172060

Andrographolide

A bicyclic diterpenoid lactone that displays anti-viral, anti-inflammatory, anti-apoptotic, and anti-hyperglycemic properties.

• Synonyma: Andrographolide, Andro
• Empirický vzorec (Hillův zápis): C₂₀H₃₀O₅
• Číslo CAS: 5508-58-7
• Molekulová hmotnost: 350.45
• UNSPSC Code: 12352200
• NACRES: NA.77
• MDL number: MFCD07778082
• Assay: ≥95% (TLC)
• Form: solid
• Storage condition: OK to freeze, protect from light

Vlastnosti

• Quality Segment: 100
• description: Merck USA index - 14, 633
• assay: ≥95% (TLC)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze, protect from light
• color: off-white
• solubility: chloroform: methanol (1:1): 10 mg/mL, DMSO: 15 mg/mL (Use only fresh DMSO.)
• shipped in: ambient
• storage temp.: 2-8°C
• SMILES string: O1CC(\C(=C/C[C@H]2[C@]3(C(C(C(CC3)O)(CO)C)CCC2=C)C)\C1=O)O
• InChI: 1S/C20H30O5/c1-12-4-7-16-19(2,9-8-17(23)20(16,3)11-21)14(12)6-5-13-15(22)10-25-18(13)24/h5,14-17,21-23H,1,4,6-11H2,2-3H3/b13-5+/t14-,15?,16?,17?,19+,20?/m1/s1
• InChI key: BOJKULTULYSRAS-ZJFCSBQFSA-N

Popis

General description

A bicyclic diterpenoid lactone that displays anti-viral, anti-inflammatory, anti-apoptotic, and anti-hyperglycemic properties. Acts as an irreversible antagonist of NF-κB and AP-1 (IC₅₀ ≤ 15 µM) activation, and prevents in vitro and in vivo T cell activation. Exerts no effect on IκBα degradation, p50 and p65 nuclear translocation. Inhibits iNOS and Mac-1 expressions and ROS production, and prevents endotoxin shock in mouse model. Further, reported to activate PI 3K/Akt pathway.

An irreversible blocker of NF-κB and AP-1 (IC₅₀ ≤ 15 µM) activation that displays anti-viral, anti-inflammatory, anti-apoptotic, and anti-hyperglycemic properties. Exerts no effect on IκBα degradation of nuclear translocation p50 and p65. Inhibits iNOS and Mac-1 expressions and ROS production, and prevents endotoxin shock in a mouse model. Reported to supress Cytochrome C release and apoptosis by activating the PI 3-K/Akt pathway.

Biochem/physiol Actions

Cell permeable: no

Primary Target
NF-κB and AP-1 activation

Product does not compete with ATP.

Reversible: no

Target IC₅₀: ≤ 15 µM against NF-κB and AP-1 activation

Packaging

Packaged under inert gas

Preparation Note

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

Other Notes

Xia, Y.F., et al. 2004. J. Immunol.173, 4207.
Chen, J.H., et al. 2004. Biochem. Pharmacol.67, 1337.
Yu, B.C., et al. 2003. Planta Med.69, 1075.

Legal Information

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

Disclaimer

Toxicity: Carcinogenic / Teratogenic (D)

Bezpečnostní informace

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