Triptolide - CAS 38748-32-2

Triptolide - CAS 38748-32-2 Catalog number: BADC-00036

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Triptolide is a diterpene triepoxide, immunosuppresive agent extracted from the Chinese herb Tripterygium wilfordii. It has immunosuppressive, anti-inflammatory, antiproliferative and antitumour effects. Triptolide is an NF-κB activation inhibitor.

Category
ADCs Cytotoxin
Product Name
Triptolide
CAS
38748-32-2
Catalog Number
BADC-00036
Molecular Formula
C20H24O6
Molecular Weight
360.40
Triptolide

Ordering Information

Catalog Number Size Price Quantity
BADC-00036 20mg $268
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Description
Triptolide is a diterpene triepoxide, immunosuppresive agent extracted from the Chinese herb Tripterygium wilfordii. It has immunosuppressive, anti-inflammatory, antiproliferative and antitumour effects. Triptolide is an NF-κB activation inhibitor.
Synonyms
NSC 163062; PG490; Trisoxireno[4b,5:6,7:8a,9]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)-; (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; (-)-Triptolide; PG 490; Triptolide
IUPAC Name
(1S,2S,4S,5S,7R,8R,9S,11S,13S)-8-hydroxy-1-methyl-7-(propan-2-yl)-3,6,10,16-tetraoxaheptacyclo[11.7.0.02,4.02,9.05,7.09,11.014,18]icos-14(18)-en-17-one
Canonical SMILES
CC(C)C12C(O1)C3C4(O3)C5(CCC6=C(C5CC7C4(C2O)O7)COC6=O)C
InChI
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
InChIKey
DFBIRQPKNDILPW-CIVMWXNOSA-N
Density
1.5±0.1 g/cm3
Solubility
Soluble in Dichloromethane (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly), Methanol
Melting Point
223-230°C
In Vitro
The triptolide-loaded microemulsions showed an enhanced in vitro permeation through mouse skins compared to an aqueous solution of 20% propylene glycol containing 0.025% triptolide. The permeation of microemulsions accorded with the Fick's first diffusion law. No obvious skin irritation was observed for the studied microemulsion ME6, but the aqueous solution of 20% propylene glycol containing 0.025% triptolide revealed the significant skin irritation. Cell growth was significantly inhibited by triptolide as observed by an inverted phase contrast microscope; the results of MTT assay indicated that triptolide inhibits HEC-1B cell proliferation in a dose and time-dependent manner.
In Vivo
Flow cytometry showed that low concentration (5 ng/ml) of triptolide induces cell cycle arrest of HEC-1B cells mainly at S phase, while higher concentration (40 or 80 ng/ml) induced cell cycle arrest of HEC-1B cells mainly at G2/M phase, and apoptosis of the cells was also induced. High-dose triptolide showed a similar tumor-inhibitory effect as cisplatin (-50%); high-dose triptolide significantly inhibited Bcl-2 and VEGF expression in the xenograft model compared to normal saline control (P<0.05). The in vivo anti-osteosarcoma effects of triptolide were verified in osteosarcoma nude mice. The in vivo associated protein expressions were detected using immunohistochemistry (IHC). The results indicated that Triptolide could significantly inhibit the proliferation of various osteosarcoma cells. Besides, it could induce their apoptosis. Triptolide triggered the mitochondrial dependent apoptotic pathway, significantly inhibited the in vivo growth of osteosarcoma cells, and caused in vivo apoptosis.
Clinical Trial Information
NCT NumberCondition Or DiseasePhaseStart DateSponsorStatus
NCT00801268Polycystic KidneyNot Applicable2015-03-30Zhi-Hong Liu, M.D.Terminated (high rate of drop-out)
NCT02115659Autosomal Dominant Polycystic Kidney Disease (ADPKD)Phase 32014-04-17Shanghai Changzheng HospitalUnknown Verified April 2014 by Mei changlin, Shanghai Changzheng Hospital. Recruitment status was Recruiting
NCT02219672AIDS/HIV PROBLEMPhase 32014-08-19Peking Union Medical CollegeUnknown Verified August 2014 by LI Taisheng, Peking Union Medical College. Recruitment status was Recruiting
NCT04896073Adenosquamous Carcinoma of the PancreasPhase 22021-11-29National Cancer Institute (NCI)Recruiting
NCT01817283HIVPhase 1, Phase 22013-03-25LI TaishengUnknown Verified March 2013 by LI Taisheng, Peking Union Medical College. Recruitment status was Recruiting
Application
ADCs Cytotoxin
Appearance
White to Off-white Powder
Purity
>98%
Quantity
Grams-Kilos
Quality Standard
Enterprise Standard
Shipping
Room temperature, or blue ice upon request.
Storage
Store at -20°C under inert atmosphere
Pictograms
Acute Toxic; Health Hazard
Signal Word
Danger
Boiling Point
601.7±55.0°C at 760 mmHg
1. Total synthesis of novel D-ring-modified triptolide analogues: structure–cytotoxic activity relationship studies on the D-ring of triptolide
Bing Zhou, Xiaomei Li, Huanyu Tang, Zehong Miao, Huijin Feng and Yuanchao Li*. Org. Biomol. Chem., 2011, 9, 3176–3179
For a long time, there have been no studies on the structure-activity relationship of the D-ring of triptolide except for two patents, describing some butenolide-modified triptolide analogues without any biological activity data, and our previous paper, reporting that an analogue (compound 6) with a five-membered unsaturated lactam ring has the same activity as the natural triptolide. So the structure-activity relationship of the D-ring is still obscure. To explore whether the five-membered unsaturated lactone ring of triptolide is completely critical to its anticancer activity, compound 3,havinga transposition butenolide, compound 4,which has a furan ring replacing the five-membered unsaturated lactone ring, and compound 5 without the planar D-ring were synthesized for SAR studies of the D-ring. The SAR studies of these tripolide analogues were performed by using ovary (SK-OV-3) and prostate (PC-3) tumor cells.
2. Computational prediction and experimental validation of low-affinity target of triptolide and its analogues
Xiufeng Liu, Kai Wang, Weijuan Zheng,* Jiahuang Li* and Zi-chun Hua*. RSC Adv.,2015, 5,34572–34579
This study was designed to investigate the potential interactions between NRs and triptolide, triptonide and triptriolide. 12 NRs were first screened through docking calculations to identify the putative molecular targets of triptolide. Then themost likely target ERa-LBD was expressed and purified in vitro. The binding capacities between ERa-LBD and three compounds were determined by Surface Plasmon Resonance (SPR) and Isothermal Titration Calorimetry (ITC) analyses. The results were further validated using reporter gene assays. These data revealed ERa act as a previously unknown binding protein of triptolide and triptonide which may provide valuable information for studying the mechanisms and structure–function relationships of these chemicals in vivo.
3. The role of breast cancer resistance protein (Bcrp/Abcg2) in triptolide-induced testis toxicity
Chunzhu Li, Guozhen Xing, Xinming Qi,* Guangji Wang*. Toxicol. Res.,2015, 4,1260–1268
Preclinical studies have revealed that triptolide has strong effects against cancer, collagen-induced arthritis, skin allograft rejection and bone marrow transplantation. Several derivatives of triptolide have entered human clinical trials for cancer and other diseases. However, the clinical uses of triptolide and its derivatives have been limited by their toxicity. Triptolide induced cumulative testis toxicity in some experimental and clinical research studies. The mechanisms of testicular injury induced by triptolide are not characterized well.

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Historical Records: Glucopiericidin A | Triptolide

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