574102

Sulindac Sulfide

A cell-permeable, active metabolite of Sulindac.

• Synonym(e): Sulindac Sulfide, (Z)-5-Fluoro-2-methyl-1-[ p-(methylthio)benzylidene]indene-3-acetic Acid
• Empirische Formel (Hill-System): C₂₀H₁₇FO₂S
• CAS-Nummer: 32004-67-4
• Molekulargewicht: 340.41
• UNSPSC Code: 51111800
• NACRES: NA.77
• MDL number: MFCD00869764
• Assay: ≥98% (TLC)
• Form: solid
• Storage condition: OK to freeze

Eigenschaften

• Quality Segment: 100
• assay: ≥98% (TLC)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze
• color: yellow-orange
• solubility: DMSO: 25 mg/mL, ethanol: 5 mg/mL
• shipped in: ambient
• storage temp.: 10-30°C
• SMILES string: Fc1cc2c(cc1)\C(=C\c3ccc(cc3)SC)\C(=C2CC(=O)O)C
• InChI: 1S/C20H17FO2S/c1-12-17(9-13-3-6-15(24-2)7-4-13)16-8-5-14(21)10-19(16)18(12)11-20(22)23/h3-10H,11H2,1-2H3,(H,22,23)/b17-9+
• InChI key: LFWHFZJPXXOYNR-RQZCQDPDSA-N

Beschreibung

General description

A cell-permeable, active metabolite of Sulindac (Cat. No. 574100). Strongly inhibits Ras-induced malignant transformation and Ras/Raf-dependent transactivation. Also decreases the Ras-induced activation of c-Raf-1 kinase. Inhibits growth and induces apoptosis in prostate cancer cell lines. Selectively inhibits COX-1 (ID₅₀ = 500 nM) compared to prostaglandin H synthase-2 (PGHS-2; COX-2; ID₅₀ = 14 µM). Preferentially inhibits the secretion of Aβ₄₂ in CHO cells stably transfected with both APP₇₅, and the PS1 mutant M146L.

An active metabolite of the non-steroidal anti-inflammatory drug Sulindac (Cat. No. 574100). Inhibits Ras signaling. Strongly inhibits Ras-induced malignant transformation and Ras/Raf-dependent transactivation. Also decreases the Ras-induced activation of c-Raf-1 kinase. Inhibits cell growth and induces apoptosis in a time-and dose-dependent manner. Selectively inhibits prostaglandin H synthase-1 (PGHS-1; COX-1; ID₅₀ = 0.5 µM) relative to prostaglandin H synthase-2 (PGHS-2; COX-2; ID₅₀ = 14 µM). Reduces Aβ₄₂ production independently of COX inhibition.

Biochem/physiol Actions

Cell permeable: yes

ID50 = 500 nM against COX-1

Product does not compete with ATP.

Reversible: no

Other Notes

Weggen, S., et al. 2001. Nature414, 212.
Lim, J.T., et al. 1999. Biochem. Pharmacol. 58, 1097.
Herrmann, C., et al. 1998. Oncogene 17, 1769.
Picariello, L., et al. 1998. Eur. J. Pharmacol. 360, 105.
Arber, N., et al. 1997. Gastroenterology 113, 1892.
Meade, E.A., et al. 1993. J. Biol. Chem. 268, 6610.

Legal Information

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

Disclaimer

Toxicity: Harmful & Carcinogenic / Teratogenic (E)

Sicherheitshinweise

• pictograms: GHS08,GHS07
• signalword: Danger
• hcodes: H302,H317,H334,H361
• pcodes: P202 - P261 - P280 - P301 + P312 - P302 + P352 - P308 + P313
• Hazard Classifications: Acute Tox. 4 Oral - Repr. 2 - Resp. Sens. 1 - Skin Sens. 1
• Lagerklasse: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable