248584-40-9Relevant academic research and scientific papers
Synthesis and Cytotoxic Activity of the Products of Addition of Thiophenol to Sesquiterpene Lactones
Anikina, L. V.,Klochkov, S. G.,Semakov, A. V.
, p. 906 - 917 (2021/08/25)
Abstract—: Derivatives of sesquiterpene lactones modified at the lactone ring with a thiophenol residue have been synthesized. The resulting conjugates with thiophenol have capacity for the oxidation–elimination reaction by the action of ROS of a tumor cell with the release of initial cytotoxic lactones. It has been proposed to use the resulting sulfur-containing conjugates as ROS-activated prodrugs of sesquiterpene lactones. The antiproliferative properties of the conjugates have been examined on tumor and pseudonormal cell lines. The cytotoxicity of the conjugates is lower than that of parent lactones; however, in some cases, as with the conjugates of alantolactone with artemisiten, it remains moderate in all tumor cell lines tested.
Phenylthio-derivatives of α-methylene-γ-lactones as pro-drugs of cytotoxic agents
Fardella, Giuseppe,Barbetti, Paolo,Grandolini, Giuliano,Chiappini, Ione,Ambrogi, Valeria,Scarcia, Vito,Furlani Candiani, Ariella
, p. 515 - 523 (2007/10/03)
A series of substituted phenylthio-derivatives of grosheimin (1), a natural cytotoxic guaianolide, were investigated with the aim of providing insight into their mechanism of action as cytotoxic agents against KB cell lines. Hydrolysis data, kinetics, in the presence and in the absence of H2O2, and the valuation of lipophilicity were correlated with cytotoxicity values and with Hammett-σ-values of substituents (R) at the thiophenol ring. These compounds behave as 'pro-drugs' which release the cytotoxic agent grosheimin by sulphur-oxidation promoted by H2O2 and subsequent retro- elimination which depends on the nature and position of the R substituent.
