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The enzyme kinetic studies, DNA protection and antioxidant activities of furan/ thiophene-2-carboxamide derivatives

Yıl 2024, Cilt: 8 Sayı: 2, 137 - 142

Şükriye Çakmak , Semiha Yenigün , Tevfik Ozen

https://doi.org/10.32571/ijct.1405155

Öz

Three furan and/or thiophene-2-carboxamide compounds, namely N-(furan-2-ylmethyl)thiophene-2-carboxamide (1), N-(furan-2-carbonyl)furan-2-carboxamide (2), and N-(Thiophene-2-ylmethyl)furan-2-carboxamide (3) were investigated the enzyme kinetic studies by urease, acetylcholinesterase (AChE), and butyrylcholinesterase (BChE). The inhibition constant (Ki) of Compound (CPD)3 by AChE was determined as 0.10 mM, and the Ki value by BChE was determined as 0.07 mM. In comparison, the Ki value of CPD1 by urease was determined as 0.10 mM. These CPDs were examined for antioxidant activity by the DPPH˙ scavenging method. CPD3 exhibited 98.93% DPPH scavenging activity compared to ascorbic acid, the positive control group. Furthermore, the DNA-protective activities of the compounds were investigated, and the DNA protection activity of CPD1 was observed to be 78%. The findings suggest that thiophene/furan carboxy amide-containing CPD1 and CPD3 might be exploited as potential structures for evaluating pharmaceuticals with greater potency.

Anahtar Kelimeler

Furan/thiophene-2-carboxamide acetylcholinesterase butyrylcholinesterase urease inhibition DNA-protective activity

Proje Numarası

TUBITAK (221Z330)

Teşekkür

All the authors are thankful to Scientific Technological Research and Applications Center (GRUMLAB) for taking the NMR spectra. This study was supported by TUBITAK (The Scientific and Technological Research Council of Turkey) (Project Number: 221Z330).

Kaynakça

  • Volodina, Y. L.; Tikhomirov, A. S.; Dezhenkova, L. G.; Ramonova, A. A.; Kononova, A. V.; Andreeva, D. V.; Kaluzhny, D. N.; Schols, D.; Moisenovich, M. M.; Shchekotikhin, A. E., 2021, Eur J Med Chem, 221, 113521.
  • Volodina, Y. L.; Tikhomirov, A. S.; Dezhenkova, L. G.; Ramonova, A. A.; Kononova, A. V.; Andreeva, D. V.; Kaluzhny, D. N.; Schols, D.; Moisenovich, M. M.; Shchekotikhin, A. E., 2021, Eur J Med Chem, 221, 113521.
  • Owa, T.; Nagasu, T., 2000, Expert Opin Ther Pat, 10 (11), 1725-1740.
  • Nan, X.; Wang, Q.-X.; Xing, S.-J.; Liang, Z.-G., 2023, J Enzym Inhib Med Ch, 38 (1), 2247183.
  • Mali, S. N.; Anand, A.; Zaki, M. E.; Al-Hussain, S. A.; Jawarkar, R. D.; Pandey, A.; Kuznetsov, A., 2023, Molecules, 28 (6), 2801.
  • Huang, E.; Zhang, L.; Xiao, C.; Meng, G.; Zhang, B.; Hu, J.; Wan, D. C.-C.; Meng, Q.; Jin, Z.; Hu, C., 2019, Chinese Chem Lett, 30 (12), 2157-2159.
  • Desantis, J.; Nannetti, G.; Massari, S.; Barreca, M. L.; Manfroni, G.; Cecchetti, V.; Palù, G.; Goracci, L.; Loregian, A.; Tabarrini, O., 2017, Eur J Med Chem, 138, 128-139.
  • Rollet-Labelle, E.; Grange, M.-J.; Elbim, C.; Marquetty, C.; Gougerot-Pocidalo, M.-A.; Pasquier, C., 1998, Free Radical Bio Med, 24 (4), 563-572.
  • Singh, P.; Vishwakarma, S. P.; Singh, R. L., 2014, J Sci Food Agr, 94 (12), 2497-2504.
  • Moskovitz, J.; Yim, M. B.; Chock, P. B., 2002, Arch Biochem Biophys, 397 (2), 354-359.
  • Sevgi, K.; Tepe, B.; Sarikurkcu, C., 2015, Food Chem Toxicol, 77, 12-21.
  • Cakmak, S.; Yenigun, S.; Ozen, T., 2023, J Iran Chem Soc, 20 (10), 2543-2553.
  • Zhang, L.; Mulrooney, S. B.; Leung, A. F.; Zeng, Y.; Ko, B. B.; Hausinger, R. P.; Sun, H., 2006, Biometals, 19 (5), 503-511.
  • Ellman, G. L.; Courtney, K. D.; Andres Jr, V.; Featherstone, R. M., 1961, Biochem Pharmacol, 7 (2), 88-95.
  • Wu, Z.; Shen, L.; Han, Q.; Lu, J.; Tang, H.; Xu, X.; Xu, H.; Huang, F.; Xie, J.; He, Z., 2017, Food Biophys, 12 (1), 78-87.
  • Blois, M. S., 1958, Nature, 181 (4617), 1199-1200.
  • Baiseitova, A.; Jenis, J.; Kim, J. Y.; Li, Z. P.; Park, K. H., 2021, Nat Prod Res, 35 (5), 880-883.
  • Başar, Y.; Demirtaş, İ.; Yenigün, S.; İpek, Y.; Özen, T.; Behçet, L., 2024, J Biomol Struct Dyn, 1-14.
  • Basar, Y.; Yenigun, S.; Gul, F.; Ozen, T.; Demirtas, I. A., M. Hakkı ; Temel, S., 2024, Int J Chem Techno, 8 (1), 62-71.
  • Gökçimen, S. Ş.; İpek, Y.; Behçet, L.; Demirtaş, İ.; Özen, T., 2024, J Biomol Struct Dyn, Published online: 12 Jan 2024, 1-18.
  • Başar, Y.; Yenigün, S.; İpek, Y.; Behçet, L.; Gül, F.; Özen, T.; Demirtaş, İ., 2023, J Biomol Struct Dyn, Published online.
  • Yenigün, S.; Başar, Y.; İpek, Y.; Behçet, L.; Özen, T.; Demirtaş, İ., 2024, J Biomol Struct Dyn, 42 (11), 5799-5816.
  • Afshari, M.; Rahimmalek, M.; Miroliaei, M.; Sabzalian, M. R.; Sadeghi, M.; Matkowski, A.; Szumny, A., 2024, Ind Crop Prod, 208, 117859.
  • Yenigun, S.; Basar, Y.; Gül, F.; Ipek, Y.; Gok, M.; Behcet, L.; Ozen, T.; Demirtas, I., 2024, ChemistrySelect, 9 (18), e202400919.
  • Yenigun, S.; Basar, Y.; Ipek, Y.; Gok, M.; Behcet, L.; Ozen, T.; Demirtas, I., 2024, Process Biochem, 143, 234-247.
  • Yenigün, S.; Ozen, T.; Başar, Y.; Ipek, Y.; Gök, M.; Behçet, L.; Demirtaş, İ., 2024, Curr Persp Med Aromatic Plants, 7 (1), 1-11.
  • Kareem, H. S.; Nordin, N.; Heidelberg, T.; Abdul-Aziz, A.; Ariffin, A., 2016, Molecules, 21 (2), 224.
  • Takahashi, O.; Kirikoshi, R., 2014, Comput Sci Disc, 7 (1), 015005.
  • Iqbal, A.; Khan, Z. A.; Shahzad, S. A.; Usman, M.; Khan, S. A.; Fauq, A. H.; Bari, A.; Sajid, M. A., 2018, Turkish J Chem, 42 (6), 1518-1533.
  • Valko, M.; Leibfritz, D.; Moncol, J.; Cronin, M. T.; Mazur, M.; Telser, J., 2007, The Int J Biochem Cell Bio, 39 (1), 44-84.
  • Azqueta, A.; Collins, A., 2016, Nutrients, 8 (12), 785.
  • Bekhouche, K.; Ozen, T.; Boussaha, S.; Koldas, S.; Yenigun, S.; Lassed, S.; Demirtas, I.; Benayache, F.; Benayache, S.; Zama, D., 2018, Bangladesh J Pharmacol, 13 (1).
  • Mondal, N. K.; Sorensen, E.; Hiivala, N.; Feller, E.; Griffith, B.; Wu, Z. J., 2013, Int J Med Sci, 10 (7), 883.
  • Ozen, T.; Yenigun, S.; Toka, M., 2022, Int J Chem Techno, 6 (1), 21-32.
  • Tuteja, N.; Singh, M. B.; Misra, M. K.; Bhalla, P. L.; Tuteja, R., 2001, Crit Rev Biochem Mol, 36 (4), 337-397.
  • Valko, M.; Izakovic, M.; Mazur, M.; Rhodes, C. J.; Telser, J., 2004, Mol Cell Biochem, 266 (1-2), 37-56.
  • Yenigun, S.; Ipek, Y.; Marah, S.; Demirtas, I.; Ozen, T., 2024, J Biomol Struct Dyn, 42 (2), 848-862.
  • De Almeida, S. M. V.; Lafayette, E. A.; Da Silva, L. P. B. G.; Amorim, C. A. d. C.; De Oliveira, T. B.; Ruiz, A. L. T. G.; De Carvalho, J. E.; De Moura, R. O.; Beltrão, E. I. C.; De Lima, M. D. C. A., 2015, Int J Mol Sci, 16 (6), 13023-13042.

Yıl 2024, Cilt: 8 Sayı: 2, 137 - 142

Şükriye Çakmak , Semiha Yenigün , Tevfik Ozen

https://doi.org/10.32571/ijct.1405155

Öz

Proje Numarası

TUBITAK (221Z330)

Kaynakça

  • Volodina, Y. L.; Tikhomirov, A. S.; Dezhenkova, L. G.; Ramonova, A. A.; Kononova, A. V.; Andreeva, D. V.; Kaluzhny, D. N.; Schols, D.; Moisenovich, M. M.; Shchekotikhin, A. E., 2021, Eur J Med Chem, 221, 113521.
  • Volodina, Y. L.; Tikhomirov, A. S.; Dezhenkova, L. G.; Ramonova, A. A.; Kononova, A. V.; Andreeva, D. V.; Kaluzhny, D. N.; Schols, D.; Moisenovich, M. M.; Shchekotikhin, A. E., 2021, Eur J Med Chem, 221, 113521.
  • Owa, T.; Nagasu, T., 2000, Expert Opin Ther Pat, 10 (11), 1725-1740.
  • Nan, X.; Wang, Q.-X.; Xing, S.-J.; Liang, Z.-G., 2023, J Enzym Inhib Med Ch, 38 (1), 2247183.
  • Mali, S. N.; Anand, A.; Zaki, M. E.; Al-Hussain, S. A.; Jawarkar, R. D.; Pandey, A.; Kuznetsov, A., 2023, Molecules, 28 (6), 2801.
  • Huang, E.; Zhang, L.; Xiao, C.; Meng, G.; Zhang, B.; Hu, J.; Wan, D. C.-C.; Meng, Q.; Jin, Z.; Hu, C., 2019, Chinese Chem Lett, 30 (12), 2157-2159.
  • Desantis, J.; Nannetti, G.; Massari, S.; Barreca, M. L.; Manfroni, G.; Cecchetti, V.; Palù, G.; Goracci, L.; Loregian, A.; Tabarrini, O., 2017, Eur J Med Chem, 138, 128-139.
  • Rollet-Labelle, E.; Grange, M.-J.; Elbim, C.; Marquetty, C.; Gougerot-Pocidalo, M.-A.; Pasquier, C., 1998, Free Radical Bio Med, 24 (4), 563-572.
  • Singh, P.; Vishwakarma, S. P.; Singh, R. L., 2014, J Sci Food Agr, 94 (12), 2497-2504.
  • Moskovitz, J.; Yim, M. B.; Chock, P. B., 2002, Arch Biochem Biophys, 397 (2), 354-359.
  • Sevgi, K.; Tepe, B.; Sarikurkcu, C., 2015, Food Chem Toxicol, 77, 12-21.
  • Cakmak, S.; Yenigun, S.; Ozen, T., 2023, J Iran Chem Soc, 20 (10), 2543-2553.
  • Zhang, L.; Mulrooney, S. B.; Leung, A. F.; Zeng, Y.; Ko, B. B.; Hausinger, R. P.; Sun, H., 2006, Biometals, 19 (5), 503-511.
  • Ellman, G. L.; Courtney, K. D.; Andres Jr, V.; Featherstone, R. M., 1961, Biochem Pharmacol, 7 (2), 88-95.
  • Wu, Z.; Shen, L.; Han, Q.; Lu, J.; Tang, H.; Xu, X.; Xu, H.; Huang, F.; Xie, J.; He, Z., 2017, Food Biophys, 12 (1), 78-87.
  • Blois, M. S., 1958, Nature, 181 (4617), 1199-1200.
  • Baiseitova, A.; Jenis, J.; Kim, J. Y.; Li, Z. P.; Park, K. H., 2021, Nat Prod Res, 35 (5), 880-883.
  • Başar, Y.; Demirtaş, İ.; Yenigün, S.; İpek, Y.; Özen, T.; Behçet, L., 2024, J Biomol Struct Dyn, 1-14.
  • Basar, Y.; Yenigun, S.; Gul, F.; Ozen, T.; Demirtas, I. A., M. Hakkı ; Temel, S., 2024, Int J Chem Techno, 8 (1), 62-71.
  • Gökçimen, S. Ş.; İpek, Y.; Behçet, L.; Demirtaş, İ.; Özen, T., 2024, J Biomol Struct Dyn, Published online: 12 Jan 2024, 1-18.
  • Başar, Y.; Yenigün, S.; İpek, Y.; Behçet, L.; Gül, F.; Özen, T.; Demirtaş, İ., 2023, J Biomol Struct Dyn, Published online.
  • Yenigün, S.; Başar, Y.; İpek, Y.; Behçet, L.; Özen, T.; Demirtaş, İ., 2024, J Biomol Struct Dyn, 42 (11), 5799-5816.
  • Afshari, M.; Rahimmalek, M.; Miroliaei, M.; Sabzalian, M. R.; Sadeghi, M.; Matkowski, A.; Szumny, A., 2024, Ind Crop Prod, 208, 117859.
  • Yenigun, S.; Basar, Y.; Gül, F.; Ipek, Y.; Gok, M.; Behcet, L.; Ozen, T.; Demirtas, I., 2024, ChemistrySelect, 9 (18), e202400919.
  • Yenigun, S.; Basar, Y.; Ipek, Y.; Gok, M.; Behcet, L.; Ozen, T.; Demirtas, I., 2024, Process Biochem, 143, 234-247.
  • Yenigün, S.; Ozen, T.; Başar, Y.; Ipek, Y.; Gök, M.; Behçet, L.; Demirtaş, İ., 2024, Curr Persp Med Aromatic Plants, 7 (1), 1-11.
  • Kareem, H. S.; Nordin, N.; Heidelberg, T.; Abdul-Aziz, A.; Ariffin, A., 2016, Molecules, 21 (2), 224.
  • Takahashi, O.; Kirikoshi, R., 2014, Comput Sci Disc, 7 (1), 015005.
  • Iqbal, A.; Khan, Z. A.; Shahzad, S. A.; Usman, M.; Khan, S. A.; Fauq, A. H.; Bari, A.; Sajid, M. A., 2018, Turkish J Chem, 42 (6), 1518-1533.
  • Valko, M.; Leibfritz, D.; Moncol, J.; Cronin, M. T.; Mazur, M.; Telser, J., 2007, The Int J Biochem Cell Bio, 39 (1), 44-84.
  • Azqueta, A.; Collins, A., 2016, Nutrients, 8 (12), 785.
  • Bekhouche, K.; Ozen, T.; Boussaha, S.; Koldas, S.; Yenigun, S.; Lassed, S.; Demirtas, I.; Benayache, F.; Benayache, S.; Zama, D., 2018, Bangladesh J Pharmacol, 13 (1).
  • Mondal, N. K.; Sorensen, E.; Hiivala, N.; Feller, E.; Griffith, B.; Wu, Z. J., 2013, Int J Med Sci, 10 (7), 883.
  • Ozen, T.; Yenigun, S.; Toka, M., 2022, Int J Chem Techno, 6 (1), 21-32.
  • Tuteja, N.; Singh, M. B.; Misra, M. K.; Bhalla, P. L.; Tuteja, R., 2001, Crit Rev Biochem Mol, 36 (4), 337-397.
  • Valko, M.; Izakovic, M.; Mazur, M.; Rhodes, C. J.; Telser, J., 2004, Mol Cell Biochem, 266 (1-2), 37-56.
  • Yenigun, S.; Ipek, Y.; Marah, S.; Demirtas, I.; Ozen, T., 2024, J Biomol Struct Dyn, 42 (2), 848-862.
  • De Almeida, S. M. V.; Lafayette, E. A.; Da Silva, L. P. B. G.; Amorim, C. A. d. C.; De Oliveira, T. B.; Ruiz, A. L. T. G.; De Carvalho, J. E.; De Moura, R. O.; Beltrão, E. I. C.; De Lima, M. D. C. A., 2015, Int J Mol Sci, 16 (6), 13023-13042.
Toplam 38 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Gıda Mühendisliği
Bölüm Makale
Yazarlar

Şükriye Çakmak 0000-0002-2221-0098

Semiha Yenigün 0000-0002-1979-5427

Tevfik Ozen 0000-0003-0133-5630

Proje Numarası TUBITAK (221Z330)
Erken Görünüm Tarihi 24 Eylül 2024
Yayımlanma Tarihi
Gönderilme Tarihi 3 Ocak 2024
Kabul Tarihi 14 Ağustos 2024
Yayımlandığı Sayı Yıl 2024 Cilt: 8 Sayı: 2

Kaynak Göster

APA Çakmak, Ş., Yenigün, S., & Ozen, T. (2024). The enzyme kinetic studies, DNA protection and antioxidant activities of furan/ thiophene-2-carboxamide derivatives. International Journal of Chemistry and Technology, 8(2), 137-142. https://doi.org/10.32571/ijct.1405155
AMA Çakmak Ş, Yenigün S, Ozen T. The enzyme kinetic studies, DNA protection and antioxidant activities of furan/ thiophene-2-carboxamide derivatives. Int. J. Chem. Technol. Eylül 2024;8(2):137-142. doi:10.32571/ijct.1405155
Chicago Çakmak, Şükriye, Semiha Yenigün, ve Tevfik Ozen. “The Enzyme Kinetic Studies, DNA Protection and Antioxidant Activities of Furan/ Thiophene-2-Carboxamide Derivatives”. International Journal of Chemistry and Technology 8, sy. 2 (Eylül 2024): 137-42. https://doi.org/10.32571/ijct.1405155.
EndNote Çakmak Ş, Yenigün S, Ozen T (01 Eylül 2024) The enzyme kinetic studies, DNA protection and antioxidant activities of furan/ thiophene-2-carboxamide derivatives. International Journal of Chemistry and Technology 8 2 137–142.
IEEE Ş. Çakmak, S. Yenigün, ve T. Ozen, “The enzyme kinetic studies, DNA protection and antioxidant activities of furan/ thiophene-2-carboxamide derivatives”, Int. J. Chem. Technol., c. 8, sy. 2, ss. 137–142, 2024, doi: 10.32571/ijct.1405155.
ISNAD Çakmak, Şükriye vd. “The Enzyme Kinetic Studies, DNA Protection and Antioxidant Activities of Furan/ Thiophene-2-Carboxamide Derivatives”. International Journal of Chemistry and Technology 8/2 (Eylül 2024), 137-142. https://doi.org/10.32571/ijct.1405155.
JAMA Çakmak Ş, Yenigün S, Ozen T. The enzyme kinetic studies, DNA protection and antioxidant activities of furan/ thiophene-2-carboxamide derivatives. Int. J. Chem. Technol. 2024;8:137–142.
MLA Çakmak, Şükriye vd. “The Enzyme Kinetic Studies, DNA Protection and Antioxidant Activities of Furan/ Thiophene-2-Carboxamide Derivatives”. International Journal of Chemistry and Technology, c. 8, sy. 2, 2024, ss. 137-42, doi:10.32571/ijct.1405155.
Vancouver Çakmak Ş, Yenigün S, Ozen T. The enzyme kinetic studies, DNA protection and antioxidant activities of furan/ thiophene-2-carboxamide derivatives. Int. J. Chem. Technol. 2024;8(2):137-42.
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