REVERSINE

ChemicalBook > CAS DataBase List > REVERSINE

Product Name: REVERSINE
CAS No.: 656820-32-5
Chemical Name: REVERSINE
Synonyms: CS-870;REVERSINE;Reversine, >96%;Reversine, >=98%;REVERSINE USP/EP/BP;Picropodophyllin (PPP);2-(4-MORPHOLINOANILINO)-6-CYCLOHEXYLAMINOPURINE;N6-CYCLOHEXYL-N2-(4-MORPHOLINOPHENYL)-9H-PURINE-2,6-DIAMINE;N6-Cyclohexyl-N2-(4-morpholinophenyl)-7H-purine-2,6-diamine;N6-CYCLOHEXYL-N2-[4-(4-MORPHOLINYL)PHENYL]-1H-PURINE-2,6-DIAMINE
CBNumber: CB5470820
Molecular Formula: C21H27N7O
Formula Weight: 393.49
MOL File: 656820-32-5.mol

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REVERSINE Property

Melting point:: 305℃ (decomposition)
Boiling point:: 736.4±70.0 °C(Predicted)
Density: 1.343±0.06 g/cm3(Predicted)
storage temp.: 2-8°C
solubility: DMSO: 7 mg/mL, soluble
form: solid
pka: 10.51±0.10(Predicted)
color: Off-white
Stability:: Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months

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Safety

Hazard Codes: Xn
Risk Statements: 22
WGK Germany: 3

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P330Rinse mouth.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: R3904
Product name: Reversine
Purity: ≥98% (HPLC), solid
Packaging: 1mg
Price: $91.6
Updated: 2024/03/01

Sigma-Aldrich

Product number: R3904
Product name: Reversine
Purity: ≥98% (HPLC), solid
Packaging: 5mg
Price: $317
Updated: 2024/03/01

Cayman Chemical

Product number: 10004412
Product name: Reversine
Purity: ≥98%
Packaging: 1mg
Price: $36
Updated: 2024/03/01

Cayman Chemical

Product number: 10004412
Product name: Reversine
Purity: ≥98%
Packaging: 5mg
Price: $155
Updated: 2024/03/01

Cayman Chemical

Product number: 10004412
Product name: Reversine
Purity: ≥98%
Packaging: 10mg
Price: $274
Updated: 2024/03/01

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REVERSINE Chemical Properties,Usage,Production

Description

Reversine is a 2,6-disubstituted purine derivative that was originally found to induce dedifferentiation of C2C12 culture myoblast cells into stem cell progenitors when used at a concentration of 5 μM for four days. Depending on cell type, reversine promotes either differentiation or dedifferentiation. For example, in NT2 neuronal and HL-60 human promyelocytic leukemia cells, it induces differentiation. It inhibits the Aurora A, B, and C kinases with IC₅₀ values of 98-876 nM and acts as an antagonist at the adenosine A₃ receptor with a K_i value of 0.66 μM. Reversine is also used for studies of chromosome segregation. It inhibits the mitotic spindle checkpoint enzyme MPS1 with IC₅₀ values of 6 and 2.8 nM for its kinase domain and full-length version, respectively). Reversine induces autophagy in WRO human follicular thyroid cancer cells and decreases Akt/mTOR signaling.

Uses

Reversine acts as a potent human A3 adenosine receptor antagonist and pan-aurora A/B/C kinase inhibitor. Used for stem cell differentiation.

Definition

ChEBI: 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.

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.

in vitro

reversine could be used to induce dedifferentiation of murine myoblasts. previous reports also showed that reversine had a role in regeneration. moreover, a recent report indicated reversine had anti-tumor capabilities for a myeloma cell line, as demonstrated by that reversine could suppress the expression of cell cycle related proteins aurora kinase a and aurora kinase b [1].

in vivo

the effects of reversine on tumor weight and volume were assessed using a murine model of cervical cancer with u14 cells, separately or combined with aspirin. the inhibition rate of cells in the combination group significantly increased; moreover, such combination could synergistically inhibit the proliferation of five cervical cancer cell lines. in the mouse model, tumor weight and volume of cervical cancer bearing mice were more reduced [1].

IC 50

150, 500 and 400 nm for aurora kinase a, b and c respectively

References

1) Chen et al. (2004), Dedifferentiation of lineage-committed cells by a small molecule; J. Am. Chem. Soc., 126 410 2) Chen et al. (2007), Reversine increases the plasticity of lineage-committed mammalian cells; Proc. Natl. Acad. Sci. USA, 104 10482 3) Perreira et al. (2005), Reversine and its 2-substituted adenine derivatives as potent and selective A3 adenosine receptor antagonists; J. Med. Chem., 48 4910

REVERSINE Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from REVERSINE manufacturers

Career Henan Chemical Co

Product: REVERSINE 656820-32-5
Price: US $2.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 100kg
Release date: 2018-12-24

656820-32-5, REVERSINERelated Search:

CYCLOPAMINE Rimonabant Ginkgolide B LY-2584702 (tosylate salt) MG-132 AVP-AEW541 Trametinib BMS-754807 Canertinib REVERSINE

9H-Purine-2,6-diamine,N6-cyclohexyl-N2-[4-(4-morpholinyl)phenyl]-

N6-Cyclohexyl-N2-(4-morpholinophenyl)-7H-purine-2,6-diamine

2-(4-MORPHOLINOANILINO)-6-CYCLOHEXYLAMINOPURINE

N6-CYCLOHEXYL-N2-(4-MORPHOLINOPHENYL)-9H-PURINE-2,6-DIAMINE

Picropodophyllin (PPP)

N6-Cyclohexyl-N2-[4-(4-morpholinyl)phenyl]-1H-purine-2,6-diamine Reversine

Reversine N6-Cyclohexyl-N2-[4-(4-morpholinyl)phenyl]-1H-purine-2,6-diamine

REVERSINE

N6-CYCLOHEXYL-N2-[4-(4-MORPHOLINYL)PHENYL]-1H-PURINE-2,6-DIAMINE

Reversine, >=98%

Reversine, >96%

CS-870

REVERSINE USP/EP/BP

656820-32-5

C21H27N7O

Inhibitors