Modifying the glycosidic linkage in digitoxin analogs provides selective cytotoxins

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 2, 2008, Pages 670-673

  Langenhan, Joseph M ^a   Engle, Jeffery M ^a   Slevin, Lauren K ^a   Fay, Lindsay R ^a   Lucker, Ryan W ^a   Smith, Kyle R ^a   Endo, Matthew M ^a  

^a SEATTLE UNIVERSITY   (United States)

Author keywords

Cardiac glycoside; Chemoselective ligation; Cytotoxicity; Glycorandomization; Glycosylation

Indexed keywords

CHLORMETHINE N OXIDE; CYTOTOXIN; DIGITOXIN; DIGITOXIN DERIVATIVE; GLYCOCONJUGATE; GLYCOSIDE; SUGAR; UNCLASSIFIED DRUG;

ARTICLE; CANCER CELL CULTURE; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CONJUGATION; CYTOTOXICITY; DRUG MECHANISM; DRUG POTENCY; DRUG SELECTIVITY; GLYCOSYLATION; HUMAN; HUMAN CELL; PROCESS OPTIMIZATION; REACTION ANALYSIS; VALIDATION PROCESS;

AMINES; CARBOHYDRATES; CYTOTOXINS; DIGITOXIN; GLYCOCONJUGATES; GLYCOSYLATION;

EID: 38149104642     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.11.058     Document Type: Article

References (41)

1. Bertozzi C.R., and Kiessling L.L. Science 291 (2001) 2357
2. Prescher J.A., Dube D.H., and Bertozzi C.R. Nature 430 (2004) 873
3. Sawa M., Hsu T.-L., Itoh T., Sugiyama M., Hanson S.R., Vogt P.K., and Wong C.-H. Proc. Natl. Acad. Sci. 103 (2006) 12371
4. van Kasteren S.I., Kramer H.B., Jensen H.H., Campbell S.J., Kirkpatrick J., Oldham N.J., Anthony D.C., and Davis B.G. Nature 446 (2007) 1105
5. Newman D.J., and Cragg G.M. J. Nat. Prod. 70 (2007) 461
6. Clardy J., and Walsh C. Nature 432 (2004) 829
7. Thorson J.S., Hosted Jr. T.J., Jiang J., Biggins J.B., and Ahlert J. Curr. Org. Chem. 5 (2001) 139
8. Paula S., Tabet M.R., and Ball Jr. W.J. Biochemistry 44 (2005) 498
9. Stenkvist B. Anti-Cancer Drugs 12 (2001) 635
10. Haux J., Klepp O., Spigset O., and Tretli S. BMC Cancer 1 (2001) 11
11. Johansson S., Lindholm P., Gullbo J., Larsson R., Bohlin L., and Claeson P. Anticancer Drugs 12 (2001) 475
12. López-Lázaro M., Pastor N., Azrak N., Ayuso M.J., Austin C.A., and Cortés F. J. Nat. Prod. 68 (2005) 1642
13. Haux J. Medical Hypotheses 59 (2002) 781
14. Yeh J.Y., Huang W.J., Kan S.F., and Wang P.S. J. Urol. 166 (2001) 1937
15. For a flexible synthetic approach that provides ready access to mono- and disaccharide analogs see:. Zhou M., and O'Doherty G.A. J. Org. Chem. 72 (2007) 2485
16. Zhou M., and O'Doherty G.A. Org. Lett. 8 (2006) 4339
17. Zhou M., and O'Doherty G.A. Org. Lett. 8 (2006) 5677
18. Thibodeaux C.J., Melancon C.E., and Liu H.-W. Nature 446 (2007) 1008
19. Blanchard S., and Thorson J.S. Curr. Opin. Chem. Biol. 10 (2006) 263
20. Langenhan J.M., Griffith B.R., and Thorson J.S. J. Nat. Prod. 68 (2005) 1696
21. Griffith B.R., Langenhan J.M., and Thorson J.S. Curr. Opin. Biotechnol. 16 (2005) 622
22. Langenhan J.M., and Thorson J.S. Curr. Org. Synth. 2 (2005) 59 and references cited therein
23. Peri F., Dumy P., and Mutter M. Tetrahedron 54 (1998) 12269
24. Carrasco M.R., Brown R.T., Doan V.H., Kandel S.M., and Lee F.C. Biopolymers 84 (2006) 414
25. Carrasco M.R., and Brown R.T. J. Org. Chem. 68 (2003) 8853
26. Carrasco M.R., Brown R.T., Serafimova I.M., and Silva O. J. Org. Chem. 68 (2003) 195
27. Carrasco M.R., Nguyen M.J., Burnell D.R., MacLaren M.D., and Hengel S.M. Tetrahedron Lett. 43 (2002) 5727
28. Peri F., and Nicotra F. Chem. Comm. (2004) 623
29. Peri F., Jimenez-Barbero J., Garcia-Aparicio V., Tvaroska I., and Nicotra F. Chem. Eur. J. 10 (2004) 1433
30. Langenhan J.M., Peters N.R., Guzei I.A., Hoffman F.M., and Thorson J.S. Proc. Natl. Acad. Sci. 102 (2005) 12305
31. Ahmed A., Peters N.R., Fitzgerald M.K., Watson Jr. J.A., Hoffmann F.M., and Thorson J.S. J. Am. Chem. Soc. 128 (2006) 14224
32. Griffith B.R., Krepel C., Fu X., Blanchard S., Ahmed A., Edmiston C.E., and Thorson J.S. J. Am. Chem. Soc. 129 (2007) 8150
33. The distribution of pyranose, and sometimes furanose, anomers in these glycosides is dependent on sugar identity, but usually a single isomer predominates (see Ref. 14a).
34. 4 404.3, observed 404.4. The undesired α isomer can be obtained by further elution with 100% EtOAc.
35. 8 550.3, obsd 550.5.
36. The isomeric mixtures were not resolved during product purification since equilibration between product isomers occurs (see Ref. 14a).
37. For years, NCI/ADR-RES cells have been misidentified as drug-resistant MCF-7 breast adenocarcinoma cells, but recently this line has been shown definitively to be a drug-resistant line derived from OVCAR-8 ovarian adenocarcinoma cells. Liscovitch M., and Ravid D. Cancer Lett. 245 (2007) 350
38. Tanigawara Y., Okumura N., Hirai M., Yasuhara M., Ueda K., Kioka N., Komano T., and Hori R. J. Pharmacol. Exp. Ther. 263 (1992) 840
39. Johnson P.H., Walker R.P., Jones S.W., Stephens K., Meurer J., Zajchowski D.A., Luke M.M., Eeckman F., Tan Y., Wong L., Parry G., Morgan Jr. T.K., McCarrick M.A., and Monforte J. Mol. Cancer Ther. 1 (2002) 1293
40. Komentiani P., Liu L., and Askari A. Mol. Pharmacol. 67 (2005) 929
41. Yang Q., Huang W., Jozwik C., Lin Y., Glasman M., Caohuy H., Srivastava M., Esposito D., Gillette W., Hartley J., and Pollard H.B. Proc. Natl. Acad. Sci. 102 (2005) 9631