Evaluation of novel Hyphodermin derivatives as Glycogen Phosphorylase a inhibitors

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 11, 2008, Pages 6172-6178

  Loughlin, Wendy A ^a   Pierens, Gregory K ^b   Petersson, Maria J ^a   Henderson, Luke C ^a   Healy, Peter C ^a  

^a GRIFFITH UNIVERSITY   (Australia)

^b UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

C Log P; Glycogen Phosphorylase a; Hydrobenzoindole carboxylic acids; Hyphodermin; Inhibitor

Indexed keywords

ENZYME INHIBITOR; FURAN DERIVATIVE; GLYCOGEN PHOSPHORYLASE; GLYCOGEN PHOSPHORYLASE INHIBITOR; HYPHODERMIN; HYPHODERMIN A; HYPHODERMIN B; HYPHODERMIN D;

ARTICLE; DRUG PENETRATION; DRUG SOLUBILITY; IC 50; LIPOPHILICITY; MOLECULAR MODEL; PHYSICAL CHEMISTRY; STRUCTURE ACTIVITY RELATION;

ALLOSTERIC REGULATION; ANIMALS; BASIDIOMYCOTA; CELL MEMBRANE PERMEABILITY; FURANS; GLYCOGEN PHOSPHORYLASE, MUSCLE FORM; HYDROGEN BONDING; ISOENZYMES; LIPIDS; MODELS, MOLECULAR; NAPHTHALENES; RABBITS; SOLUBILITY; SURFACE PROPERTIES;

EID: 44449105030     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.04.047     Document Type: Article

References (48)

1. Oikonomakos N.G. Curr. Protein Pept. Sci. 3 (2002) 561
2. Henke B.R., and Sparks S.M. Mini-Rev. Med. Chem. 6 (2006) 845
3. Treadway J.L., Mendys P., and Hoover D.J. Expert Opin. Invest. Drugs 10 (2001) 439
4. Martin J.L., Velugaraja K.R., Johnson L.N., Fleet G.W.J., Ramsden N.G., Bruce I., Orchard M.G., Oikonomakos N.G., Papageorgiou A.C., Leonidas D.D., and Tsitoura H.S. Biochemistry 30 (1991) 10101
5. Sprang S.R., Goldsmith E.J., Fletterick R.J., Withers S.G., and Madsen N.B. Biochemistry 21 (1982) 5364
6. Somsak L., Nagy V., Hadady Z., Docsa T., and Gergely P. Curr. Pharm. Des. 9 (2003) 1177
7. Ekstrom J.L., Pauly T.A., Carty M.D., Soeller W.C., Culp J., Danley D.E., Hoover D.J., Treadway J.L., Gibbs E.M., Fletterick R.J., Day Y.S.N., Myszka D.G., and Rath V.L. Chem. Biol. 9 (2002) 915
8. Martin W.H., Hoover D.J., Armento S.J., Stock I.A., McPherson R.K., Danley D.E., Stevenson R.W., Barrett E.J., and Treadway J.L. Proc. Natl. Acad. Sci. U.S.A. 95 (1998) 1776
9. Oikonomakos N.G., Skamnaki V.T., Tsitsanou K.E., Gavalas N.G., and Johnson L.N. Structure 8 (2000) 575
10. Rath V.L., Ammirati M., Danley D.E., Ekstrom J.L., Gibbs E.M., Hynes T.R., Mathiowetz A.M., McPherson R.K., Olson T.V., Treadway J.L., and Hoover D.J. Chem. Biol. 7 (2000) 677
11. Chrysina E.D., Kosmopoulou M.N., Tiradis C., Kardakaris R., Bischler N., Leonidas D.D., Hadady Z., Somsak L., Docsa T., Gergley P., and Oikonomakos N.G. Protein Sci. 14 (2005) 873
12. Hoover D.J., Lefkowitz-Snow S., Burgess-Henry J.L., Martin W.H., Armento S.J., Stock I.A., McPherson R.K., Genereux P.E., Gibbs E.M., and Treadway J.L. J. Med. Chem. 41 (1998) 2934
13. Barf T. Mini-Rev. Med. Chem. 4 (2004) 897
14. Baker D.J., Greenhaff P.L., and Timmons J.A. Expert Opin. Ther. Patents 16 (2006) 459
15. For example:. Koch M.A., and Waldmann H. Drug Discov. Today 10 (2005) 471
16. Henkel, T.; Mueller, H.; Schmidt, D.; Wollweber, H. Ger. Offen.; DE 19611366 A1; Chem. Abstr. 1997, 127, 260060.
17. Henderson L.C., Loughlin W.A., Jenkins I.D., Healy P.C., and Campitelli M.R. J. Org. Chem. 71 (2006) 2384
18. Petersson M.J., Marchal C., Loughlin W.A., Jenkins I.D., Healy P.C., and Almesåker A. Tetrahedron 63 (2007) 1395
19. Loughlin W.A., Jenkins I.D., Henderson L.C., Campitelli M.R., and Healy P.C. J. Org. Chem. 73 (2008) 3435
20. QikProp; 2.5 ed.; Schrödinger: LLC, New York, NY, 2005.
21. Tetko I.V., Gasteiger J., Todeschini R., Mauri A., Livingstone D., Ertl P., Palyulin V.A., Radchenko E.V., Zefirov N.S., Makarenko A.S., Tanchuk V.Y., and Prokopenko V.V. J. Comput. Aided Mol. Des. 19 (2005) 453
22. VCCLAB, Virtual Computational Chemistry Laboratory, http://www.vcclab.org, 2005.
23. Oprea T.I.I. J. Comput. Aided Mol. Des. 16 (2002) 325
24. Avdeef A. Curr. Top. Med. Chem. 1 (2001) 277-351
25. Balakin K.V., Savchuk N.P., and Tetko I.V. Curr. Med. Chem. 13 (2006) 223
26. Lipinski C.A., Lombardo F., Dominy B.W., and Feeney P.J. Adv. Drug Deliv. Rev. 46 (2001) 3
27. Kerns E.H. J. Pharm. Sci. 90 (2001) 1838
28. Caron G., and Ermondi G. Mini-Rev. Med. Chem. 3 (2003) 821
29. Tetko I.V., Tanchuk V.Y., and Villa A.E.P. J. Chem. Inf. Comput. Sci 41 (2001) 1407
30. Tetko I.V., and Poda G.I. J. Med. Chem. 47 (2004) 5601
31. Raevsky O.A., Fetisov V.I., Trepalina E.P., McFarland J.W., and Schaper K.-J. Quant. Struct. Act. Relat. 19 (2000) 366
32. Lipinski C.A., Lombardo F., Dominy B.W., and Feeney P.J. Adv. Drug Deliv. Rev. 23 (1997) 3
33. Teague S.J., Davis A.M., Leeson P.D., and Oprea T. Angew. Chem., Int. Ed. Engl. 38 (1999) 3743
34. Artursson P., and Karlsson J. Biochem. Biophys. Res. Commun. 175 (1991) 880
35. Jorgensen W.L., and Duffy E.M. Adv. Drug Deliv. Rev. 54 (2002) 355
36. Zhoa Y.H., Abraham M.H., Lee J., Hersey A., Luscombe C.N., Beck G., Sherborne B., and Cooper I. Pharm. Res. 19 (2002) 1446
37. Martin Y.C. J. Med. Chem. 48 (2005) 3164
38. Darvas F., Keseru G., Papp A., Dorman G., Urge L., and Krajcsi P. Curr. Top. Med. Chem. 2 (2002) 1287
39. Ghose A.K., Herbertz T., Salvino J.M., and Mallamo J.P. Drug Discov. Today 11 (2006) 1107
40. Muegge I. Med. Res. Rev. 23 (2003) 302
41. Veber D.F., Johnson S.R., Cheng H.-Y., Smith B.R., Ward K.W., and Kapple K.D. J. Med. Chem. 45 (2002) 2615
42. Refsgaard H.H.F., Jensen B.F., Brockhoff P.B., Padkjr S.B., Guldbrandt M., and Christensen M.S. J. Med. Chem. 48 (2005) 805
43. Yoshida F., and Topliss J.G. J. Med. Chem. 43 (2000) 2575
44. Engers H.D., Shechosky S., and Madsen N.B. Can. J. Biochem. 48 (1970) 746-754
45. Leach A.R., Hann M.M., Burrows J.N., and Griffen E.J. Mol. BioSyst. 2 (2006) 429
46. MacroModel, version 8.0, Schrodinger, LLC, New York, NY, 2007.
47. Lanzetta P.A., Alvarez L.J., Reinach P.S., and Candia O.A. Anal. Biochem. 100 (1979) 95
48. Hess H.H., and Derr J.E. Anal. Biochem. 63 (1975) 607