Synthesis, Anticancer Activity and Carbonic Anhydrase Inhibitory Activity of new Thiadiazole-hydrazone Derivatives-Reference-Cited by-同舟云学术

Synthesis, Anticancer Activity and Carbonic Anhydrase Inhibitory Activity of new Thiadiazole-hydrazone Derivatives

Published:2023-06-30 Issue:2 Volume:44 Page:258-262
ISSN:2587-2680
Container-title:Cumhuriyet Science Journal
language:
Short-container-title:

Author:

BOSTANCI Hayrani Eren¹^ORCID,ACAR ÇEVİK Ulviye²^ORCID

Affiliation:

1. SİVAS CUMHURİYET ÜNİVERSİTESİ, ECZACILIK FAKÜLTESİ, ECZACILIK PR.

2. ANADOLU UNIVERSITY, FACULTY OF PHARMACY, PHARMACY PR.

Abstract

In five steps, new compounds 5a, 5b of thiadiazole-hydrazone derivatives were synthesized. Various spectral methods, such as 1H NMR, 13C NMR, and elemental analyses, were used to clarify the structures of the compounds. Three cancer cell lines (MCF7, MDA, and HT-29) and one healthy cell line (L929) were tested for the cytotoxicity activity of synthetic compounds, as well as their inhibitory action against carbonic anhydrase I and II isoenzymes (hCA I and hCA II). Among them, the compound 5b exhibited remarkable CA inhibitory activities compared to a standard inhibitor with IC50 values at of 27 µM for hCA I and 33,46 µM for hCA II. The compounds have been found to be ineffective against cancer cell lines. Furthermore, the compounds were found to be non-toxic to the healthy cell line.

Publisher

Cumhuriyet University

Subject

General Medicine

Reference31 articles.

1. [1] Tapera M., Kekeçmuhammed H., Tüzün B., Sarıpınar E., Koçyiğit Ü. M., Yıldırım E., Doğen M., Zorlu Y., Synthesis, carbonic anhydrase inhibitory activity, anticancer activity and molecular docking studies of new imidazolyl hydrazone derivatives, J. Mol. Struct., 1269 (2022) 133816.

2. [2] Bilginer S., Bardaweel S. K., Demir Y., Gulcin I., & Kazaz C., Synthesis, cytotoxicities, and carbonic anhydrase inhibition activities of pyrazoline–benzenesulfonamide derivatives harboring phenol/polyphenol moieties, Med. Chem. Res., (2022) 1-11.

3. [3] Bonardi A., Bua S., Combs J., Lomelino C., Andring J., Osman S. M., Toti A., Mannelli L.D.C., Gratteri P., Ghelardini C., McKennac R., Nocentini A., The three-tails approach as a new strategy to improve selectivity of action of sulphonamide inhibitors against tumour-associated carbonic anhydrase IX and XII, J. Enzyme Inhib. Med. Chem., 37(2022) 930-939.

4. [4] Arrighi G., Puerta A., Petrini A., Hicke F. J., Nocentini A., Fernandes M. X., Padron J.M., Supuran C.T., Fernandes-Bolanos J.M., López Ó., Squaramide-Tethered Sulfonamides and Coumarins: Synthesis, Inhibition of Tumor-Associated CAs IX and XII and Docking Simulations, Int. J. Mol. Sci., 23 (2022) 7685.

5. [5] Tawfik H. O., Petreni A., Supuran C. T., & El-Hamamsy M. H., Discovery of new carbonic anhydrase IX inhibitors as anticancer agents by toning the hydrophobic and hydrophilic rims of the active site to encounter the dual-tail approach, Eur. J. Med. Chem., 232 (2022) 114190.