T3652

Triptolide

from Tripterygium wilfordii, ≥98% (HPLC), solid, immunosuppressant

• Synonym(s): PG 490
• Empirical Formula (Hill Notation): C₂₀H₂₄O₆
• CAS Number: 38748-32-2
• Molecular Weight: 360.40
• MDL number: MFCD00210565
• UNSPSC Code: 12352200
• PubChem Substance ID: 24900156
• NACRES: NA.77

Properties

• Product Name: Triptolide, from Tripterygium wilfordii, ≥98% (HPLC), solid
• biological source: Tripterygium wilfordii
• Assay: ≥98% (HPLC)
• form: solid
• color: white to off-white
• solubility: DMSO: soluble
• storage temp.: 2-8°C
• SMILES string: O=C1OCC2=C1CC[C@]3(C)[C@]4(O5)[C@@H]5[C@H]6[C@@](O6)(C(C)C)[C@@H](O)[C@]4(O7)[C@@H]7C[C@]32[H]
• InChI: 1S/C20H24O6/c1-8(2)18-13(25-18)14-20(26-14)17(3)5-4-9-10(7-23-15(9)21)11(17)6-12-19(20,24-12)16(18)22/h8,11-14,16,22H,4-7H2,1-3H3/t11?,12-,13-,14-,16+,17-,18-,19+,20+/m0/s1
• InChI key: DFBIRQPKNDILPW-KTGKZQHOSA-N

Description

Application

Triptolide has been used as a NF-κB inhibitor to study the inhibition of cell invasion and angiogenesis in human thyroid cancer cells⁶. Triptolide has also been used to study its apoptotic effects in anaplastic thyroid cancer cells⁷.

Biochem/physiol Actions

Triptolide is a diterpene triepoxide, the principal active ingredient in extracts from the Chinese herb Tripterygium wilfordii hook (TwHF). It is a potent immunosuppressant and anti-inflammatory. Triptolide has been shown to inhibit the expression of IL-2 in activated T cells at the level of purine-box/nuclear factor and NF-κB mediated transcription activation. It synergizes with cyclosporin A in promoting graft survival in animal models and in suppression of graft versus host disease in allogeneic bone marrow transplants. In addition, it induces apoptosis in tumor cells and potentiates tumor necrosis factor (TNF_α) induction of apoptosis in part through the suppression of c-IAP₂ and c-IAP₁ induction.

Preparation Note

Triptolide is soluble in DMSO. The stock solution should be stored in DMSO at -20 deg C after reconstitution.

Safety Information

• Pictograms: GHS06,GHS08
• Signal Word: Danger
• Hazard Statements: H300 + H330,H361f
• Precautionary Statements: P202 - P260 - P264 - P270 - P271 - P304 + P340 + P310
• Hazard Classifications: Acute Tox. 1 Inhalation - Acute Tox. 1 Oral - Repr. 2
• Storage Class Code: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves