Novel 3-amino-2-hydroxy acids containing protease inhibitors. Part 1: Synthesis and kinetic characterization as aminopeptidase P inhibitors

Bioorganic and Medicinal Chemistry

Volumn 13, Issue 16, 2005, Pages 4806-4820

  Stöckel Maschek, Angela ^a   Stiebitz, Beate ^a   Koelsch, Regine ^a   Neubert, Klaus ^a  

^a MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

Author keywords

Aminopeptidase P; Bestatin; Mixed type inhibition; Slow binding inhibition

Indexed keywords

3 AMINO 2 HYDROXY 4 PEHYLBUTANOYLPROLINE; 3 AMINO 2 HYDROXY 4 PHENYLBUTANOIC ACID PYRROLIDIDE; 3 AMINO 2 HYDROXY 4 PHENYLBUTANOIC ACID THIAZOLIDIDE HYDROBROMIDE; 3 AMINO 2 HYDROXY 4 PHENYLBUTANOYLPROLINE METHYL ESTER; 3 AMINO 2 HYDROXY 4 PHENYLBUTANOYLPROLINE METHYL ESTER HYDROBROMIDE; 3 AMINO 2 HYDROXY 4 PHENYLBUTANOYLPROLINE TRIFLUOROACETATE; 3 AMINO 2 HYDROXY 4 PHENYLBUTANOYLPROLYLPHENYLALANINE METHYL ESTER; 3 AMINO 2 HYDROXY 5 METHYLHEXANOIC ACID THIAZOLIDIDE HYDROBROMIDE; 3 AMINO 2 HYDROXY 5 METHYLHEXANOYLPROLINE TRIFLUOROACETATE; 4 BENZYL 3 HYDROXY 1,5 DIAZABICYCLO[5.3.0]DECAN 2,6 DIONE; AMINOPEPTIDASE P; BESTATIN; HYDROXYACID; NANOPARTICLE; PROTEINASE INHIBITOR; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CHEMICAL REACTION KINETICS; CONTROLLED STUDY; DRUG BINDING; DRUG MECHANISM; DRUG POTENCY; DRUG SYNTHESIS; ENZYME INHIBITION; ESCHERICHIA COLI; INTESTINE; NONHUMAN; RAT;

AMINO ACIDS; AMINOPEPTIDASES; ANIMALS; BINDING SITES; ESCHERICHIA COLI; KINETICS; LEUCINE; PROLINE; PROTEASE INHIBITORS; PYRROLES; RATS; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY; THIAZOLES;

ESCHERICHIA COLI;

EID: 21744462243     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.05.040     Document Type: Article

References (48)

1. A. Yaron, and D. Mlynar Biochem. Biophys. Res. Commun. 32 1968 658 663
2. J. Lasch, R. Koelsch, A.-M. Ladhoff, and B. Hartrodt Biomed. Biochim. Acta 45 1986 833 843
3. N.M. Hooper, J. Hryszko, and A.J. Turner Biochem. J. 267 1990 509 515
4. H.-T. Harbeck, and R. Mentlein Eur. J. Biochem. 198 1991 451 458
5. I. Mars, and V. Monnet Biochim. Biophys. Acta 1243 1995 209 215
6. N.M. Hooper, and A.J. Turner FEBS Lett. 229 1988 340 344
7. W.H. Simmons, and A.T. Orawski J. Biol. Chem. 267 1992 4897 4903
8. I. Rusu, and A. Yaron Eur. J. Biochem. 210 1992 93 100
9. M.C.J. Wilce, C.S. Bond, N.E. Dixon, H.C. Freeman, J.M. Guss, P.E. Lilley, and J.A. Wilce Proc. Natl. Acad. Sci. U.S.A. 95 1998 3472 3477
10. L. Zhang, M.J. Crossley, N.E. Dixon, P.J. Ellis, M.L. Fisher, G.F. King, P.E. Lilley, D. MacLachlan, R.J. Pace, and H.C. Freeman J. Biol. Inorg. Chem. 3 1998 470 483
11. N.D. Rawlings, and A. Barrett J. Methods Enzymol. 248 1995 183 228
12. J.F. Bazan, L.H. Weaver, S.L. Roderick, R. Huber, and B.W. Matthews Proc. Nat. Acad. Sci. U.S.A. 91 1994 2473 2477
13. A. Yaron, and F. Naider Crit. Rev. Biochem. Mol. Biol. 28 1993 31 81
14. S.-I. Kitamura, L.A. Carbini, O.A. Carretero, W.H. Simmons, and A.G. Scicli Br. J. Pharmacol. 114 1995 6 7
15. M.M. Prechel, A.T. Orawski, V.W. Maggiora, and H. Simmons J. Pharmacol. Exp. Ther. 275 1995 1136 1142
16. K.C. Nicolaou, W.-M. Dai, and R.K. Guy Angew. Chem. 106 1994 38 69
17. K.C. Nicolaou, and R.K. Guy Angew. Chem. 107 1995 2247 2259
18. H. Umezawa, T. Aoyagi, H. Suda, M. Hamada, and T. Takeuchi J. Antibiot. 29 1976 97 99
19. T. Mimoto, J. Imai, N. Hattori, O. Takahashi, S. Kisanuki, Y. Nagano, M. Shintani, H. Hayashi, H. Sakikawa, K. Akaji, and Y. Kiso Chem. Pharm. Bull. 39 1991 2465 2467
20. T. Mimoto, J. Imai, S. Tanaka, N. Hattori, S. Kisanuki, K. Akaji, and Y. Kiso Chem. Pharm. Bull. 39 1991 3088 3090
21. S.H. Wilkes, and J.M. Prescott J. Biol. Chem. 260 1985 13154 13162
22. S. Yoshida, Y. Nakamura, H. Naganawa, T. Aoyagi, and T. Takeuchi J. Antibiot. XLIII 1990 149 153
23. S.J. Hecker, and K.M. Werner J. Org. Chem. 58 1993 1762 1765
24. H. Kim, and W.N. Lipscomb Adv. Enzymol. 68 1994 153 213
25. D.H. Rich, B.J. Moon, and S. Harbeson J. Med. Chem. 27 1984 417 422
26. T. Yoshimoto, A.T. Orawski, and W.H. Simmons Arch. Biochem. Biophys. 311 1994 28 34
27. J.-A. Fehrentz, and B. Castro Synthesis 1983 676 678
28. R. Herranz, J. Castro-Pichel, S. Vinuesa, and M.T. Garcia-Lopez J. Org. Chem. 55 1990 2232 2234
29. B.D. Sykes, E.B. Robertson, H.B. Dunford, and D. Konasewich Biochemistry 5 1966 697 701
30. S. Johne, and D. Gröger Pharmazie 32 1977 1 15
31. M. Sakurai, S. Higashida, M. Sugano, T. Komai, R. Yagi, Y. Ozawa, H. Handa, T. Nishigaki, and Y. Yabe Bioorg. Med. Chem. 2 1994 807 825
32. I.H. Segel Enzyme kinetics. Behavior and analysis of rapid equilibrium and steady-state enzyme systems 1993 John Wiley, Wiley Classics Library 161 176
33. L.L. Maggiora, A.T. Orawski, and W.H. Simmons J. Med. Chem. 42 1999 2394 2402
34. J.F. Morrison, and C.T. Walsh Adv. Enzymol. 61 1988 201 301
35. T. Aoyagi, T. Wada, K. Yamamoto, F. Kojima, M. Nagai, S. Harada, and H. Umezawa J. Appl. Biochem. 6 1984 212 221
36. A. Stöckel-Maschek, C. Mrestani-Klaus, B. Stiebitz, H.-U. Demuth, and K. Neubert Biochim. Biophys. Acta 1479 2000 15 31
37. W.T. Lowther, and B.W. Matthews Biochim. Biophys. Acta 1477 2000 157 167
38. W.T. Lowther, and B.W. Matthews Chem. Rev. 102 2002 4581 4607
39. M.J. Maher, M. Ghosh, A.M. Grunden, A.L. Menon, M.W.W. Adams, H.C. Freeman, and J. Guss Biochemistry 43 2004 2771 2783
40. N. Sträter, and W.N. Lipscomb Biochemistry 34 1995 14792 14800
41. H. Kim, and W.N. Lipscomb Biochemistry 32 1993 8465 8478
42. S.C. Graham, M.J. Maher, W.H. Simmons, H.C. Freeman, and J.M. Guss Acta Cryst. Sect. D 60 2004 1770 1779
43. J.-Y. Li, L.-L. Chen, Y.-M. Cui, Q.-L. Luo, J. Li, F.-J. Nan, and Q.-Z. Ye Biochem. Biophys. Res. Commun. 307 2003 172 179
44. J. Lasch, R. Koelsch, T. Steinmetzer, U. Neumann, and H.-U. Demuth FEBS Lett. 227 1988 171 174
45. A. Stöckel-Maschek, B. Stiebitz, R. Koelsch, and K. Neubert Anal. Biochem. 322 2003 60 67
46. T. Yoshimoto, H. Tone, T. Honda, K. Osatomi, R. Kobayashi, and D. Tsuru J. Biochem. 105 1989 412 416
47. Gottwald, S.; Martin-Luther-Universität Halle-Wittenberg, Thesis, 1996.
48. S.E. Szedlacsek, and R.G. Duggleby Methods Enzymol. 249 1995 144 180