T3652

Triptolide

Name: Triptolide
Brand: SIGMA

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

Synonym(s):

PG 490

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All Photos(3)

About This Item

Empirical Formula (Hill Notation):

C₂₀H₂₄O₆

CAS Number:

38748-32-2

Molecular Weight:

360.40

UNSPSC Code:

12352200

PubChem Substance ID:

24900156

NACRES:

NA.77

MDL number:

MFCD00210565

Product Name

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

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

biological source

Tripterygium wilfordii

assay

≥98% (HPLC)

form

solid

color

white to off-white

solubility

DMSO: soluble

storage temp.

2-8°C

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Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

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.

pictograms

GHS06,GHS08

signalword

Danger

hcodes

H300 + H330,H361f

pcodes

P202 - P260 - P264 - P270 - P271 - P304 + P340 + P310

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 1 Oral - Repr. 2

Storage Class

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

ppe

Eyeshields, Gloves, type N95 (US)

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Triptolide disrupts the actin-based Sertoli-germ cells adherens junctions by inhibiting Rho GTPases expression.

Xiang Wang et al.

Toxicology and applied pharmacology, 310, 32-40 (2016-08-25)

Triptolide (TP), derived from the medicinal plant Triterygium wilfordii Hook. f. (TWHF), is a diterpene triepoxide with variety biological and pharmacological activities. However, TP has been restricted in clinical application due to its narrow therapeutic window especially in reproductive system.

Triptolide attenuates lipopolysaccharide-induced inflammatory responses in human endothelial cells: involvement of NF-κB pathway.

Chundong Song et al.

BMC complementary and alternative medicine, 19(1), 198-198 (2019-08-04)

Endothelial cell inflammation is a central event in the pathogenesis of numerous cardiovascular diseases, including sepsis and atherosclerosis. Triptolide, a principal bioactive ingredient of Traditional Chinese Medicine Tripterygium wilfordii Hook.F., displays anti-inflammatory actions in vivo. However, the mechanisms underlying these

Triptolide inhibits tumor growth by induction of cellular senescence.

Ruidong Li et al.

Oncology reports, 37(1), 442-448 (2016-11-24)

Cellular senescence, an irreversible growth arrest of cells, is involved in protection against cancer. Triptolide (TPL) plays an important role in immunosuppressive, anti-fertility, anti-cystogenesis and anticancer activities. However, effect and mechanism of TPL on cellular senescence-associated antitumor is rarely reported.

RNA polymerase II-independent recruitment of SPT6L at transcription start sites in Arabidopsis.

Chen Chen et al.

Nucleic acids research, 47(13), 6714-6725 (2019-05-28)

SPT6 is a conserved elongation factor that is associated with phosphorylated RNA polymerase II (RNAPII) during transcription. Recent transcriptome analysis in yeast mutants revealed its potential role in the control of transcription initiation at genic promoters. However, the mechanism by

Synergistic cytotoxicity of BIIB021 with triptolide through suppression of PI3K/Akt/mTOR and NF-κB signal pathways in thyroid carcinoma cells.

Si Hyoung Kim et al.

Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 83, 22-32 (2016-10-25)

The effec.t of BIIB021, a novel heat shock protein 90 (hsp90) inhibitor, on survival of thyroid carcinoma cells has not been evaluated. In this study, the impact of BIIB021 alone or in combination with the histone acetyltransferase inhibitor triptolide on

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