Azido derivatives of sesquiterpene lactones: Synthesis, anticancer proliferation, and chemistry of nitrogen-centered radicals DOI Creative Commons

Yahaira Reyes,

Enoch K. Larrey,

Rupak Pathak

и другие.

Results in Chemistry, Год журнала: 2024, Номер 9, С. 101643 - 101643

Опубликована: Июль 1, 2024

Sesquiterpene lactones (SLs) such as parthenolide (PTL) and dehydroleucodine (DhL) selectively kill cancer cells without exerting normal tissue toxicity, potentially due to presence of α-methylene-γ-lactone (αMγL) fragment. We hypothesize that the addition an azido group αMγL fragment PTL or DhL further augments their anticancer properties well radiation sensitivity cells. Azido-SLs containing at C14 methyl position (i.e., azido-melampomagnolide B, AzMMB) while preserving mechanistically crucial exomethylene unit were also prepared. Sham-irradiated unirradiated control) irradiated human breast (MCF7) treated with different concentrations azido-PTL (AzPTL) azido-DhL (AzDhL) along parental SLs. Proliferation rate MCF7 measured by MTT-assay, colony forming ability was determined formation assay. Both AzPTL AzDhL significantly suppress proliferation MCF-7 suppressed ability, not cellular proliferation, following irradiation a greater extent than lower (5 10 μM). Electron spin resonance (ESR) studies performed employing gamma-irradiated homogeneous supercooled aqueous solutions investigate radical through radiation-mediated prehydrated electrons azide follow subsequent reactions these radicals. In AzPTL, tertiary carbon-centered plausibly via metastable aminyl observed, whereas produced both π-aminyl α-azidoalkyl These radicals may contribute antitumor activities AzDhL.

Язык: Английский

Azido derivatives of sesquiterpene lactones: Synthesis, anticancer proliferation, and chemistry of nitrogen-centered radicals DOI Creative Commons

Yahaira Reyes,

Enoch K. Larrey,

Rupak Pathak

и другие.

Results in Chemistry, Год журнала: 2024, Номер 9, С. 101643 - 101643

Опубликована: Июль 1, 2024

Sesquiterpene lactones (SLs) such as parthenolide (PTL) and dehydroleucodine (DhL) selectively kill cancer cells without exerting normal tissue toxicity, potentially due to presence of α-methylene-γ-lactone (αMγL) fragment. We hypothesize that the addition an azido group αMγL fragment PTL or DhL further augments their anticancer properties well radiation sensitivity cells. Azido-SLs containing at C14 methyl position (i.e., azido-melampomagnolide B, AzMMB) while preserving mechanistically crucial exomethylene unit were also prepared. Sham-irradiated unirradiated control) irradiated human breast (MCF7) treated with different concentrations azido-PTL (AzPTL) azido-DhL (AzDhL) along parental SLs. Proliferation rate MCF7 measured by MTT-assay, colony forming ability was determined formation assay. Both AzPTL AzDhL significantly suppress proliferation MCF-7 suppressed ability, not cellular proliferation, following irradiation a greater extent than lower (5 10 μM). Electron spin resonance (ESR) studies performed employing gamma-irradiated homogeneous supercooled aqueous solutions investigate radical through radiation-mediated prehydrated electrons azide follow subsequent reactions these radicals. In AzPTL, tertiary carbon-centered plausibly via metastable aminyl observed, whereas produced both π-aminyl α-azidoalkyl These radicals may contribute antitumor activities AzDhL.

Язык: Английский

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