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Metal-containing Coordination Complexes (MCCs): Assessment of Biological Activity with Helicobacter pylori Caused Gastric Ulcer

Year 2022, , 768 - 775, 31.08.2022
https://doi.org/10.16984/saufenbilder.1068212

Abstract

The ulcer is a vital disease that unfavorably affects human health globally. Helicobacter pylori, a reason forhave an antibacterial effect against ulcers and some stomach disorders, live on using the urease enzyme and induces the condition to occur. Metal coordination complexes (MCC) are used in numerous industrial areas and the health field. Cyanide bridged metal complexes are also applied in several places. In the current study, antibacterial characteristic of (C1), [Ni(bishydeten)2Ag(CN)2][Ag(CN)2].H2O), and (C2), ([Ni(hydeten)2Ag(CN)2][Ag(CN)2], MCC were analyzed by disk diffusion and broth dilution broth and urease enzyme inhibition assays were performed. As a result of both antibacterial tests, C1 and C2 were observed to provide favorable effects. The synthesized compounds have effective inhibitory potential with IC50 value between 26.65±1.21 and 12.37±0.87 µM for urease.

Supporting Institution

TÜBİTAK

Project Number

1919B011902147

Thanks

We would like to thank TÜBİTAK for supporting this project.

References

  • [1] J. E. Everhart, “Recent developments in the epidemiology of Helicobacter pylori,” Gastroenterology Clinics of North America, vol. 29, no. 3, pp. 559-578, 2000.
  • [2] P. Malfertheiner, F. Megraud, C. A. O'morain, J. P. Gisbert, E. J. Kuipers, A. T. Axon, E. M. El-Omar, “Management of Helicobacter pylori infection—the Maastricht V/Florence consensus report,” Gut, vol. 66, no.1, pp. 6-30, 2017.
  • [3] W. R. Gransden, “Topley and Wilson's Microbiology and Microbial Infections, (CD-ROM),” Journal of Clinical Pathology, vol. 52, no. 3, pp. 237, 1999.
  • [4] F. Mégraud, “Advantages and disadvantages of current diagnostic tests for the detection of Helicobacter pylori,” Scandinavian journal of gastroenterology, vol 31, no. sup215, pp. 57-62, 1996.
  • [5] P. Taslimi, I. Gulcin, B. Ozgeris, S. Goksu, F. Tumer, S. H. Alwasel, C. T. Supuran, “The human carbonic anhydrase isoenzymes I and II (hCA I and II) inhibition effects of trimethoxyindane derivatives,” Journal of enzyme inhibition and medicinal chemistry, vol. 31, no. 1, pp. 152-157, 2016.
  • [6] D. Barman, V. Kumar, S. Roy, S.C. Mandal, “Clinical enzymes and their application,” Aquaculture. pp. 12-13, 2011.
  • [7] X. Huang, S. Jiang, M. Liu, “Metal ion modulated organization and function of the Langmuir− Blodgett films of amphiphilic diacetylene: photopolymerization, thermochromism, and supramolecular chirality,” The Journal of Physical Chemistry B, vol. 109, no. 1, pp. 114-119, 2005.
  • [8] H. Aghabozorg, F. Manteghi, S. Sheshmani, “A brief review on structural concepts of novel supramolecular proton transfer compounds and their metal complexes,” Journal of the Iranian Chemical Society, vol. 5, no. 2, pp. 184-227, 2008.
  • [9] H. İlkimen, C. Yenikaya, “Salisilik asit türevleri ile 2-aminobenzotiyazol türevlerinin karışık ligandlı Cu (II) komplekslerinin sentezi ve karakterizasyonu,” Pamukkale Üniversitesi Mühendislik Bilimleri Dergisi, vol. 23, no. 7, pp. 899-907, 2017.
  • [10] N. Korkmaz, A. Aydın, A. Karadağ, Y. Yanar, Y. Maaşoğlu, E. Şahin, Ş. Tekin, “New bimetallic dicyanidoargentate (I)-based coordination compounds: Synthesis, characterization, biological activities, and DNA-BSA binding affinities,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, vol. 173, pp. 1007-1022, 2017.
  • [11] L. Ronconi, P. J. Sadler, “Using coordination chemistry to design new medicines,” Coordination Chemistry Reviews, vol. 251, no. 13-14, pp. 1633-1648, 2007.
  • [12] E. Meggers, “Exploring biologically relevant chemical space with metal complexes,” Current opinion in chemical biology, vol. 11 no. 3, pp. 287-292, 2007.
  • [13] P. C. Bruijnincx, P. J. Sadler, “New trends for metal complexes with anticancer activity,” Current opinion in chemical biology, vol. 12, no. 2, pp. 197-206, 2008.
  • [14] I. Ott, R. Gust, “Non platinum metal complexes as anti‐cancer drugs,” Archiv der Pharmazie: An International Journal Pharmaceutical and Medicinal Chemistry, vol. 340, no. 3, pp. 117-126, 2007.
  • [15] E. R. T. Tiekink, “Anti-cancer potential of gold complexes,” Inflammopharmacology, vol. 16, no. 3, pp. 138-142, 2008.
  • [16] I. Kostova, “Ruthenium complexes as anticancer agents,” Current Medicinal Chemistry, vol. 13, no. 9, pp. 1085-1107, 2006.
  • [17] D. Y. Graham, M. Miftahussurur, “Helicobacter pylori urease for diagnosis of Helicobacter pylori infection: A mini-review,” Journal of Advanced Research, vol. 13, pp. 51-57, 2018.
  • [18] G. M. El-Sherbiny, M. K. Elbestawy, “A review–plant essential oils active against Helicobacter pylori,” Journal of Essential Oil Research, pp. 1-13, 2022.
  • [19] D. Kısa, N. Korkmaz, P. Taslimi, B. Tuzun, Ş. Tekin, A. Karadag, F. Şen, “Bioactivity and molecular docking studies of some nickel complexes: New analogues for the treatment of Alzheimer, glaucoma and epileptic diseases,” Bioorganic Chemistry, vol. 101, no. 104066, 2020.
  • [20] J. Hudzicki, “Kirby-Bauer disk diffusion susceptibility test protocol” 2009.
  • [21] J.M. Andrews, Determination of minimum inhibitory concentrations, Journal of Antimicrobial Chemotherapy, vol. 49, pp. 1049–1049, 2002.
  • [22] M. Ikram, S. Rehman, F. Subhan, M. N. Akhtar, M. O. Sinnokrot, “Synthesis, characterization, thermal degradation and urease inhibitory studies of the new hydrazide based Schiff base ligand 2-(2-hydroxyphenyl)-3-{[(E)-(2-hydroxyphenyl)methylidene]amino}-2,3-dihydroquinazolin-4(1H)-one,” Open Chemistry, vol. 15, pp. 308–319, 2017.
  • [23] N. Korkmaz, A. Karadağ, A. Aydın, Y. Yanar, İ. Karaman, Ş. Tekin, “Synthesis and characterization of two novel dicyanidoargentate (I) complexes containing N-(2-hydroxyethyl) ethylenediamine exhibiting significant biological activity,” New Journal of Chemistry, vol. 38, no. 10, pp. 4760-4773, 2014.
  • [24] A. Karadağ, N. Korkmaz, A. Aydın, Ş. Tekin, Y. Yanar, Y. Yerli, Ş. A. Korkmaz, “In vitro biological properties and predicted DNA–BSA interaction of three new dicyanidoargentate (i)-based complexes: synthesis and characterization,” New Journal of Chemistry, vol. 42, no. 6, pp. 4679-4692, 2018.
  • [25] A. Karadağ, N. Korkmaz, A. Aydın, H. Akbaş, Ş. Tekin, Y. Yerli, F. Şen, “Metalo components exhibiting significant anticancer and antibacterial properties: a novel sandwich-type like polymeric structure,” Scientific reports, vol. 10, no. 1, pp. 1-17, 2020.
  • [26] EUCAST (2022). The European Committee on Antimicrobial Susceptibility Testing. Breakpoint tables for interpretation of MICs and zone diameters. Version 12.0, 2022. http://www.eucast.org.
  • [27] S. Ahmad, S. Nadeem, A. Anwar, A. Hameed, S. A. Tirmizi, W. Zierkiewicz, M. A. Alotaibi, “Synthesis, characterization, DFT calculations and antibacterial activity of palladium (II) cyanide complexes with thioamides,” Journal of Molecular Structure, vol. 1141, pp. 204-212, 2017.
  • [28] S. Aslam, A. A. Isab, M. A. Alotaibi, M. Saleem, M. Monim-ul-Mehboob, S. Ahmad, N. Trendafilova, “Synthesis, spectroscopic characterization, DFT calculations and antimicrobial properties of silver (I) complexes of 2, 2′-bipyridine and 1, 10-phenanthroline,” Polyhedron, vol. 115, pp. 212-218, 2016.
  • [29] M. N. Uddin, J. Akter, M. A. Manchur, “Cyano Bridged Bimetallic Compounds of the Type M2+-NC-Fe3+ (M= Co, Ni, Cu, Zn, Cd) Using the [Fe (CN) 6] 3-Building Block and their Antibacterial Evaluation,” Orbital: The Electronic Journal of Chemistry, vol. 5, no. 4, pp. 257-263, 2014.
  • [30] W. Chen, Y. Li, Y. Cui, X. Zhang, H. L. Zhu, Q. Zeng, "Synthesis, molecular docking and biological evaluation of Schiff base transition metal complexes as potential urease inhibitors," European Journal of Medicinal Chemistry, vol. 45, pp. 4473–4478, 2010.
  • [31] Y. Cui, X. Dong, Y. Li, Z. Li, W. Chen, "Synthesis, structures and urease inhibition studies of Schiff base metal complexes derived from 3,5-dibromosalicylaldehyde," Eur. J. Med. Chem., vol. 58, pp. 323–331, 2012.
  • [32] Z. You, H. Yu, Z. Li, W. Zhai, Y. Jiang, A. Li, S. Guo, K. Li, C. Lv, C. Zhang, "Inhibition studies of Jack bean urease with hydrazones and their copper(II) complexes," Inorganica Chimica. Acta., vol. 480, pp. 120–126, 2018.
  • [33] J. Matysiak, A. Skrzypek, M. Karpińska, K. Czarnecka, P. Szymański, M. Bajda, A. Niewiadomy, "Biological evaluation, molecular docking, and sar studies of novel 2-(2,4-dihydroxyphenyl)-1h- benzimidazole analogues," Biomolecules, vol. 9, pp. 1–17, 2019.
Year 2022, , 768 - 775, 31.08.2022
https://doi.org/10.16984/saufenbilder.1068212

Abstract

Project Number

1919B011902147

References

  • [1] J. E. Everhart, “Recent developments in the epidemiology of Helicobacter pylori,” Gastroenterology Clinics of North America, vol. 29, no. 3, pp. 559-578, 2000.
  • [2] P. Malfertheiner, F. Megraud, C. A. O'morain, J. P. Gisbert, E. J. Kuipers, A. T. Axon, E. M. El-Omar, “Management of Helicobacter pylori infection—the Maastricht V/Florence consensus report,” Gut, vol. 66, no.1, pp. 6-30, 2017.
  • [3] W. R. Gransden, “Topley and Wilson's Microbiology and Microbial Infections, (CD-ROM),” Journal of Clinical Pathology, vol. 52, no. 3, pp. 237, 1999.
  • [4] F. Mégraud, “Advantages and disadvantages of current diagnostic tests for the detection of Helicobacter pylori,” Scandinavian journal of gastroenterology, vol 31, no. sup215, pp. 57-62, 1996.
  • [5] P. Taslimi, I. Gulcin, B. Ozgeris, S. Goksu, F. Tumer, S. H. Alwasel, C. T. Supuran, “The human carbonic anhydrase isoenzymes I and II (hCA I and II) inhibition effects of trimethoxyindane derivatives,” Journal of enzyme inhibition and medicinal chemistry, vol. 31, no. 1, pp. 152-157, 2016.
  • [6] D. Barman, V. Kumar, S. Roy, S.C. Mandal, “Clinical enzymes and their application,” Aquaculture. pp. 12-13, 2011.
  • [7] X. Huang, S. Jiang, M. Liu, “Metal ion modulated organization and function of the Langmuir− Blodgett films of amphiphilic diacetylene: photopolymerization, thermochromism, and supramolecular chirality,” The Journal of Physical Chemistry B, vol. 109, no. 1, pp. 114-119, 2005.
  • [8] H. Aghabozorg, F. Manteghi, S. Sheshmani, “A brief review on structural concepts of novel supramolecular proton transfer compounds and their metal complexes,” Journal of the Iranian Chemical Society, vol. 5, no. 2, pp. 184-227, 2008.
  • [9] H. İlkimen, C. Yenikaya, “Salisilik asit türevleri ile 2-aminobenzotiyazol türevlerinin karışık ligandlı Cu (II) komplekslerinin sentezi ve karakterizasyonu,” Pamukkale Üniversitesi Mühendislik Bilimleri Dergisi, vol. 23, no. 7, pp. 899-907, 2017.
  • [10] N. Korkmaz, A. Aydın, A. Karadağ, Y. Yanar, Y. Maaşoğlu, E. Şahin, Ş. Tekin, “New bimetallic dicyanidoargentate (I)-based coordination compounds: Synthesis, characterization, biological activities, and DNA-BSA binding affinities,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, vol. 173, pp. 1007-1022, 2017.
  • [11] L. Ronconi, P. J. Sadler, “Using coordination chemistry to design new medicines,” Coordination Chemistry Reviews, vol. 251, no. 13-14, pp. 1633-1648, 2007.
  • [12] E. Meggers, “Exploring biologically relevant chemical space with metal complexes,” Current opinion in chemical biology, vol. 11 no. 3, pp. 287-292, 2007.
  • [13] P. C. Bruijnincx, P. J. Sadler, “New trends for metal complexes with anticancer activity,” Current opinion in chemical biology, vol. 12, no. 2, pp. 197-206, 2008.
  • [14] I. Ott, R. Gust, “Non platinum metal complexes as anti‐cancer drugs,” Archiv der Pharmazie: An International Journal Pharmaceutical and Medicinal Chemistry, vol. 340, no. 3, pp. 117-126, 2007.
  • [15] E. R. T. Tiekink, “Anti-cancer potential of gold complexes,” Inflammopharmacology, vol. 16, no. 3, pp. 138-142, 2008.
  • [16] I. Kostova, “Ruthenium complexes as anticancer agents,” Current Medicinal Chemistry, vol. 13, no. 9, pp. 1085-1107, 2006.
  • [17] D. Y. Graham, M. Miftahussurur, “Helicobacter pylori urease for diagnosis of Helicobacter pylori infection: A mini-review,” Journal of Advanced Research, vol. 13, pp. 51-57, 2018.
  • [18] G. M. El-Sherbiny, M. K. Elbestawy, “A review–plant essential oils active against Helicobacter pylori,” Journal of Essential Oil Research, pp. 1-13, 2022.
  • [19] D. Kısa, N. Korkmaz, P. Taslimi, B. Tuzun, Ş. Tekin, A. Karadag, F. Şen, “Bioactivity and molecular docking studies of some nickel complexes: New analogues for the treatment of Alzheimer, glaucoma and epileptic diseases,” Bioorganic Chemistry, vol. 101, no. 104066, 2020.
  • [20] J. Hudzicki, “Kirby-Bauer disk diffusion susceptibility test protocol” 2009.
  • [21] J.M. Andrews, Determination of minimum inhibitory concentrations, Journal of Antimicrobial Chemotherapy, vol. 49, pp. 1049–1049, 2002.
  • [22] M. Ikram, S. Rehman, F. Subhan, M. N. Akhtar, M. O. Sinnokrot, “Synthesis, characterization, thermal degradation and urease inhibitory studies of the new hydrazide based Schiff base ligand 2-(2-hydroxyphenyl)-3-{[(E)-(2-hydroxyphenyl)methylidene]amino}-2,3-dihydroquinazolin-4(1H)-one,” Open Chemistry, vol. 15, pp. 308–319, 2017.
  • [23] N. Korkmaz, A. Karadağ, A. Aydın, Y. Yanar, İ. Karaman, Ş. Tekin, “Synthesis and characterization of two novel dicyanidoargentate (I) complexes containing N-(2-hydroxyethyl) ethylenediamine exhibiting significant biological activity,” New Journal of Chemistry, vol. 38, no. 10, pp. 4760-4773, 2014.
  • [24] A. Karadağ, N. Korkmaz, A. Aydın, Ş. Tekin, Y. Yanar, Y. Yerli, Ş. A. Korkmaz, “In vitro biological properties and predicted DNA–BSA interaction of three new dicyanidoargentate (i)-based complexes: synthesis and characterization,” New Journal of Chemistry, vol. 42, no. 6, pp. 4679-4692, 2018.
  • [25] A. Karadağ, N. Korkmaz, A. Aydın, H. Akbaş, Ş. Tekin, Y. Yerli, F. Şen, “Metalo components exhibiting significant anticancer and antibacterial properties: a novel sandwich-type like polymeric structure,” Scientific reports, vol. 10, no. 1, pp. 1-17, 2020.
  • [26] EUCAST (2022). The European Committee on Antimicrobial Susceptibility Testing. Breakpoint tables for interpretation of MICs and zone diameters. Version 12.0, 2022. http://www.eucast.org.
  • [27] S. Ahmad, S. Nadeem, A. Anwar, A. Hameed, S. A. Tirmizi, W. Zierkiewicz, M. A. Alotaibi, “Synthesis, characterization, DFT calculations and antibacterial activity of palladium (II) cyanide complexes with thioamides,” Journal of Molecular Structure, vol. 1141, pp. 204-212, 2017.
  • [28] S. Aslam, A. A. Isab, M. A. Alotaibi, M. Saleem, M. Monim-ul-Mehboob, S. Ahmad, N. Trendafilova, “Synthesis, spectroscopic characterization, DFT calculations and antimicrobial properties of silver (I) complexes of 2, 2′-bipyridine and 1, 10-phenanthroline,” Polyhedron, vol. 115, pp. 212-218, 2016.
  • [29] M. N. Uddin, J. Akter, M. A. Manchur, “Cyano Bridged Bimetallic Compounds of the Type M2+-NC-Fe3+ (M= Co, Ni, Cu, Zn, Cd) Using the [Fe (CN) 6] 3-Building Block and their Antibacterial Evaluation,” Orbital: The Electronic Journal of Chemistry, vol. 5, no. 4, pp. 257-263, 2014.
  • [30] W. Chen, Y. Li, Y. Cui, X. Zhang, H. L. Zhu, Q. Zeng, "Synthesis, molecular docking and biological evaluation of Schiff base transition metal complexes as potential urease inhibitors," European Journal of Medicinal Chemistry, vol. 45, pp. 4473–4478, 2010.
  • [31] Y. Cui, X. Dong, Y. Li, Z. Li, W. Chen, "Synthesis, structures and urease inhibition studies of Schiff base metal complexes derived from 3,5-dibromosalicylaldehyde," Eur. J. Med. Chem., vol. 58, pp. 323–331, 2012.
  • [32] Z. You, H. Yu, Z. Li, W. Zhai, Y. Jiang, A. Li, S. Guo, K. Li, C. Lv, C. Zhang, "Inhibition studies of Jack bean urease with hydrazones and their copper(II) complexes," Inorganica Chimica. Acta., vol. 480, pp. 120–126, 2018.
  • [33] J. Matysiak, A. Skrzypek, M. Karpińska, K. Czarnecka, P. Szymański, M. Bajda, A. Niewiadomy, "Biological evaluation, molecular docking, and sar studies of novel 2-(2,4-dihydroxyphenyl)-1h- benzimidazole analogues," Biomolecules, vol. 9, pp. 1–17, 2019.
There are 33 citations in total.

Details

Primary Language English
Subjects Structural Biology
Journal Section Research Articles
Authors

Dursun Kısa 0000-0002-7681-2385

Yusuf Ceylan 0000-0001-8186-7252

Merve Yıldırım This is me 0000-0003-1427-9666

Sümeyra Durgun 0000-0001-6437-5512

Nesrin Korkmaz 0000-0002-7896-1042

Project Number 1919B011902147
Publication Date August 31, 2022
Submission Date February 5, 2022
Acceptance Date June 16, 2022
Published in Issue Year 2022

Cite

APA Kısa, D., Ceylan, Y., Yıldırım, M., Durgun, S., et al. (2022). Metal-containing Coordination Complexes (MCCs): Assessment of Biological Activity with Helicobacter pylori Caused Gastric Ulcer. Sakarya University Journal of Science, 26(4), 768-775. https://doi.org/10.16984/saufenbilder.1068212
AMA Kısa D, Ceylan Y, Yıldırım M, Durgun S, Korkmaz N. Metal-containing Coordination Complexes (MCCs): Assessment of Biological Activity with Helicobacter pylori Caused Gastric Ulcer. SAUJS. August 2022;26(4):768-775. doi:10.16984/saufenbilder.1068212
Chicago Kısa, Dursun, Yusuf Ceylan, Merve Yıldırım, Sümeyra Durgun, and Nesrin Korkmaz. “Metal-Containing Coordination Complexes (MCCs): Assessment of Biological Activity With Helicobacter Pylori Caused Gastric Ulcer”. Sakarya University Journal of Science 26, no. 4 (August 2022): 768-75. https://doi.org/10.16984/saufenbilder.1068212.
EndNote Kısa D, Ceylan Y, Yıldırım M, Durgun S, Korkmaz N (August 1, 2022) Metal-containing Coordination Complexes (MCCs): Assessment of Biological Activity with Helicobacter pylori Caused Gastric Ulcer. Sakarya University Journal of Science 26 4 768–775.
IEEE D. Kısa, Y. Ceylan, M. Yıldırım, S. Durgun, and N. Korkmaz, “Metal-containing Coordination Complexes (MCCs): Assessment of Biological Activity with Helicobacter pylori Caused Gastric Ulcer”, SAUJS, vol. 26, no. 4, pp. 768–775, 2022, doi: 10.16984/saufenbilder.1068212.
ISNAD Kısa, Dursun et al. “Metal-Containing Coordination Complexes (MCCs): Assessment of Biological Activity With Helicobacter Pylori Caused Gastric Ulcer”. Sakarya University Journal of Science 26/4 (August 2022), 768-775. https://doi.org/10.16984/saufenbilder.1068212.
JAMA Kısa D, Ceylan Y, Yıldırım M, Durgun S, Korkmaz N. Metal-containing Coordination Complexes (MCCs): Assessment of Biological Activity with Helicobacter pylori Caused Gastric Ulcer. SAUJS. 2022;26:768–775.
MLA Kısa, Dursun et al. “Metal-Containing Coordination Complexes (MCCs): Assessment of Biological Activity With Helicobacter Pylori Caused Gastric Ulcer”. Sakarya University Journal of Science, vol. 26, no. 4, 2022, pp. 768-75, doi:10.16984/saufenbilder.1068212.
Vancouver Kısa D, Ceylan Y, Yıldırım M, Durgun S, Korkmaz N. Metal-containing Coordination Complexes (MCCs): Assessment of Biological Activity with Helicobacter pylori Caused Gastric Ulcer. SAUJS. 2022;26(4):768-75.

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