UNBS-1450

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MedKoo CAT#: 528304

CAS#: 676541-58-5

Description: UNBS-1450, also known as UBS-1450, is a sodium channel antagonist potentially for the treatment of cancer. UNBS-1450 is a hemi-synthetic cardenolide derived from 2″-oxovorusharin extracted from the plant Calotropis procera, which is effective against various cancer cell types with an excellent differential toxicity. At low nanomolar concentrations, UNBS-1450 induces apoptotic cell death. UNBS-1450 inhibits NF-κB transactivation and triggers apoptosis by cleavage of pro-caspases 8, 9 and 3/7, by decreasing expression of anti-apoptotic Mcl-1 and by recruitment of pro-apoptotic Bak and Bax protein eventually resulting in cell death.


Price and Availability

Size Price Shipping out time Quantity
Inquire bulk and customized quantity

Pricing updated 2020-10-29. Prices are subject to change without notice.

UNBS-1450 (UBS-1450) is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 528304
Name: UNBS-1450
CAS#: 676541-58-5
Chemical Formula: C31H43NO9S
Exact Mass: 605.2659
Molecular Weight: 605.743
Elemental Analysis: C, 61.47; H, 7.16; N, 2.31; O, 23.77; S, 5.29


Synonym: UNBS-1450, UNBS 1450, UNBS1450, UBS-1450, UBS1450, UBS 1450

IUPAC/Chemical Name: (1R,3aS,3bR,5aS,6aS,7aS,9R,11S,11aR,12aS,13aR,13bS,15aR)-3a,11a-dihydroxy-13a-(hydroxymethyl)-9,15a-dimethyl-1-(5-oxo-2,5-dihydrofuran-3-yl)icosahydro-1H-spiro[cyclopenta[7,8]phenanthro[2,3-b]pyrano[3,2-e][1,4]dioxine-11,2'-thiazolidin]-4'-one

InChi Key: GRINEMOQBRCRRY-OVGHKGCDSA-N

InChi Code: InChI=1S/C31H43NO9S/c1-16-11-30(32-24(34)14-42-30)31(37)26(39-16)40-22-10-18-3-4-21-20(28(18,15-33)12-23(22)41-31)5-7-27(2)19(6-8-29(21,27)36)17-9-25(35)38-13-17/h9,16,18-23,26,33,36-37H,3-8,10-15H2,1-2H3,(H,32,34)/t16-,18+,19-,20+,21-,22+,23+,26+,27-,28-,29+,30+,31-/m1/s1

SMILES Code: O=C1OCC([C@H]2CC[C@]3(O)[C@]4([H])CC[C@@]5([H])C[C@@]6([H])[C@](O[C@@]([C@@](O6)([H])O[C@H](C)C7)(O)[C@]7(SC8)NC8=O)([H])C[C@]5(CO)[C@@]4([H])CC[C@]23C)=C1


Technical Data

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


References

1: Schoner W, Scheiner-Bobis G. Endogenous and exogenous cardiac glycosides: their roles in hypertension, salt metabolism, and cell growth. Am J Physiol Cell Physiol. 2007 Aug;293(2):C509-36. Review. PubMed PMID: 17494630.

2: Cerella C, Muller F, Gaigneaux A, Radogna F, Viry E, Chateauvieux S, Dicato M, Diederich M. Early downregulation of Mcl-1 regulates apoptosis triggered by cardiac glycoside UNBS1450. Cell Death Dis. 2015 Jun 11;6:e1782. doi: 10.1038/cddis.2015.134. PubMed PMID: 26068790; PubMed Central PMCID: PMC4669823.

3: Muller F, Cerella C, Radogna F, Dicato M, Diederich M. Effects of Natural Products on Mcl-1 Expression and Function. Curr Med Chem. 2015;22(30):3447-61. Review. PubMed PMID: 26179996.

4: Juncker T, Cerella C, Teiten MH, Morceau F, Schumacher M, Ghelfi J, Gaascht F, Schnekenburger M, Henry E, Dicato M, Diederich M. UNBS1450, a steroid cardiac glycoside inducing apoptotic cell death in human leukemia cells. Biochem Pharmacol. 2011 Jan 1;81(1):13-23. doi: 10.1016/j.bcp.2010.08.025. PubMed PMID: 20849830.

5: Mijatovic T, Jungwirth U, Heffeter P, Hoda MA, Dornetshuber R, Kiss R, Berger W. The Na+/K+-ATPase is the Achilles heel of multi-drug-resistant cancer cells. Cancer Lett. 2009 Sep 8;282(1):30-4. doi: 10.1016/j.canlet.2009.02.048. PubMed PMID: 19339106.

6: Juncker T, Schumacher M, Dicato M, Diederich M. UNBS1450 from Calotropis procera as a regulator of signaling pathways involved in proliferation and cell death. Biochem Pharmacol. 2009 Jul 1;78(1):1-10. doi: 10.1016/j.bcp.2009.01.018. PubMed PMID: 19447218.

7: Mathieu V, Pirker C, Martin de Lassalle E, Vernier M, Mijatovic T, DeNeve N, Gaussin JF, Dehoux M, Lefranc F, Berger W, Kiss R. The sodium pump alpha1 sub-unit: a disease progression-related target for metastatic melanoma treatment. J Cell Mol Med. 2009 Sep;13(9B):3960-72. doi: 10.1111/j.1582-4934.2009.00708.x. PubMed PMID: 19243476; PubMed Central PMCID: PMC4516543.

8: Lefranc F, Mijatovic T, Kiss R. [The sodium pump could constitute a new target to combat glioblastomas]. Bull Cancer. 2008 Mar;95(3):271-81. doi: 10.1684/bdc.2008.0597. French. PubMed PMID: 18390407.

9: Lefranc F, Mijatovic T, Kondo Y, Sauvage S, Roland I, Debeir O, Krstic D, Vasic V, Gailly P, Kondo S, Blanco G, Kiss R. Targeting the alpha 1 subunit of the sodium pump to combat glioblastoma cells. Neurosurgery. 2008 Jan;62(1):211-21; discussion 221-2. doi: 10.1227/01.NEU.0000311080.43024.0E. PubMed PMID: 18300910.

10: Mijatovic T, Roland I, Van Quaquebeke E, Nilsson B, Mathieu A, Van Vynckt F, Darro F, Blanco G, Facchini V, Kiss R. The alpha1 subunit of the sodium pump could represent a novel target to combat non-small cell lung cancers. J Pathol. 2007 Jun;212(2):170-9. PubMed PMID: 17471453.

11: Mijatovic T, De Nève N, Gailly P, Mathieu V, Haibe-Kains B, Bontempi G, Lapeira J, Decaestecker C, Facchini V, Kiss R. Nucleolus and c-Myc: potential targets of cardenolide-mediated antitumor activity. Mol Cancer Ther. 2008 May;7(5):1285-96. doi: 10.1158/1535-7163.MCT-07-2241. PubMed PMID: 18483316.

12: Lefranc F, Kiss R. The sodium pump alpha1 subunit as a potential target to combat apoptosis-resistant glioblastomas. Neoplasia. 2008 Mar;10(3):198-206. Review. PubMed PMID: 18323016; PubMed Central PMCID: PMC2259449.

13: Mijatovic T, Mathieu V, Gaussin JF, De Nève N, Ribaucour F, Van Quaquebeke E, Dumont P, Darro F, Kiss R. Cardenolide-induced lysosomal membrane permeabilization demonstrates therapeutic benefits in experimental human non-small cell lung cancers. Neoplasia. 2006 May;8(5):402-12. PubMed PMID: 16790089; PubMed Central PMCID: PMC1592454.

14: Mijatovic T, Op De Beeck A, Van Quaquebeke E, Dewelle J, Darro F, de Launoit Y, Kiss R. The cardenolide UNBS1450 is able to deactivate nuclear factor kappaB-mediated cytoprotective effects in human non-small cell lung cancer cells. Mol Cancer Ther. 2006 Feb;5(2):391-9. PubMed PMID: 16505114.