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Article
2023

Synthesis, characterization, theoretical and experimental anticancer evaluation of novel cocrystals of 5-fluorouracil and Schiff bases against SW480 colorectal carcinoma

Abstract (English)

The chemotherapeutic agent known as 5-fluorouracil (5-FU) is an artificial fluoropyrimidine antimetabolite that has been widely used for its antineoplastic properties. Cocrystals of 5-fluorouracil (5-FU) with five different Schiff bases (benzylidene-urea (BU), benzylidene-aniline (BA), salicylidene-aniline (SA), salicylidene-phenylhydrazine (SPH), and para-hydroxy benzylideneaniline (HBA)) are reported in this study. The newly synthesized cocrystals were analyzed by FTIR and PXRD. In this study, we investigated the antitumor efficacy of 5-FU derivatives in SW480 colon cancer cells via MTT assay at varying dose concentrations. Molecular docking was performed to predict the binding mechanism of TS with various 5-FU complexes. FTIR revealed the presence of respective functional groups in the prepared cocrystals. The frequencies (v) of N-H (3220.24 cm−1) and carbonyl groups (1662.38 cm−1) in the spectrum of 5-FU shifted considerably in all derivative cocrystal new interactions. There was a noticeable transformation in the PXRD peak of 5-FU at 2θ = 28.37° in all derivatives. The novelty of the present study lies in the fact that 5-FU-BA showed an anticancer potential IC50 (6.4731) far higher than that of 5-FU (12.116), almost comparable to that of the reference drug doxorubicin (3.3159), against SW480 cancel cell lines, followed by 5-Fu-HBA (10.2174). The inhibition rates of 5-FU-BA and 5-FU-HBA were highest among the derivatives (99.85% and 99.37%, respectively) in comparison with doxorubicin (97.103%). The results revealed that the synthesized 5-FU cocrystals have promising antitumor efficacy compared with previously reported 5-FU and 5-FU. The activities of the cocrystals were rationalized by a molecular modeling approach to envisage binding modes with the target cancer protein.

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Pharmaceutics, 15 (2023), 7, 1929. https://doi.org/10.3390/pharmaceutics15071929. ISSN: 1999-4923
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660 Chemical engineerin

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@article{Jubeen2023, url = {https://hohpublica.uni-hohenheim.de/handle/123456789/16226}, doi = {10.3390/pharmaceutics15071929}, author = {Jubeen, Farhat and Jabeen, Ishrat and Aftab, Usman et al.}, title = {Synthesis, characterization, theoretical and experimental anticancer evaluation of novel cocrystals of 5-fluorouracil and Schiff bases against SW480 colorectal carcinoma}, journal = {Pharmaceutics}, year = {2023}, volume = {15}, number = {7}, }