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

Ordering Information

Catalog Number	Size	Price	Quantity
BADC-00036	20 mg	$285

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Products Information
Reference Reading

Description

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 Number	Condition Or Disease	Phase	Start Date	Sponsor	Status
NCT00801268	Polycystic Kidney	Not Applicable	2015-03-30	Zhi-Hong Liu, M.D.	Terminated (high rate of drop-out)
NCT02115659	Autosomal Dominant Polycystic Kidney Disease (ADPKD)	Phase 3	2014-04-17	Shanghai Changzheng Hospital	Unknown Verified April 2014 by Mei changlin, Shanghai Changzheng Hospital. Recruitment status was Recruiting
NCT02219672	AIDS/HIV PROBLEM	Phase 3	2014-08-19	Peking Union Medical College	Unknown Verified August 2014 by LI Taisheng, Peking Union Medical College. Recruitment status was Recruiting
NCT04896073	Adenosquamous Carcinoma of the Pancreas	Phase 2	2021-11-29	National Cancer Institute (NCI)	Recruiting
NCT01817283	HIV	Phase 1, Phase 2	2013-03-25	LI Taisheng	Unknown 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.