Taspine
| Code | Size | Price |
|---|
| AG-CN2-0544-M001 | 1 mg | £90.00 |
Quantity:
| AG-CN2-0544-M005 | 5 mg | £330.00 |
Quantity:
| AG-CN2-0544-M010 | 10 mg | £540.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
Ambient
Storage:
Short term: +20°C. Long term: -20°C
Documents
Further Information
Alternate Names/Synonyms:
Thaspine; NSC 76022; NSC 618155; NSC 688259
Appearance:
White to off-white solid.
CAS:
602-07-3
EClass:
32160000
Form (Short):
solid
Handling Advice:
Keep cool and dry. Protect from light and oxygen.
InChi:
InChI=1S/C20H19NO6/c1-21(2)8-7-10-9-13(25-4)18-16-14(10)20(23)27-17-12(24-3)6-5-11(15(16)17)19(22)26-18/h5-6,9H,7-8H2,1-4H3
InChiKey:
MTAWKURMWOXCEO-UHFFFAOYSA-N
Long Description:
Chemical. CAS: 602-07-3. Formula: C20H19NO6. MW: 369.4. Taspine is an alkaloid with multifunctional pharmacological properties, including apoptosis-inducing, anti-angiogenic, anticancer, cytotoxic, anti-inflammatory and wound-healing activities, thereby modulating multiple targets. Taspine is a potent acetylcholinesterase (AChE) inhibitor and wound healing promoter (cicatrizant), by regulating the expression of keratinocyte growth factor (KGF; FGF-7) in early phases. Taspine has anticancer properties targeting DNA topoisomerase IB and was shown to be a dual topoisomerase inhibitor. Taspine is an apoptosis-inducing compound. It induces conformational activation of the pro-apoptotic proteins Bak and Bax, mitochondrial cytochrome c release and mitochondrial membrane permeabilization. It induced tumor apoptosis in vitro and in vivo. Taspine can inhibit tumor angiogenesis acting as a multi-target VEGFR-2 inhibitor. Taspine was shown to downregulate VEGF expression and inhibit the proliferation of vascular endothelial cells through PI3 kinase and MAPK signaling pathways. The anti-angiogenic activity of taspine may depend on its EGF secretion properties and therefore the modulation of the EGFR signaling pathways, mediating MAPK (Erk1/2) but Akt signals. Taspine is a human P2X4 receptor inhibitor, mediating its effect through PI3-kinase inhibition. Activation of P2X4 is associated with inflammation involving peripheral and central inflammatory cell types. It also has been shown to act as a potent TLR2 antagonist, contributing to its anti-inflammatory properties.
MDL:
MFCD09837996
Molecular Formula:
C20H19NO6
Molecular Weight:
369.4
Package Type:
Vial
Product Description:
Taspine is an alkaloid with multifunctional pharmacological properties, including apoptosis-inducing, anti-angiogenic, anticancer, cytotoxic, anti-inflammatory and wound-healing activities, thereby modulating multiple targets. Taspine is a potent acetylcholinesterase (AChE) inhibitor and wound healing promoter (cicatrizant), by regulating the expression of keratinocyte growth factor (KGF; FGF-7) in early phases. Taspine has anticancer properties targeting DNA topoisomerase IB and was shown to be a dual topoisomerase inhibitor. Taspine is an apoptosis-inducing compound. It induces conformational activation of the pro-apoptotic proteins Bak and Bax, mitochondrial cytochrome c release and mitochondrial membrane permeabilization. It induced tumor apoptosis in vitro and in vivo. Taspine can inhibit tumor angiogenesis acting as a multi-target VEGFR-2 inhibitor. Taspine was shown to downregulate VEGF expression and inhibit the proliferation of vascular endothelial cells through PI3 kinase and MAPK signaling pathways. The anti-angiogenic activity of taspine may depend on its EGF secretion properties and therefore the modulation of the EGFR signaling pathways, mediating MAPK (Erk1/2) but Akt signals. Taspine is a human P2X4 receptor inhibitor, mediating its effect through PI3-kinase inhibition. Activation of P2X4 is associated with inflammation involving peripheral and central inflammatory cell types. It also has been shown to act as a potent TLR2 antagonist, contributing to its anti-inflammatory properties.
Purity:
>98% (1H-NMR)
SMILES:
CN(CCC1=CC(OC)=C(O2)C(C3=C(C2=O)C=CC(OC)=C3O4)=C1C4=O)C
Solubility Chemicals:
Soluble in ethanol, methanol, chloroform or DMSO. Insoluble in water.
Source / Host:
Isolated from Croton lechleri.
Transportation:
Non-hazardous
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C.
References
South American plants II: taspine isolation and anti-inflammatory activity: G.P. Perdue, et al.; J. Pharm. Sci. 68, 124 (1979) | Taspine is the cicatrizant principle in Sangre de Grado extracted from Croton lechleri: A.J. Vaisberg, et al.; Planta Med. 55, 140 (1989) | Enhancement of wound healing by the alkaloid taspine defining mechanism of action: B.H. Porras-Reyes, et al.; Proc. Soc. Exp. Biol. Med. 203, 18 (1993) | Total Synthesis of Taspine: T.R. Kelly & R.L. Xie; J. Org. Chem. 63, 8045 (1998) | Taspine: Bioactivity-Guided Isolation and Molecular Ligand - Target Insight of a Potent Acetylcholinesterase Inhibitor from Magnolia x soulangiana: J.M. Rollinger, et al.; J. Nat. Prod. 69, 1341 (2006) | Taspine downregulates VEGF expression and inhibits proliferation of vascular endothelial cells through PI3 kinase and MAP kinase signaling pathways: J. Zhao, et al.; Biomed. Pharmacother. 62, 383 (2008) | Suppression of tumor-induced angiogenesis by taspine isolated from Radix et Rhizoma Leonticis and its mechanism of action in vitro: Y. Zhang, et al.; Cancer Lett. 262, 103 (2008) | Identification of a Novel Topoisomerase Inhibitor Effective in Cells Overexpressing Drug Efflux Transporters: W. Fayad, et al.; PLoS One 4, e7238 (2009) | Antitumor activity of taspine by modulating the EGFR signaling pathway of Erk1/2 and Akt in vitro and in vivo: Y. Zhang, et al.; Planta Med. 77, 1774 (2011) | Effects of taspine on proliferation and apoptosis by regulating caspase-3 expression and the ratio of Bax/Bcl-2 in A431 cells: Y. Zhang, et al.; Phytother. Res. 25, 357 (2011) | Revealing multi-binding sites for taspine to VEGFR-2 by cell membrane chromatography zonal elution: H. Du, et al.; J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 887-888, 67 (2012) | A natural anticancer agent thaspine targets human topoisomerase IB: S. Castelli, et al.; Anticancer Agents Med. Chem. 13, 356 (2013) | Taspine is a natural product that suppresses P2X4 receptor activity via phosphoinositide 3-kinase inhibition: I.B. Nadzirin, et al.; Br. J. Pharmacol. 178, 4859 (2021) | Effect of Taspine hydrochloride on the repair of rat skin wounds by regulating keratinocyte growth factor signal: X. Wang, et al.; Bioengineered 13, 789 (2022) | Discovery of novel aporphine alkaloid derivative as potent TLR2 antagonist reversing macrophage polarization and neutrophil infiltration against acute inflammation: J. Yang, et al.; Acta Pharm. Sin. B. 13, 3782 (2023)