... ADORA1(134), ADORA2A(135), ADORA2B(136), ADORA3(140)
rat ... Adora3(25370)
Application
Reversine has been used as a monopolar spindle 1 (Mps1) kinase inhibitor or mitotic spindle assembly checkpoint (SAC) inhibitor:
- to study the need of mitotic arrest for combretastatin A4 (CA4)-mediated cytotoxicity
- to study the contribution of SAC activation to epstein-barr virus (EBV) replication
- to induce chromosome mis-segregation
Biochem/physiol Actions
Reversine is an A3 adenosine receptor antagonist, Aurora kinase inhibitor, and Mps1 kinase inhibitor.
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.
Preparation Note
According to other sources, stock solutions of Reversine in DMSO are stable refrigerated for short term only. For long term storage aliquotes should be stable at -20°C for up to 2 years. Solution storage at ambient temperature is not recommended.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Xianlong Chen et al.
Journal of bone oncology, 46, 100601-100601 (2024-05-06)
Reversine, or 2-(4-morpholinoanilino)-6-cyclohexylaminopurine, is a 2,6-disubstituted purine derivative. This small molecule shows anti-tumor potential by playing a central role in the inhibition of several kinases related to cell cycle regulation and cytokinesis. In this study, systematic review demonstrated the feasibility
Chromosome mis-segregation generates cell-cycle-arrested cells with complex karyotypes that are eliminated by the immune system
Santaguida S, et al.
Developmental Cell, 41(6), 638-651 (2017)
Krishna K Sarangapani et al.
The Journal of cell biology, 220(12) (2021-10-15)
Dividing cells detect and correct erroneous kinetochore-microtubule attachments during mitosis, thereby avoiding chromosome missegregation. The Aurora B kinase phosphorylates microtubule-binding elements specifically at incorrectly attached kinetochores, promoting their release and providing another chance for proper attachments to form. However, growing
Global Trade Item Number
| SKU | GTIN |
|---|---|
| R3904-1MG | 04061826676776 |
| R3904-5MG | 04061832925332 |