FSL0754

Structure

• InChI=1S/C29H44O12/c1-13-22(34)23(35)24(36)25(40-13)41-15-8-19(32)28(12-30)21-17(3-5-27(28,37)9-15)29(38)6-4-16(14-7-20(33)39-11-14)26(29,2)10-18(21)31/h7,13,15-19,21-25,30-32,34-38H,3-6,8-12H2,1-2H3/t13-,15-,16+,17?,18+,19+,21?,22-,23+,24+,25-,26+,27-,28+,29-/m0/s1
• InChIKey=LPMXVESGRSUGHW-XPXORLBYSA-N

Synonyms

• (-)-Ouabain
• 11018-89-6
• MS0A0456
• ouabain

Origin

Acokanthera oubaio
Strophanthus gratus

Biological activities

An increase in intracellular sodium and calcium concentrations

Therapeutic

Cardiotonic

Target

Sodium/potassium-transporting ATPase

Assay information

Inhibition of human Na⁺/K⁺-ATPase α1β1 (K_d = 13.3 ± 5.2 nM), α2β1 (K_d = 32.8 ± 15.7 nM), α3β1 (K_d = 16.7 ± 1.8 nM)
Induction for the apoptosis in MDA-MB-231 breast cancer cells by increasing free calcium concentration and by activating caspase-3 (IC₅₀ = 150 nM (24h), 90 nM (48 h))
Antiproliferative and apoptotic effects in several cancer cell lines, including 1. Small cell lung cancer cell: H69 AR (IC₅₀ = 45 nM, MRP-associated resistance), NCl-H69 (IC₅₀ = 70 nM, parental resistance); 2. Histiocy
Cytoprotective effects of cardiac glycosides in human tumor cell at the low concentrations (0.1-10 nM)

References

• Prassas I, Diamandis EP
  Novel therapeutic applications of cardiac glycosides.
  Nat Rev Drug Discov, 7(11): 926-935 (2008)  18948999  doi: 10.1038/nrd2682
• 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, 30(10): 1216-1224 (2007)  18038900
• Mucaji P, Nagy M, Grancai D
  [Ouabain: from an arrow poison to a new steroidal hormone].
  Ceska Slov Farm, 54(5): 207-210 (2005)  16209434
• Müller-Ehmsen J, Juvvadi P, Thompson CB, Tumyan L, Croyle M, Lingrel JB, Schwinger RH, McDonough AA, Farley RA
  Ouabain and substrate affinities of human Na(+)-K(+)-ATPase alpha(1)beta(1), alpha(2)beta(1), and alpha(3)beta(1) when expressed separately in yeast cells.
  Am J Physiol Cell Physiol, 281(4): C1355-C1364 (2001)  11546674
• Johansson S, Lindholm P, Gullbo J, Larsson R, Bohlin L, Claeson P
  Cytotoxicity of digitoxin and related cardiac glycosides in human tumor cells.
  Anticancer Drugs, 12(5): 475-483 (2001)  11395576
• RISING JD
  Digitalis glycosides, ouabain and strophanthin in general practice.
  J Kans Med Soc, 49(1): 14-19 (1948)  18897678