Proscillaridin
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MedKoo CAT#: 561872

CAS#: 466-06-8

Description: Proscillaridin, also known as Proscillaridin A, is a cardiotonic glycoside. It potently disrupts topoisomerase I and II activity.


Chemical Structure

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Proscillaridin
CAS# 466-06-8

Theoretical Analysis

MedKoo Cat#: 561872
Name: Proscillaridin
CAS#: 466-06-8
Chemical Formula: C30H42O8
Exact Mass: 530.29
Molecular Weight: 530.650
Elemental Analysis: C, 67.90; H, 7.98; O, 24.12

Price and Availability

Size Price Availability Quantity
5mg USD 350 2 Weeks
10mg USD 600 2 Weeks
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Synonym: Proscillaridin; Proscillaridin A; Proscillaridina; Caradrin;

IUPAC/Chemical Name: 5-[(3S,8R,9S,10R,13R,14S,17R)-14-Hydroxy-10,13-dimethyl-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-1,2,3,6,7,8,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one

InChi Key: MYEJFUXQJGHEQK-ALRJYLEOSA-N

InChi Code: InChI=1S/C30H42O8/c1-16-24(32)25(33)26(34)27(37-16)38-19-8-11-28(2)18(14-19)5-6-22-21(28)9-12-29(3)20(10-13-30(22,29)35)17-4-7-23(31)36-15-17/h4,7,14-16,19-22,24-27,32-35H,5-6,8-13H2,1-3H3/t16-,19-,20+,21-,22+,24-,25+,26+,27-,28-,29+,30-/m0/s1

SMILES Code: O=C1C=CC([C@H]2CC[C@]3(O)[C@]4([H])CCC5=C[C@@H](O[C@@H]6O[C@@H](C)[C@H](O)[C@@H](O)[C@H]6O)CC[C@]5(C)[C@@]4([H])CC[C@]23C)=CO1

Appearance: Solid powder

Purity: >90 % (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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 530.65 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:
In vitro protocol:
In vivo protocol:

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1: Lin YT, Wang CK, Yang SC, Hsu SC, Lin H, Chang FP, Kuo TC, Shen CN, Chiang PM, Hsiao M, Lu FL, Lu J. Elimination of undifferentiated human embryonic stem cells by cardiac glycosides. Sci Rep. 2017 Jul 13;7(1):5289. doi: 10.1038/s41598-017-05616-2. PubMed PMID: 28706279; PubMed Central PMCID: PMC5509667.

2: Raynal NJ, Da Costa EM, Lee JT, Gharibyan V, Ahmed S, Zhang H, Sato T, Malouf GG, Issa JJ. Repositioning FDA-Approved Drugs in Combination with Epigenetic Drugs to Reprogram Colon Cancer Epigenome. Mol Cancer Ther. 2017 Feb;16(2):397-407. doi: 10.1158/1535-7163.MCT-16-0588. Epub 2016 Dec 15. PubMed PMID: 27980103; PubMed Central PMCID: PMC5292054.

3: Gozalpour E, Wilmer MJ, Bilos A, Masereeuw R, Russel FG, Koenderink JB. Heterogeneous transport of digitalis-like compounds by P-glycoprotein in vesicular and cellular assays. Toxicol In Vitro. 2016 Apr;32:138-45. doi: 10.1016/j.tiv.2015.12.009. Epub 2015 Dec 17. PubMed PMID: 26708294.

4: Okuyama-Dobashi K, Kasai H, Tanaka T, Yamashita A, Yasumoto J, Chen W, Okamoto T, Maekawa S, Watashi K, Wakita T, Ryo A, Suzuki T, Matsuura Y, Enomoto N, Moriishi K. Hepatitis B virus efficiently infects non-adherent hepatoma cells via human sodium taurocholate cotransporting polypeptide. Sci Rep. 2015 Nov 23;5:17047. doi: 10.1038/srep17047. PubMed PMID: 26592202; PubMed Central PMCID: PMC4655410.

5: Delebinski CI, Georgi S, Kleinsimon S, Twardziok M, Kopp B, Melzig MF, Seifert G. Analysis of proliferation and apoptotic induction by 20 steroid glycosides in 143B osteosarcoma cells in vitro. Cell Prolif. 2015 Oct;48(5):600-10. doi: 10.1111/cpr.12208. Epub 2015 Aug 24. PubMed PMID: 26300346.

6: 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.

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: Denicolaï E, Baeza-Kallee N, Tchoghandjian A, Carré M, Colin C, Jiglaire CJ, Mercurio S, Beclin C, Figarella-Branger D. Proscillaridin A is cytotoxic for glioblastoma cell lines and controls tumor xenograft growth in vivo. Oncotarget. 2014 Nov 15;5(21):10934-48. PubMed PMID: 25400117; PubMed Central PMCID: PMC4279420.

9: Gozalpour E, Greupink R, Bilos A, Verweij V, van den Heuvel JJ, Masereeuw R, Russel FG, Koenderink JB. Convallatoxin: a new P-glycoprotein substrate. Eur J Pharmacol. 2014 Dec 5;744:18-27. doi: 10.1016/j.ejphar.2014.09.031. Epub 2014 Sep 28. PubMed PMID: 25264938.

10: Gozalpour E, Greupink R, Wortelboer HM, Bilos A, Schreurs M, Russel FG, Koenderink JB. Interaction of digitalis-like compounds with liver uptake transporters NTCP, OATP1B1, and OATP1B3. Mol Pharm. 2014 Jun 2;11(6):1844-55. doi: 10.1021/mp400699p. Epub 2014 May 6. PubMed PMID: 24754247.

11: El-Seedi HR, Burman R, Mansour A, Turki Z, Boulos L, Gullbo J, Göransson U. The traditional medical uses and cytotoxic activities of sixty-one Egyptian plants: discovery of an active cardiac glycoside from Urginea maritima. J Ethnopharmacol. 2013 Feb 13;145(3):746-57. doi: 10.1016/j.jep.2012.12.007. Epub 2012 Dec 8. PubMed PMID: 23228916.

12: Gozalpour E, Wittgen HG, van den Heuvel JJ, Greupink R, Russel FG, Koenderink JB. Interaction of digitalis-like compounds with p-glycoprotein. Toxicol Sci. 2013 Feb;131(2):502-11. doi: 10.1093/toxsci/kfs307. Epub 2012 Oct 26. PubMed PMID: 23104431.

13: Winnicka K, Bielawska A, Bielawski K. Inhibition of DNA topoisomerases I and II by G3 PAMAM-NH2 dendrimer-modified digoxin and proscillaridin A conjugates in a cell free system. Acta Pol Pharm. 2010 Nov-Dec;67(6):630-4. PubMed PMID: 21229879.

14: Winnicka K, Bielawski K, Bielawska A. Synthesis and cytotoxic activity of G3 PAMAM-NH(2) dendrimer-modified digoxin and proscillaridin A conjugates in breast cancer cells. Pharmacol Rep. 2010 Mar-Apr;62(2):414-23. PubMed PMID: 20508299.

15: Winnicka K, Bielawski K, Bielawska A, Miltyk W. Dual effects of ouabain, digoxin and proscillaridin A on the regulation of apoptosis in human fibroblasts. Nat Prod Res. 2010 Feb;24(3):274-85. doi: 10.1080/14786410902991878. PubMed PMID: 20140806.

16: Felth J, Rickardson L, Rosén J, Wickström M, Fryknäs M, Lindskog M, Bohlin L, Gullbo J. Cytotoxic effects of cardiac glycosides in colon cancer cells, alone and in combination with standard chemotherapeutic drugs. J Nat Prod. 2009 Nov;72(11):1969-74. doi: 10.1021/np900210m. PubMed PMID: 19894733.

17: Zhang H, Qian DZ, Tan YS, Lee K, Gao P, Ren YR, Rey S, Hammers H, Chang D, Pili R, Dang CV, Liu JO, Semenza GL. Digoxin and other cardiac glycosides inhibit HIF-1alpha synthesis and block tumor growth. Proc Natl Acad Sci U S A. 2008 Dec 16;105(50):19579-86. doi: 10.1073/pnas.0809763105. Epub 2008 Nov 19. PubMed PMID: 19020076; PubMed Central PMCID: PMC2604945.

18: Winnicka K, Bielawski K, Bielawska A, Surazyński A. Antiproliferative activity of derivatives of ouabain, digoxin and proscillaridin A in human MCF-7 and MDA-MB-231 breast cancer cells. Biol Pharm Bull. 2008 Jun;31(6):1131-40. PubMed PMID: 18520043.

19: Winnicka K, Bielawski K, Bielawska A, Miltyk W. Apoptosis-mediated cytotoxicity of ouabain, digoxin and proscillaridin A in the estrogen independent MDA-MB-231 breast cancer cells. Arch Pharm Res. 2007 Oct;30(10):1216-24. PubMed PMID: 18038900.

20: Bielawski K, Winnicka K, Bielawska A. Inhibition of DNA topoisomerases I and II, and growth inhibition of breast cancer MCF-7 cells by ouabain, digoxin and proscillaridin A. Biol Pharm Bull. 2006 Jul;29(7):1493-7. PubMed PMID: 16819197.