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MedKoo Cat#: 559166 | Name: Lanatoside

Description:

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

Lanatoside is an FDA approved cardiac glycoside was identified as a candidate anti-dengue compound.

Chemical Structure

Lanatoside
Lanatoside
CAS#11014-59-8

Theoretical Analysis

MedKoo Cat#: 559166

Name: Lanatoside

CAS#: 11014-59-8

Chemical Formula: C49H76O19

Exact Mass: 968.4981

Molecular Weight: 969.12

Elemental Analysis: C, 60.73; H, 7.90; O, 31.37

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 #
No Data
Synonym
Lanatoside; ABC lanatoside complex; Lantoside;
IUPAC/Chemical Name
(2R,3R,4S)-6-(((2R,3S,4S)-4-hydroxy-6-(((2R,3S,4S)-4-hydroxy-6-(((3S,9S,10S,13R,17R)-14-hydroxy-10,13-dimethyl-17-(5-oxo-2,5-dihydrofuran-3-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)-2-methyltetrahydro-2H-pyran-3-yl)oxy)-2-methyltetrahydro-2H-pyran-3-yl)oxy)-2-methyl-3-(((3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-4-yl acetate
InChi Key
YFGQJKBUXPKSAW-ZUDKKNPISA-N
InChi Code
InChI=1S/C49H76O19/c1-22-43(66-38-18-33(53)44(23(2)61-38)67-39-19-34(63-25(4)51)45(24(3)62-39)68-46-42(57)41(56)40(55)35(20-50)65-46)32(52)17-37(60-22)64-28-9-12-47(5)27(16-28)7-8-31-30(47)10-13-48(6)29(11-14-49(31,48)58)26-15-36(54)59-21-26/h15,22-24,27-35,37-46,50,52-53,55-58H,7-14,16-21H2,1-6H3/t22-,23-,24-,27?,28+,29-,30+,31?,32+,33+,34+,35+,37?,38?,39?,40+,41-,42+,43-,44-,45-,46?,47+,48-,49?/m1/s1
SMILES Code
C[C@@H]1[C@@H](OC2C[C@H](O)[C@H](OC3C[C@H](OC(C)=O)[C@H](OC4[C@@H](O)[C@H](O)[C@@H](O)[C@H](CO)O4)[C@@H](C)O3)[C@@H](C)O2)[C@@H](O)CC(O[C@H]5CC[C@]6(C)[C@H]7CC[C@]8(C)[C@@H](C9=CC(OC9)=O)CCC8(O)C7CCC6C5)O1
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
>3 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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 969.12 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: Kang MA, Kim MS, Kim W, Um JH, Shin YJ, Song JY, Jeong JH. Lanatoside C suppressed colorectal cancer cell growth by inducing mitochondrial dysfunction and increased radiation sensitivity by impairing DNA damage repair. Oncotarget. 2016 Feb 2;7(5):6074-87. doi: 10.18632/oncotarget.6832. PubMed PMID: 26756216; PubMed Central PMCID: PMC4868741. 2: Shi H, Mao X, Zhong Y, Liu Y, Zhao X, Yu K, Zhu R, Wei Y, Zhu J, Sun H, Mao Y, Zeng Q. Lanatoside C Promotes Foam Cell Formation and Atherosclerosis. Sci Rep. 2016 Jan 29;6:20154. doi: 10.1038/srep20154. PubMed PMID: 26821916; PubMed Central PMCID: PMC4731744. 3: Durmaz I, Guven EB, Ersahin T, Ozturk M, Calis I, Cetin-Atalay R. Liver cancer cells are sensitive to Lanatoside C induced cell death independent of their PTEN status. Phytomedicine. 2016 Jan 15;23(1):42-51. doi: 10.1016/j.phymed.2015.11.012. Epub 2015 Dec 12. PubMed PMID: 26902406. 4: Cheung YY, Chen KC, Chen H, Seng EK, Chu JJ. Antiviral activity of lanatoside C against dengue virus infection. Antiviral Res. 2014 Nov;111:93-9. doi: 10.1016/j.antiviral.2014.09.007. Epub 2014 Sep 22. PubMed PMID: 25251726. 5: Crommentuijn MH, Maguire CA, Niers JM, Vandertop WP, Badr CE, Würdinger T, Tannous BA. Intracranial AAV-sTRAIL combined with lanatoside C prolongs survival in an orthotopic xenograft mouse model of invasive glioblastoma. Mol Oncol. 2016 Apr;10(4):625-34. doi: 10.1016/j.molonc.2015.11.011. Epub 2015 Dec 11. PubMed PMID: 26708508; PubMed Central PMCID: PMC4826802. 6: Ueda Y, Mishiro K, Yoshida K, Furuta T, Kawabata T. Regioselective diversification of a cardiac glycoside, lanatoside C, by organocatalysis. J Org Chem. 2012 Sep 21;77(18):7850-7. Epub 2012 Sep 4. PubMed PMID: 22870937. 7: Badr CE, Wurdinger T, Nilsson J, Niers JM, Whalen M, Degterev A, Tannous BA. Lanatoside C sensitizes glioblastoma cells to tumor necrosis factor-related apoptosis-inducing ligand and induces an alternative cell death pathway. Neuro Oncol. 2011 Nov;13(11):1213-24. doi: 10.1093/neuonc/nor067. Epub 2011 Jul 13. PubMed PMID: 21757445; PubMed Central PMCID: PMC3199161. 8: Chao MW, Chen TH, Huang HL, Chang YW, HuangFu WC, Lee YC, Teng CM, Pan SL. Lanatoside C, a cardiac glycoside, acts through protein kinase Cδ to cause apoptosis of human hepatocellular carcinoma cells. Sci Rep. 2017 Apr 7;7:46134. doi: 10.1038/srep46134. PubMed PMID: 28387249; PubMed Central PMCID: PMC5384006. 9: Aldous S, Thomas R. Absorption and metabolism of lanatoside C. II. Fate after oral administration. Clin Pharmacol Ther. 1977 Jun;21(6):647-58. PubMed PMID: 862307. 10: Saito H, Kawaguchi W, Iwata M, Maekawa K, Tanimoto T, Okada S. [Lanatoside C Reference Standard (Control 981) of National Institute of Health Sciences]. Kokuritsu Iyakuhin Shokuhin Eisei Kenkyusho Hokoku. 1999;(117):192-4. Japanese. PubMed PMID: 10939857. 11: Hu Y, Yu K, Wang G, Zhang D, Shi C, Ding Y, Hong D, Zhang D, He H, Sun L, Zheng JN, Sun S, Qian F. Lanatoside C inhibits cell proliferation and induces apoptosis through attenuating Wnt/β-catenin/c-Myc signaling pathway in human gastric cancer cell. Biochem Pharmacol. 2018 Apr;150:280-292. doi: 10.1016/j.bcp.2018.02.023. Epub 2018 Feb 21. PubMed PMID: 29475060. 12: Hammarström L, Smith CI, Persson U. Functional characterization of lanatoside-C-responsive cells. Scand J Immunol. 1978;8(3):263-71. PubMed PMID: 309177. 13: Bodem G, Ochs H, Hahn E, Dengler HJ. [Clinical study of the biological availability of lanatoside C and digoxin in long-term tests]. Schweiz Med Wochenschr. 1977 May 14;107(19):658-66. German. PubMed PMID: 867012. 14: De Luca B, Cerciello A, Monda M. Cortical control of neurally-mediated arrhythmogenic properties of desacetyl lanatoside C: the role of the posterior hypothalamus. Neuropharmacology. 1982 Nov;21(11):1211-4. PubMed PMID: 7177346. 15: Karjalainen J, Ojala K. Therapeutic and toxic lanatoside C serum concentrations in hospital patients. Klin Wochenschr. 1975 Jul 15;53(14):685-6. PubMed PMID: 1219181. 16: CORSI V. [Effect of lanatoside C in auricular flutter and fibrillation]. Cuore Circ. 1951 Oct;35(5):257-82. Undetermined Language. PubMed PMID: 14905896. 17: Matos L, Békés M, Polák G, Rausch J, Török E. Comparative study of the cardiac and peripheral vascular effects of strophantin K and lanatoside C in coronary heart disease. Eur J Clin Pharmacol. 1975 Oct 10;9(1):27-37. PubMed PMID: 1233250. 18: BROWN BT, RANGER D, WRIGHT SE. The excretory products of lanatoside C and digitoxin in the rat. J Pharmacol Exp Ther. 1955 Mar;113(3):353-8. PubMed PMID: 14368503. 19: Raineri A, Palazzoadriano M, Battaglia A. [Action of desacetyl-lanatoside C on acetylcholinesterase activity of the rat myocardium]. Boll Soc Ital Biol Sper. 1967 Apr 30;43(8):398-401. Italian. PubMed PMID: 6050477. 20: VAN BUREN E. The use of lanatoside C in the treatment of congestive heart failure. J Med Assoc Ga. 1946 Jan;35:9-11. PubMed PMID: 21011254.