Some coumarins and benzoxazinones as potent paraoxonase 1 inhibitors

References

• Draganov DI, La Du BN. Pharmacogenetics of paraoxonases: a brief review. Naunyn Schmiedebergs Arch Pharmacol 2004;369:78–88
   PubMed Web of Science ®Google Scholar
• Goswani B, Tayal D, Gupta N, Mallika V. Paraoxonase: a multifaceted biomolecule. Clin Chim Acta 2009;410:1–12
   PubMed Web of Science ®Google Scholar
• Van Himbergen TM, Van Tits LJH, Roest M, Stalenhoef AFH. The story of PON1: how an organophosphate-hydrolysing enzyme is becoming a player in cardiovascular medicine. Neth J Med 2006;64:34–8
   PubMed Web of Science ®Google Scholar
• Aharoni A, Gaidukov L, Khersonsky O, et al. The ‘evolvability' of promiscuous protein functions. Nat Genet 2005;37:73–6
   PubMed Web of Science ®Google Scholar
• Khersonsky O, Tawfik DS. Structure-reactivity studies of serum paraoxonase PON1 suggest that its native activity is lactonase. Biochemistry 2005;44:6371–8
   PubMed Web of Science ®Google Scholar
• Rochua D, Chobriere E, Massono P. Human paraoxonase: a promising approach for pre-treatment and therapy of organophosphorus poisoning. Toxicology 2007;233:459
   Web of Science ®Google Scholar
• Alici HA, Ekinci D, Beydemir S. Intravenous anaesthetics inhibit human serum paraoxonase (PON1) activity in vitro and in vivo. Clin Biochem 2008;41:1384–90
   PubMed Web of Science ®Google Scholar
• Mackness MI, Arrol S, Durrington PN. Paraoxonase prevents accumulation of lipoperoxides in low-density-lipoprotein. FEBS Lett 1991;286:152–4
   PubMed Web of Science ®Google Scholar
• Reddy ST, Wadleigh DJ, Grijalva V, et al. Human paraoxonase-3 is an HDL-associated enzyme with biological activity similar to paraoxonase-1 protein but it is not regulated by oxidizing lipids. Arterioscler Thromb Vasc Biol 2001;21:542–7
   PubMed Web of Science ®Google Scholar
• Rozenberg O, Aviram M. S-Glutathionation regulates HDL-associated paraoxonase1 (PON1) activity. Biochem Biophys Res Comm 2006;351:492–8
   PubMed Web of Science ®Google Scholar
• Billecke S, Draganov D, Counsell R, et al. Human serum paraoxonase (PON1) isozymes Q and R hydrolyze lactones and cyclic carbonate esters. Drug Metab Dispos 2000;28:1335–41
   PubMed Web of Science ®Google Scholar
• Harel M, Aharoni A, Gaidukov L, et al. Structure and evolution of the serum paraoxonase family of detoxifying and anti-atherosclerotic enzymes. Nat Struct Mol Biol 2004;11:412–19
   PubMed Web of Science ®Google Scholar
• Kockar F, Sinan S, Yildirim H, Arslan O. Differential effects of some antibiotics on paraoxonase enzyme activity on human hepatoma cells (Hep62) in vitro. J. Enzyme Inhib Med Chem 2010;25:715–19
   PubMed Web of Science ®Google Scholar
• Erzengin M, Basaran I, Cakir U, et al. In vitro inhibition effects of some dihydroxycoumarin compounds on purified human serum paraoxonase I (PON1). Appl Biochem Biotechnol 2012;168:1540–8
   PubMed Web of Science ®Google Scholar
• Senturk M, Ekinci D, Alici HA, Beydemir S. Paraoxonase-1, an organophosphate detoxifier and cardioprotective enzyme is inhibited by anasthetics: an in vitro and in vivo insight. Pest Biochem Physiol 2011;11:206–11
   Web of Science ®Google Scholar
• Turkes C, Soyut H, Beydemir S. Effect of calcium channel blockers on paraoxonase-1 (PON1) activity and oxidative stress. Pharmacol Rep 2014;66:74–80
   PubMed Web of Science ®Google Scholar
• Pla A, Rodrigo L, Hernandez AF, et al. Effect of metal ions and calcium on purified PON1 and PON3 from rat liver. Chem Biol Interact 2007;167:63–70
   PubMed Web of Science ®Google Scholar
• Gencer N, Arslan O. In vitro effects of some pesticides on PON1Q192 and PON1R192 isoenzymes from human serum. Fresen Environ Bull 2011;20:590–6
   Web of Science ®Google Scholar
• Gebauer M. Synthesis and structure-activity relationship of novel warfarin derivatives. Bioorg Med Chem 2007;25:2414–20
   Web of Science ®Google Scholar
• Lacy A, O’Kennedy R. Studies on coumarins and coumarin-related compounds to determine their therapeutic role in the treatment of cancer. Curr Pharm Des 2004;10:3797–811
   PubMed Web of Science ®Google Scholar
• Kontogiorgis CA, Detsi A, Hadjipavlou-Litina D. Coumarin-based drugs: a patent review. Expert Opin Ther Patents 2012;22:437–54
   PubMed Web of Science ®Google Scholar
• Saidu NEB, Valente S, Bana E, et al. Coumarin polysulfides inhibit cell growth and induce apoptosis in HCT116 colon cancer cells. Bioorg Med Chem 2012;20:1584–93
   PubMed Web of Science ®Google Scholar
• Zhao H, Neamati N, Hong H, et al. Coumarin-based inhibitors of HIV integrase. J Med Chem 1997;40:242–9
   PubMed Web of Science ®Google Scholar
• Yu D, Suzuki M, Xie L, et al. Recent progress in the development of coumarin derivatives as potent anti-HIV agents. Med Res Rev 2003;23:322–45
   PubMed Web of Science ®Google Scholar
• Kontogiorgis CA, Hadjipavlou-Litina D. Synthesis and anti-inflammatory activity of coumarin derivatives. J Med Chem 2005;48:6400–8
   PubMed Web of Science ®Google Scholar
• Smyth T, Ramaehandran VN, Smyth WF. A study of the antimicrobial activity of selected naturally occurring and synthetic coumarins. Int J Antimicrob Agents 2009;33:421–6
   PubMed Web of Science ®Google Scholar
• Li Z, Li J, Qu D, et al. Synthesis and pharmacological evaluations of 4-hydroxycoumarin derivatives as a new class of anti-Staphylococcus aureus agents. J Pharm Pharmacol 2014;67:573–82
   PubMed Web of Science ®Google Scholar
• Khan KM, Saify ZS, Hayat S, et al. Synthesis, antioxidant and insectisidal activities of some coumarin derivatives. J Chem Soc Pak 2002;24:226–31
   Web of Science ®Google Scholar
• Khan KM, Saify ZS, Khan MZ, et al. Synthesis of coumarin derivatives with cytotoxic, antibacterial and antifungal activities. J Enzyme Inhib Med Chem 2004;19:373–9
   PubMed Web of Science ®Google Scholar
• Haq Z, Lodhi MA, Nawaz SA, et al. 3S-QSAR CoMFA studies on bis-coumarin analogues as urease inhibitor: a strategic design in anti-urease agents. Bioorg Med Chem 2008;16:3456–61
   PubMed Web of Science ®Google Scholar
• Khan KM, Rahim F, Wadood A, et al. Synthesis and molecular docking studies of potent α-glucosidase inhibitors based on biscoumarin skeleton. Eur J Med Chem 2014;81:245–52
   PubMed Web of Science ®Google Scholar
• Khan KM, Fakhri MI, Shaikh NN, et al. Glucuronidase inhibitory studies on coumarin derivatives. Med Chem 2014;10:778–82
   PubMed Web of Science ®Google Scholar
• Maresca A, Temperini C, Vu H, et al. Non-zinc mediated inhibition of carbonic anhydrases: coumarins are a new class of suicide inhibitors. J Am Chem Soc 2009;131:3057–62
   PubMed Web of Science ®Google Scholar
• Kajino M, Shibouta Y, Nishikawa K, Megura K. Synthesis and biological activities of new 2-substitue 1,4-benzoxazinone derivatives. Chem Pharm Bull 1991;38:2896–908
   Web of Science ®Google Scholar
• Katsura Y, Nishino S, Takasugi H. Studies on antiulcer drugs. I. Synthesis and antiulcer activities of imidazo[1,2-alpha]pyridinyl-2-oxobenzoxazolidines-3-oxo-2H-1,4-benzoxazines and related compounds. Chem Pharm Bull 1991;39:2937–43
   PubMed Web of Science ®Google Scholar
• Turk CF, Krapcho J, Miche IM, Weinryb I. Synthesis and central nervous system activity of 2-arylidene-4-aminoalkyl-2H-1,4-benzoxazin-3(4H)-ones and related compounds. J Med Chem 1997;20:729–32
   Web of Science ®Google Scholar
• Fringuelli R, Giocche N, Milanese L, et al. Bulky 1,4-benzoxazine derivatives with antifungal activity. Bioorg Med Chem 2009;17:3838–46
   PubMed Web of Science ®Google Scholar
• Li X, Liu N, Zhang H, et al. Synthesis and SAR studies of benzoxazine MenB inhibitors: novel antibacterial agent against Mycobacterium tuberculosis. Bioorg Med Chem Lett 2010;2:6306–9
   Web of Science ®Google Scholar
• Gokce B, Gencer N, Arslan O, et al. In vitro inhibiton effect of some coumarin compounds on purified human serum paraoxonase 1 (PON1). J Enzyme Inhib Med Chem 2015. [Epub ahead of print]. Doi: 10.3109/14756366.2015.1043297
   Web of Science ®Google Scholar
• Karatas MO, Uslu H, Sari S, et al. Coumarin or benzoxazionone based novel carbonic anhydrase inhibitors: synthesis, molecular docking and anticonvulsant studies. J Enzyme Inhib Med Chem 2015. [Epub ahead of print]. Doi: 10.3109/14756366.2015.1063624
   Web of Science ®Google Scholar
• Gan KN, Smolen A, Eckerson HW, La Du BN. Purification of human serum paraoxonase/arylesterase. Evidence for one esterase catalyzing both activities. Drug Metab Dispos 1991;19:100–6
   PubMed Web of Science ®Google Scholar
• Sinan S, Kockar F, Arslan O. Novel purification strategy for human PON1 and inhibition of the activity by cephalosporin and aminoglikozide derived antibiotics. Biochimie 2006;88:565–74
   PubMed Web of Science ®Google Scholar
• Bradford MM. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 1976;72:248–54
   PubMed Web of Science ®Google Scholar
• Laemmli DK. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 1970;227:680–5
   PubMed Web of Science ®Google Scholar
• Karatas MO, Alici B, Cakir U, et al. Synthesis and carbonic anhydrase inhibitory properties of novel coumarin derivatives. J Enzyme Inhib Med Chem 2013;28:299–304
   PubMed Web of Science ®Google Scholar
• Arslan M, Gencer N, Arslan O, et al. In vitro efficacy of some cattle drugs on bovine serum paraoxonase 1 (PON1) activity. J Enzyme Inhib Med Chem 2012;27:722–9
   PubMed Web of Science ®Google Scholar
• Sayin D, Cakir DT, Gencer N, et al. Effects of some metals on paraoxonase activity from shark Scyliorhinus canicula. J Enzyme Inhib Med Chem 2012;27:595–8
   PubMed Web of Science ®Google Scholar