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R3904

Sigma-Aldrich

Reversine

≥98% (HPLC), solid

Synonym(s):

2-(4-Morpholinoanilino)-6-cyclohexylaminopurine

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About This Item

Empirical Formula (Hill Notation):
C21H27N7O
CAS Number:
656820-32-5
Molecular Weight:
393.49
MDL number:
MFCD07784513
UNSPSC Code:
12352200
PubChem Substance ID:
24724590
NACRES:
NA.77

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 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.

Storage and Stability

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
G N Subramanian et al.
Molecular human reproduction, 27(2) (2020-12-19)
Premature loss of ovarian activity before 40 years of age is known as primary ovarian insufficiency (POI) and occurs in ∼1% of women. A more subtle decline in ovarian activity, known as premature ovarian ageing (POA), occurs in ∼10% of women.
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)
Structurally simplified biphenyl combretastatin A4 derivatives retain in vitro anti-cancer activity dependent on mitotic arrest.
Tarade D, et al.
PLoS ONE, 12(3), e0171806-e0171806 (2017)
Federica Schiavoni et al.
Nature communications, 13(1), 1731-1731 (2022-04-03)
Aneuploidy results in decreased cellular fitness in many species and model systems. However, aneuploidy is commonly found in cancer cells and often correlates with aggressive growth, suggesting that the impact of aneuploidy on cellular fitness is context dependent. The BRG1
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