Convenient route to benzo[1,2,3]selenadiazole–isoxazole hybrids and evaluation of their in vitro cytotoxicity

Oubella, Ali; Fawzi, Mourad; Bimoussa, Abdoullah; Ousidi, Abdellah N'ait; Auhmani, Aziz; Riahi, Abdelkhalek; Robert, Anthony; Firdoussi, Larbi El; Morjani, Hamid; Itto, My Youssef Ait

doi:10.1007/s11696-022-02083-6

Cited by 12 publications

(7 citation statements)

References 61 publications

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“…The cytotoxic activity was evaluated using the MTT assay. [39][40][41][42][43] Doxorubicin (DOX) was used as a positive, and the IC 50 values are presented in Table 1.…”

Section: In Vitro Anti-proliferative Activitymentioning

confidence: 99%

Synthesis and Biological Evaluation of Novel Thiazole Analogs with Both Anti‐Proliferative and Mechanistic Analyses and Molecular Docking Studies

et al. 2022

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Herein, we report the synthesis of a novel series of βhimachalene derivatives, including semicarbazones, thiosemicarbazones, and thiazoles. The structures of these compounds were elucidated by NMR, IR, and HRMS analysis methods. The in vitro antitumor activity of these compounds was evaluated by the MTT assay against four human cancer cell lines, such as fibrosarcoma (HT-1080), breast adenocarcinoma (MCF-7 and MDA-MB-231), and lung carcinoma (A-549), and the results indicated that all compounds showed moderate to significant cytotoxic activities against all cancer cell lines with IC 50 values ranging from 7.19 � 0.30 to 50 μM. The mechanism of action of the most cytotoxic compounds 2 b and 7 b suggested that they induced apoptosis through caspase-3/7 activation, and elicited G2/M-phase arrest with the loss of mitochondrial membrane potential in HT-1080 cells. The molecular docking showed that compounds 2 b and 7 b activated the caspase-3 by forming a stable protein-ligand complex.

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“…The cytotoxic activity was evaluated using the MTT assay. [39][40][41][42][43] Doxorubicin (DOX) was used as a positive, and the IC 50 values are presented in Table 1.…”

Section: In Vitro Anti-proliferative Activitymentioning

confidence: 99%

Synthesis and Biological Evaluation of Novel Thiazole Analogs with Both Anti‐Proliferative and Mechanistic Analyses and Molecular Docking Studies

et al. 2022

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“…In comparison to conventional chemotherapeutic agents, organoselenium compounds such as 10–14 have excellent cytotoxic properties with low side effects [ 99 , 102 , 105 , 106 , 109 ]. Recent studies have also pointed to selenium-based nanomedicines, suggesting the design of selenium nanoparticles as an efficient strategy to improve drug delivery and thus cancer treatment [ 190 ].…”

Section: Discussionmentioning

confidence: 99%

“…Five benzo[1,2,3]selenodiazole hybrids with an isoxazole moiety were obtained by Oubella et al [ 109 ]. Isoxazole derivatives (e.g., luminespid ) [ 110 ] are described as potent anticancer compounds [ 111 ]; thus, combining this moiety with selenium-containing derivatives may allow for compounds with greater anticancer activity.…”

Section: Selenium-containing Compounds As Therapeutic Agentsmentioning

confidence: 99%

“…Isoxazole derivatives (e.g., luminespid ) [ 110 ] are described as potent anticancer compounds [ 111 ]; thus, combining this moiety with selenium-containing derivatives may allow for compounds with greater anticancer activity. The final five benzoselenadizole-isoxazoles were estimated by MTT assay on four tumour lines (HT1080, A549, MCF-7 and MDA-MB-231) [ 109 ]. Results (after 24 h) showed lower cytotoxic activity of these compounds (IC 50 from 18.7 to >100 µM) in comparison with their semicarbazone precursors (IC 50 from 10.9 to 21.6 µM) with the most promising compound in this series represented by 14 ( Figure 7 ).…”

Section: Selenium-containing Compounds As Therapeutic Agentsmentioning

confidence: 99%

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Selenium-Containing Agents Acting on Cancer—A New Hope?

et al. 2022

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Selenium-containing agents are more and more considered as an innovative potential treatment option for cancer. Light is shed not only on the considerable advancements made in understanding the complex biology and chemistry related to selenium-containing small molecules but also on Se-nanoparticles. Numerous Se-containing agents have been widely investigated in recent years in cancer therapy in relation to tumour development and dissemination, drug delivery, multidrug resistance (MDR) and immune system-related (anti)cancer effects. Despite numerous efforts, Se-agents apart from selenocysteine and selenomethionine have not yet reached clinical trials for cancer therapy. The purpose of this review is to provide a concise critical overview of the current state of the art in the development of highly potent target-specific Se-containing agents.

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“…[20,21] They have also been used as useful intermediate supports in organic synthesis. [22,23] At the structural level, many research have shown that the major biological properties of 1,3,4-thiadiazole are due to the presence of the toxophoric ═N-C-S moiety. [24,25] In addition, the interaction of thiadiazoles with several proteins in a noncovalent manner has been attributed to the sulfur atom of the compounds.…”

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confidence: 99%

Novel isoxazoline‐linked 1,3,4‐thiadiazole hybrids as anticancer agents: Design, synthesis, biological evaluation, molecular docking, and molecular dynamics simulation

Oubella

Byadi

Bimoussa

et al. 2022

Archiv der Pharmazie

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In the current study, natural (R)‐carvone was utilized as a starting material for the efficient synthesis of two series of isoxazoline derivatives bearing the 1,3,4‐thiadiazole moiety. The new compounds were obtained in good yields and were characterized by 1H and 13C NMR and HRMS analysis. The newly synthesized monoterpenic isoxazoline 1,3,4‐thiadiazole and their thiosemicarbazone intermediate derivatives were evaluated for their anticancer activity in four cancer cell lines (HT‐1080, A‐549, MCF‐7, and MDA‐MB‐231). Most of the synthesized compounds exhibited moderate to high anticancer effects. Compound 13c showed the highest anticancer activity with IC50 values ranging from 19.33 ± 1.81 to 34.81 ± 3.03 µM. Further investigation revealed that compounds 12e and 13c could inhibit the cell growth of HT‐1080 and MCF‐7 cells by inducing apoptosis through caspase‐3/7 activation. The apoptotic effect was accompanied by an S phase and G2/M cell cycle arrest for 13c and 12e, respectively. Compounds 12e and 13c were assessed in silico using molecular docking and molecular dynamics. We found that compound 13c is moderately active against the caspase‐3 protein, which triggers apoptosis via intrinsic and extrinsic routes, making compound 13c a promising candidate to activate the proapoptotic protein (caspase‐3).

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Convenient route to benzo[1,2,3]selenadiazole–isoxazole hybrids and evaluation of their in vitro cytotoxicity

Cited by 12 publications

References 61 publications

Synthesis and Biological Evaluation of Novel Thiazole Analogs with Both Anti‐Proliferative and Mechanistic Analyses and Molecular Docking Studies

Synthesis and Biological Evaluation of Novel Thiazole Analogs with Both Anti‐Proliferative and Mechanistic Analyses and Molecular Docking Studies

Selenium-Containing Agents Acting on Cancer—A New Hope?

Novel isoxazoline‐linked 1,3,4‐thiadiazole hybrids as anticancer agents: Design, synthesis, biological evaluation, molecular docking, and molecular dynamics simulation

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