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Synthesis, FT-IR, DFT and in silico Antibacterial Activity Studies of Silver Nitrate Complex of Chlorzoxazone

Year 2024, , 52 - 61, 12.12.2024
https://doi.org/10.5281/zenodo.14344088

Abstract

In this study, it was aimed to produce a new potential antibacterial agent using Chlorzoxazone and silver nitrate. Within the scope of the study, CZX.AgNO3 structure was synthesized by chemical synthesis methods. The structure was experimentally characterized by FT-IR and elemental analysis. In addition, the optimized structure and vibration frequencies were determined by the DFT method. After characterization, ADME and toxicity parameters of the new molecule were revealed using in silico methods. In order to determine the antibacterial effect of the molecule, molecular docking studies were performed on gram+ Staphylococcus aureus bacteria, and the results were compared with the frequently used antibiotic clindamycin. The results revealed the ADME, toxicity, and antibacterial effect of CZX.AgNO3 is quite superior.

References

  • Aveledo, R., Aveledo, A., Lago, N., Mato, M. M., & Legido, J. L. (2023). Antibacterial activity of silver nitrate on Pseudomonas aeruginosa bacteria using Calvet calorimetry. Journal of Thermal Analysis and Calorimetry, 148(4), 1639-1646.
  • Bai, Y., & Ma, X. (2020). Chlorzoxazone exhibits neuroprotection against Alzheimer’s disease by attenuating neuroinflammation and neurodegeneration in vitro and in vivo. International Immunopharmacology, 88, 106790.
  • Banerjee, P., Kemmler, E., Dunkel, M., & Preissner, R. (2024). ProTox 3.0: a webserver for the prediction of toxicity of chemicals. Nucleic Acids Research, gkae303.
  • Bilkan, M. T., Yurdakul, Ş., Demircioğlu, Z., & Büyükgüngör, O. (2016). Crystal structure, FT-IR, FT-Raman and DFT studies on a novel compound [C10H9N3] 4AgNO3. Journal of Organometallic Chemistry, 805, 108-116.
  • Bitencourt-Ferreira, G., & de Azevedo, W. F. (2019). Molegro virtual docker for docking. Docking screens for drug discovery, 149-167.
  • Creteanu, A., Lisa, G., Vasile, C., Popescu, M. C., Pamfil, D., Lungu, C. N., ... & Tantaru, G. (2024). New Hydrophilic Matrix Tablets for the Controlled Released of Chlorzoxazone. International Journal of Molecular Sciences, 25(10), 5137.
  • Deng, L., Li, H., Su, X., Zhang, Y., Xu, H., Fan, L., ... & Zhao, R. C. (2020). Chlorzoxazone, a small molecule drug, augments immunosuppressive capacity of mesenchymal stem cells via modulation of FOXO3 phosphorylation. Cell Death & Disease, 11(3), 158.
  • Dennington, R. D., Keith, T. A., & Millam, J. M. (2008). GaussView 5.0, Gaussian. Inc., Wallingford, 20. Eady, M., Setia, G., Park, B., Wang, B., & Sundaram, J. (2023). Biopolymer encapsulated silver nitrate nanoparticle substrates with surface-enhanced Raman spectroscopy (SERS) for Salmonella detection from chicken rinse. International Journal of Food Microbiology, 391, 110158.
  • Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., ... & Cioslowski, J. (2010). Gaussian 09 Revision B. 01 M., and Revision A. 02 SMP J. Gaussian, Inc., Wallingford, CT.
  • Gnanasambandan, T., Gunasekaran, S., & Seshadri, S. (2014). FT-IR, FT-Raman, UV–Vis spectral and normal coordinate analysis of chlorzoxazone. Journal of Molecular Structure, 1061, 124-133.
  • Gutmańska, K., Ciborska, A., Hnatejko, Z., & Dołęga, A. (2022). Nitrate and nitrite silver complexes with weakly coordinating nitriles. Polyhedron, 220, 115831.
  • İde, S., & Topaç, A. (1997). Tautomeric investigations and crystal structure analysis of chlorzoxazone. Journal of chemical crystallography, 27, 303-306.
  • Jamróz, M. H., (2004). Vibrational Energy Distribution Analysis. VEDA 4, Warsaw.
  • Karan, Y. B., & Erenler, R. (2024). Synthesis of Silver Nanoparticles Using Potato Cultivars with Their Antioxidant Activity. Communications in Soil Science and Plant Analysis, 1-9.
  • Megalamani, M. B., Patil, Y. N., & Nandibewoor, S. T. (2023). YSZ/MoS2 modified carbon based sensor for the determination of muscle relaxant agent chlorzoxazone: A novel electroanalytical strategy. Inorganic Chemistry Communications, 155, 111074.
  • Pereira, S. P., Boyle, D., Nogueira, A. J., & Handy, R. D. (2023). Comparison of toxicity of silver nanomaterials and silver nitrate on developing zebrafish embryos: Bioavailability, osmoregulatory and oxidative stress. Chemosphere, 139236.
  • Sekito, T., Sadahira, T., Watanabe, T., Maruyama, Y., Watanabe, T., Iwata, T., ... & Watanabe, M. (2022). Medical uses for silver nitrate in the urinary tract. World Academy of Sciences Journal, 4(1), 1-6.
  • Seul, S. C. (2004) Bioinformatics and Molecular Design Research Center;. PreADMET program.
  • Stewart, J. T., & Janicki, C. A. (1987). Chlorzoxazone. In Analytical profiles of drug substances (Vol. 16, pp. 119-144). Academic Press.
  • Skrejborg, P., Petersen, K. K., Beck, J., Ulrich, M., Simonsen, O., Nielsen, P. T., ... & Laursen, M. (2020). Investigating the effect of perioperative chlorzoxazone on acute postoperative pain after total hip and knee replacement surgery. The Clinical Journal of Pain, 36(5), 352-358.
  • Tang, P., Li, S., Wang, L., Yang, H., Yan, J., & Li, H. (2015). Inclusion complexes of chlorzoxazone with β-and hydroxypropyl-β-cyclodextrin: characterization, dissolution, and cytotoxicity. Carbohydrate polymers, 131, 297-305.

Chlorzoxazone Molekülünün Gümüş Nitrat Bileşiğinin Sentezlenmesi, FT-IR, DFT ve in silico Antibakteriyel Çalışmaları

Year 2024, , 52 - 61, 12.12.2024
https://doi.org/10.5281/zenodo.14344088

Abstract

Bu çalışmada, Klorzoksazon ve gümüş nitrat kullanılarak yeni bir potansiyel antibakteriyel ajan üretilmesi amaçlanmıştır. Çalışma kapsamında, CZX.AgNO3 yapısı kimyasal sentez yöntemleri ile sentezlenmiştir. Yapı, FT-IR ve elementel analiz ile deneysel olarak karakterize edilmiştir. Ayrıca, optimize edilmiş yapı ve titreşim frekansları DFT yöntemi ile belirlenmiştir. Karakterizasyon sonrasında yeni molekülün ADME ve toksisite parametreleri in silico yöntemler kullanılarak ortaya çıkarılmıştır. Molekülün antibakteriyel etkisini belirlemek amacıyla gram+ Staphylococcus aureus bakterileri üzerinde moleküler yerleştirme çalışmaları yapılmış ve sonuçlar sıklıkla kullanılan antibiyotik klindamisin ile karşılaştırılmıştır. Sonuçlar CZX.AgNO3'ün ADME, toksisite ve antibakteriyel etkisinin oldukça üstün olduğunu ortaya koymuştur.

References

  • Aveledo, R., Aveledo, A., Lago, N., Mato, M. M., & Legido, J. L. (2023). Antibacterial activity of silver nitrate on Pseudomonas aeruginosa bacteria using Calvet calorimetry. Journal of Thermal Analysis and Calorimetry, 148(4), 1639-1646.
  • Bai, Y., & Ma, X. (2020). Chlorzoxazone exhibits neuroprotection against Alzheimer’s disease by attenuating neuroinflammation and neurodegeneration in vitro and in vivo. International Immunopharmacology, 88, 106790.
  • Banerjee, P., Kemmler, E., Dunkel, M., & Preissner, R. (2024). ProTox 3.0: a webserver for the prediction of toxicity of chemicals. Nucleic Acids Research, gkae303.
  • Bilkan, M. T., Yurdakul, Ş., Demircioğlu, Z., & Büyükgüngör, O. (2016). Crystal structure, FT-IR, FT-Raman and DFT studies on a novel compound [C10H9N3] 4AgNO3. Journal of Organometallic Chemistry, 805, 108-116.
  • Bitencourt-Ferreira, G., & de Azevedo, W. F. (2019). Molegro virtual docker for docking. Docking screens for drug discovery, 149-167.
  • Creteanu, A., Lisa, G., Vasile, C., Popescu, M. C., Pamfil, D., Lungu, C. N., ... & Tantaru, G. (2024). New Hydrophilic Matrix Tablets for the Controlled Released of Chlorzoxazone. International Journal of Molecular Sciences, 25(10), 5137.
  • Deng, L., Li, H., Su, X., Zhang, Y., Xu, H., Fan, L., ... & Zhao, R. C. (2020). Chlorzoxazone, a small molecule drug, augments immunosuppressive capacity of mesenchymal stem cells via modulation of FOXO3 phosphorylation. Cell Death & Disease, 11(3), 158.
  • Dennington, R. D., Keith, T. A., & Millam, J. M. (2008). GaussView 5.0, Gaussian. Inc., Wallingford, 20. Eady, M., Setia, G., Park, B., Wang, B., & Sundaram, J. (2023). Biopolymer encapsulated silver nitrate nanoparticle substrates with surface-enhanced Raman spectroscopy (SERS) for Salmonella detection from chicken rinse. International Journal of Food Microbiology, 391, 110158.
  • Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., ... & Cioslowski, J. (2010). Gaussian 09 Revision B. 01 M., and Revision A. 02 SMP J. Gaussian, Inc., Wallingford, CT.
  • Gnanasambandan, T., Gunasekaran, S., & Seshadri, S. (2014). FT-IR, FT-Raman, UV–Vis spectral and normal coordinate analysis of chlorzoxazone. Journal of Molecular Structure, 1061, 124-133.
  • Gutmańska, K., Ciborska, A., Hnatejko, Z., & Dołęga, A. (2022). Nitrate and nitrite silver complexes with weakly coordinating nitriles. Polyhedron, 220, 115831.
  • İde, S., & Topaç, A. (1997). Tautomeric investigations and crystal structure analysis of chlorzoxazone. Journal of chemical crystallography, 27, 303-306.
  • Jamróz, M. H., (2004). Vibrational Energy Distribution Analysis. VEDA 4, Warsaw.
  • Karan, Y. B., & Erenler, R. (2024). Synthesis of Silver Nanoparticles Using Potato Cultivars with Their Antioxidant Activity. Communications in Soil Science and Plant Analysis, 1-9.
  • Megalamani, M. B., Patil, Y. N., & Nandibewoor, S. T. (2023). YSZ/MoS2 modified carbon based sensor for the determination of muscle relaxant agent chlorzoxazone: A novel electroanalytical strategy. Inorganic Chemistry Communications, 155, 111074.
  • Pereira, S. P., Boyle, D., Nogueira, A. J., & Handy, R. D. (2023). Comparison of toxicity of silver nanomaterials and silver nitrate on developing zebrafish embryos: Bioavailability, osmoregulatory and oxidative stress. Chemosphere, 139236.
  • Sekito, T., Sadahira, T., Watanabe, T., Maruyama, Y., Watanabe, T., Iwata, T., ... & Watanabe, M. (2022). Medical uses for silver nitrate in the urinary tract. World Academy of Sciences Journal, 4(1), 1-6.
  • Seul, S. C. (2004) Bioinformatics and Molecular Design Research Center;. PreADMET program.
  • Stewart, J. T., & Janicki, C. A. (1987). Chlorzoxazone. In Analytical profiles of drug substances (Vol. 16, pp. 119-144). Academic Press.
  • Skrejborg, P., Petersen, K. K., Beck, J., Ulrich, M., Simonsen, O., Nielsen, P. T., ... & Laursen, M. (2020). Investigating the effect of perioperative chlorzoxazone on acute postoperative pain after total hip and knee replacement surgery. The Clinical Journal of Pain, 36(5), 352-358.
  • Tang, P., Li, S., Wang, L., Yang, H., Yan, J., & Li, H. (2015). Inclusion complexes of chlorzoxazone with β-and hydroxypropyl-β-cyclodextrin: characterization, dissolution, and cytotoxicity. Carbohydrate polymers, 131, 297-305.
There are 21 citations in total.

Details

Primary Language English
Subjects Atomic and Molecular Physics
Journal Section Research Articles
Authors

Mustafa Tuğfan Bilkan 0000-0002-0306-1509

Zehra Çakıl 0009-0006-5727-8216

Elçin Özgür Büyükatalay

Early Pub Date December 10, 2024
Publication Date December 12, 2024
Submission Date October 10, 2024
Acceptance Date November 12, 2024
Published in Issue Year 2024

Cite

APA Bilkan, M. T., Çakıl, Z., & Büyükatalay, E. Ö. (2024). Synthesis, FT-IR, DFT and in silico Antibacterial Activity Studies of Silver Nitrate Complex of Chlorzoxazone. Journal of Anatolian Physics and Astronomy, 3(2), 52-61. https://doi.org/10.5281/zenodo.14344088