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Carbonic anhydrase inhibition and antioxidant activity of the axially naphthoxazin group substituted silicon phthalocyanines

Cilt: 12 Sayı: 1 15 Ocak 2022
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Carbonic anhydrase inhibition and antioxidant activity of the axially naphthoxazin group substituted silicon phthalocyanines

Abstract

Silicon phthalocyanines are an interesting subclass of phthalocyanines. They are abundant and have extremely low toxicity levels. The low solubility of silicon phthalocyanine is the major obstacle to its use in many different applications. Therefore, in a previous study, two axially substituted silicon phthalocyanines were synthesized to increase their solubility. In this study, these axially substituted silicon phthalocyanines were evaluated for carbonic anhydrase inhibition and antioxidant activities. The carbonic anhydrase (CA) inhibition potential of silicon phthalocyanines was evaluated by esterase activity. The antioxidant activity was tested by 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging and ferric ion (III) reducing/antioxidant power (FRAP) assays. The silicon phthalocyanines had significant CA inhibitory activity [50% inhibitory values (IC50): 495 ± 12.74 nM and 857 ± 13.03 nM for H4-Si and H3-Si, respectively]. According to the antioxidant studies, 50% scavenging concentration (SC50) values of DPPH• assay were 2.29 ± 0.06 µg/mL and 1.39 ± 0.43 µg/mL for H3-Si and H4-Si and Trolox Equivalent Antioxidant Capacity (TEAC) values of FRAP test were 259.33 ± 48.27 µM and 342.00 ± 44.40 for H3-Si µM and H4-Si, respectively. Consequently, silicon phthalocyanine compounds are considered to have great potential for their use in various fields such as food and medicine.

Keywords

Antioxidant , Carbonic anhydrase , Esterase activity , Inhibitor , Silicon phthalocyanines

Kaynakça

  1. Agirtaş, M.S., Cabir, B., Gümüş, S., Özdemir, S. and Dündar, A. (2018). Synthesis and antioxidant, aggregation, and electronic properties of 6-tert-butyl-1,4-benzodioxine substituted phthalocyanines. Turkish Journal of Chemistry, 42, 100-111. https://doi.org/10.3906/kim-1605-59
  2. Aktaş Karaçelik, A., Efe, D., Çakır, V. and Bıyıklıoğlu, Z. (2021). Aksiyal disübstitüe silisyum ftalosiyaninlerin biyolojik aktivitelerinin belirlenmesi. Journal of the Institute of Science and Technology, 11(2), 1302-1310. https://doi.org/10.21597/jist.804539
  3. Alkan Türkuçar, S., Aktaş Karaçelik. A. and Karaköse, M. (2021). Phenolic compounds, essential oil composition, and antioxidant activity of Angelica purpurascens (Avé-Lall.) Gill. Turkish Journal of Chemistry, 45(3), 956-966. https://doi.org/10.3906/kim-2101-28
  4. Arslan, T., Biyiklioglu, Z. and Şentürk, M. (2018). The synthesis of axially disubstituted silicon phthalocyanines, their quaternized derivatives and first inhibitory effect on human cytosolic carbonic anhydrase isozymes hCA I and II, RSC Advances, 8, 10172-10178. https://doi.org/10.1039/C7RA13674A
  5. Arslan, T., Çakır, N., Keleş, T., Biyiklioglu, Z. and Senturk, M. (2019). Triazole substituted metal-free, metallo-phthalocyanines and their water soluble derivatives as potential cholinesterases inhibitors: Design, synthesis and in vitro inhibition study. Bioorganic Chemistry, 90, 103100. https://doi.org/10.1016/j.bioorg.2019.103100
  6. Barut, B., Demirbaş, Ü., Özel, A. and Kantekin, H. (2017a). Novel water soluble morpholine substituted Zn(II) phthalocyanine: Synthesis, characterization, DNA/BSA binding, DNA photocleavage and topoisomerase I inhibition. International Journal of Biological Macromolecules, 105(1), 499-508. https://doi.org/10.1016/j.ijbiomac.2017.07.072
  7. Barut, B., Demirbaş, Ü., Şenocak, A., Özel, A. and Kantekin, H. (2017b). Water soluble axially morpholine disubstituted silicon phthalocyanines: Synthesis, characterisation, DNA/BSA binding, DNA photocleavage properties. Synthetic Metals, 229, 22-32. https://doi.org/10.1016/j.synthmet.2017.05.006
  8. Baş, H. and Biyiklioglu, Z. (2015). Non-aggregated axially naphthoxazin group substituted silicon phthalocyanines: Synthesis and electrochemistry. Journal of Organometallic Chemistry, 791, 238-243. https://doi.org/10.1016/j.jorganchem.2015.05.015
  9. Benzie, I.F.F. and Strain, J.J. (1996). The ferric reducing ability of plasma (FRAP) as a measure of “antioxidant power”: the FRAP assay. Analytical Biochemistry, 239(1), 70-76. https://doi.org/10.1006/abio.1996.0292
  10. Bispo, M., Pereira, P.M.R., Setaro, F., Rodríguez-Morgade, M.S, Fernandes, R., Torres, T. and Tomé, J. P.C. (2018). A galactose dendritic silicon (IV) phthalocyanine as a photosensitizing agent in cancer photodynamic therapy. ChemPlusChem, 83(9), 855-860. https://doi.org/10.1002/cplu.201800370

Kaynak Göster

APA
Aktaş Karaçelik, A., Çakır, V., Baş, H., & Bıyıklıoğlu, Z. (2022). Carbonic anhydrase inhibition and antioxidant activity of the axially naphthoxazin group substituted silicon phthalocyanines. Gümüşhane Üniversitesi Fen Bilimleri Dergisi, 12(1), 227-234. https://doi.org/10.17714/gumusfenbil.1001784