Synthesis and pharmacological evaluation of new methyloxiranylmethoxyxanthone analogues

Woo, Sang-Wook; Kang, Da Hye; Nam, Jung Min; Lee, Chong Soon; Ha, Eun Mi; Lee, Eung Seok; Kwon, Young Joo; Na, Younghwa

doi:10.1016/j.ejmech.2010.06.017

Cited by 17 publications

(7 citation statements)

References 24 publications

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“…The results are shown in Table 2 (compounds of series A and B), Table 3 (compounds of series C) and Table 4 (compounds of series D). Methylseleninic acid (MSA) in PC-3 and etoposide in PC-3 and MCF-7 were used as controls in the cytotoxic assays [ 40 , 41 , 42 ].…”

Section: Resultsmentioning

confidence: 99%

Antioxidant-Prooxidant Properties of a New Organoselenium Compound Library

et al. 2010

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The present study describes the biological evaluation of a library of 59 organo-selenium compounds as superoxide (O2─) generators and cytotoxic agents in human prostate cancer cells (PC-3) and in breast adenocarcinoma (MCF-7). In order to corroborate that the biological activity for selenium compounds depends on the chemical form, a broad structural variety is presented. These structures include selenocyanates, diselenides, selenoalkyl functional moieties and eight newly synthesized symmetrically substituted dithioselenites and selenylureas. Eleven of the derivatives tested showed high levels of superoxide generation in vitro via oxidation of reduced glutathione (GSH) and nine of them were more catalytic than the reference compound, diselenodipropionic acid. Eighteen of the library compounds inhibited cell growth more than or similar to reference chemotherapeutic drugs in PC-3 and eleven were more potent cytotoxic agents than etoposide in the MCF-7 cell line. Considering both parameters (superoxide generation and cell cytotoxicity) compounds B1, C6 and C9 displayed the best therapeutic profiles. Considering that many diselenide compounds can generate superoxide (O2─) in vitro via oxidation of GSH and other thiols, the analogue B1, that contains a diselenide moiety, was selected for a preliminary mechanistic investigation, which . revealed that B1 has apoptogenic effects similar to camptothecin mediated by reactive oxygen species (ROS) in lymphocytic leukemia cells (CCRF-CEM) and affected the MCF-7 cell-cycle in G2/M and S-phases.

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Section: Resultsmentioning

confidence: 99%

Antioxidant-Prooxidant Properties of a New Organoselenium Compound Library

et al. 2010

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“…Meanwhile, an additional 2-epoxypropyl group at C-1 position (compound 1b) drastically improved the IC 50 values to 3.28 and 23.3 µM against MCF-7 and HeLa cells, respectively [102]. It was also reported that xanthone derivatives with halohydrin, methoxy, and amino substituents at C-3 and C-5 positions were also active for topoisomerase inhibition [103,104]. Furthermore, it was reported that DNA crosslinking occurred on the targeted cancer cells after the treatment with the epoxy-xanthones.…”

Section: In Vitro Anticancer Assay Of Xanthone Derivativesmentioning

confidence: 98%

An Update on the Anticancer Activity of Xanthone Derivatives: A Review

et al. 2021

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The annual number of cancer deaths continues increasing every day; thus, it is urgent to search for and find active, selective, and efficient anticancer drugs as soon as possible. Among the available anticancer drugs, almost all of them contain heterocyclic moiety in their chemical structure. Xanthone is a heterocyclic compound with a dibenzo-γ-pyrone framework and well-known to have “privileged structures” for anticancer activities against several cancer cell lines. The wide anticancer activity of xanthones is produced by caspase activation, RNA binding, DNA cross-linking, as well as P-gp, kinase, aromatase, and topoisomerase inhibition. This anticancer activity depends on the type, number, and position of the attached functional groups in the xanthone skeleton. This review discusses the recent advances in the anticancer activity of xanthone derivatives, both from natural products isolation and synthesis methods, as the anticancer agent through in vitro, in vivo, and clinical assays.

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“…Up to now, many benzoxanthone analogues for prospective drug candidates have been obtained [ 5 , 6 , 7 , 8 ]. Some benzoxanthone derivatives have been used as topoisomerase inhibitors and DNA cross-linkers [ 9 , 10 ]. Hurley synthesized bisfuranoxanthones and found the compounds possessed high antitumor activity [ 11 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Anticancer Efficacy Evaluation of Benzoxanthone Compounds toward Gastric Cancer SGC-7901

Fu¹,

Xu²,

Liu³

et al. 2022

Molecules

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Three benzoxanthone derivatives were synthesized through a new photochemical strategy. The in vitro cytotoxic activity of these compounds was evaluated by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay, and their partition coefficients (logP) were measured by shake flask method. The pKa values of the compounds were detected by potentionmetric titration. The interaction of the compounds with calf thymus DNA (CT-DNA) was investigated by electronic absorption, luminescence spectra and viscosity. A molecular docking analysis was performed. The antitumor efficacy of the compounds was evaluated by cell apoptosis, cell cycle arrest, intracellular Ca2+ concentrations and reactive oxygen species (ROS) levels. The mitochondrial membrane potential was assayed using JC-1 (5,5′,6,6′-tetrachloro-1,1,3′,3′-tetraethyl-imidacarbocyanine iodide) as the fluorescence probe. The expression of Bcl-2 family protein, caspase 3 and poly ADP-ribose polymerase (PARP) was explored by western blot. The results showed that the compounds induced apoptosis through a ROS-mediated mitochondrial dysfunction pathway. This work provides an efficient approach to synthesize benzoxanthone derivatives, and is helpful for understanding the apoptotic mechanism.

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Synthesis and pharmacological evaluation of new methyloxiranylmethoxyxanthone analogues

Cited by 17 publications

References 24 publications

Antioxidant-Prooxidant Properties of a New Organoselenium Compound Library

Antioxidant-Prooxidant Properties of a New Organoselenium Compound Library

An Update on the Anticancer Activity of Xanthone Derivatives: A Review

Synthesis, Characterization and Anticancer Efficacy Evaluation of Benzoxanthone Compounds toward Gastric Cancer SGC-7901

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