New coumarin derivatives as carbonic anhydrase inhibitors

References

• Anand P, Singh B, Singh N. 2012. A review on coumarins as acetylcholinesterase inhibitors for Alzheimer's disease. Bioorg Med Chem. 20:1175–1180.
   PubMed Web of Science ®Google Scholar
• Arslan O, Nalbantoglu B, Demir N, Ozdemir H, Küfrevioglu OI. 1996. A new method for the purification of carbonic anhydrase isozymes by affinity chromatography. Turk J Med Sci. 26:163–166.
   Google Scholar
• Arslan M, Gencer N, Arslan O, Guler OO. 2012. In vitro efficacy of some cattle drugs on bovine serum paraoxonase 1 (PON1) activity. J Enzyme Inhib and Med Chem. 27:722–729.
   PubMed Web of Science ®Google Scholar
• Ashida M, Brey P. 1995. Role of the integument in insect defense: pro-phenol oxidase cascade in the cuticular matrix. Proc Natl Acad Sci USA. 92:10698–10702.
   PubMed Web of Science ®Google Scholar
• Aydemir T, Kavrayan D. 2009. Purification and characterization of glutathione-s-transferase from chicken erythrocyte. Artif Cells Blood Substit Immobil Biotechnol. 37:92–100.
   PubMed Web of Science ®Google Scholar
• Bayram T, Arslan O, Ugras HI, Cakir U, Ozensoy O. 2007. Purification of carbonic anhydrase from dog erytrocytes and investigation of in vitro inhibition effects by various compounds. J Enzyme Inhib Med Chem. 22:739–744.
   PubMed Web of Science ®Google Scholar
• Borras J, Scozzafava A, Menabuoni L, Mincione F, Briganti F, Mincione G, Supuran CT. 1999. 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. 7: 2397–2406.
   PubMed Web of Science ®Google Scholar
• Bytyqi-Damoni A, Genc H, Zengin M, Beyaztas S, Gencer N, Arslan O. 2012. In vitro effect of novel β-lactam compounds on xanthine oxidase enzyme activity. Artif Cells Blood Substit Immobil Biotechnol. 40:369–377.
   PubMed Web of Science ®Google Scholar
• Carta F, Maresca A, Scozzafava A, Supuran CT. 2012. Novel coumarins and 2-thioxo-coumarins as inhibitors of the tumor-associated carbonic anhydrases IX and XII. Bioorg & Med Chem. 20:2266–2273.
   PubMed Web of Science ®Google Scholar
• Cicek B, Ergun A, Gencer N. 2012. Synthesis and evaluation in vitro effects of some macro cyclic thiocrown ethers on erythrocyte carbonic anhydrase I and II” Asian. J Chem. 24:3729–3731.
   Web of Science ®Google Scholar
• Demirel LA, Tarhan L. 2004. Dismutation properties of purified and GDA modified CuZnSOD from chicken heart. Artif Cells Blood Substit Immobil Biotechnol. 32:609–624.
   PubMed Web of Science ®Google Scholar
• Demir D, Gencer N, Er A. 2012. Purification and characterization of prophenoloxidase from Galleria mellonella L. Artif Cells Blood Substit Immobil Biotechnol. 40:369–377.
   PubMedGoogle Scholar
• Ebbesen P, Pettersen EO, Gorr TA, Jobst G, Williams K, Kienninger J, et al. 2009. Taking advantage of tumor cell adaptations to hypoxia for developing new tumor markers and treatment strategies. J Enzyme Inhib Med Chem. 24:1–39.
   PubMed Web of Science ®Google Scholar
• Gencer N, Arslan O. 2011. In Vitro Effects of Some Pesticides on PON1Q192 and PON1R192 Isoenzymes from Human Serum. Fresen Envir Bull. 20:590–596.
   Web of Science ®Google Scholar
• Gencer N, Ergun A, Demir D. 2012a. In vitro effects of some pesticides on human erythrocyte carbonic anhydrase activity. Fresen Environ Bull. 21:549–552.
   Web of Science ®Google Scholar
• Gencer N, Ergun A, Demir D. 2012b. In vitro effects of some anabolic compounds on erythrocyte carbonic anhydrase I and II. J Enzyme Inhib and Medicinal Chem. 27:208–210.
   PubMed Web of Science ®Google Scholar
• Gokce B, Gencer N, Arslan O, Turkoglu SA, Alper M, Kockar F. 2012. Evaluation of in vitro effects of some analgesic drugs on erythrocyte and recombinant carbonic anhydrase I and II. J Enzyme Inhib Med Chem. 27: 37–42.
   PubMed Web of Science ®Google Scholar
• Gumus A, Karadeniz S, Ugras HI, Bulut M, Cakir U, Gören AC. 2010. Synthesis, complexation, and biological activity studies of 4-aminomethyl-7,8-dihydroxy coumarines and their crown ether derivatives. J Heteroc Chem. 47:1127–1133.
   Web of Science ®Google Scholar
• Gupta SP, Kumaran S. 2005. 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. 20:251–259.
   PubMed Web of Science ®Google Scholar
• Hindi KM, Panzenr MJ, Tessier CA, Cannon CL, Youngs WJ. 2009. The medicinal applications of imidazolium carbene-metal complexes. Chem Rev. 109:3859–3884.
   PubMed Web of Science ®Google Scholar
• Karatas MO, Alici B, Cakir U, Cetinkaya E, Demir D, Ergun A, Gencer N, Arslan O. 2013. Synthesis and carbonic anhydrase inhibitory properties of novel coumarin derivatives. J Enzyme Inhib Med Chem. 28:317–322.
   Web of Science ®Google Scholar
• Khan KM, Shah Z, Ahmad VU, Ambreen N, Khan M, Taha M, et al. (2012). 6-Nitrobenzimidazole derivatives: potential phosphodiesterase inhibitors: synthesis and structure-activity relationship. Bioorg Med Chem. 20:1521–1526.
   PubMed Web of Science ®Google Scholar
• Lehtonen J, Shen B, Vihinen M, Casini A, Scozzafava A, Supuran CT, et al. 2004. Characterization of CA XIII, a novel member of the carbonic anhydrase isozyme family. J Biol Chem. 279:2719–2727.
   PubMed Web of Science ®Google Scholar
• Maren TH. 1960. A simplified micromethod for the determination of carbonic anhydrase and its inhibitors. J Pharm Exp Ther. 130:2629–2634.
   Web of Science ®Google Scholar
• Maresca A, Temperini C, Vu H, Pham NB, Poulsen SA, Scozzafava A, Quinn RJ, Supuran CT. 2009. Nonzinc mediated inhibition of carbonic anhydrases: coumarins are a new class of suicide inhibitors. J Am Chem Soc. 131:3057–3062.
   PubMed Web of Science ®Google Scholar
• Maresca A, Temperini C, Pochet L, Masereel B, Scozzafava A, Supuran CT. 2010. Deciphering the mechanism of carbonic anhydrase inhibition with coumarins and thiocoumarins. J Med Chem. 53:335–344.
   PubMed Web of Science ®Google Scholar
• McKiernan JM, Buttyan R, Stifelman MD, Kutz AG, Chen MW, Olsson CA, Sawczuk IS. 1997. Expression of the tumor-associated gene MN: a potential biomarker for human renal cell carcinoma. Cancer Res. 57:2362–2365.
   PubMed Web of Science ®Google Scholar
• Nair SK, Ludwig PA, Christianson DW. (1994). 2-site binding of phenol in the active-site of human carbonic-anhydrase-ii - structural implications for substrate association. J Am Chem Soc. 116:3659–3660.
   Web of Science ®Google Scholar
• 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 (FL) USA: CRC Press, pp. 25–43.
   Google Scholar
• Nishimori I, Vullo D, Innocenti A, Scozzafava A, Mastrolorenzo A, Supuran CT. 2005a. Carbonic anhydrase inhibitors. The mitochondrial isozyme VB as a new target for sulfonamide and sulfamate inhibitors. J Med Chem. 48:7860–7866.
   PubMed Web of Science ®Google Scholar
• Nishimori I, Vullo D, Innocenti A, Scozzafava A, Mastrolorenzo A, Supuran CT. 2005b. Carbonic anhydrase inhibitors: inhibition of the transmembrane isozyme XIV with sulfonamides. Bioorg Med Chem Lett. 15:3828–3833.
   PubMed Web of Science ®Google Scholar
• Nishimori I, Minakuchia T, Onishia S, Vullob D, Cecchib A, Scozzafavab A, Supuran CT. 2007a. Carbonic anhydrase inhibitors: cloning, characterization, and inhibition studies of the cytosolic isozyme III with sulfonamides. Bioorg Med Chem. 15: 7229–7236.
   PubMed Web of Science ®Google Scholar
• Nishimori I, Minakuchi T, Onishi S, Vullo D, Scozzafava A, Supuran CT. 2007b. 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. 50:381–388.
   PubMed Web of Science ®Google Scholar
• Ozdemir I, Sahin N, Demir S, Cetinkaya B. 2005. In situ generated 1- alkylbenzimidazole-palladium catalyst for the Suzuki coupling of aryl chlorides. J Molec Catal. 234:181–185.
   Web of Science ®Google Scholar
• Pastorekova S, Parkkila S, Pastorek J, Supuran CT. 2004. Carbonic anhydrases: current state of the art, therapeutic applications and future prospects. J Enzyme Inhib Med Chem. 19:199–229.
   PubMed Web of Science ®Google Scholar
• Sayin D, Cakir DT, Gencer N, Arslan O. 2012. Effects of some metals on Paraoxonase activity from shark Scyliorhinus canicula. J Enzyme Inhib Med Chem. 27:595–598.
   PubMed Web of Science ®Google Scholar
• Scozzafava A, Mastrolorenzo A, Supuran CT. 2006. Carbonic anhydrase inhibitors and activators and their use in therapy. Expert Opin Ther Pat. 16:1627–1664.
   Web of Science ®Google Scholar
• Smith KS, Ferry JG. 2000. Prokaryotic carbonic anhydrases. FEMS Microbiol Rev. 24:335–366.
   PubMed Web of Science ®Google Scholar
• Sonmez F, Sevmezler S, Atahan A, Ceylan M, Demir D, Gencer N, Arslan O, Kucukislamoglu M. 2011. Evaluation of new chalcone derivatives as polyphenol oxidase inhibitors. Bioorg Med Chem Lett. 21:7479–7482.
   PubMed Web of Science ®Google Scholar
• Stams T, Christianson DW. 2000. The carbonic anhydrases—new horizons (Chegwidden WR, Carter ND, Edwards YH, Eds), pp. 159–174.
   Google Scholar
• Supuran CT. 2008. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov. 7:168–181.
   PubMed Web of Science ®Google Scholar
• Supuran CT. 2010. Carbonic anhydrase inhibitors. Bioorg Med Chem Lett. 20:3467–3474.
   PubMed Web of Science ®Google Scholar
• Supuran CT, Scozzafava A, Casini A. 2003. Carbonic anhydrase inhibitors. Med Res Rev. 23:146–189.
   PubMed Web of Science ®Google Scholar
• Temperini C, Innocenti A, Scozzafava A, Parkkila S, Supuran CT. 2010. 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. 53:850–854.
   PubMed Web of Science ®Google Scholar
• Thiry A, Dogne JM, Masereel B, Supuran CT. 2006. Targeting tumor-associated carbonic anhydrase IX in cancer therapy. Trends Pharmacol Sci. 27:566–573.
   PubMed Web of Science ®Google Scholar
• Tischer M, Pradel G, Ohlsen K, Hilzgrabe U. 2012. Quaternary ammonium salts and their antimicrobial potential: targets or nonspecific interactions?Chem Med Chem. 7:22–31.
   Google Scholar
• Vullo D, Franchi M, Gallori E, Pastorek J, Scozzafava A, Pastorekova S, Supuran CT. 2003. Carbonic anhydrase inhibitors: inhibition of the tumor-associated isozyme IX with aromatic and heterocyclic sulfonamides. Bioorg Med Chem Lett. 13:1005–1009.
   PubMed Web of Science ®Google Scholar
• Vullo D, Franchi M, Gallori E, Antel J, Scozzafava A, Supuran CT. 2004. Carbonic anhydrase inhibitors. Inhibition of mitochondrial isozyme V with aromatic and heterocyclic sulfonamides. J Med Chem. 47:1272–1279.
   PubMed Web of Science ®Google Scholar
• Vullo D, Voipiob J, Innocenti A, Riverab C, Rankib H, Scozzafavaa A, Kailab K, Supuran CT. 2005a. Carbonic anhydrase inhibitors. Inhibition of the human cytosolic isozyme VII with aromatic and heterocyclic sulfonamides. Bioorg Med Chem Lett. 15:971–976.
   PubMed Web of Science ®Google Scholar
• Vullo D, Innocenti A, Nishimori I, Pastorek J, Scozzafava A, Pastorekova S, Supuran CT. 2005b. 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. 15:963–969.
   PubMed Web of Science ®Google Scholar
• Vu H, Pham NB, Quinn RJ. 2008. Direct screening of natural product extracts using mass spectrometry. J Biomol Screen. 13: 265–275.
   PubMed Web of Science ®Google Scholar