Celastrol CAS 34157-83-0

Introduction：Basic information about Celastrol CAS 34157-83-0, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Celastrol Basic information

• Product Name: Celastrol
• Synonyms: TRIPTERIN;(2r,4as,6as,6ar,14as,14br)-10-hydroxy-2,4a,6a,6a,9,14a-hexamethyl-11-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylic acid;3-HYDROXY-9BETA,13ALPHA-DIMETHYL-2-OXO-24,25,26-TRINOROLEANA-1(10),3,5,7-TETRAEN-29-OIC ACID;3-HYDROXY-24-NOR-2-OXO-1(10),3,5,7-FRIEDELATETRAEN-29-OIC ACID;Tripterine;24,25,26-Trinoroleana-1(10),3,5,7-tetraen-29-oicacid, 3-hydroxy-9,13-dimethyl-2-oxo-, (9β,13α,14β,20α)-;(9,13a,14,20a)-3-Hydroxy-9,13-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oic Acid;3-Hydroxy-2-oxo- 24-nor-D:A-friedooleana-1(10),3,5,7-tetraen-29-oic Acid
• CAS: 34157-83-0
• MF: C29H38O4
• MW: 450.61
• EINECS: 636-472-5
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;ProteasomeInhibitors;Natural Anti-cancer Medical Materials and It's Derivatives;Miscellaneous Natural Products;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Steroids;34157-83-0
• Mol File: 34157-83-0.mol

Celastrol Chemical Properties

• Melting point: 219-230°C
• Boiling point: 645.7±55.0 °C(Predicted)
• density: 1.2
• storage temp.: -20°C
• solubility: DMSO: >10mg/mL
• form: solid
• pka: 4.78±0.70(Predicted)
• color: red
• λmax: 424nm(MeOH)(lit.)
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 1 month.
• InChIKey: KQJSQWZMSAGSHN-JJWQIEBTSA-N
• SMILES: [C@]12(C)CC[C@@]3(C)CC[C@@](C)(C(=O)O)C[C@@]3([H])[C@]1(C)CC[C@@]1(C)C3=CC(C(O)=C(C)C3=CC=C21)=O |&1:0,4,8,14,16,20,r|
• LogP: 7.080 (est)
• CAS DataBase Reference: 34157-83-0(CAS DataBase Reference)

Safety Information

• Hazard Codes: T
• Risk Statements: 25
• Safety Statements: 45-24/25
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 2
• RTECS: YJ7900000
• HS Code: 29189900
• Storage Class: 11 - Combustible Solids

Celastrol Usage And Synthesis

Pharmacological effects

• Tripterine is a natural product with a variety of biological activity. It has a strong antioxidant effect, anti-cancer neovascularization effect as well as anti-rheumatoid effect. It is mainly isolated from the root bark of the celastraceae plant, Tripterygium wilfordii. It is one of the active ingredients contained in the rheumatoid-treatment drug Tripterygium tablet, Tripterygium Glycosides tablets and other preparations.
• The major activity and pharmacological effects of Tripterine:
• Cytotoxic activity. In vitro, it has non-specific cytotoxic activity against P388 and a group of human cancer cell lines.
• Immune regulation. It could significantly inhibit the formation of hemolytic plaque cells in mouse spleen cells and significantly inhibit the mice delayed-type hypersensitivity.
• Anti-inflammatory effect. At a dose of 0.5mg/kg, it could result in significant inhibition of the formation of rat cotton granuloma. At a dose of 0.1~1.0μg/mL, it could suppress the production of PGE2 induced by the yeast sugar; at a dose of 1.0μg/mL, it can inhibit the macrophage phagocytosis.
• The anti-oxidation effect of tripterine is 15 times that of tocopherol with an IC50 of 7μM. Inhibit the peroxidation occurring inside and outside of the mitochondrial membrane, direct removing the free radicals.
• Tripterine can extend the sleep time of mice triggered by the pentobarbital sodium.
• Immunosuppressive effect: inhibit the spleen cell proliferation of mice induced by PHA, ConA and LPS, further inhibiting the lymphocyte proliferation.
• It can inhibit the in vitro sperm fertilization capacity of guinea pig with the activity being significantly stronger than acetic acid gossypol.
• Anti-arthritic effect, it will inhibit the activity of interleukin-1 of inside and outside the mouse intraperitoneal macrophages, inhibit the production of interleukin-2 by mouse spleen cells and lower the level of PGE2 produced by rabbit synovial cells.

Source: ChemicalBook Editorial.

Application

Celastrol is an effective proteasome inhibitor. It has been confirmed that it is capable of inducing apoptosis of cancer cells through inhibiting proteasome activity.

Description

Celastrol (34157-83-0) displays potent antioxidant and anti-inflammatory activity. Inhibits NFkB (IC50=270 nM). ?It induces heat shock response and cytoprotection in various cells. Inhibits 20S proteasome chymotrypsin activity (IC50=2.5 mM). Induces autophagy by targeting AR/miR-101 in prostate cancer cells.4 Induces UPR-dependent cell death in cancer cells.5 Cell permeable.

Chemical Properties

Orange Red Solid

Uses

antineoplastic, NO synthesis inhibitor, chaperone stimulant

Uses

Celastrol is an antioxidant natural product which inhibits the growth of human glioma xenografts in nude mice through suppressing VEGFR expression. Used for clinical treatment for rheumatoid arthritis, was demonstrated to have antiangiogenic activity, and be inhibitory against mice tumor growth by a few recent studies. Celastrol also has been shown to have the power to kill tumor cells and can work as an anticarcinogen. It is also a leptin sensitizer with the potential to reduce weight in obesity.

Uses

Celastrol can be used as an antioxidant onstrated to have antiangiogenic activity, and be inhibitory against mice tumor growth by a few recent studies.

Uses

An antioxidant natural product Celastrol inhibits the growth of human glioma xenografts in nude mice through suppressing VEGFR expression. Used for clinical treatment for rheumatoid arthritis, was demonstrated to have antiangiogenic activity, and be

Definition

ChEBI: A pentacyclic triterpenoid that is 24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oic acid bearing an oxo substituent at position 2, a hydroxy substituent at position 3 and two methyl groups at positions 9 and 13. An antioxidant and anti-inflammatory agent. otently inhibits lipid peroxidation in mitochondria and inhibits TNF-alpha-induced NFkappaB activation. Also shown to inhibit topoisomerase II activity in vitro (IC50 = 7.41 muM).

General Description

This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

Biological Activity

Antioxidant and anti-inflammatory agent. Potently inhibits lipid peroxidation in mitochondria and inhibits TNF- α -induced NF κ B activation. Also shown to inhibit topoisomerase II activity in vitro (IC 50 = 7.41 μ M).

Biochem/physiol Actions

Celastrol is a potent antioxidant, and anti-inflammatory agent. It is a novel HSP90 inhibitor (disrupts Hsp90/Cdc37 complex), that exhibits anticancer (anti-angiogenic - suppresses VEGFR expression); antioxidant (inhibits lipid peroxidation) and anti-inflammatory activity (suppresses iNOS and inflammatory cytokine production).

storage

+4°C

References

[1] GAUTAM SETHI. Celastrol, a novel triterpene, potentiates TNF-induced apoptosis and suppresses invasion of tumor cells by inhibiting NF-kappaB-regulated gene products and TAK1-mediated NF-kappaB activation.[J]. Blood, 2007, 109 7: 2727-2735. DOI:10.1182/blood-2006-10-050807
[2] SANDY D WESTERHEIDE. Celastrols as inducers of the heat shock response and cytoprotection.[J]. The Journal of Biological Chemistry, 2004, 279 53: 56053-56060. DOI:10.1074/jbc.m409267200
[3] HUANJIE YANG. Celastrol, a triterpene extracted from the Chinese “Thunder of God Vine,” is a potent proteasome inhibitor and suppresses human prostate cancer growth in nude mice.[J]. Cancer research, 2006, 66 9: 4758-4765. DOI:10.1158/0008-5472.can-05-4529
[4] JIANQUAN GUO. Celastrol Induces Autophagy by Targeting AR/miR-101 in Prostate Cancer Cells.[J]. PLoS ONE, 2015: e0140745. DOI:10.1371/journal.pone.0140745
[5] ANDREW M. FRIBLEY . Celastrol induces unfolded protein response-dependent cell death in head and neck cancer[J]. Experimental cell research, 2015, 330 2: Pages 412-422. DOI:10.1016/j.yexcr.2014.08.014