Design, Synthesis, Molecular Docking, and Biological Evaluation of New Emodin Anthraquinone Derivatives as Potential Antitumor Substances

Abstract

The emodin anthraquinone derivatives are generally used in traditional Chinese medicine due to their various pharmacological activities. In the present study, a series of emodin anthraquinone derivatives have been designed and synthesized, among which 1,3‐dihydroxy‐6,8‐dimethoxyanthracene‐9,10‐dione is a natural compound that has been synthesized for the very first time, and 1,3‐dimethoxy‐5,8‐dimethylanthracene‐9,10‐dione is a compound that has never been reported earlier. Interestingly, while total seven of these compounds showed neuraminidase inhibitory activity in influenza virus with inhibition rate more than 50 %, specific four compounds exhibited significant inhibition of tumor cell proliferation. The further results demonstrate that 1,3‐dimethoxy‐5,8‐dimethylanthracene‐9,10‐dione showed the best anticancer activity among all the synthesized compounds by inducing highest apoptosis rate to HCT116 cancer cells and arresting their G0/G1 cell cycle phase, through elevation of intracellular level of reactive oxygen species (ROS). Moreover, the binding of 1,3‐dimethoxy‐5,8‐dimethylanthracene‐9,10‐dione with BSA protein has thoroughly been investigated. Altogether, this study suggests the neuraminidase inhibitory activity and antitumor potential of the new emodin anthraquinone derivatives.

Journey of anthraquinones as anticancer agents – a systematic review of recent literature

“…Moreover, it displayed good apoptosis induction by G0/G1 cell cycle arrest and increased the reaction oxygen species at an intracellular level. 84 In another study, Li et al evaluated S. lycopersici . Associated with D. gemmacea and isolated two new anthraquinone derivatives, alterporriol Y and macrosporin 2-O-α- d -glucopyranoside.…”

Is Emodin with Anticancer Effects Completely Innocent? Two Sides of the Coin

“…The binding of 1,3-dimethoxy-5,8-dimethyltracene-9,10-dione with the BSA protein has also been extensively studied. Therefore, this research suggested the neuraminidase inhibitory effect and antitumor activity of the novel emodin anthraquinone derivatives [181]. A novel series of emodin derivatives was contrived and assessed for their in vitro proliferative effect.…”

The Health Benefits of Emodin, a Natural Anthraquinone Derived from Rhubarb—A Summary Update

“…The most recent research results indicate that emodin regulates cell cycle in non-small lung cancer (NSCLC) through hyaluronan synthase 2 (HA2)-HA-CD44/receptor for the hyaluronic acid-mediated motility (RHAMM) interaction-dependent signaling pathway [38]. Li et al [39] synthesized new emodin derivatives, which were further tested for antitumor activity against HCT116 cancer cells.…”