Abstract
Several indolylquinone analogues of perezone, a natural sesquiterpene quinone, were characterized in this work by theoretical methods. In addition, some physicochemical, toxicological and metabolic properties were predicted using bioinformatics software. The predicted physicochemical properties are in agreement with the solubility and cLogP values, the penetration across the cell membrane, and absorption values, as well as with a possible apoptosis-activated mechanism of cytotoxic action. The toxicological predictions suggest no mutagenic, tumorigenic or reproductive effects of the four target molecules. Complementarily, the results of a performed docking study show high scoring values and hydrogen bonding values in agreement with the cytotoxicity IC50 value ranking, i.e., indolylmenadione > indolylperezone > indolylplumbagine > indolylisoperezone. Consequently, it is possible to suggest an appropriate apoptotic pathway for each compound. Finally, potential metabolic pathways of the molecules were proposed.
Highlights
Many secondary metabolites isolated from plant specimens are quinones [1]
Our research group recently reported the cytotoxic activity of 1–4 (Figure 2a) in a human breast cancer cell line (MDA-MB-231) [23]
58.33 kcal/mol) and largest reactivity. These results suggest a possible correlation between the chemical stability and the breast cancer cell cytotoxicity
Summary
Many secondary metabolites isolated from plant specimens are quinones [1]. Perezone or pipitzaoic acid (Figure 1), obtained from specimens of the roots of Perezia (currently Acourtia) byRío de la Loza, is reportedly the first secondary metabolite isolated in the New World [2]. The molecule has been the focus of many chemical, structural and biological studies [3,4,5,6,7,8] It has been used in an interesting green route for the production of various derivatives [9] and many of its pharmacological effects have been reported [10,11,12,13,14]. As the indolylquinone moiety is present in many natural products with interesting biological activities [15,16], the promising pharmaceutical use of the indolylquinones has attracted attention for the synthesis of new molecules of this class
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
