Biologically active sulfur-containing polyamides as promising anticancer materials

Gadeer R Ashour; Sara A Alqarni; Youssef O Al-Ghamdi; W Abd El-Fattah; Abeer M Alosaimi; Mahmoud A Hussein

doi:10.1080/15685551.2023.2205734

Biologically active sulfur-containing polyamides as promising anticancer materials

Des Monomers Polym. 2023 May 9;26(1):150-162. doi: 10.1080/15685551.2023.2205734. eCollection 2023.

Authors

Gadeer R Ashour¹, Sara A Alqarni², Youssef O Al-Ghamdi³, W Abd El-Fattah^{4

5}, Abeer M Alosaimi⁶, Mahmoud A Hussein^{7

8}

Affiliations

¹ Department of Chemistry, Faculty of Applied Sciences, Umm Al Qura University, Makkah, Saudi Arabia.
² Department of Chemistry, College of Science, University of Jeddah, Jeddah, Saudi Arabia.
³ Department of Chemistry, College of Science Al-zulfi, Majmaah University, Al-Majmaah, Saudi Arabia.
⁴ Chemistry Department, College of Science, IMSIU (Imam Mohammad Ibn Saud Islamic University), Riyadh, kingdom of Saudi Arabia.
⁵ Chemistry Department, Faculty of Science, Port-Said University, Port-Said, Egypt.
⁶ Department of Chemistry, Faculty of Science, Taif University, Taif, Saudi Arabia.
⁷ Chemistry Department, Faculty of Science, King Abdulaziz University, Jeddah, Saudi Arabia.
⁸ Polymer Chemistry Lab. Chemistry Department, Faculty of Science, Assiut University, Assiut, Egypt.

Abstract

Thiazol-based molecules have practically infinite biological implementation. Today, there are many medical applications for compounds containing the thiazole moiety owing to their presence in most clinically applied anticancer drugs, such as dasatinib, dabrafenib, ixabepilone, patellamide A and epothilone. In this study, the polycondensation, of a new group of thiazole-containing polyamides with the formulas PA_1-4 was carried out by the interaction of 2-aminothiazole diphenyl sulfide and variable diacid chlorides in dimethyl formamide in the presence of potassium carbonate anhydrous as a catalyst. Fourier transform-infrared spectroscopy (FTIR) was initially used to figure out the PA_1-4 structures, which were further characterized using solubility, gel permeation chromatography (GPC), X-ray diffraction analyses (XRD) and scanning electron microscopy (SEM). The solubility results revealed that the presence of heteroaromatic thiazole ring units and sulfur content in the polyamides main chain, made the solubility easier as it increases the chain packing distance. From the values of average molecular weight, it was clear that all synthesized polyamides have almost the same chain length which ranged from 37,561.80 to 39,827.66. Moreover, the thermogravimetric analysis (TGA) confirm that PA_1-4 were thermally stable even at high temperatures especially the polyamides which were synthesized from aromatic diacid chlorides. Furthermore, the newly synthesized polyamides were investigated for their antimicrobial properties against different species of Gram-positive and Gram-negative bacteria and also against different fungi. The results revealed that compound PA₂ showed the highest antibacterial activity. Also, their inhibitory activity against breast carcinoma cells (MCF-7 cell line) and colon carcinoma cells (HCT cell line) was evaluated. It was clear that there was an enhancement in the anticancer activity for the synthesized polyamides owing to the presence of the thiazole moiety as well as sulfur linkage. According to the results of the 50% inhibitory concentration (IC50), the synthesized polymers were found to be more active against the MCF-7 cell line than the HCT cell line.

Keywords: Sulfur-containing polyamides; anticancer agents; biological interest; polyamide derivatives; thermal properties.

Publication types

Review