Stereochemical survey of digitoxin monosaccharides

ACS Medicinal Chemistry Letters

Volumn 2, Issue 1, 2011, Pages 73-78

  Wang, Hua Yu Leo ^a   Xin, Wenjun ^b   Zhou, Maoquan ^b   Stueckle, Todd A ^b   Rojanasakul, Yon ^b   O'Doherty, George A ^a  

^a NORTHEASTERN UNIVERSITY   (United States)

^b WEST VIRGINIA UNIVERSITY   (United States)

Author keywords

amicetose; apoptosis; cancer; Digitoxin; digitoxin monosaccharide; NCI H460; rhamnose

Indexed keywords

ALPHA LEVO AMICETOSE; ALPHA LEVO RHAMNOSE; BETA DEXTRO DIGITOXOSE; DIGITOXIGENIN; DIGITOXIN; MONOSACCHARIDE; SUGAR; UNCLASSIFIED DRUG;

APOPTOSIS; ARTICLE; CONCENTRATION RESPONSE; CYTOTOXICITY; DRUG POTENCY; DRUG SYNTHESIS; GLYCOSYLATION; HUMAN; HUMAN CELL; PRIORITY JOURNAL; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 78651507653     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml100219d     Document Type: Article

References (32)

1. Greeff, K. Cardiac Glycosides, Part 1: Experimental Pharmacology. Handbook of Experimental Pharmacology; Springer-Verlag: Berlin, NY, 1981; Vol. 56.
2. Stenkvist, B.; Bengtsson, E.; Eriksson, O.; Holmquist, J.; Nordin, B.; Westman-Naeser, S. Cardiac glycosides and breast cancer Lancet 1979, 1, 563
3. Stenkvist, B.; Bengtsson, E.; Dahlqvist, B.; Eriksson, O.; Jarkrans, T.; Nordin, B. Cardiac glycosides and breast cancer, revisited N. Engl. J. Med. 1982, 306, 484
4. Newman, R. A.; Yang, P.; Pawlus, A. D.; Block, K. I. Cardiac Glycosides as Novel Cancer Therapeutic Agents Mol. Interventions 2008, 8, 36-49
5. Haux, J.; Solheim, O.; Isaksen, T.; Angelsen, A. Digitoxin, in non-toxic concentrations, inhibits proliferation and induces cell death in prostate cancer cell lines Z. Onkol. 2000, 32, 11-16
6. +-ATPase J. Biol. Chem. 2000, 275, 27832-27837
7. +-ATPase-Mediated Signal Transduction: From Protein Interaction to Cellular Function Mol. Interventions 2003, 3, 157-168
8. Arispe, N.; Diaz, J. C.; Simakova, O.; Pollard, H. B. Heart failure drug digitoxin induces calcium uptake into cells by forming transmembrane calcium channels Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 2610-2615
9. 2+ concentrations J. Biol. Chem. 2000, 275, 27838-27844
10. Saunders, R.; Scheiner-Bobis, G. Ouabain stimulates endothelin release and expression in human endothelial cells without inhibiting the sodium pump Eur. J. Biochem. 2004, 271, 1054-1062
11. Lopez-Lazaro, M.; Pastor, N.; Azrak, S. S.; Ayuso, M. J.; Austin, C. A.; Cortes, F. Digitoxin Inhibits the Growth of Cancer Cell Lines at Concentrations Commonly Found in Cardiac Patients J. Nat. Prod. 2005, 68, 1642-1645
12. Yoda, A. Structure-Activity Relationships of Cardiotonic Steroids for the inhibition of Sodium-and Potassium-Dependent Adenosine Triphosphatase Mol. Pharmacol. 1973, 9, 51-60
13. Smith, P.; Brown, L.; Boutagy, J.; Thomas, R. Cardenolide Analogues. Synthesis and Biological Activity of Glucosides of C17b-Modified Derivatives of Digitoxigenin J. Med. Chem. 1982, 25, 1222-1226
14. Fullerton, D. S.; Kihara, M.; Deffo, T.; Kitatsuji, E.; Ahmed, K.; Simat, B.; From, A. H. L.; Rohrer, D. C. Cardiac Glycosides. A Systematic Study of Digitoxigenin D-Glycosides J. Med. Chem. 1984, 27, 256-261
15. Griffith, B. R.; Langenhan, J. M.; Thorson, J. S. Sweetening natural products via glycorandomization Curr. Opin. Biotechnol. 2005, 16, 622-630
16. Langenhan, L. M.; Peters, N. R.; Guzei, I. A.; Hoffmann, M.; Thorson, J. S. Enhancing the anticancer properties of cardiac glycosides by neoglycorandomization Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 12305-12310
17. Iyer, A. K. V.; Zhou, M.; Azad, N.; Elbaz, H.; Wang, L.; Rogalsky, D. K.; Rojanasakul, Y.; O'Doherty, G. A.; Langenhan, J. M. A Direct Comparison of the Anticancer Activities of Digitoxin MeON-Neoglycosides and O-Glycosides: Oligosaccharide Chain Length-Dependent Induction of Caspase-9-Mediated Apoptosis ACS Med. Chem. Lett. 2010, 1, 326-330
18. Babu, R. S.; O'Doherty, G. A. A Palladium-Catalyzed Glycosylation Reaction: The De Novo Synthesis of Natural and Unnatural Glycosides J. Am. Chem. Soc. 2003, 125, 12406-12407
19. Shan, M.; O'Doherty, G. A. De Novo Asymmetric Syntheses of SL0101 and its Analogues via a Palladium-Catalyzed Glycosylation Org. Lett. 2006, 8, 5149-5152
20. Zhou, M.; O'Doherty, G. A. De Novo Synthesis of the Trisaccharide Subunit of Landomycins A and E Org. Lett. 2008, 10, 2283-2286
21. Yu, X.; O'Doherty, G. A. De Novo Asymmetric Synthesis and Biological Evaluation of the Trisaccharide Portion of PI-080 and Vineomycin B2 Org. Lett. 2008, 10, 4529-4532
22. Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. Ruthenium(II)-Catalyzed Asymmetric Transfer Hydrogenation of Ketones Using a Formic Acid-Triethylamine Mixture J. Am. Chem. Soc. 1996, 118, 2521-2522
23. Li, M.; O'Doherty, G. A. An enantioselective synthesis of phomopsolide D Tetrahedron Lett. 2004, 45, 6407-6411
24. Achmatowicz, O.; Bukowski, P.; Szechner, B.; Zwierzchowska, Z.; Zamojski, A. Synthesis of methyl 2,3-dideoxy-DL-alk-2-enopyranosides from furan compounds: A general approach to the total synthesis of monosaccharides Tetrahedron 1971, 27, 1973-1996
25. Guo, H.; O'Doherty, G. A. De Novo Asymmetric Synthesis of Daumone via a Palladium-Catalyzed Glycosylation Org. Lett. 2005, 7, 3921-3924
26. 4 oxidation of olefins to cis-1,2-glycols using tertiary amine oxides as the oxidant Tetrahedron Lett. 1976, 17, 1973-1976
27. Haukaas, M. H.; O'Doherty, G. A. Enantioselective Synthesis of 2-Deoxy-and 2,3-Dideoxyhexoses Org. Lett. 2002, 4, 1771-1774
28. Buszek, K. R.; Brown, N. Improved Method for the Diimide Reduction of Multiple Bonds on Solid-Supported Substrates J. Org. Chem. 2007, 72, 3125-3128
29. Zhou, M.; O'Doherty, G. A. A Stereoselective Synthesis of Digitoxin and Digitoxigen Mono-and Bisdigitoxoside from Digitoxigenin via a Palladium-Catalyzed Glycosylation Org. Lett. 2006, 8, 4339-4342
30. Zhou, M.; O'Doherty, G. A. De Novo Approach to 2-Deoxy-β-glycosides: Asymmetric Syntheses of Digoxose and Digitoxin J. Org. Chem. 2007, 72, 2485-2493
31. Myers, A. G.; Zheng, B. An efficient method for the reductive transposition of allylic alcohols Tetrahedron Lett. 1996, 37, 4841-4844
32. Rathore, H.; From, A. H. L.; Ahmed, K.; Fullerton, D. S. Cardiac Glycosides. 7. Sugar Stereochemistry and Cardiac Glycoside Activity J. Med. Chem. 1986, 29, 1945-1952