Triptolide

Modify Date: 2024-01-01 21:30:21

Triptolide Structure
Triptolide structure
Common Name Triptolide
CAS Number 38748-32-2 Molecular Weight 360.401
Density 1.5±0.1 g/cm3 Boiling Point 601.7±55.0 °C at 760 mmHg
Molecular Formula C20H24O6 Melting Point 226-227°C
MSDS USA Flash Point 220.7±25.0 °C

 Use of Triptolide


Triptolide is a diterpenoid triepoxide extracted from the root of Tripterygium wilfordii with immunosuppressive, anti-inflammatory and antiproliferative effects. Triptolide is a NF-κB activation inhibitor.

 Names

Name triptolide
Synonym More Synonyms

 Triptolide Biological Activity

Description Triptolide is a diterpenoid triepoxide extracted from the root of Tripterygium wilfordii with immunosuppressive, anti-inflammatory and antiproliferative effects. Triptolide is a NF-κB activation inhibitor.
Related Catalog
Target

HSP90

MDM-2/p53:47-73 nM (IC50)

In Vitro Triptolide induces apoptosis in cultured and primary Chronic Lymphocytic Leukemia (CLL) B-cells. Treatment of CD19+ B cells with Triptolide, induces a dose-dependent increase in apoptosis in cultured and primary CLL cells. Triptolide is selectively toxic to both high risk (n=5) and low risk CLL (n=12) B cells (10 to 50 nM range) while largely sparing normal B-cells (n=5). Consistent with the inhibition of heat-shock induced HSP transcription, treatment with Triptolide attenuates heat-shock induced expression of HSPs[1]. Triptolide is a natural product derived from the Chinese plant Tripterygium wilfordii, is reported to exhibit antitumor effects in a broad range of cancers. Triptolide inhibits MDM2 expression in a dose-dependent manner, even at low concentrations spanning 20-100 nM in acute lymphoblastic leukemia (ALL) cells. Triptolide exhibits strongly cytotoxic activity in all 8 cell lines having native MDM2 overexpression, with IC50 values range from 47 to 73 nM. Triptolide exhibits much less cytotoxic effect on EU-4 cells that express very low level of MDM2, while it effectively kill these cells when MDM2 is stably transfected (IC50 values: 725 nM vs. 88 nM)[2]. Differentiated PC12 cells are incubated with different concentrations of Triptolide (0.01, 0.1, and 1 nM) in the presence of 10 μM Aβ25-35 for 24 hours and MTT assay is used to detect the effect of Triptolide. The results show that Aβ25-35 can decrease the cell viability and when treated with Triptolide the viability of differentiated PC12 cells is significantly increased. The results indicate that Triptolide can alleviate cellular damage caused by Aβ25-35, which means that Triptolide has a neuroprotective effect[3].
In Vivo The Triptolide (TP) plasma concentrations are declined rapidly in mice after receive an intravenous dose. After 2h of injection, the Triptolide concentrations are dropped below the lower limit of quantification for all three groups. A comparison of the parameters is made between the control and the treated groups to assess the effect of P-gp inhibition on the Triptolide exposure and elimination. Treatment with the mdr1a-siRNA can significantly enhance the Triptolide plasma exposure, with the Cmax increases from 413±74 to 510±94 ng/mL (P<0.05) and the AUC from 103.5±9.6 to 154.3±30.2 ng•h/mL (P<0.05). In the concomitant group with Tariquidar, the significantly increased AUC is also noted, from 103.5±9.6 of the control to 145.9±24.6 ng•h/mL of the Triptolide+Tariquidar group (P<0.05). Accordingly, the total body clearance of Triptolide in mice is remarkably decreased, from 9564±1024.2 mL/min/kg of the control to 6576.4±1438.5 (P<0.05) and 5755.4±1200.1 mL/min/kg (P<0.05) for Triptolide+Tariquidar and Triptolide+mdr1a-siRNA groups, respectively[4].
Cell Assay The viability of differentiated PC12 cells treated with different concentrations of Triptolide. After differentiated PC12 cells are cultured on 96-well plates with RPMI 1640 medium for stabilization, differentiated PC12 cells are incubated with different concentrations of Triptolide (0.01, 0.1, and 1 nM) for 24 hours. The concentrations in this study are chosen. Then cell viability is determined by the MTT assay. Each condition and experiment is repeated three times[3].
Animal Admin Mice[4] Male BALB/C mice (weight, 18-22 g) are used. For Triptolide (TP) plasma kinetic study and toxicological evaluation, mice are divided into four groups (n=5 each) to collect blood and tissue samples: (1) normal+saline group; (2) 1.0 mg/kg Triptolide+15 nmol negative control (NC) siRNA-siRNA group; (3) 1.0 mg/kg Triptolide+15 nmol mdr1a-siRNA group; (4) 1.0 mg/kg Triptolide+10 mg/kg Tariquidar group. In order to avoid the complication caused by drug absorption or possible intestinal first-pass effect, Triptolide and the inhibitor are intravenously administrated to mice. The siRNA group is intravenously injected with NC-siRNA or mdr1a-siRNA 2 days before Triptolide dose. For Triptolide+Tariquidar group, the mice are received an intravenous Tariquidar dose 20 min prior to the Triptolide injection. Blood samples are collected at 2, 5, 10, 15, 30, 60 and 120 min after Triptolide dosing. To assess the liver exposure of Triptolide, liver tissue samples are collected from another set of mice at 5, 30, 60 and 120 min after dosing. Three Triptolide groups are design for this experiment, including Triptolide+NC-siRNA group, Triptolide+mdr1a-siRNA group and Triptolide+Tariquidar group. The liver tissue samples are weighed and then homogenized in 10 volume (w:v) of ice-cold saline. The concentrations of Triptolide in plasma and liver tissue are measured by a validated LC-MS/MS method.
References

[1]. Ganguly S, et al. Targeting HSF1 disrupts HSP90 chaperone function in chronic lymphocytic leukemia. Oncotarget. 2015 Oct 13;6(31):31767-79.

[2]. Huang M, et al. Triptolide inhibits MDM2 and induces apoptosis in acute lymphoblastic leukemia cells through a p53-independent pathway. Mol Cancer Ther. 2013 Feb;12(2):184-94.

[3]. Xu P, et al. Triptolide Inhibited Cytotoxicity of Differentiated PC12 Cells Induced by Amyloid-Beta25-35 via the Autophagy Pathway.PLoS One. 2015 Nov 10;10(11):e0142719.

[4]. Kong LL, et al. Inhibition of P-glycoprotein Gene Expression and Function Enhances Triptolide-induced Hepatotoxicity in Mice.Sci Rep. 2015 Jul 2;5:11747.

[5]. Zhang W, et al. Triptolide Combined with Radiotherapy for the Treatment of Nasopharyngeal Carcinoma via NF-κB-Related Mechanism. Int J Mol Sci. 2016 Dec 19;17(12). pii: E2139.

 Chemical & Physical Properties

Density 1.5±0.1 g/cm3
Boiling Point 601.7±55.0 °C at 760 mmHg
Melting Point 226-227°C
Molecular Formula C20H24O6
Molecular Weight 360.401
Flash Point 220.7±25.0 °C
Exact Mass 360.157288
PSA 84.12000
LogP 1.27
Vapour Pressure 0.0±3.9 mmHg at 25°C
Index of Refraction 1.647
Storage condition 2-8°C
Water Solubility DMSO: soluble

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
YK7751000
CHEMICAL NAME :
Triptolide
CAS REGISTRY NUMBER :
38748-32-2
LAST UPDATED :
199412
DATA ITEMS CITED :
3
MOLECULAR FORMULA :
C20-H24-O6
MOLECULAR WEIGHT :
360.44

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
900 ug/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - food intake (animal) Lungs, Thorax, or Respiration - other changes
REFERENCE :
CYLPDN Zhongguo Yaoli Xuebao. Acta Pharmacologica Sinica. Chinese Journal of Pharmacology. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1980- Volume(issue)/page/year: 2,70,1981
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
800 ug/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - food intake (animal) Lungs, Thorax, or Respiration - other changes
REFERENCE :
CYLPDN Zhongguo Yaoli Xuebao. Acta Pharmacologica Sinica. Chinese Journal of Pharmacology. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1980- Volume(issue)/page/year: 2,70,1981 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
1120 ug/kg/7D-I
TOXIC EFFECTS :
Blood - changes in bone marrow (not otherwise specified) Blood - changes in erythrocyte (RBC) count Nutritional and Gross Metabolic - weight loss or decreased weight gain
REFERENCE :
CYLPDN Zhongguo Yaoli Xuebao. Acta Pharmacologica Sinica. Chinese Journal of Pharmacology. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1980- Volume(issue)/page/year: 2,70,1981

 Safety Information

Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes T+
Safety Phrases 22-24/25
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS YK7751000

 Synthetic Route

~31%

Triptolide Structure

Triptolide

CAS#:38748-32-2

Literature: Aoyagi, Yutaka; Hitotsuyanagi, Yukio; Hasuda, Tomoyo; Fukaya, Haruhiko; Takeya, Koichi; Aiyama, Ritsuo; Matsuzaki, Takeshi; Hashimoto, Shusuke Bioorganic and Medicinal Chemistry Letters, 2011 , vol. 21, # 10 p. 3046 - 3049

~49%

Triptolide Structure

Triptolide

CAS#:38748-32-2

Literature: Yang, Dan; Ye, Xiang-Yang; Xu, Ming Journal of Organic Chemistry, 2000 , vol. 65, # 7 p. 2208 - 2217

~%

Triptolide Structure

Triptolide

CAS#:38748-32-2

Literature: Yang, Dan; Ye, Xiang-Yang; Xu, Ming Journal of Organic Chemistry, 2000 , vol. 65, # 7 p. 2208 - 2217

~%

Triptolide Structure

Triptolide

CAS#:38748-32-2

Literature: Yang, Dan; Ye, Xiang-Yang; Xu, Ming Journal of Organic Chemistry, 2000 , vol. 65, # 7 p. 2208 - 2217

~%

Triptolide Structure

Triptolide

CAS#:38748-32-2

Literature: Yang, Dan; Ye, Xiang-Yang; Xu, Ming Journal of Organic Chemistry, 2000 , vol. 65, # 7 p. 2208 - 2217

~%

Triptolide Structure

Triptolide

CAS#:38748-32-2

Literature: Yang, Dan; Ye, Xiang-Yang; Xu, Ming Journal of Organic Chemistry, 2000 , vol. 65, # 7 p. 2208 - 2217

~%

Triptolide Structure

Triptolide

CAS#:38748-32-2

Literature: Yang, Dan; Ye, Xiang-Yang; Xu, Ming Journal of Organic Chemistry, 2000 , vol. 65, # 7 p. 2208 - 2217

~28%

Triptolide Structure

Triptolide

CAS#:38748-32-2

Detail
Literature: Aoyagi, Yutaka; Hitotsuyanagi, Yukio; Hasuda, Tomoyo; Fukaya, Haruhiko; Takeya, Koichi; Aiyama, Ritsuo; Matsuzaki, Takeshi; Hashimoto, Shusuke Bioorganic and Medicinal Chemistry Letters, 2011 , vol. 21, # 10 p. 3046 - 3049

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 Synonyms

MFCD00210565
(3bS,4aS,5aS,6R,6aR,7aS,7bS,8aS,8bS)-6-Hydroxy-6a-isopropyl-8b-methyl-3b,4,4a,6,6a,7a,7b,8b,9,10-decahydrotrisoxireno[6,7:8a,9:4b,5]phenanthro[1,2-c]furan-1(3H)-one
(3bS,4aS,5aS,6R,6aR,7aS,7bS,8aS,8bS)-3b,4,4a,6,6a,7a,7b,8b,9,10-decahydro-6-hydroxy-8b-methyl-6a-(1-methylethyl)trisoxireno[4b,5:6,7:8a,9]phenanthro[1,2-c]furan-1(3H)-one
triptolid
Triptolide (PG490)
EINECS 300-006-3
(3bS,4aS,5aS,6R,6aR,7aS,7bS,8aS,8bS)-6-hydroxy-8b-methyl-6a-(propan-2-yl)-3b,4,4a,6,6a,7a,7b,8b,9,10-decahydrotrisoxireno[6,7:8a,9:4b,5]phenanthro[1,2-c]furan-1(3H)-one
(3bS,4aS,5aS,6R,6aR,7aS,7bS,8aS,8bS)-3b,4,4a,6,6a,7a,7b,8b,9,10-decahydro-6-hydroxy-6a-isopropyl-8b-methyltrisoxireno[6,7:8a,9:4b,5]phenanthro[1,2-c]furan-1(3H)-one
TRIPTOLIDE TLC
Triptolide
Trisoxireno[6,7:8a,9:4b,5]phenanthro[1,2-c]furan-1(3H)-one, 3b,4,4a,6,6a,7a,7b,8b,9,10-decahydro-6-hydroxy-8b-methyl-6a-(1-methylethyl)-, (3bS,4aS,5aS,6R,6aR,7aS,7bS,8aS,8bS)-
Triptolide(PG490)
,7as,7bs,8as,8bs)
PG490
triptergium wilfordii
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