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Research Article

Synthesis and carbonic anhydrase inhibitory properties of novel coumarin derivatives

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Pages 299-304 | Received 09 Feb 2012, Accepted 14 Mar 2012, Published online: 18 Apr 2012

References

  • Maresca A, Temperini C, Vu H, Pham NB, Poulsen SA, Scozzafava A et al. Non-zinc mediated inhibition of carbonic anhydrases: Coumarins are a new class of suicide inhibitors. J Am Chem Soc 2009;131:3057–3062.
  • Maresca A, Temperini C, Pochet L, Masereel B, Scozzafava A, Supuran CT. Deciphering the mechanism of carbonic anhydrase inhibition with coumarins and thiocoumarins. J Med Chem 2010;53:335–344.
  • Barker HA, Smyth RD, Weissbach H, Toohey JI, Ladd JN, Volcani BE. Isolation and properties of crystalline cobamide coenzymes containing benzimidazole or 5, 6-dimethylbenzimidazole. J Biol Chem 1960;235:480–488.
  • Ozdemir I, Demir S, Cetinkaya B, Gourlaouen C, Maseras F, Bruneau C et al. Direct arylation of arene C-H bonds by cooperative action of NHcarbene-ruthenium(II) catalyst and carbonate via proton abstraction mechanism. J Am Chem Soc 2008;130:1156–1157.
  • Hindi KM, Panzner MJ, Tessier CA, Cannon CL, Youngs WJ. The medicinal applications of imidazolium carbene-metal complexes. Chem Rev 2009;109:3859–3884.
  • Supuran CT. Carbonic anhydrases: Novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov 2008;7:168–181.
  • Thiry A, Dogné JM, Masereel B, Supuran CT. Targeting tumor-associated carbonic anhydrase IX in cancer therapy. Trends Pharmacol Sci 2006;27:566–573.
  • McKiernan JM, Buttyan R, Bander NH, Stifelman MD, Katz AE, Chen MW et al. Expression of the tumor-associated gene MN: A potential biomarker for human renal cell carcinoma. Cancer Res 1997;57:2362–2365.
  • Scozzafava A, Mastrolorenzo A, Supuran CT. Carbonic anhydrase inhibitors and activators and their use in therapy. Expert Opin Ther Pat 2006;16:1627–1664.
  • Supuran CT, Scozzafava A, Casini A. Carbonic anhydrase inhibitors. Med Res Rev 2003;23:146–189.
  • Smith KS, Ferry JG. Prokaryotic carbonic anhydrases. FEMS Microbiol Rev 2000;24:335–366.
  • Stams T, Christianson DW. (2000). X-ray crystallographic studies of mammalian carbonic anhydrase isozymes. In: Chegwidden WR, Carter ND, Edwards YH, eds. X-ray crystallographic studies of mammalian carbonic anhydrase isozymes. The Carbonic Anhydrases: New Horizons. Boston: Birkhauser Verlag, 159–174.
  • Pastorekova S, Parkkila S, Pastorek J, Supuran CT. Carbonic anhydrases: Current state of the art, therapeutic applications and future prospects. J Enzyme Inhib Med Chem 2004;19:199–229.
  • Nishimori I, Minakuchi T, Onishi S, Vullo D, Cecchi A, Scozzafava A et al. Carbonic anhydrase inhibitors: Cloning, characterization, and inhibition studies of the cytosolic isozyme III with sulfonamides. Bioorg Med Chem 2007;15:7229–7236.
  • Vullo D, Franchi M, Gallori E, Antel J, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors. Inhibition of mitochondrial isozyme V with aromatic and heterocyclic sulfonamides. J Med Chem 2004;47:1272–1279.
  • Nishimori I, Vullo D, Innocenti A, Scozzafava A, Mastrolorenzo A, Supuran CT. Carbonic anhydrase inhibitors. The mitochondrial isozyme VB as a new target for sulfonamide and sulfamate inhibitors. J Med Chem 2005;48:7860–7866.
  • Nishimori I, Minakuchi T, Onishi S, Vullo D, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors. DNA cloning, characterization, and inhibition studies of the human secretory isoform VI, a new target for sulfonamide and sulfamate inhibitors. J Med Chem 2007;50:381–388.
  • Vullo D, Voipio J, Innocenti A, Rivera C, Ranki H, Scozzafava A et al. Carbonic anhydrase inhibitors. Inhibition of the human cytosolic isozyme VII with aromatic and heterocyclic sulfonamides. Bioorg Med Chem Lett 2005;15:971–976.
  • Nishimori I. (2004). Acatalytic CAs: Carbonic anhydrase-related proteins. In: Supuran CT, Scozzafava A, Conway J, eds. Carbonic anhydrase—Its inhibitors and activators. Boca Raton: CRC Press, 25–43.
  • Vullo D, Franchi M, Gallori E, Pastorek J, Scozzafava A, Pastorekova S et al. Carbonic anhydrase inhibitors: Inhibition of the tumor-associated isozyme IX with aromatic and heterocyclic sulfonamides. Bioorg Med Chem Lett 2003;13:1005–1009.
  • Vullo D, Innocenti A, Nishimori I, Pastorek J, Scozzafava A, Pastoreková S et al. Carbonic anhydrase inhibitors. Inhibition of the transmembrane isozyme XII with sulfonamides-a new target for the design of antitumor and antiglaucoma drugs? Bioorg Med Chem Lett 2005;15:963–969.
  • Lehtonen J, Shen B, Vihinen M, Casini A, Scozzafava A, Supuran CT et al. Characterization of CA XIII, a novel member of the carbonic anhydrase isozyme family. J Biol Chem 2004;279:2719–2727.
  • Nishimori I, Vullo D, Innocenti A, Scozzafava A, Mastrolorenzo A, Supuran CT. Carbonic anhydrase inhibitors: Inhibition of the transmembrane isozyme XIV with sulfonamides. Bioorg Med Chem Lett 2005;15:3828–3833.
  • Ashida M, Brey PT. Role of the integument in insect defense: Pro-phenol oxidase cascade in the cuticular matrix. Proc Natl Acad Sci USA 1995;92:10698–10702.
  • Gumus A, Karadeniz Ş, Uğraş Hİ, Bulut M, Çakır Ü, Gören AC. Synthesis, complexation, and biological activity studies of 4-aminomethyl-7,8-dihydroxy coumarines and their crown ether derivatives. J Heteroc Chem 2010;47:1127–1133.
  • Borras J, Scozzafava A, Menabuoni L, Mincione F, Briganti F, Mincione G et al. Carbonic anhydrase inhibitors: Synthesis of water-soluble, topically effective intraocular pressure lowering aromatic/heterocyclic sulfonamides containing 8-quinoline-sulfonyl moieties: Is the tail more important than the ring? Bioorg Med Chem 1999;7:2397–2406.
  • Ozdemir İ, Şahin N, Gök Y, Demir S, Çetinkaya B. In situ generated 1-alkylbenzimidazole-palladium catalyst for the Suzuki coupling of aryl chlorides. J Molec Catal 2005;234:181–185.
  • Arslan O, Nalbantoglu B, Demir N, Ozdemir H, Küfrevioglu OI. A new method for the purification of carbonic anhydrase isozymes by affinity chromatography. Turk J Med Sci 1996;26:163–166.
  • Maren TH. A simplified micromethod for the determination of carbonic anhydrase and its inhibitors. J Pharm Exp Ther 1960;130:2629–2634.
  • Ebbesen P, Pettersen EO, Gorr TA, Jobst G, Williams K, Kieninger J et al. Taking advantage of tumor cell adaptations to hypoxia for developing new tumor markers and treatment strategies. J Enzyme Inhib Med Chem 2009;24 Suppl 1:1–39.
  • Nair SK, Ludwig PA, Christianson DW. 2-site binding of phenol in the active-site of human carbonic-anhydrase-ii - structural implications for substrate association. J Am Chem Soc 1994;116:3659–3660.
  • Temperini C, Innocenti A, Scozzafava A, Parkkila S, Supuran CT. The coumarin-binding site in carbonic anhydrase accommodates structurally diverse inhibitors: The antiepileptic lacosamide as an example and lead molecule for novel classes of carbonic anhydrase inhibitors. J Med Chem 2010;53:850–854.
  • Vu H, Pham NB, Quinn RJ. Direct screening of natural product extracts using mass spectrometry. J Biomol Screen 2008;13:265–275.
  • Bayram T, Arslan O, Ugras HI, Cakir U, Ozensoy O. Purification of carbonic anhydrase from dog erythrocytes and investigation ofin vitroinhibition by various compounds. J Enzyme Inhib Med Chem 2007;22:739–744.
  • Gupta SP, Kumaran S. A quantitative structure-activity relationship study on some aromatic/heterocyclic sulfonamides and their charged derivatives acting as carbonic anhydrase inhibitors. J Enzyme Inhib Med Chem 2005;20:251–259.
  • Aydemir T, Kavrayan D. Purification and characterization of glutathione-s-transferase from chicken erythrocyte. Artif Cells Blood Substit Immobil Biotechnol 2009;37:92–100.
  • Gencer N, Arslan O. In vitro effects of some pesticides on PON1Q192 and PON1R192 isoenzymes from human serum. Fresen Envir Bull 2011;20:590–596.
  • Gençer N, Arslan O. Purification human PON1Q192 and PON1R192 isoenzymes by hydrophobic interaction chromatography and investigation of the inhibition by metals. J Chromatogr B Analyt Technol Biomed Life Sci 2009;877:134–140.
  • Sinan S, Gencer N, Turan Y, Arslan O. In vitro inhibition of the carbonic anhydrase from saanen goat (capra hircus) with pesticides. Pest Biochem Phys 2007;88:307–311.
  • Kiranoglu S, Sinan S, Gencer N, Köckar F, Arslan O. In vivoeffects of oral contraceptives on paraoxonase, catalase and carbonic anhydrase enzyme activities on mouse. Biol Pharm Bull 2007;30:1048–1051.
  • Sinan S, Kockar F, Gencer N, Yildirim H, Arslan O. Amphenicol and macrolide derived antibiotics inhibit paraoxonase enzyme activity in human serum and human hepatoma cells (HepG2) in vitro. Biochemistry Mosc 2006;71:46–50.

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