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Year 2019, Volume: 6 Issue: 2, 253 - 260, 15.06.2019
https://doi.org/10.18596/jotcsa.546960

Abstract

References

  • 1. Klasen H. Historical review of the use of silver in the treatment of burns. I. Early uses. Burns. 2000;26;117-30.
  • 2. Moyer CA, Brentano L, Gravens DL, Margraf HW, Monafo WW. Treatment of large human burns with 0.5 per cent silver nitrate solution. Arch Surg. 1965;90:812-67.
  • 3. Fox CL. Silver sulfadiazine- A new topical therapy for Pseudomonas in Burns. Arch Surg. 1968;96:184-8.
  • 4. Medici S, Peana M, Crisponi G, Nurchi VM, Lachowicz JI, Remelli M, Zoroddu MA. Silver coordination compounds: A new horizon in medicine. Coord Chem Rev. 2016;327-328:349-59.
  • 5. Allison SJ, Sadiq M, Baronou E, Cooper PA, Dunnill C, Georgopoulos NT, Latif A, Shepherd S, Shnyder SD, Stratford IJ, Wheelhouse RT, Willans CE, Phillips RM. Preclinical anti-cancer activity and multiple mechanisms of action of a cationic silver complex bearing N-heterocyclic carbene ligands. Cancer Lett. 2017;403:98-107.
  • 6. Teyssot ML, Jarrouse AS, Manin M, Chevry A, Roche S, Norre F, Beaudoin C, Morel L, Boyer D, Mahiou R, Gautier A. Metal-NHC complexes: a survey of anti-cancer properties. Dalton Trans. 2009;2009:6894-902.
  • 7. Liu W, Gust R. Metal N-heterocyclic carbene complexes as potential antitumor metallodrug. Chem Soc Rev. 2013;42:755-73.
  • 8. Rowan R, Tallon T, Sheahan AM, Curran R, McCann M, Kavanagh K, Devereux M, McKee V. ‘Silver bullet’ in antimicrobial chemotherapy: Synthesis, characterisation and biological screening of some new Ag(I)-containing imidazole complexes. Polyhedron. 2006;25:1771-8.
  • 9. Ray S, Mohan R, Singh JK, Samantaray MK, Shaikh MM, Panda D, Ghosh P. Anticancer and antimicrobial metallopharmaceutical agents based on palladium, gold, and silver N-heterocyclic carbene complexes. J Am Chem Soc. 2007;129: 15042-53.
  • 10. Ainscough EW, Brodie AM, Freeman GH, Plieger PG. Structural studies on tribenzylphosphane sulphide complexes of copper(I) and silver(I). Polyhedron. 2016;106:40-3.
  • 11. Yadav G, Ganguly S. Structure activity relationship (SAR) study of benzimidazole scaffold for different biological activities: A mini-review. Eur J Med Chem. 2015;97:419-43.
  • 12. Song D, Ma S. Recent development of benzimidazole-containing antibacterial agents. ChemMedChem. 2016;11:646-59.
  • 13. Gaba M, Mohan C. Development of drug-based imidazole and benzimidazole bioactive heterocycles: recent advances and future directions. Med Chem Res. 2016;25:173-210.
  • 14. Rylands L, Welsh A, Maepa K, Stringer T, Taylor D, Chibale K, Smith GS. Structure-activity relationship studies of antiplasmodial cyclometallated ruthenium(II), rhodium(III), and iridium(III) complexes of 2-phenylbenzimidazole. Eur J. Med Chem. 2019;161:11-21.
  • 15. Gozelle M, Süloğlu AK, Selmaoğlu G, Ramazanoğlu N, Açık L, Gümüş F. Studies on the synthesis, characterization, cytotoxic activities and plasmid DNA binding of platinum(II) complexes having 2-substituted benzimidazole ligands. Polyhedron. 2019;161:298-308.
  • 16. Su WY, Pan RK, Song JL, Li GB, Liu SG. Synthesis, crystal structures and cytotoxic activity of two zinc(II) complexes derived from benzimidazole derivatives. Polyhedron. 2019;161: 268-75.
  • 17. Sarı Y, Akkoç S, Gök Y, Sifniotis V, Özdemi İ, Günal S, Kayser V. Benzimidazolium-based novel silver N-heterocyclic carbene complexes: synthesis, characterization and in vitro antimicrobial activity. J Enzyme Inhib Med Chem. 2016;31:1527-30.
  • 18. Touj N, Özdemir İ, Yaşar S, Hamdi N. An Efficient (NHC) copper(I)-catalyst for azide-alkyne cycloaddition reactions for the synthesis of 1,2,3-trisubstituted triazoles: Click chemistry. Inorg Chim Acta. 2017;467:21-32.
  • 19. Kaloğlu N, Kaloğlu M, Tahir MN, Arıcı C, Bruneau C, Doucet H, Dixneuf PH, Çetinkaya B, Özdemir İ. Synthesis of N-heterocyclic carbene-palladium-PEPPSI complexes and their catalytic activity in the direct C-H bond activation. J Organomet Chem. 2018;867:404-12.
  • 20. Şahin-Bölükbaşı S, Şahin N, Tahir MN, Arıcı C, Çevik E, Gürbüz N, Özdemir İ, Cummings BS. Novel N-heterocyclic carbene silver(I) complexes: Synthesis, structural characterisation, and anticancer activity. Inorg Chim Acta. 2019;486:711-8.
  • 21. Aktaş A, Celepci D, Kaya R, Taslimi P, Gök Y, Aygün M, Gülçin İ. Novel morpholine liganded Pd-based N-heterocyclic carbene complexes: Synthesis, characterization, crystal structure, antidiabetic and anticholinergic properties. Polyhedron. 2019;159:345-54.
  • 22. Supuran CT, Scozzafava A, Casini A. Carbonic anhydrase inhibitors. Med Res Rev. 2003;23:146-89.
  • 23. Supuran CT. Carbonic anhydrase inhibitors. Bioorg Med Chem Lett. 2010;20:3467-74.
  • 24. Kupriyanova E, Pronind N, Los D. Carbonic anhydrase- a universal enzyme of carbon-based life. Photosynthetica. 2017;55:3-19.
  • 25. Aggarwal M, Kondeti B, McKenna R. Anticonvulsant/antiepileptic carbonic anhydrase inhibitors: a patent review. Expert Opin Ther Pat. 2013;23:717-24.
  • 26. Scozzafava A, Supuran CT, Carta F. Antiobesity carbonic anhydrase inhibitors: a literature and patent review. Expert Opin Ther Pat. 2013;23:725-35.
  • 27. Monti BM, Supuran CT, De Simone G. Anticancer carbonic anhydrase inhibitors: a patent review (2008-2013). Expert Opin Ther Pat. 2013;23:737-49.
  • 28. Özdemir İ, Şahin N, Gök Y, Demir S, Çetinkaya B. In situ generated 1-alkylbenzimidazole palladium catalyst for the Suzuki coupling of aryl chlorides. J Mol Catal A-Chem. 2005;234:181-5.
  • 29. Arslan O, Nalbantoğlu B, Demir N, Özdemir H, Küfrevioğlu Öİ. A new method for the purification of carbonic anhydrase isozymes by affinity chromatography. Turk J Med Sci. 1996;26:167-70.
  • 30. Verpoorte JA, Mehta S, Edsall JT. Esterase activities of human carbonic anhydrases B and C. J Biol Chem. 1967;242:4221-9.
  • 31. Karlık Ö, Balcıoğlu S, Karataş MO, Ateş B, Alıcı B, Özdemir N. Synthesis, structural characterization and cytotoxicity studies of T-shaped silver(I) complexes derived from 1-benzyl-3H-benzimidazolium p-toluenesulfonates. Polyhedron. 2018;142:63-70.
  • 32. Wu H, Zhang Y, Chen C, Zhang J, Bai Y, Shi F, Wang X. DNA binding studies and antioxidant activities of two-, three- and four- coordinate silver(I) complexes containing bis(2-benzimidazolyl)aniline derivatives. New J Chem. 2014;38:3688-98.
  • 33. Lee CK, Hsu KM, Tsai CH, Lai CK, Lin IJB. Liquid crystals of silver complexes derived from simple 1-alkylimidazoles. Dalton Trans. 2004;2004:1120-6.
  • 34. Büyükkıdan N, Bülbül M, Kasımoğulları R, Büyükkıdan B. Synthesis and characterization of metal complexes of heterocyclic sulphonamide as carbonic anhydrase inhibitors. J Enzyem Inhib Med Chem. 2013;28:311-5.
  • 35. Scozzafava A, Briganti F, Ilies MA, Supuran CT. Carbonic anhydrase inhibitors: Synthesis of membrane-impermeant low molecular weight sulfonamides possessing in vivo selectivity for the membrane-bound versus cytosolic isozymes. J Med Chem. 2000;43:292-300.
  • 36. Casey JR, Morgan PE, Vullo D, Scozzafava A, Mastrolorenzo A, Supuran CT. Carbonic anhydrase inhibitors. Design of selective, membrane-impermeant inhibitors targeting the human tumor-associated isozyme IX. J Med Chem. 2004;49:2337-47.
  • 37. Güzel Ö, Maresca A, Scozzafava A, Salman A, Balaban AT, Supuran CT. Discovery of low nanomolar and subnanomolar inhibitors of the Mycobacterial β-carbonic anhydrases Rv1284 Rv3273. J Med Chem. 2009;52:4063-7.
  • 38. Akocak S, Ilies MA. Targeting carbonic anhydrases. London:Future Science;2014:35-51.

Synthesis, Characterization, and Carbonic Anhydrase Inhibitory Properties of Silver(I) Complexes of Benzimidazole Derivatives

Year 2019, Volume: 6 Issue: 2, 253 - 260, 15.06.2019
https://doi.org/10.18596/jotcsa.546960

Abstract

The antimicrobial properties of silver compounds
and biological properties of benzimidazole derivatives have been well known for
many years. In the present study, in terms of their biological potential, six
novel silver(I)-N-alkylbenzimidazole derivatives were synthesized in order to
examine their carbonic anhydrase (CA) inhibitory properties. All complexes were
characterized by the combination of 1H NMR, 13C NMR, mass, FT-IR spectroscopic
methods and elemental analyses. The inhibitory properties of all complexes were
tested on the esterase activity of human CA I and II (hCA I and hCA II).
Acetazolamide was used as a standard. All complexes inhibited the hCA I and hCA
II activity in the range of 27.37-29.58 µM and 20.93-27.25 µM, respectively. 

References

  • 1. Klasen H. Historical review of the use of silver in the treatment of burns. I. Early uses. Burns. 2000;26;117-30.
  • 2. Moyer CA, Brentano L, Gravens DL, Margraf HW, Monafo WW. Treatment of large human burns with 0.5 per cent silver nitrate solution. Arch Surg. 1965;90:812-67.
  • 3. Fox CL. Silver sulfadiazine- A new topical therapy for Pseudomonas in Burns. Arch Surg. 1968;96:184-8.
  • 4. Medici S, Peana M, Crisponi G, Nurchi VM, Lachowicz JI, Remelli M, Zoroddu MA. Silver coordination compounds: A new horizon in medicine. Coord Chem Rev. 2016;327-328:349-59.
  • 5. Allison SJ, Sadiq M, Baronou E, Cooper PA, Dunnill C, Georgopoulos NT, Latif A, Shepherd S, Shnyder SD, Stratford IJ, Wheelhouse RT, Willans CE, Phillips RM. Preclinical anti-cancer activity and multiple mechanisms of action of a cationic silver complex bearing N-heterocyclic carbene ligands. Cancer Lett. 2017;403:98-107.
  • 6. Teyssot ML, Jarrouse AS, Manin M, Chevry A, Roche S, Norre F, Beaudoin C, Morel L, Boyer D, Mahiou R, Gautier A. Metal-NHC complexes: a survey of anti-cancer properties. Dalton Trans. 2009;2009:6894-902.
  • 7. Liu W, Gust R. Metal N-heterocyclic carbene complexes as potential antitumor metallodrug. Chem Soc Rev. 2013;42:755-73.
  • 8. Rowan R, Tallon T, Sheahan AM, Curran R, McCann M, Kavanagh K, Devereux M, McKee V. ‘Silver bullet’ in antimicrobial chemotherapy: Synthesis, characterisation and biological screening of some new Ag(I)-containing imidazole complexes. Polyhedron. 2006;25:1771-8.
  • 9. Ray S, Mohan R, Singh JK, Samantaray MK, Shaikh MM, Panda D, Ghosh P. Anticancer and antimicrobial metallopharmaceutical agents based on palladium, gold, and silver N-heterocyclic carbene complexes. J Am Chem Soc. 2007;129: 15042-53.
  • 10. Ainscough EW, Brodie AM, Freeman GH, Plieger PG. Structural studies on tribenzylphosphane sulphide complexes of copper(I) and silver(I). Polyhedron. 2016;106:40-3.
  • 11. Yadav G, Ganguly S. Structure activity relationship (SAR) study of benzimidazole scaffold for different biological activities: A mini-review. Eur J Med Chem. 2015;97:419-43.
  • 12. Song D, Ma S. Recent development of benzimidazole-containing antibacterial agents. ChemMedChem. 2016;11:646-59.
  • 13. Gaba M, Mohan C. Development of drug-based imidazole and benzimidazole bioactive heterocycles: recent advances and future directions. Med Chem Res. 2016;25:173-210.
  • 14. Rylands L, Welsh A, Maepa K, Stringer T, Taylor D, Chibale K, Smith GS. Structure-activity relationship studies of antiplasmodial cyclometallated ruthenium(II), rhodium(III), and iridium(III) complexes of 2-phenylbenzimidazole. Eur J. Med Chem. 2019;161:11-21.
  • 15. Gozelle M, Süloğlu AK, Selmaoğlu G, Ramazanoğlu N, Açık L, Gümüş F. Studies on the synthesis, characterization, cytotoxic activities and plasmid DNA binding of platinum(II) complexes having 2-substituted benzimidazole ligands. Polyhedron. 2019;161:298-308.
  • 16. Su WY, Pan RK, Song JL, Li GB, Liu SG. Synthesis, crystal structures and cytotoxic activity of two zinc(II) complexes derived from benzimidazole derivatives. Polyhedron. 2019;161: 268-75.
  • 17. Sarı Y, Akkoç S, Gök Y, Sifniotis V, Özdemi İ, Günal S, Kayser V. Benzimidazolium-based novel silver N-heterocyclic carbene complexes: synthesis, characterization and in vitro antimicrobial activity. J Enzyme Inhib Med Chem. 2016;31:1527-30.
  • 18. Touj N, Özdemir İ, Yaşar S, Hamdi N. An Efficient (NHC) copper(I)-catalyst for azide-alkyne cycloaddition reactions for the synthesis of 1,2,3-trisubstituted triazoles: Click chemistry. Inorg Chim Acta. 2017;467:21-32.
  • 19. Kaloğlu N, Kaloğlu M, Tahir MN, Arıcı C, Bruneau C, Doucet H, Dixneuf PH, Çetinkaya B, Özdemir İ. Synthesis of N-heterocyclic carbene-palladium-PEPPSI complexes and their catalytic activity in the direct C-H bond activation. J Organomet Chem. 2018;867:404-12.
  • 20. Şahin-Bölükbaşı S, Şahin N, Tahir MN, Arıcı C, Çevik E, Gürbüz N, Özdemir İ, Cummings BS. Novel N-heterocyclic carbene silver(I) complexes: Synthesis, structural characterisation, and anticancer activity. Inorg Chim Acta. 2019;486:711-8.
  • 21. Aktaş A, Celepci D, Kaya R, Taslimi P, Gök Y, Aygün M, Gülçin İ. Novel morpholine liganded Pd-based N-heterocyclic carbene complexes: Synthesis, characterization, crystal structure, antidiabetic and anticholinergic properties. Polyhedron. 2019;159:345-54.
  • 22. Supuran CT, Scozzafava A, Casini A. Carbonic anhydrase inhibitors. Med Res Rev. 2003;23:146-89.
  • 23. Supuran CT. Carbonic anhydrase inhibitors. Bioorg Med Chem Lett. 2010;20:3467-74.
  • 24. Kupriyanova E, Pronind N, Los D. Carbonic anhydrase- a universal enzyme of carbon-based life. Photosynthetica. 2017;55:3-19.
  • 25. Aggarwal M, Kondeti B, McKenna R. Anticonvulsant/antiepileptic carbonic anhydrase inhibitors: a patent review. Expert Opin Ther Pat. 2013;23:717-24.
  • 26. Scozzafava A, Supuran CT, Carta F. Antiobesity carbonic anhydrase inhibitors: a literature and patent review. Expert Opin Ther Pat. 2013;23:725-35.
  • 27. Monti BM, Supuran CT, De Simone G. Anticancer carbonic anhydrase inhibitors: a patent review (2008-2013). Expert Opin Ther Pat. 2013;23:737-49.
  • 28. Özdemir İ, Şahin N, Gök Y, Demir S, Çetinkaya B. In situ generated 1-alkylbenzimidazole palladium catalyst for the Suzuki coupling of aryl chlorides. J Mol Catal A-Chem. 2005;234:181-5.
  • 29. Arslan O, Nalbantoğlu B, Demir N, Özdemir H, Küfrevioğlu Öİ. A new method for the purification of carbonic anhydrase isozymes by affinity chromatography. Turk J Med Sci. 1996;26:167-70.
  • 30. Verpoorte JA, Mehta S, Edsall JT. Esterase activities of human carbonic anhydrases B and C. J Biol Chem. 1967;242:4221-9.
  • 31. Karlık Ö, Balcıoğlu S, Karataş MO, Ateş B, Alıcı B, Özdemir N. Synthesis, structural characterization and cytotoxicity studies of T-shaped silver(I) complexes derived from 1-benzyl-3H-benzimidazolium p-toluenesulfonates. Polyhedron. 2018;142:63-70.
  • 32. Wu H, Zhang Y, Chen C, Zhang J, Bai Y, Shi F, Wang X. DNA binding studies and antioxidant activities of two-, three- and four- coordinate silver(I) complexes containing bis(2-benzimidazolyl)aniline derivatives. New J Chem. 2014;38:3688-98.
  • 33. Lee CK, Hsu KM, Tsai CH, Lai CK, Lin IJB. Liquid crystals of silver complexes derived from simple 1-alkylimidazoles. Dalton Trans. 2004;2004:1120-6.
  • 34. Büyükkıdan N, Bülbül M, Kasımoğulları R, Büyükkıdan B. Synthesis and characterization of metal complexes of heterocyclic sulphonamide as carbonic anhydrase inhibitors. J Enzyem Inhib Med Chem. 2013;28:311-5.
  • 35. Scozzafava A, Briganti F, Ilies MA, Supuran CT. Carbonic anhydrase inhibitors: Synthesis of membrane-impermeant low molecular weight sulfonamides possessing in vivo selectivity for the membrane-bound versus cytosolic isozymes. J Med Chem. 2000;43:292-300.
  • 36. Casey JR, Morgan PE, Vullo D, Scozzafava A, Mastrolorenzo A, Supuran CT. Carbonic anhydrase inhibitors. Design of selective, membrane-impermeant inhibitors targeting the human tumor-associated isozyme IX. J Med Chem. 2004;49:2337-47.
  • 37. Güzel Ö, Maresca A, Scozzafava A, Salman A, Balaban AT, Supuran CT. Discovery of low nanomolar and subnanomolar inhibitors of the Mycobacterial β-carbonic anhydrases Rv1284 Rv3273. J Med Chem. 2009;52:4063-7.
  • 38. Akocak S, Ilies MA. Targeting carbonic anhydrases. London:Future Science;2014:35-51.
There are 38 citations in total.

Details

Primary Language English
Journal Section Articles
Authors

Mert Ogun Karataş 0000-0001-8500-2088

Adem Ergün 0000-0003-4647-6058

Publication Date June 15, 2019
Submission Date March 29, 2019
Acceptance Date May 21, 2019
Published in Issue Year 2019 Volume: 6 Issue: 2

Cite

Vancouver Karataş MO, Ergün A. Synthesis, Characterization, and Carbonic Anhydrase Inhibitory Properties of Silver(I) Complexes of Benzimidazole Derivatives. JOTCSA. 2019;6(2):253-60.