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Synthesis, biological evaluation (antioxidant, antimicrobial, enzyme inhibition, and cytotoxic) and molecular docking study of hydroxy methoxy benzoin/benzil analogous

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info:eu-repo/semantics/closedAccess

Tarih

2021

Yazar

Yaylı, Nurettin
Kılıç, Gözde
Kahriman, Nuran
Kanbolat, Şeyda
Bozdeveci, Arif
Karaoğlu, Şengül Alpay
Aliyazıcıoğlu, Rezzan
Sellitepe, Hasan Erdinç
Doğan, İnci Selin
Aydın, Ali
Tatar, Gizem

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Künye

Yaylı, N., Kılıç, G., Kahriman, N., Kanbolat, Ş., Bozdeveci, A., Alpay Karaoğlu, Ş., Aliyazıcıoğlu, R., Erdinç Sellitepe, H., Selin Doğan, İ., Aydın, A., & Tatar, G. (2021). Synthesis, biological evaluation (antioxidant, antimicrobial, enzyme inhibition, and cytotoxic) and molecular docking study of hydroxy methoxy benzoin/benzil analogous. Bioorganic Chemistry, 115, 105183. https://doi.org/10.1016/j.bioorg.2021.105183

Özet

In this work, due to the biological activity evaluation, a series of hydroxy methoxy benzoins (1–8), benzils (10–16) and methoxy benzoin/benzil-O-β-D-glucosides (17–28) were synthesized. Antioxidant (FRAP, CUPRAC, DPPH), antimicrobial (16 microorganisms, and two yeast), enzyme inhibition (α-amylase, α-glucosidase, AChE, BChE, and tyrosinase) of all synthesized benzoin/benzil analogs were investigated. Benzoins (1–8) showed the most effective antioxidant properties compared to all three methods. Compound 28 against α-amylase, compound 9 against α-glucosidase, compound 11 against AChE, compound 2 against BChE, and compound 13 against tyrosinase showed the best activities with the better or similar IC50 values as used standards. Hydroxy methoxy benzoin compounds (1–8) among all four groups were seen as the most effective against the tested microorganism. Molecular docking analysis showed that all tested compounds 1–28 (0.01–2.22 µM) had the best binding affinity against AChE enzyme. Cytotoxic effects of the many of compounds (1–16, 21, and 24) also investigated and it was found that they caused different effects in different cells. The LDH tests of compounds 1a + b, 4, 7, 8, 9, 11, 12, 21, and 24, seemed to be effective compared to the positive control cisplatin. The cytotoxicity of compounds 6 (9.24%) for MCF7 cancer cells, 8 (5.16%) and 4 (8.26%) for HT29 cancer cells, 24 (9.84%) for Hep3B cells and 8 (8.52%), 7 (5.70%), 4 (6.94) and 9 (7.22%) for C6 cells were at normal values. And also cytotoxic activity of four compounds (5, 9, 21, and 24) among the all synthetic groups, were evaluated to the HeLa and RPE. Compound 5 showed anticancer activity on HeLa and RPE cancer cells as much as or better than cisplatin which was used as standard. © 2021 Elsevier Inc.

Kaynak

Bioorganic Chemistry

Cilt

115

Bağlantı

https://doi.org/10.1016/j.bioorg.2021.105183
https://hdl.handle.net/11436/7218

Koleksiyonlar

  • FEF, Biyoloji Bölümü Koleksiyonu [588]
  • PubMed İndeksli Yayınlar Koleksiyonu [2443]
  • Scopus İndeksli Yayınlar Koleksiyonu [5931]



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