Design and synthesis of sulfur-containing butylated hydroxytoluene: antioxidant potency and selective anticancer agent

Abstract

In the present study, a series of multipotent antioxidants (MPAOs), namely sulfur-containing BHT (S-BHT), derivatives were rationally designed and synthesized, and their inhibitory activities against free radicals and human cancer cell lines, HT29 (colon cancer) and MCF7 (breast cancer) were further evaluated. The experimental results showed that the Six out-of-eight S-BHT compounds had excellent antioxidant activity against DPPH radical with major enhancement compared to BHT. Among them, compounds 2b, 2a and 3b attained over 45% lower IC 50 values than BHT. In vitro cytotoxicity, MTT assay was carried out using two human cancer cell lines, HT29 (colon cancer) and MCF7 (breast cancer) in addition to their non-tumorigenic counterparts to explore selectivity. In line with antioxidant activity, compounds 2a and 2b displayed the highest cytotoxicity effect on both cancer types. Interestingly, 2b not only exhibited superior cancer inhibition but also scored high selectivity index (SI = 5.2, 12.5) in colon and breast tissues, respectively, exceeding that of the standard chemotherapeutic drugs used 5-Fluorouracil (5-FU) and Tamoxifen (Tmx), with lower IC 50 values. The results indicated that the symmetric S-BHT derivatives were significantly enhanced by the antioxidant potency and their ability as useful and promising selective anticancer agents.

Semicarbazide and thiosemicarbazide containing butylated hydroxytoluene moiety: new potential antioxidant additives for synthetic lubricating oil

“…DPPH radical scavenging assay had been carried out according to protocol reported by Ahmad et al with some modifications. 17 Around 0.2 mM of DPPH solution in methanol was added to various concentrations; 10, 20, 40 and 60 μM of antioxidant samples. A negative control (no sample) is using same concentration of DPPH solution.…”

Antioxidants for the Treatment of Breast Cancer: Are We There Yet?

“…Interestingly, BHT, together with BHA, PG and BuPB, showed both estrogenic and anti-estrogenic effects in breast cancer [ 184 ]. S-BHT, a derivative of BHT, demonstrated a potent antioxidant effect as a free radical scavenger and inhibitory activity against human colon and breast cancer cell lines [ 185 ]. Currently, in clinical trials, only NAC is being studied in breast cancer patients, as shown in Table 11 .…”

Synthesis, Redox Properties and Antibacterial Activity of Hindered Phenols Linked to Heterocycles

“…Experimental data report on the cytotoxicity against tumor lines of epithelioid carcinoma of the cervix uteri (M-Hela) and breast adenocarcinoma (MCF-7) of 2,6-diaminopyridine derivatives [21]. Symmetric S-BHT derivatives containing 1,3,4-thiadiazole fragments showed antioxidant potency and potential to be useful and promising selective agents against breast and colon cancer [22].…”