Triptonide
Triptonide
CAS: 38647-11-9
Molecular Formula: C20H22O6
Triptonide - Names and Identifiers
| Name | Triptonide |
| Synonyms | PG 492 Triptonide TRIPTONIDE troptonide NSC 165677 14-Deoxy-14-oxotriptolide Triptolide,14-deoxy-14-oxo TRIPTONIDE(PRIMARY STANDARD) Triptolide, 14-deoxy-14-oxo- |
| CAS | 38647-11-9 |
| InChI | InChI=1/C20H22O6/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/h8,11-14H,4-7H2,1-3H3/t11-,12-,13-,14-,17-,18-,19+,20+/m0/s1 |
Triptonide - Physico-chemical Properties
| Molecular Formula | C20H22O6 |
| Molar Mass | 358.39 |
| Density | 1.48±0.1 g/cm3(Predicted) |
| Melting Point | 251～252℃ |
| Boling Point | 581.1±50.0 °C(Predicted) |
| Specific Rotation(α) | -175°(C=0.148，chloroform) |
| Flash Point | 257.8°C |
| Solubility | Chloroform, dichloromethane, ethyl acetate, DMSO, acetone, etc. Insoluble in water. |
| Vapor Presure | 1.7E-13mmHg at 25°C |
| Appearance | Powder; colorless (dichloromethane-ether) |
| Color | Off-White to Pale Beige |
| Storage Condition | Inert atmosphere,Store in freezer, under -20°C |
| Refractive Index | 1.637 |
| MDL | MFCD00210566 |
| Physical and Chemical Properties | Yellow crystalline powder, soluble in methanol, ethanol, DMSO and other organic solvents, derived from Tripterygium wilfordii. |
| In vitro study | Triptonide blocks Wnt/β-catenin signaling via C-terminal transactivation domain of β-catenin, and promots apoptosis in Wnt-dependent cancer cells. Triptonide potently inhibits the proliferation of human B-lymphoma Raji and T-lymphoma Jurkat cells with IC 50 of 5.7 nM and 4.8 nM, respectively. Triptonide (2.5-10 nM; 6 days) significantly suppresses B-lymphoma cell colony-forming capability. Triptonide (20 nM; 3 days) promotes apoptosis through activation of PARP and caspase 3, but reduction of BCL2 protein levels in the lymphoma cells. Triptonide (5-10 nM; 72 hours) markedly reduces both total and phosphorylated Lyn proteins, and diminishes Lyn downstream ERK and ATK signal pathways. Cell Proliferation Assay Cell Line: B-lymphoma Raji cells, T-lymphoma Jurkat cells Concentration: 0-80 nM Incubation Time: 3 days, 6 days Result: Inhibited lymphoma cell tumorigenic capability in a dose-dependent manner. Apoptosis Analysis Cell Line: Raji cells Concentration: 5 nM, 10 nM, 20 nM Incubation Time: 3 days Result: Did not significantly induce apoptosis at the effective tumor growth-inhibitory (2.5-10 nM); moderately induced lymphoma cell apoptosis (20 nM). Western Blot Analysis Cell Line: Raji cells Concentration: 5 nM, 10 nM, 20 nM Incubation Time: 3 days Result: Did not vigorously activated pro-apoptotic proteins PARP and caspase 3 in lymphoma cells (5-10 nM); significantly activated PARP and caspase 3 (20 nM); significantly reduced anti-apoptotic BCL2 levels. RT-PCR Cell Line: Raji cells Concentration: 5 nM, 10 nM Incubation Time: 72 hours Result: Significantly diminished Lyn mRNA levels in the lymphoma cells. |
| In vivo study | Triptonide (5 mg/kg; i.p.; daily; for 34 days) exerts a strong anti-lymphoma effect in mice. Animal Model: Eight-week-old female NOD/SCID mice (18-22 g), with 3 x 10 7 Raji cells xenograft Dosage: 5 mg/kg Administration: Intraperitoneal injection, daily, for 34 days Result: Potently inhibited lymphoma cell growth and tumorigenic capability. |
Triptonide - Reference
| Reference Show more | 1. Liu, Xiufeng, et al. "Computational prediction and experimental validation of low-affinity target of triptolide and its analogues." RSC advances 5.44 (2015): 34572-34579.DOI https://doi.org/10.1039/C4RA17009A 2. [IF=3.361] Xiufeng Liu et al."Computational prediction and experimental validation of low-affinity target of triptolide and its analogues."Rsc Adv. 2015 Apr;5(44):34572-34579 |
Triptonide - Reference Information
| Overview | triptolide is a diterpene compound isolated from Tripterygium wilfordii, it is structurally similar to triptolide, and its activity is also equivalent, and its structural formula is as follows. Triptolide has anti-male fertility effect and certain influence on immune function. |
| biological activity | Triptonide (NSC 165677;PG 492) is a natural product identified from Tripterygium wilfordii. Triptonate is a Wnt signaling inhibitor with an IC50 of approximately 0.3 nM. Tripltonide has immunosuppressive, anti-inflammatory, antifertility, neuroprotective and anti-lymphoma effects. |
| Target | TargetValue Wnt/β-catenin () |
| Target | Value |
| in vitro study | tripltonide blocks Wnt/β-catenin signaling via C- terminal transaction domain of β-catenin, and advances apoptosis in Wnt-dependent cancer cells. Tripltonide potently inhibit the propagation of human B- lyphohoma Raji and T-lymphoma Jurkat cells with IC 50 of 5.7 nM and 4.8 nM, review. Tripltonide (2.5-10 nM; 6 days) significant limitations B- lymphoma cell colony-forming capability. Tripltonide (20 nM; 3 days) promotes apoptosis through activation of PARP and caspase 3, but reduction of BCL2 protein levels in the lymphoma cells. Triptonide (5-10 nM; 72 hours) markedly reduces both total and phosphorylated Lyn proteins, and diminishes Lyn downstream ERK and ATK signal pathways. Cell Proliferation Assay Cell Line: B- lymphoma Raji cells, T-lymphoma Jurkat cells Concentration: 0-80 nM Incubation Time: 3 days, 6 days Result: Inhibited lymphoma cell tumorigenic capability in a dose-dependent manner. Apoptosis Analysis Cell Line: Raji cells Concentration: 5 nM, 10 nM, 20 nM Incubation Time: 3 days Result: Did not significantly induce apoptosis at the effective tumor growth-inhibitory (2.5-10 nM); moderately induced lymphoma cell apoptosis (20 nM). Western Blot Analysis Cell Line: Raji cells Concentration: 5 nM, 10 nM, 20 nM Incubation Time: 3 days Result: Did not vigorously activated pro-apoptotic proteins PARP and caspase 3 in lymphoma cells (5-10 nM); significantly activated PARP and caspase 3 (20 nM); significantly reduced anti-apoptotic BCL2 levels. RT-PCR Cell Line: Raji cells Concentration: 5 nM, 10 nM Incubation Time: 72 hours Result: Significantly diminished Lyn mRNA levels in the lymphoma cells. |
| Cell Line: | B-lymphoma Raji cells, T-lymphoma Jurkat cells Raji cells Raji cells Raji cells |
| Concentration: | 0-80 nM 5 nM, 10 nM, 20 nM 5 nM, 10 nM, 20 nM 5 nM, 10 nM |
| Incubation Time: | 3 days, 6 days 3 days 3 days 72 hours |
| Result: | Inhibited lymphoma cell tumorigenic capability in a dose-dependent manner. Did not significantly induce apoptosis at the effective tumor growth-inhibitory (2.5-10 nM); moderately induced lymphoma cell apoptosis (20 nM). Did not vigorously activated pro-apoptotic proteins PARP and caspase 3 in lymphoma cells (5-10 nM); significantly activated PARP and caspase 3 (20 nM); significantly reduced anti-apoptotic BCL2 levels. Significantly diminished Lyn mRNA levels in the lymphoma cells. Potently inhibited lymphoma cell growth and tumorigenic capability. |
| in vivo studies | Triptonide (5 mg/kg; I. p.; daily; for 34 days) exerts a strong anti-lymphoma effect in mice. Animal Model: Eight-week-old female NOD/SCID mice (18-22g), with 3 x 10 7 Raji cells xenograft Dosage: 5 mg/kg Administration: Intraperitoneal injection, daily, for 34 days Result: Potently inhibited lymphoma cell growth and tumorigenic capability. |
| Animal Model: | Eight-week-old female NOD/SCID mice (18-22 g), with 3 x 10 7 Raji cells xenograft |
| Dosage: | 5 mg/kg |
| Administration: | Intraperitoneal injection, daily, for 34 days |
| Chemical properties | yellow crystalline powder, soluble in methanol, ethanol, DMSO and other organic solvents, derived from Tripterygium wilfordii. |
| Use | Triptolide has anti-tumor immunomodulatory and anti-inflammatory effects. for content determination/identification/pharmacological experiments. Pharmacological Efficacy: treatment of leprosy reaction, treatment of rheumatoid arthritis, treatment of tuberculosis and other chronic lung disease. |
Last Update：2024-04-10 22:29:15
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