5.33575

Rigosertib

• Synonym(e): Rigosertib, Sodium ( E)-2-(2-methoxy-5-((2,4,6-trimethoxystyrylsulfonyl)methyl)phenylamino)acetate, ON01910, Na, Estybon
• Empirische Formel (Hill-System): C₂₁H₂₄NNaO₈S
• CAS-Nummer: 592542-60-4
• Molekulargewicht: 473.47
• MDL number: MFCD11655911
• UNSPSC Code: 12352200
• NACRES: NA.77
• Assay: ≥98% (HPLC)
• Form: solid
• Storage condition: OK to freeze, protect from light

Eigenschaften

• assay: ≥98% (HPLC)
• Quality Segment: 100
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze, protect from light
• color: off-white
• solubility: DMSO: 50 mg/mL
• storage temp.: 2-8°C
• SMILES string: [Na+].[S](=O)(=O)(Cc2cc(c(cc2)OC)NCC(=O)[O-])\C=C\c1c(cc(cc1OC)OC)OC
• InChI: 1S/C21H25NO8S.Na/c1-27-15-10-19(29-3)16(20(11-15)30-4)7-8-31(25,26)13-14-5-6-18(28-2)17(9-14)22-12-21(23)24;/h5-11,22H,12-13H2,1-4H3,(H,23,24);/q;+1/p-1/b8-7+;
• InChI key: VLQLUZFVFXYXQE-USRGLUTNSA-M

Beschreibung

General description

A cell-permeable, nontoxic benzylstyrylsulfone based compound with anti-tumor and radiosensitizing properties. Potently suppresses PI 3-K/Akt/mTOR signaling pathway and activates Cdc25C phosphatases. Acts as an allosteric, substrate-competitive, and reversible inhibitor of multiple protein kinases (IC₅₀ = 32, 42, 182, 18 and 155 nM against Bcr-Abl, Flt1, Fyn, PDGFR, and Src, respectively). Induces DNA damage and blocks microtubule formation. Also shown to cause mitotic arrest and apoptosis in multiple types of cancer cells (GI₅₀ = 30 - 200 nM) and blocks cell cycle at G2/M phase. Effective against several multi-drug resistance tumor cells (IC₅₀ = 50-100 nM). Suppresses the growth of BT20 tumor xenografts in mice and improves their survival rate (200 mg/kg, i.v. Q2D X 20 schedule). However, it displays limited oral bioavailability.

Rigosertib, CAS 592542-60-4, is a cell-permeable, potent suppressor of PI 3-K/Akt/mTOR signaling. Allosterically inhibits several key protein kinases that are over active in many cancer cells.

Biochem/physiol Actions

Cell permeable: yes

Primary Target
PI 3-K/Akt/mTOR signaling

Target IC₅₀: 32, 42, 182, 18 and 155 nM against Bcr-Abl, Flt1, Fyn, PDGFR, and Src, respectively

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Lu, T., et al. 2015. Mol. Pharmacol.87, 18.
Ramana Reddy, M.V., et al. 2011. J. Med. Chem.54, 6254.
Gumireddy, K., et al. 2005. Cancer Cell7, 275.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

Sicherheitshinweise

• Lagerklasse: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable