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MedKoo Cat#: 407366 | Name: Thaspine HCl

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Thaspine, also known as NSC 135784, is a natural compound and a potent topoisomerase IB inhibitor. Taspine downregulates VEGF expression and inhibits proliferation of vascular endothelial cells through PI3 kinase and MAP kinase signaling pathways. Taspine isolated from Radix et Rhizoma Leonticis inhibits proliferation and migration of endothelial cells as well as chicken chorioallantoic membrane neovascularisation. Croton lechleri sap and isolated alkaloid taspine exhibit inhibition against human melanoma SK23 and colon cancer HT29 cell lines.

Chemical Structure

Thaspine HCl
Thaspine HCl
CAS#74578-01-1

Theoretical Analysis

MedKoo Cat#: 407366

Name: Thaspine HCl

CAS#: 74578-01-1

Chemical Formula: C20H20ClNO6

Exact Mass:

Molecular Weight: 405.83

Elemental Analysis: C, 59.19; H, 4.97; Cl, 8.74; N, 3.45; O, 23.65

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
74578-01-1 (free base); 35115-50-5 (HCl)
Synonym
Thaspine; Thaspine HCl, NSC 135784; NSC-135784; NSC135784.
IUPAC/Chemical Name
1-(2-(Dimethylamino)ethyl)-3,8-dimethoxychromeno(5,4,3-cde)chromene-5,10-dione hydrochloride
InChi Key
ORYWNHKVTVKCMC-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H19NO6.ClH/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;1H
SMILES Code
O=C1C2=CC=C(OC)C(O3)=C2C4=C(O1)C(OC)=CC(CCN(C)C)=C4C3=O.[H]Cl
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 405.83 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Castelli S, Katkar P, Vassallo O, Falconi M, Linder S, Desideri A. A natural anticancer agent thaspine targets human topoisomerase IB. Anticancer Agents Med Chem. 2013 Feb;13(2):356-63. PubMed PMID: 22931416. 2: Montopoli M, Bertin R, Chen Z, Bolcato J, Caparrotta L, Froldi G. Croton lechleri sap and isolated alkaloid taspine exhibit inhibition against human melanoma SK23 and colon cancer HT29 cell lines. J Ethnopharmacol. 2012 Dec 18;144(3):747-53. doi: 10.1016/j.jep.2012.10.032. PubMed PMID: 23123266. 3: Zhang Y, Zheng L, Zhang J, Dai B, Wang N, Chen Y, He L. Antitumor activity of taspine by modulating the EGFR signaling pathway of Erk1/2 and Akt in vitro and in vivo. Planta Med. 2011 Nov;77(16):1774-81. doi: 10.1055/s-0030-1271132. PubMed PMID: 21614750. 4: Zhan Y, Zhang Y, Chen Y, Wang N, Zheng L, He L. Activity of taspine isolated from Radix et Rhizoma Leonticis against estrogen-receptor-positive breast cancer. Fitoterapia. 2011 Sep;82(6):896-902. doi: 10.1016/j.fitote.2011.05.004. PubMed PMID: 21605638. 5: Du H, Wang S, Ren J, Lv N, He L. Revealing multi-binding sites for taspine to VEGFR-2 by cell membrane chromatography zonal elution. J Chromatogr B Analyt Technol Biomed Life Sci. 2012 Mar 1;887-888:67-72. doi: 10.1016/j.jchromb.2012.01.011. PubMed PMID: 22321409. 6: Dai B, Wang W, Liu R, Wang H, Zhang Y. Novel taspine derivative 12k inhibits cell growth and induces apoptosis in lung cell carcinoma. Biomed Pharmacother. 2015 Mar;70:227-33. doi: 10.1016/j.biopha.2015.01.024. PubMed PMID: 25776505. 7: Liu R, Wang W, Dai B, Liu Y, Zhang Y. Taspine derivative TAS9 regulates cell growth and metastasis of human hepatocellular carcinoma. Mol Med Rep. 2015 Nov;12(5):7735-41. doi: 10.3892/mmr.2015.4398. PubMed PMID: 26459497. 8: Zhang YM, He LC. [Study on thaspine in inducing apoptosis of A549 cell]. Zhong Yao Cai. 2007 Apr;30(4):429-32. Chinese. PubMed PMID: 17674796. 9: Zhao J, Zhao L, Chen W, He L, Li X. Taspine downregulates VEGF expression and inhibits proliferation of vascular endothelial cells through PI3 kinase and MAP kinase signaling pathways. Biomed Pharmacother. 2008 Jul-Aug;62(6):383-9. PubMed PMID: 17826025. 10: Zhang YM, Wang N, Dai BL, He LC. [Effect of taspine derivatives on human liver cancer SMMC7721]. Zhong Yao Cai. 2011 Jul;34(7):1094-7. Chinese. PubMed PMID: 22066407. 11: Zhang J, Zhang Y, Zhang S, Wang S, He L. Discovery of novel taspine derivatives as antiangiogenic agents. Bioorg Med Chem Lett. 2010 Jan 15;20(2):718-21. doi: 10.1016/j.bmcl.2009.11.073. Erratum in: Bioorg Med Chem Lett. 2010 Mar 1;20(5):1797. PubMed PMID: 20006929. 12: Lu W, He LC, Zeng XM. HPLC method for the pharmacokinetics and tissue distribution of taspine solution and taspine liposome after intravenous administrations to mice. J Pharm Biomed Anal. 2008 Jan 7;46(1):170-6. PubMed PMID: 17889477. 13: Zhang Y, He L, Meng L, Luo W, Xu X. Suppression of tumor-induced angiogenesis by taspine isolated from Radix et Rhizoma Leonticis and its mechanism of action in vitro. Cancer Lett. 2008 Apr 8;262(1):103-13. doi: 10.1016/j.canlet.2007.11.035. PubMed PMID: 18180095. 14: Zhang J, Zhang Y, Shan Y, Li N, Ma W, He L. Synthesis and preliminary biological evaluation of novel taspine derivatives as anticancer agents. Eur J Med Chem. 2010 Jul;45(7):2798-805. doi: 10.1016/j.ejmech.2010.03.001. PubMed PMID: 20304537. 15: Zhang Y, He L, Meng L, Luo W. Taspine isolated from Radix et Rhizoma Leonticis inhibits proliferation and migration of endothelial cells as well as chicken chorioallantoic membrane neovascularisation. Vascul Pharmacol. 2008 Feb-Mar;48(2-3):129-37. doi: 10.1016/j.vph.2008.01.008. PubMed PMID: 18304881. 16: Zhang Y, Zhang J, Dai B, Wang N, He L. Anti-proliferative and apoptotic effects of the novel taspine derivative tas41 in the Caco-2 cell line. Environ Toxicol Pharmacol. 2011 May;31(3):406-15. doi: 10.1016/j.etap.2011.02.001. PubMed PMID: 21787711. 17: Zhang Y, He L, Zhou Y. Taspine isolated from Radix et Rhizoma Leonticis inhibits growth of human umbilical vein endothelial cell (HUVEC) by inducing its apoptosis. Phytomedicine. 2008 Jan;15(1-2):112-9. PubMed PMID: 17976967. 18: Zhang YM, He LC, Wang HY. [Inhibitory effect of taspine on mouse S180 sarcoma and its mechanism]. Zhongguo Zhong Yao Za Zhi. 2007 May;32(10):953-6. Chinese. PubMed PMID: 17655156. 19: Fayad W, Fryknäs M, Brnjic S, Olofsson MH, Larsson R, Linder S. Identification of a novel topoisomerase inhibitor effective in cells overexpressing drug efflux transporters. PLoS One. 2009 Oct 2;4(10):e7238. doi: 10.1371/journal.pone.0007238. PubMed PMID: 19798419; PubMed Central PMCID: PMC2749935. 20: Dong Y, He L, Chen F. [Enhancement of wound healing by taspine and its effect on fibroblast]. Zhong Yao Cai. 2005 Jul;28(7):579-82. Chinese. PubMed PMID: 16252727.

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