954
Views
6
CrossRef citations to date
0
Altmetric
Research Article

A novel proton transfer salt of 2-amino-6-sulfamoylbenzothiazole and its metal complexes: the evaluation of their inhibition effects on human cytosolic carbonic anhydrases

, , , , , & show all
Pages 231-239 | Received 27 May 2016, Accepted 20 Sep 2016, Published online: 19 Jan 2017

References

  • Achaiah G, Goud NS, Kumar KP, Mayuri P. Review on 2-substituted benzothiazoles: diversity of synthetic methods and biological activities. Int J Pharm Sci Res 2016;7:1375–82.
  • Yadav PS, Senthilkumar GP. Benzothiazole: different methods of synthesis and diverse biological activities. Int J Pharma Sci Drug Res 2011;3:01–7.
  • Alterio V, Di Fiore A, Ambrosio KD, et al. Multiple binding modes of inhibitors to carbonic anhydrases: how to design specific drugs targeting 15 different isoforms?. Chem Rev 2012;112:4421–68.
  • Scozzafava A, Kalın P, Supuran CT, et al. The impact of hydroquinone on acetylcholine esterase and certain human carbonic anhydrase isoenzymes (hCA I, II, IX, and XII). J Enzym Inhib Med Chem 2015;30:941–6.
  • Supuran CT. Structure and function of carbonic anhydrases. Biochem J 2016;473:2023–32.
  • Demirdağ R, Yerlikaya E, Şentürk M, et al. Heavy metal ion inhibition studies of human, sheep and fish α-carbonic anhydrases. J Enzyme Inhib Med Chem 2013;28:278–82.
  • Henry RP, Swenson ER. The distribution and physiological significance of carbonic anhydrase in vertebrate gas exchange organs. Respir Physiol 2000;121:1–12.
  • Lee SW, Park SB, Jeong SK, et al. On carbon dioxide storage based on biomineralization strategies. Micron 2010;41:273–82.
  • Fisher SZ, Aggarwal M, Kovalevsky AY, et al. Neutron diffraction of acetazolamide-bound human carbonic anhydrase II reveals atomic details of drug binding. J Am Chem Soc 2012;134:14726–9.
  • Hassan MI, Shajee B, Waheed A, et al. Structure, function and applications of carbonic anhydrase isozymes. Bioorg Med Chem 2013;21:1570–82.
  • Le Roy N, Jackson DJ, Marie B, et al. The evolution of metazoan α-carbonic anhydrases and their roles in calcium carbonate biomineralization. Front Zool 2014;11:75–90.
  • Supuran CT. Carbonic anhydrase inhibitors. Bioorg Med Chem Lett 2010;20:3467–74.
  • Balseven H, İşgör MM, Mert S, et al. Facile synthesis and characterization of novel pyrazole-sulfonamides and their inhibition effects on human carbonic anhydrase isoenzymes. Bioorg Med Chem 2013;21:21–7.
  • Supuran CT. How many carbonic anhydrase inhibition mechanisms exist? J Enzyme Inhib Med Chem 2016;31:345–60.
  • Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov 2008;7:168–81.
  • Netland PA. Glaucoma medical therapy principles and management. China: Oxford; 2008:9–36.
  • Yenikaya C, Sarı M, Bülbül M, et al. Synthesis, characterization and antiglaucoma activity of a novel proton transfer compound and a mixed-ligand Zn(II) complex. Bioorg Med Chem 2010;18:930–8.
  • Masini E, Carta F, Scozzafava A, Supuran CT. Antiglaucoma carbonic anhydrase inhibitors: a patent review. Expert Opin Ther Pat 2013;23:705–16.
  • Fabrizi F, Mincione F, Somma T, et al. A new approach to antiglaucoma drugs: carbonic anhydrase inhibitors with or without NO donating moieties. Mechanism of action and preliminary pharmacology. J Enzym Inhib Med Chem 2012;27:138–47.
  • Başar E, Tunca E, Bülbül M, Kaya M. Synthesis of novel sulfonamides under mild conditions with effective inhibitory activity against the carbonic anhydrase isoforms I and II. J Enzym Inhib Med Chem 2016;31:1356–61.
  • Aditama R, Mujahidin D, Syah YM, Hertadi R. Docking and molecular dynamics simulation of carbonic anhydrase II inhibitors from phenolic and flavonoid group. Procedia Chem 2015;16:357–64.
  • İlkimen H, Yenikaya C, Sarı M, et al. Synthesis and characterization of a proton transfer salt between dipicolinic acid and 2-amino-6-methylbenzothiazole and its complexes, and their inhibition studies on carbonic anhydrase isoenzyme. Polyhedron 2013;61:56–64.
  • İlkimen H, Yenikaya C, Sarı M, et al. Synthesis and characterization of a proton transfer salt between 2,6-pyridinedicarboxylic acid and 2-aminobenzothiazole, and its complexes and their inhibition studies on carbonic anhydrase isoenzymes. J Enzym Inhib Med Chem 2014;29:353–61.
  • İlkimen H, Yenikaya C, Sarı M, et al. Synthesis and characterization of some metal complexes of a proton transfer salt, and their inhibition studies on carbonic anhydrase isoenzymes and the evaluation of the results by statistical analysis. J Enzyme Inhib Med Chem 2014;29:695–701.
  • İlkimen H, Yenikaya C, Sarı M, et al. Synthesis, characterization and biological activities of metal(II) dipicolinate complexes derived from pyridine-2,6-dicarboxylic acid and 2-(piperazin-1-yl)ethanol. J Enzyme Inhib Med Chem 2015;30:195–203.
  • Kaufmann HP, Buckmann JH. Über die rhodanierung des sulfanilamids und einige benzthiazolyl-sulfonamide. Arch Pharm 1941;279:194–209.
  • Anderegg G, Bottari E. Pyridinderivate als komplexbildner VII. Über die koordinationstendenz von substituierten dipicolinat-ionen. Helvetica Chimica Acta 1965;48:887–92.
  • Bruker, SADABS, Bruker AXS Inc. Madison; 2005.
  • Sheldrick GM, SHELXS97 AND SHEXL97. Program for crystal structure solution and refinement. Germany: University of Gottingen; 1997.
  • Farrugia LJ. ORTEP-3 for Windows – a version of ORTEP-III with a graphical user interface (GUI). J Appl Cryst 1997;30:565.
  • Rickli EE, Ghazanfar SA, Gibbson BH, Edsall JT. Carbonic anhydrases from human erythrocytes. Preparation and properties of two enzymes. J Biol Chem 1964;239:1065–1068.
  • 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;72:248–254.
  • Laemmli UK. Cleavage of structural proteins during the assembly of the head of Bacteriophage T4. Nature 1970;227:680–685.
  • Wilbur KM, Anderson NG. Electrometric and colorimetric determination of carbonic anhydrase. J Biol Chem 1948;176:147–154.
  • Verpoorte JA, Mehta S, Edsall JT. Esterase activities of human carbonic anhydrases B and C. J Biol Chem 1967;242:4221–4229.
  • Yenikaya C, İlkimen H, Demirel MM, et al. Preparation of two maleic acid sulfonamide salts and their Cu(II) complexes and antiglaucoma activity studies. J Brazilian Chem Soc 2016;27:1706–14.
  • Cook D. Vibrational spectra of pyridinium salts. Canadian J Chem 1961;39:2009–2024.
  • Nakamoto K. Infrared and raman spectra of inorganic and coordination compounds. 5th ed. New York: Interscience-Wiley; 1997:59.
  • Geary WJ. The use of conductivity measurements in organic solvents for the characterisation of coordination compounds. Coord Chem Rev 1971;7:81–121.