Captopril analogues as metallo-β-lactamase inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 26, Issue 6, 2016, Pages 1589-1593

  Yusof, Yusralina ^a   Tan, Daniel T C ^a   Arjomandi, Omid Khalili ^a   Schenk, Gerhard ^a   McGeary, Ross P ^a  

^a UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

Antibiotic resistance; Captopril; IMP 1 inhibitor; Metallo lactamase

Indexed keywords

BETA LACTAMASE INHIBITOR; CAPTOPRIL; BETA LACTAMASE; BETA-LACTAMASE IMP-1;

ARTICLE; COMPETITIVE INHIBITION; CRYSTAL STRUCTURE; DRUG HYDROLYSIS; DRUG POTENCY; DRUG SYNTHESIS; STRUCTURE ACTIVITY RELATION; ANALOGS AND DERIVATIVES; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; METABOLISM; MOLECULAR DOCKING; SYNTHESIS;

BETA-LACTAMASE INHIBITORS; BETA-LACTAMASES; CAPTOPRIL; DOSE-RESPONSE RELATIONSHIP, DRUG; MOLECULAR DOCKING SIMULATION; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84979026616     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2016.02.007     Document Type: Article

References (37)

1. 1 King, D.T., Strynadka, N.C.J., Future Med. Chem., 5, 2013, 1243.
2. 2 Drawz, S.M., Bonomo, R.A., Clin. Microbiol. Rev., 23, 2010, 160.
3. 3 Ball, P., Int. J. Antimicrob. Agents, 30, 2007, S113.
4. 4(a) Vella, P., Miraula, M., Phelan, E., Leung, E.W.W., Ely, F., Ollis, D.L., McGeary, R.P., Schenk, G., Mitic, N.J.B.I.C., J. Biol. Inorg. Chem., 18, 2013, 855.
5. 4(b) Hou, C.-F.D., Phelan, E.K., Miraula, M., Ollis, D.L., Schenk, G., Mitic, N., Am. J. Mol. Biol., 4, 2014, 11.
6. 5(a) Bebrone, C., Biochem. Pharmacol., 74, 2007, 1686.
7. 5(b) Crowder, M.W., Spencer, J., Vila, A.J., Acc. Chem. Res., 39, 2006, 721.
8. 5(c) Phelan, E.K., Miraula, M., Selleck, C., Ollis, D.L., Schenk, G., Mitic, N., Am. J. Mol. Biol., 4, 2014, 89.
9. 5(d) Mitić, N., Miraula, M., Selleck, C., Hadler, K.S., Uribe, E., Pedroso, M.M., Schenk, G., Christo, Z.C., (eds.) Advances in Protein Chemistry and Structural Biology, Vol. 97, 2014, Academic Press.
10. 6 McGeary, R.P., Schenk, G., Guddat, L.W., Eur. J. Med. Chem., 76, 2014, 132.
11. 7(a) Toney, J.H., Hammond, G.G., Fitzgerald, P.M.D., Sharma, N., Balkovec, J.M., Rouen, G.P., Olson, S.H., Hammond, M.L., Greenlee, M.L., Gao, Y.-D., J. Biol. Chem., 276, 2001, 31913.
12. 7(b) Nauton, L., Kahn, R., Garau, G., Hernandez, J.F., Dideberg, O., J. Mol. Biol., 375, 2008, 257.
13. 7(c) Olsen, L., Jost, S., Adolph, H.-W., Pettersson, I., Hemmingsen, L., Jorgensen, F.S., Bioorg. Med. Chem., 14, 2006, 2627.
14. 7(d) Feng, L., Yang, K.-W., Zhou, L.-S., Xiao, J.-M., Yang, X., Zhai, L., Zhang, Y.-L., Crowder, M.W., Bioorg. Med. Chem. Lett., 22, 2012, 5185.
15. 7(e) Hiraiwa, Y., Saito, J., Watanabe, T., Yamada, M., Morinaka, A., Fukushima, T., Kudo, T., Bioorg. Med. Chem. Lett., 24, 2014, 4891.
16. 8(a) Goto, M., Takahashi, T., Yamashita, F., Koreeda, A., Mori, H., Ohta, M., Arakawa, Y., Biol. Pharm. Bull., 20, 1997, 1136.
17. 8(b) Mollard, C., Moali, C., Papamicael, C., Damblon, C., Vessilier, S., Amicosante, G., Schofield, C.J., Galleni, M., Frère, J.-M., Roberts, G.C.K., J. Biol. Chem., 276, 2001, 45015.
18. 8(c) Hammond, G.G., Huber, J.L., Greenlee, M.L., Laub, J.B., Young, K., Silver, L.L., Balkovec, J.M., Pryor, K.D., Wu, J.K., Leiting, B., Pompliano, D.L., Toney, J.H., FEMS Microbiol. Lett., 179, 1999, 289.
19. 8(d) Hussein, W.M., Fatahala, S.S., Mohamed, Z.M., McGeary, R.P., Schenk, G., Ollis, D.L., Mohamed, M.S., Chem. Biol. Drug Des., 80, 2012, 500.
20. 8(e) Faridoon, S., Hussein, W.M., Vella, P., Ul Islam, N., Ollis, D.L., Schenk, G., McGeary, R.P., Bioorg. Med. Chem. Lett., 22, 2012, 380.
21. 8(f) Mohamed, M.S., Hussein, W.M., McGeary, R.P., Vella, P., Schenk, G., Abd El-hameed, R.H., Eur. J. Med. Chem., 46, 2011, 6075.
22. 8(g) Li, N., Xu, Y., Xia, Q., Bai, C., Wang, T., Wang, L., He, D., Xie, N., Li, L., Wang, J., Zhou, H.-G., Xu, F., Yang, C., Zhang, Q., Yin, Z., Guo, Y., Chen, Y., Bioorg. Med. Chem. Lett., 24, 2014, 386.
23. 9 Cushman, D.W., Ondetti, M.A., Nat. Med. (N. Y.), 5, 1999, 1110.
24. 10(a) Heinz, U., Bauer, R., Wommer, S., Meyer-Klaucke, W., Papamichaels, C., Bateson, J., Adolph, H.-W., J. Biol. Chem., 278, 2003, 20659.
25. 10(b) Lienard, B.M.R., Garau, G., Horsfall, L., Karsisiotis, A.I., Damblon, C., Lassaux, P., Papamicael, C., Roberts, G.C.K., Galleni, M., Dideberg, O., Frere, J.-M., Schofield, C.J., Org. Biomol. Chem., 6, 2008, 2282.
26. 11 Vella, P., Hussein, W.M., Leung, E.W.W., Clayton, D., Ollis, D.L., Mitic, N., Schenk, G., McGeary, R.P., Bioorg. Med. Chem. Lett., 21, 2011, 3282.
27. 12(a) Brem, J., van Berkel, S.S., Zollman, D., Lee, S.Y., Gileadi, O., McHugh, P.J., Walsh, T.R., McDonough, M.A., Schofield, C.J., Antimicrob. Agents Chemother., 60, 2016, 142.
28. 12(b) Rydzik, A.M., Brem, J., van Berkel, S.S., Pfeffer, I., Makena, A., Claridge, T.D.W., Schofield, C.J., Angew. Chem., Int. Ed., 53, 2014, 3129.
29. 13(a) Garcia-Saez, I., Hopkins, J., Papamicael, C., Franceschini, N., Amicosante, G., Rossolini, G.M., Galleni, M., Frere, J.-M., Dideberg, O., J. Biol. Chem., 278, 2003, 23868.
30. 13(b) King, D.T., Worrall, L.J., Gruninger, R., Strynadka, N.C.J., J. Am. Chem. Soc., 134, 2012, 11362.
31. 14 Garcia-Saez, I., Mercuri, P.S., Papamicael, C., Kahn, R., Frere, J.M., Galleni, M., Rossolini, G.M., Dideberg, O., J. Mol. Biol., 325, 2003, 651.
32. 15 Lewis, A., Ryan, M.D., Gani, D., J. Chem. Soc., Perkin Trans. 1, 1998, 3767.
33. 16 Amelia Santos, M., Marques, S., Gil, M., Tegoni, M., Scozzafava, A., Supuran, C.T., J. Enzyme Inhib. Med. Chem., 18, 2003, 233.
34. 17 Hazlehurst, L.; McLaughlin, M.; Jain, P.; Dalton, W. S. WO2011115688A2, 2011.
35. 18 Han, G., Tamaki, M., Hruby, V.J., J. Peptide Res., 58, 2001, 338.
36. 19 Zajdel, P., Nomezine, G., Masurier, N., Amblard, M., Pawlowski, M., Martinez, J., Subra, G., Chem.—Eur. J., 16, 2010, 7547.
37. 20 Fast, W., Sutton, L.D., Biochim. Biophys. Acta, Proteins Proteomics, 1834, 2013, 1648.