Lanatoside C
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MedKoo CAT#: 525374

CAS#: 17575-22-3

Description: Lanatoside C is an anticancer agent, acting through protein kinase C-delta (PKCdelta) to cause apoptosis of human hepatocellular carcinoma cells.

Chemical Structure

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Lanatoside C
CAS# 17575-22-3
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 525374
Name: Lanatoside C
CAS#: 17575-22-3
Chemical Formula: C49H76O20
Exact Mass: 984.49
Molecular Weight: 985.127
Elemental Analysis: C, 59.74; H, 7.78; O, 32.48

Price and Availability

Size Price Availability Quantity
100mg USD 350 2 Weeks
1g USD 1350 2 Weeks
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Synonym: Lanatoside C

IUPAC/Chemical Name: [(2R,3R,4S,6S)-6-[(2R,3S,4S,6S)-6-[(2R,3S,4S,6R)-6-[[(3S,5R,8R,9S,10S,12R,13S,14S,17R)-12,14-dihydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]-4-hydroxy-2-methyloxan-3-yl]oxy-4-hydroxy-2-methyloxan-3-yl]oxy-2-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-4-yl] acetate

InChi Key: JAYAGJDXJIDEKI-PTGWOZRBSA-N

InChi Code: InChI=1S/C49H76O20/c1-21-43(67-38-17-32(53)44(22(2)62-38)68-39-18-33(64-24(4)51)45(23(3)63-39)69-46-42(58)41(57)40(56)34(19-50)66-46)31(52)16-37(61-21)65-27-9-11-47(5)26(14-27)7-8-29-30(47)15-35(54)48(6)28(10-12-49(29,48)59)25-13-36(55)60-20-25/h13,21-23,26-35,37-46,50,52-54,56-59H,7-12,14-20H2,1-6H3/t21-,22-,23-,26-,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: CC(O[C@@H]1[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](C)O[C@@H](O[C@@H]3[C@@H](C)O[C@@H](O[C@@H]4[C@@H](C)O[C@@H](O[C@H]5CC[C@]6(C)[C@@]7([H])C[C@@H](O)[C@]8(C)[C@@H](C9=CC(OC9)=O)CC[C@]8(O)[C@]7([H])CC[C@]6([H])C5)C[C@@H]4O)C[C@@H]3O)C1)=O

Appearance: Solid powder

Purity: >95% (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:

Product Data:
Product Data
Instruction:
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Biological target: Lanatoside C is a cardiac glycoside, can be used in the treatment of congestive heart failure and cardiac arrhythmia.Lanatoside C has an IC50 of 0.19 μM for dengue virus infection in HuH-7 cells.
In vitro activity: In the present study, lanatoside C, an FDA-approved cardiac glycoside used for the treatment of heart failure, was demonstrated to have anti-proliferative and cytotoxic effects on cervical cancer cells, with abrogation of cell migration in a dose-dependent manner. Lanatoside C also triggered cell apoptosis by enhancing reactive oxygen species production and reducing the mitochondrial membrane potential, which induced cell cycle arrest at the S and G2/M phases. Reference: Oncol Lett. 2021 Oct;22(4):740. https://pubmed.ncbi.nlm.nih.gov/34466152/
In vivo activity: The proliferation of cultured pulmonary fibroblasts isolated from BLM-induced PF mice was suppressed by lanatoside C, as hypothesized, through the induction of cell apoptosis and cell cycle arrest at the G2/M phase. In addition, TGF-β1-induced migration in lung fibroblasts was also impeded after lanatoside C treatment. Together, these data revealed that lanatoside C alleviated BLM-induced pulmonary fibrosis in mice via attenuation of growth and differentiation of fibroblasts, suggesting that it has potential as a candidate therapy for PF patients. Reference: Clin Exp Pharmacol Physiol. 2019 Jun;46(6):575-586. https://pubmed.ncbi.nlm.nih.gov/30854687/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 50.0 50.75
Ethanol 2.0 2.03

Preparing Stock Solutions

The following data is based on the product molecular weight 985.13 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
Formulation protocol: 1. Duan Y, Chen L, Shao J, Jiang C, Zhao Y, Li Y, Ke H, Zhang R, Zhu J, Yu M. Lanatoside C inhibits human cervical cancer cell proliferation and induces cell apoptosis by a reduction of the JAK2/STAT6/SOCS2 signaling pathway. Oncol Lett. 2021 Oct;22(4):740. doi: 10.3892/ol.2021.13001. Epub 2021 Aug 17. PMID: 34466152; PMCID: PMC8387865. 2. Reddy D, Kumavath R, Ghosh P, Barh D. Lanatoside C Induces G2/M Cell Cycle Arrest and Suppresses Cancer Cell Growth by Attenuating MAPK, Wnt, JAK-STAT, and PI3K/AKT/mTOR Signaling Pathways. Biomolecules. 2019 Nov 27;9(12):792. doi: 10.3390/biom9120792. PMID: 31783627; PMCID: PMC6995510. 3. Nie Y, Zhang D, Jin Z, Li B, Wang X, Che H, You Y, Qian X, Zhang Y, Zhao P, Chai G. Lanatoside C protects mice against bleomycin-induced pulmonary fibrosis through suppression of fibroblast proliferation and differentiation. Clin Exp Pharmacol Physiol. 2019 Jun;46(6):575-586. doi: 10.1111/1440-1681.13081. Epub 2019 Apr 7. PMID: 30854687. 4. 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. PMID: 26821916; PMCID: PMC4731744.
In vitro protocol: 1. Duan Y, Chen L, Shao J, Jiang C, Zhao Y, Li Y, Ke H, Zhang R, Zhu J, Yu M. Lanatoside C inhibits human cervical cancer cell proliferation and induces cell apoptosis by a reduction of the JAK2/STAT6/SOCS2 signaling pathway. Oncol Lett. 2021 Oct;22(4):740. doi: 10.3892/ol.2021.13001. Epub 2021 Aug 17. PMID: 34466152; PMCID: PMC8387865. 2. Reddy D, Kumavath R, Ghosh P, Barh D. Lanatoside C Induces G2/M Cell Cycle Arrest and Suppresses Cancer Cell Growth by Attenuating MAPK, Wnt, JAK-STAT, and PI3K/AKT/mTOR Signaling Pathways. Biomolecules. 2019 Nov 27;9(12):792. doi: 10.3390/biom9120792. PMID: 31783627; PMCID: PMC6995510.
In vivo protocol: 1. Nie Y, Zhang D, Jin Z, Li B, Wang X, Che H, You Y, Qian X, Zhang Y, Zhao P, Chai G. Lanatoside C protects mice against bleomycin-induced pulmonary fibrosis through suppression of fibroblast proliferation and differentiation. Clin Exp Pharmacol Physiol. 2019 Jun;46(6):575-586. doi: 10.1111/1440-1681.13081. Epub 2019 Apr 7. PMID: 30854687. 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. PMID: 26821916; PMCID: PMC4731744.

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1: 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.

2: 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.

3: 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.

4: 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.

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: Wang W, Liu H, Yang J, Shen Y. Acute Pulmonary Edema After Cranioplasty. J Neurosurg Anesthesiol. 2016 Jan;28(1):84. doi: 10.1097/ANA.0000000000000197. PubMed PMID: 26083423.

7: Carlier J, Guitton J, Romeuf L, Bévalot F, Boyer B, Fanton L, Gaillard Y. Screening approach by ultra-high performance liquid chromatography-tandem mass spectrometry for the blood quantification of thirty-four toxic principles of plant origin. Application to forensic toxicology. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Jan 15;975:65-76. doi: 10.1016/j.jchromb.2014.10.028. Epub 2014 Nov 1. PubMed PMID: 25438245.

8: 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.

9: Aparna V, Dineshkumar K, Mohanalakshmi N, Velmurugan D, Hopper W. Identification of natural compound inhibitors for multidrug efflux pumps of Escherichia coli and Pseudomonas aeruginosa using in silico high-throughput virtual screening and in vitro validation. PLoS One. 2014 Jul 15;9(7):e101840. doi: 10.1371/journal.pone.0101840. eCollection 2014. PubMed PMID: 25025665; PubMed Central PMCID: PMC4099075.

10: Cingoz GS, Verma SK, Gurel E. Hydrogen peroxide-induced antioxidant activities and cardiotonic glycoside accumulation in callus cultures of endemic Digitalis species. Plant Physiol Biochem. 2014 Sep;82:89-94. doi: 10.1016/j.plaphy.2014.05.008. Epub 2014 May 28. PubMed PMID: 24915111.

11: Teng J, Hejazi S, Badr CE, Tannous BA. Systemic anticancer neural stem cells in combination with a cardiac glycoside for glioblastoma therapy. Stem Cells. 2014 Aug;32(8):2021-32. doi: 10.1002/stem.1727. Erratum in: Stem Cells. 2016 Jan;34(1):252. PubMed PMID: 24801379; PubMed Central PMCID: PMC4454401.

12: Bao H, Wang J, Zhou D, Han Z, Su L, Zhang Y, Ye X, Xu C, Wang Y, Li Q. Protein-protein interaction network analysis in chronic obstructive pulmonary disease. Lung. 2014 Feb;192(1):87-93. doi: 10.1007/s00408-013-9509-x. Epub 2013 Nov 17. Retraction in: Bao H, Wang J, Zhou D, Han Z, Su L, Zhang Y, Ye X, Xu C, Wang Y, Li Q. Lung. 2015 Oct;193(5):869. PubMed PMID: 24241792.

13: Sahin G, Verma SK, Gurel E. Calcium and magnesium elimination enhances accumulation of cardenolides in callus cultures of endemic Digitalis species of Turkey. Plant Physiol Biochem. 2013 Dec;73:139-43. doi: 10.1016/j.plaphy.2013.09.007. Epub 2013 Sep 24. PubMed PMID: 24095920.

14: 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.

15: 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.

16: Roscani MG, Zanati SG, Magalhães CG, Borges VT, Matsubara BB. Digitalis-like induced arrhythmia in a patient with rheumatic mitral regurgitation complicated by preeclampsia. Hypertens Pregnancy. 2010 Jan;29(2):148-52. doi: 10.3109/10641950902928571. PubMed PMID: 19891530.

17: Pellati F, Bruni R, Bellardi MG, Bertaccini A, Benvenuti S. Optimization and validation of a high-performance liquid chromatography method for the analysis of cardiac glycosides in Digitalis lanata. J Chromatogr A. 2009 Apr 10;1216(15):3260-9. doi: 10.1016/j.chroma.2009.02.042. Epub 2009 Feb 21. PubMed PMID: 19268961.

18: Guillarme D, Grata E, Glauser G, Wolfender JL, Veuthey JL, Rudaz S. Some solutions to obtain very efficient separations in isocratic and gradient modes using small particles size and ultra-high pressure. J Chromatogr A. 2009 Apr 10;1216(15):3232-43. doi: 10.1016/j.chroma.2009.02.032. Epub 2009 Feb 21. PubMed PMID: 19251260.

19: Chen DY, Cao J, Zhu BP. Drug therapy of paroxysmal atrial fibrillation in the elderly over 75 years old. Chin Med Sci J. 2006 Mar;21(1):16-9. PubMed PMID: 16615278.

20: Zamotaev IuN, Kremnev IuA, Podshibiakin SE. [Cardiac glycosides in complex treatment of patients with heart failure and supraventricular arrhythmias]. Klin Med (Mosk). 2005;83(7):59-63. Russian. PubMed PMID: 16117429.