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.

General Information

Category
ADCs Cytotoxin
Product Name
Triptolide
CAS
38748-32-2
Catalog Number
BADC-00036
Molecular Formula
C20H24O6
Molecular Weight
360.4

Chemical Structure

  • Triptolide

Ordering Information

Catalog Number Size Price Stock Quantity
BADC-00036 20mg $268 In stock
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Purity
>98%
Appearance
white solid powder
Synonyms
PG490; PG 490; PG-490
Application
ADCs Cytotoxin
Quality Standard
Enterprise Standard
Shipping
Room temperature, or blue ice upon request.
Melting Point
>220ºC (dec.)
Canonical SMILES
CC(C)C12C(O1)C3C4(O3)C5(CCC6=C(C5CC7C4(C2O)O7)COC6=O)C
InChI Key
DFBIRQPKNDILPW-CIVMWXNOSA-N
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
Quantity
Grams-Kilos
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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