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Research Article

Characterisation of hydrazides and hydrazine derivatives as novel aspartic protease inhibitors

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Pages 673-678 | Received 26 Jan 2009, Accepted 17 Nov 2009, Published online: 11 Jan 2010

References

  • Davies DR. The structure and function of the aspartic proteinases. Ann Rev Biophys BioPhys Chem 1990;19:189–215.
  • Eder J, Hommel U, Cumin F, Martoglio B, Gerhartz B. Aspartic proteases in drug discovery. Curr Pharm Des 2007;13:271–285.
  • Schechter I, Berger A. On the size of the active site in proteases. I. Papain. Biochem Biophys Res Commun 1967;27:157–162.
  • Kay J, Dunn BM. Substrate specificity and inhibitors of aspartic proteinases. Scand J Clin Lab Invest 1992;52:23–30.
  • Zurcher M, Gottschalk T, Meyer S, Bur D, Deiderich F. Exploring the flap pocket of the antimalarial target plasmepsin II: The ‘55% rule’ applied to enzymes. Chem Med Chem 2008;3:237–240.
  • De Clercq E. Strategies in the design of antiviral drugs. Nat Rev Drug Discov 2002;1:13–25.
  • Jedinak A, Maliar T. Inhibitors of proteases as anticancer drugs. Neoplasma 2005;52:185–192.
  • Azim MK, Zaidi ZH. Molecular modeling of human procathepsin E: analysis of salt-bridge interactions between propeptide and enzyme segment. Biochem Biophys Res Commun 1999;264:825–832.
  • Ersmark K, Samuelsson B, Hallberg A. Plasmepsins as potential targets for new antimalarial therapy. Med Res Rev 2006;26:626–666.
  • Cooper JD, Russell C, Mitchison HM. Progress towards understanding disease mechanisms in small vertebrate models of neuronal ceroid lipofuscinosis. Biochem Biophys Acta 2006;1762:873–889.
  • Liu J, Istvan ES, Gluzman IY, Gross J, Goldberg DE. Plasmodium falciparum ensures its amino acid supply with multiple acquisition pathways and redundant proteolytic enzyme systems. Proc Natl Acad Sci USA 2006;103:8840–8845.
  • Bjelic S, Nervall M, Gutierrez-de-Teran H, Ersmark K, Hallberg A, Aqvist J. Computational inhibitor design against malaria plasmepsins. Cell Mol Life Sci 2007;64:2285–2305.
  • Bjelic S, Nervall M, Gutierrez-de-Teran H, Ersmark K, Hallberg A, Aqvist J. Potent, low-molecular-weight non-peptide inhibitors of malarial aspartyl protease plasmepsin II. J Med Chem 1999;42:1428–1440.
  • Dahlgren A, Kvarnstrom I, Vrang L, Hamelink E, Hallberg A, Rosenquist A, Samuelsson B. New inhibitors of the malaria aspartyl proteases plasmepsin I and II. Bioorg Med Chem 2003;11:3423–3437.
  • Corminboeuf O, Dunet G, Hafsi M, Grimont J, Grisostomi C, Meyer S, Binkert C, Bur D, Jones A, Prade L, Brun R, Boss C. Inhibitors of plasmepsin II-potential antimalarial agents. Bioorg Med Chem Lett 2006;16:6194–6199.
  • Muthas D, Noteberg D, Sabnis YA, Hamelink E, Vrang L, Samuelsson B, Karlen A, Hallberg A. Synthesis, biological evaluation, and modeling studies of inhibitors aimed at the malarial proteases plasmepsins I and II. Bioorg Med Chem 2005;13:5371–5390.
  • Hidaka K, Kimura T, Ruben AJ, Uemura T, Kamiya M, Kiso A, Okamoto T, Tsuchiya Y, Hayashi Y, Freire E, Kiso Y. Antimalarial activity enhancement in hydroxymethylcarbonyl (HMC) isostere-based dipeptidomimetics targeting malarial aspartic protease plasmepsin. Bioorg Med Chem 2008;16:10049–10060.
  • Jiang S, Prigge ST, Wei L, Gao Y-E, Hudson TH, Gerena L, Dame JB, Kyle DE. New class of small nonpeptidyl compounds blocks Plasmodium falciparum development in vitro by inhibiting plasmepsins. Antimicrob Agents Chemother 2001;45:2577–2584.
  • Azim MK, Ahmed W, Khan IA, Rao NA, Khan KM. Identification of acridinyl hydrazides as potent aspartic protease inhibitors. Bioorg Med Chem Lett 2008;18:3011–3015.
  • Blum A, Bottcher J, Sammet B, Luksch T, Heine A, Klebe G, Deiderich WE, Achiral oligoamines as versatile tool for the development of aspartic protease inhibitors. Bioorg Med Chem 2008;16:8574–8586.
  • Luksch T, Chan NS, Brass S, Sotriffer CA, Klebe G, Deitderich WE. Computer-aided design and synthesis of nonpeptidic plasmepsin II and IV inhibitors. ChemMedChem 2008;3:1323–1336.
  • Ciugureanu C, Ungureanu M, Grosu G. The antibacterial action of new hydrazide derivatives. Rev Med Chir 1993;97:433–437.
  • Waisser K, Houngbedji N, Odlerrova Z, Thiel W, Mayer R. Antitubercular agents. Thiohydrazides, potential antitubercular agents. Pharmazie 1990;45:141–142.
  • Khan MK, Rasheed M, Zia-Ullah Hayat, S, Kaukab F, Choudhary MI, Atta-ur-Rahman Perveen, S. Synthesis and in vitro leishmanicidal activity of some hydrazides and their analogues. Bioorg Med Chem 2003;11:1381–1387.
  • Cardellini M, Claudi F, Grifantini M, Gulini U, Martelli S. Indolizine derivatives with biological activity I: N’-substituted hydrazides of indolizine-2-carboxylic acid. J Pharm Sci 1977;66:259–262.
  • Rarey M, Kramer B, Lengauer T, Klebe G. A fast flexible docking method using an incremental construction algorithm. J Mol Biol 1996;261:470–489.
  • Silva AM, Lee AY, Gulnik SV, Maier P, Collins J, Bhat TN, Collins PJ, Cachau RE, Luker KE, Gluzman IY, Francis SE, Oksman A, Goldberg DE, Erickson JW. Structure and inhibition of plasmepsin II, a hemoglobin-degrading enzyme from Plasmodium falciparum. Proc Natl Acad Sci USA 1996;93:10034–10039.
  • Baldwin ET, Bhat TN, Gulnik S, Hosur MV, Sowder RC II, Cachau RE, Collins J, Silva AM, Erickson JW. Crystal structures of native and inhibited forms of human cathepsin D: Implications for lysosomal targeting and drug design. Proc Natl Acad Sci USA 1993;90:6796–6800.
  • Bohm H-J. The development of a simple empirical scoring function to estimate the binding constant for a protein-ligand complex of known three-dimensional structure. J Comput-Aided Mol Design 1994;8:243–256.
  • Teran-de-Gutierrez H, Nervall M, Ersmark K, Liu P, Janka LK, Dunn B, Hallberg A, Advist J. Inhibitor binding to the plasmepsin IV aspartic protease from Plasmodium falciparum. Biochemistry 2006;45:10529–10541.

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