Inhibition of dipeptidyl peptidase-IV (DPP-IV) by atorvastatin

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 2, 2008, Pages 479-484

  Taldone, Tony ^a   Zito, S William ^a   Talele, Tanaji T ^a  

^a ST JOHN'S UNIVERSITY   (United States)

Author keywords

Diabetes; Molecular modeling; Statin

Indexed keywords

ATORVASTATIN; DIPEPTIDYL PEPTIDASE IV; DIPEPTIDYL PEPTIDASE IV INHIBITOR; FLUINDOSTATIN; GASTRIC INHIBITORY POLYPEPTIDE; GLIBENCLAMIDE; GLUCAGON LIKE PEPTIDE 1; GLUCOSE; INCRETIN; ISOLEUCINE THIAZOLIDIDE; NATEGLINIDE; ROSIGLITAZONE; ROSUVASTATIN; SAXAGLIPTIN; SITAGLIPTIN; TOLBUTAMIDE; TROGLITAZONE; VALINE PYRROLIDIDE; VILDAGLIPTIN;

ARTICLE; BINDING AFFINITY; COMPETITIVE INHIBITION; DRUG SPECIFICITY; DRUG USE; ENZYME INACTIVATION; ENZYME INHIBITION; GLUCOSE METABOLISM; HORMONAL REGULATION; HYDROPHOBICITY; HYPOLIPEMIA; IC 50; IN VITRO STUDY; INHIBITION KINETICS; NON INSULIN DEPENDENT DIABETES MELLITUS; NONHUMAN; REACTION OPTIMIZATION; STRUCTURE ACTIVITY RELATION; SWINE;

ANTIGENS, CD26; CATALYTIC DOMAIN; HEPTANOIC ACIDS; HYDROGEN BONDING; HYDROLYSIS; MODELS, MOLECULAR; PROTEASE INHIBITORS; PYRROLES;

SUS;

EID: 38149003701     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.11.107     Document Type: Article

References (36)

1. Kreymann B., Williams G., Ghatei M.A., and Bloom S.R. Lancet 2 (1987) 1300
2. Dupre J., Ross S.A., Watson D., and Brown J.C. J. Clin. Endocrinol. Metab. 37 (1973) 826
3. Nauck M.A., Homberger E., Siegel E.G., Allen R.C., Eaton R.P., Ebert R., and Creutzfeldt W. J. Clin. Endocrinol. Metab. 63 (1986) 492
4. Nauck M., Stockmann F., Ebert R., and Creutzfeldt W. Diabetologia 29 (1986) 46
5. Ahrén B., Landin-Olsson M., Jansson P., Svensson M., Holmes D., and Schweizer A. J. Clin. Endocrinol. Metab. 89 (2004) 2078
6. Weber A.E. J. Med. Chem. 47 (2004) 4135
7. Demuth H., McIntosh C.H.S., and Pederson R.A. Biochim. Biophys. Acta 1751 (2005) 33
8. Neubert, K.; Born, I.; Faust, J.; Heins, J.; Barth, A.; Demuth, H. U.; Rahfeld, J. U.; Steinmetzer, T. German Patent Application. Number DD 296 075 A5, 1983.
9. Schön E., Born I., Demuth H.U., Faust J., Neubert K., Steinmetzer T., Barth A., and Ansorge S. Biol. Chem. Hoppe-Seyler 372 (1991) 305
10. Villhauer E.B., Brinkman J.A., Naderi G.B., Burkey B.F., Dunning B.E., Prasad K., Mangold B.L., Russell M.E., and Hughes T.E. J. Med. Chem. 46 (2003) 2774
11. Augeri D.J., Robl J.A., Betebenner D.A., Magnin D.R., Khanna A., Robertson J.G., Wang A., Simpkins L.M., Taunk P., Huang Q., Han S.P., Abboa-Offei B., Cap M., Xin L., Tao L., Tozzo E., Welzel G.E., Egan D.M., Marcinkeviciene J., Chang S.Y., Biller S.A., Kirby M.S., Parker R.A., and Hamann L.G. J. Med. Chem. 48 (2005) 5025
12. Kim D., Wang L., Beconi M., Eiermann G.J., Fisher M.H., He H., Hickey G.J., Kowalchick J.E., Leiting B., Lyons K., Marsilio F., McCann M.E., Patel R.A., Petrov A., Scapin G., Patel S.B., Roy R.S., Wu J.K., Wyvratt M.J., Zhang B.B., Zhu L., Thornberry N.A., and Weber A.E. J. Med. Chem. 48 (2005) 141
13. Biftu T., Feng D., Qian X., Liang G.B., Kieczykowski G., Eiermann G., He H., Leiting B., Lyons K., Petrov A., Sinha-Roy R., Zhang B., Scapin G., Patel S., Gao Y.D., Singh S., Wu J., Zhang X., Thornberry N.A., and Weber A.E. Bioorg. Med. Chem. Lett. 17 (2007) 49
14. Mannucci A., Ognibene A., Cremasco F., Bardini G., Mencucci A., Pierazzuoli E., Ciani S., Messeri G., and Rotella C.M. Diabetes Care 24 (2001) 489
15. Lindsay J.R., Duffy N.A., McKillop A.M., Ardill J., O'Harte F.P.M., Flatt P.R., and Bell P.M. Diabetic Med. 22 (2005) 654
16. Green B.D., Irwin N., Duffy N.A., Gault V.A., O'Harte F.P.M., and Flatt P.R. Eur. J. Pharmacol. 547 (2006) 192
17. Hinke S.S., Kuhn-Wache K., Hoffmann T., Pederson R.A., McIntosh C.H.S., and Demuth H. Biochem. Biophys. Res. Commun. 291 (2002) 1302
18. Lenhard J.M., Croom D.K., and Minnick D.T. Biochem. Biophys. Res. Commun. 324 (2004) 92
19. We did not observe inhibition by metformin up to 3.3 mM, however, there was some attenuation of activity at 10 mM (12.7 ± 0.6%) and 30 mM (21.9 ± 0.6 %).
20. Duffy N.A., Green B.D., Irwin N., Gault V.A., McKillop A.M., O'Harte F.P.M., and Flatt P.R. Eur. J. Pharmacol. 568 (2007) 278
21. We did not observe any inhibition from several sulfonylureas (glybenclamide, glypizide, tolazamide and tolbutamide) at 500 μM.
22. Croom K.F., and Plosker G.L. Drugs 65 (2005) 137
23. McGovern S.L., Caselli E., Grigorieff N., and Shoichet B.K. J. Med. Chem. 45 (2002) 1712
24. McGovern S.L., and Shoichet B.K. J. Med. Chem. 46 (2003) 1478
25. Seidler J., McGovern S.L., Doman T.N., and Shoichet B.K. J. Med. Chem. 46 (2003) 4477
26. Ryan A.J., Gray N.M., Lowe P.N., and Chung C. J. Med. Chem. 46 (2003) 3448
27. Neugebauer J.M. Methods Enzymol. 182 (1990) 239
28. -4 M and were prepared in MeOH. The assay was run by mixing 15 μl of MeOH, 10 μl of control or inhibitor and 50 μl of substrate to appropriate wells. Twenty microliters of enzyme solution was added to commence the reaction. Following an incubation period of 15 min at 37 °C, 25 μl of 25% acetic acid (in methanol) was added to each well to halt the reaction and absorbance at 405 nm was determined using a microplate reader. The assay was performed in duplicate three times and with appropriate blanks and controls. All concentrations refer to final assay values. The data were analyzed with GraphPad Prism version 4 by globally fitting it to the untransformed equations for competitive, noncompetitive, and uncompetitive inhibition.
29. Schrodinger, L. L. C., New York.
30. Jorgensen W.L., Maxwell D.S., and Tirado-Rives J. J. Am. Chem. Soc. 118 (1996) 11225
31. Bytheway I., Cochran S., and Chem J.M. J. Med. Chem. 47 (2004) 1683
32. Chen H., Lyne P.D., Giordanetto F., Lovell T., and Li J. J. Chem. Inf. Model. 46 (2006) 401
33. Friesner R.A., Banks J.L., Murphy R.B., Halgren T.A., Klicic J.J., Mainz D.T., Repasky M.P., Knoll E.H., Shelley M., Perry J.K., Shaw D.E., Francis P., and Shenkin P.S. J. Med. Chem. 47 (2004) 1739
34. Halgren T.A., Murphy R.B., Friesner R.A., Beard H.S., Frye L.L., Pollard W.T., and Banks J.L. J. Med. Chem. 47 (2004) 1750
35. Eldridge M.D., Murray C.W., Auton T.R., Paolini G.V., and Mee R.P. J. Comput.-Aided Mol. Des. 11 (1997) 425
36. Thoma R., Löffler B., Stihle M., Huber W., Ruf A., and Hennig M. Structure 11 (2003) 947