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. 2023 Mar 23;18(3):e0283289.
doi: 10.1371/journal.pone.0283289. eCollection 2023.

Synthesis of novel sulphamethoxazole derivatives and exploration of their anticancer and antimicrobial properties

Rita Vaickelionienė  1 , Vilma Petrikaitė  2   3 , Irena Vaškevičienė  4 , Alvydas Pavilonis  5 , Vytautas Mickevičius  1
Affiliations

Synthesis of novel sulphamethoxazole derivatives and exploration of their anticancer and antimicrobial properties

Rita Vaickelionienė et al. PLoS One. .

Abstract

A series of new derivatives based on sulfamethoxazole were designed and synthesized in this study. The structures of the new compounds were confirmed based on a comprehensive characterization of spectral data by applied IR and 1H as well as 13C NMR spectroscopy. The prepared compounds were tested for their anticancer and antimicrobial properties. Hydrazone 16b demonstrated convincing anticancer effect against all tested cell cultures such as human prostate carcinoma PPC-1 and human kidney carcinoma CaKi-1 cell lines, and human fibroblasts HF, n = 3. The most promising compound 16b showed higher activity against CaKi-1 cell line than the anticancer drugs axitinib and pazopanib used to treat renal cancer. Also, it was more active in the PPC-1 cell line compared to the approved PARP inhibitor Olaparib. Hydrazone 16b was also found to possess good antimicrobial properties against gram-positive bacteria strains of Staphylococcus aureus, Staphylococcus epidermidis, as well as Bacillus cereus.

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Conflict of interest statement

The authors have declared that no competing interests exist.

Figures

Fig 1
Fig 1. Isoxazole-based pharmaceuticals.
Fig 2
Fig 2. Effect of compounds on cancer cell viability at 100 μM concentration against human prostate carcinoma PPC-1, human kidney carcinoma CaKi-1 cell lines, and human fibroblasts HF, n = 3.
Fig 3
Fig 3. EC50 values of the most active sulfamethoxazole derivatives 15e, 15k, 16b, and 16d, obtained by MTT assay, after 72 hours of incubation, n = 3.
Fig 4
Fig 4. Antimicrobial activity of compound 16b in a liquid medium, expressed as half maximal effect concentration (EC50 values), n = 3.
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