Polyphenol fatty acid esters as serine protease inhibitors: a quantum-chemical QSAR analysis

References

• Fear G, Komarnytsky S, Raskin I. Protease inhibitors and their peptidomimetic derivatives as potential drugs. Pharmacol Ther 2007; 113: 354–368.
   PubMed Web of Science ®Google Scholar
• Leung D, Abbenante G, Fairlie DP. Protease inhibitors: current status and future prospects. J Med Chem 2000; 43: 305–341.
   PubMed Web of Science ®Google Scholar
• Clark JM, Elrod K, Jenkins TE, Katz BA, Moore WR, Stroud RM. Potentiating metal mediated serine protease inhibitors with cobalt or zinc ions. US Patent 6255091 (2001.
   Google Scholar
• Wang Y. The role and regulation of urokinase-type plasminogen activator receptor gene expression in cancer invasion and metastasis. Med Res Rev 2001; 21: 146–170.
   PubMed Web of Science ®Google Scholar
• Hagio T, Kishikawa K, Kawabata K, Tasaka S, Hashimoto S, Hasegawa N et al. Inhibition of neutrophil elastase reduces lung injury and bacterial count in hamsters. Pulm Pharmacol Ther 2008; 21: 884–891.
   PubMed Web of Science ®Google Scholar
• Gresele P, Agnelli G. Novel approaches to the treatment of thrombosis. Trends Pharmacol Sci 2002; 23: 25–32.
   PubMed Web of Science ®Google Scholar
• Birt DF, Hendrich S, Wang W. Dietary agents in cancer prevention: flavonoids and isoflavonoids. Pharmacol Ther 2001; 90: 157–177.
   PubMed Web of Science ®Google Scholar
• Lerch MM, Gorelick FS. Early trypsinogen activation in acute pancreatitis. Med Clin North Am 2000; 84: 549–63, viii.
   PubMed Web of Science ®Google Scholar
• Markus G, Kohga S, Camiolo SM, Madeja JM, Ambrus JL, Karakousis C. Plasminogen activators in human malignant melanoma. J Natl Cancer Inst 1984; 72: 1213–1222.
   PubMedGoogle Scholar
• Middleton E Jr, Kandaswami C, Theoharides TC. The effects of plant flavonoids on mammalian cells: implications for inflammation, heart disease, and cancer. Pharmacol Rev 2000; 52: 673–751.
   PubMed Web of Science ®Google Scholar
• Maliar T, Jedinák A, Kadrabová J, Sturdík E. Structural aspects of flavonoids as trypsin inhibitors. Eur J Med Chem 2004; 39: 241–248.
   PubMed Web of Science ®Google Scholar
• Maliar T, Baláz S, Tandlich R, Sturdík E. Viral proteinases–possible targets of antiviral drugs. Acta Virol 2002; 46: 131–140.
   PubMed Web of Science ®Google Scholar
• Mantle D, Falkous G, Perry EK. Effect of flavonoids on protease activities in human skeletal muscle tissue in vitro. Clin Chim Acta 1999; 285: 13–20.
   PubMed Web of Science ®Google Scholar
• Puri RN, Colman RW. Thrombin- and cathepsin G-induced platelet aggregation: effect of protein kinase C inhibitors. Anal Biochem 1993; 210: 50–57.
   PubMed Web of Science ®Google Scholar
• Mozzicafreddo M, Cuccioloni M, Eleuteri AM, Fioretti E, Angeletti M. Flavonoids inhibit the amidolytic activity of human thrombin. Biochimie 2006; 88: 1297–1306.
   PubMed Web of Science ®Google Scholar
• Parellada J, Guinea M. Flavonoid inhibitors of trypsin and leucine aminopeptidase: a proposed mathematical model for IC50 estimation. J Nat Prod 1995; 58: 823–829.
   PubMed Web of Science ®Google Scholar
• Viskupicova J, Danihelova M, Ondrejovic M, Liptaj T, Sturdik E. Lipophilic rutin derivatives for antioxidant protection of oil–based foods. Food Chem 2010; 123: 45–50.
   Web of Science ®Google Scholar
• Katsoura MH, Polydera AC, Tsironis L, Tselepis AD, Stamatis H. Use of ionic liquids as media for the biocatalytic preparation of flavonoid derivatives with antioxidant potency. J Biotechnol 2006; 123: 491–503.
   PubMed Web of Science ®Google Scholar
• Mellou F, Loutrari H, Stamatis H, Roussos C, Kolisis FN. Enzymatic esterification of flavonoids with unsaturated fatty acids: effect of novel esters on vascular endothelial growth factor release from K562 cells. Process Biochem 2006; 41: 2029–2034.
   Web of Science ®Google Scholar
• Mellou F, Lazari D, Skaltsa H, Tselepis AD, Kolisis FN, Stamatis H. Biocatalytic preparation of acylated derivatives of flavonoid glycosides enhances their antioxidant and antimicrobial activity. J Biotechnol 2005; 116: 295–304.
   PubMed Web of Science ®Google Scholar
• Suda I, Oki T, Masuda M, Nishiba Y, Furuta S, Matsugano K et al. Direct absorption of acylated anthocyanin in purple-fleshed sweet potato into rats. J Agric Food Chem 2002; 50: 1672–1676.
   PubMed Web of Science ®Google Scholar
• Lin SF, Lin YH, Lin M, Kao YF, Wang RW, Teng LW et al. Synthesis and structure-activity relationship of 3-O-acylated (-)-epigallocatechins as 5a-reductase inhibitors. Eur J Med Chem 2010; 45: 6068–6076.
   PubMed Web of Science ®Google Scholar
• Salem JH, Chevalot I, Harscoat–Schiavo C, Paris C, Fick M, Humeau C. Biological activities of flavonoids from N. retusa and their acylated derivatives. Food Chem 2011; 124: 486–494.
   Web of Science ®Google Scholar
• Augustyniak A, Bartosz G, Cipak A, Duburs G, Horáková L, Luczaj W et al. Natural and synthetic antioxidants: an updated overview. Free Radic Res 2010; 44: 1216–1262.
   PubMed Web of Science ®Google Scholar
• Viskupicova J, Strosova M, Sturdik E, Horakova L. Modulating effect of flavonoids and their derivatives on sarcoplasmic reticulum Ca2+-ATPase oxidized by hypochloric acid and peroxynitrite. Neuro Endocrinol Lett 2009; 30 Suppl 1: 148–151.
   PubMedGoogle Scholar
• Viskupicova J, Psenakova I, Maliar T. Biotransformation of flavonoids using Candida antarctica lipase. Nova Biotechnol 2005; 5: 83–94 [In Slovak].
   Google Scholar
• Coleman PL, Green GD. A coupled photometric assay for plasminogen activator. Meth Enzymol 1981; 80 Pt C: 408–414.
   PubMedGoogle Scholar
• Lottenberg R, Christensen U, Jackson CM, Coleman PL. Assay of coagulation proteases using peptide chromogenic and fluorogenic substrates. Meth Enzymol 1981; 80 Pt C: 341–361.
   PubMedGoogle Scholar
• Nieuwenhuizen W, Wijngaards G, Groeneveld E. Synthetic substrates and the discrimination between urokinase and tissue plasminogen activator activity. Thromb Res 1977; 11: 87–89.
   PubMed Web of Science ®Google Scholar
• Erlanger BF, Kokowsky N, Cohen W. The preparation and properties of two new chromogenic substrates of trypsin. Arch Biochem Biophys 1961; 95: 271–278.
   PubMed Web of Science ®Google Scholar
• Ward JH. Hierarchical grouping to optimize an objective. J Am Stat Assoc 1963; 58: 236–244.
   Web of Science ®Google Scholar
• Pedretti A, Villa L, Vistoli G. VEGA–an open platform to develop chemo-bio-informatics applications, using plug-in architecture and script programming. J Comput Aided Mol Des 2004; 18: 167–173.
   PubMed Web of Science ®Google Scholar
• Lee J, Koo N, Min DB. Reactive oxygen species, aging, and antioxidative nutraceuticals. Comp Rev Food Sci Food Safety 2004; 3: 2–33.
   Web of Science ®Google Scholar
• Ardhaoui M, Falcimaigne A, Engasser J–M, Moussou P, Pauly G, Ghoul M. Acylation of natural flavonoids using lipase of Candida antarctica as biocatalyst. J Mol Catal B Enzym 2004; 29: 63–67.
   Web of Science ®Google Scholar
• Stein RL, Strimpler AM, Hori H, Powers JC. Catalysis by human leukocyte elastase: mechanistic insights into specificity requirements. Biochemistry 1987; 26: 1301–1305.
   PubMed Web of Science ®Google Scholar
• Stein RL, Strimpler AM, Edwards PD, Lewis JJ, Mauger RC, Schwartz JA et al. Mechanism of slow-binding inhibition of human leukocyte elastase by trifluoromethyl ketones. Biochemistry 1987; 26: 2682–2689.
   PubMed Web of Science ®Google Scholar
• Jedinák A, Maliar T, Grancai D, Nagy M. Inhibition activities of natural products on serine proteases. Phytother Res 2006; 20: 214–217.
   PubMed Web of Science ®Google Scholar
• Jagadeeshwar Rao R, Tiwari AK, Kumar US, Reddy SV, Ali AZ, Rao JM. Novel 3-O-acyl mesquitol analogues as free-radical scavengers and enzyme inhibitors: synthesis, biological evaluation and structure-activity relationship. Bioorg Med Chem Lett 2003; 13: 2777–2780.
   PubMed Web of Science ®Google Scholar
• Kinoshita T, Lepp Z, Kawai Y, Terao J, Chuman H. An integrated database of flavonoids. Biofactors 2006; 26: 179–188.
   PubMed Web of Science ®Google Scholar
• Grabowski K, Schneider G. Properties and architecture of drugs and natural products revisited. Curr Chem Biol 2007; 1: 115–127.
   Google Scholar