Synthesis and biological evaluation of benzyl styrylsulfonyl derivatives as potent anticancer mitotic inhibitors

Chahrour, Osama; Abdalla, Ashraf N.; Lam, Frankie; Midgley, Carol A.; Wang, Shudong

doi:10.1016/j.bmcl.2011.03.041

Cited by 17 publications

(9 citation statements)

References 15 publications

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“…Antiproliferative effect of various thymoquinone analogues was tested with six human cell lines and the lead compound, ON01910, blocked the cancer cells and, furthermore, molecule OC2-23 was ten times more effective than the lead compound, ON01910 [155]. The other derivatives of thymoquinone such as 4-acylhydrazones and 6-Alkyl were also tested for growth inhibition in human HL-60 leukemia, 518A2 melanoma, KB-V1/Vb1 cervix, and MCF-7/Topo breast carcinoma cells.…”

Section: Role Of Analogues Of Tq In Cancermentioning

confidence: 99%

“…A recent study showed that Poloxin, a synthetic derivative of thymoquinone play a role in the induction of mitotic arrest and prolongs the mitotic duration, accompanied by Plk1's (member of Polo-like kinases) mislocalization at kinetochores and centrosomes with reduced γ -tubulin [ 154 ]. Antiproliferative effect of various thymoquinone analogues was tested with six human cell lines and the lead compound, ON01910, blocked the cancer cells and, furthermore, molecule OC2-23 was ten times more effective than the lead compound, ON01910 [ 155 ]. The other derivatives of thymoquinone such as 4-acylhydrazones and 6-Alkyl were also tested for growth inhibition in human HL-60 leukemia, 518A2 melanoma, KB-V1/Vb1 cervix, and MCF-7/Topo breast carcinoma cells.…”

Section: Role Of Analogues Of Tq In Cancermentioning

confidence: 99%

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Therapeutic Implications of Black Seed and Its Constituent Thymoquinone in the Prevention of Cancer through Inactivation and Activation of Molecular Pathways

Rahmani

Alzohairy

Khan

et al. 2014

Evidence-Based Complementary and Alternative Medicine

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The cancer is probably the most dreaded disease in both men and women and also major health problem worldwide. Despite its high prevalence, the exact molecular mechanisms of the development and progression are not fully understood. The current chemotherapy/radiotherapy regime used to treat cancer shows adverse side effect and may alter gene functions. Natural products are generally safe, effective, and less expensive substitutes of anticancer chemotherapeutics. Based on previous studies of their potential therapeutic uses, Nigella sativa and its constituents may be proved as good therapeutic options in the prevention of cancer. Black seeds are used as staple food in the Middle Eastern Countries for thousands of years and also in the treatment of diseases. Earlier studies have shown that N. sativa and its constituent thymoquinone (TQ) have important roles in the prevention and treatment of cancer by modulating cell signaling pathways. In this review, we summarize the role of N. sativa and its constituents TQ in the prevention of cancer through the activation or inactivation of molecular cell signaling pathways.

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Section: Role Of Analogues Of Tq In Cancermentioning

confidence: 99%

Section: Role Of Analogues Of Tq In Cancermentioning

confidence: 99%

Therapeutic Implications of Black Seed and Its Constituent Thymoquinone in the Prevention of Cancer through Inactivation and Activation of Molecular Pathways

Rahmani

Alzohairy

Khan

et al. 2014

Evidence-Based Complementary and Alternative Medicine

View full text Add to dashboard Cite

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“…Compounds 5a – 2p were synthesized from the reaction of 2a – 2b with 4a – 4o in the presence of TEA [ 25 ]. Finally, the sulfides 5a – 5p were oxidized to obtain the corresponding sulfoxides ( 6a – 6p ) with H 2 O 2 in acetic acid [ 27 ]. All the synthesized compounds were purified using recrystallization or silica gel column chromatography.…”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis and Preliminary Biological Evaluation of Novel Benzyl Sulfoxide 2-Indolinone Derivatives as Anticancer Agents

et al. 2017

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In this work, a series of novel benzyl sulfoxide 2-indolinone derivatives was designed and synthesized as potent anticancer agents. Tyrosine kinase inhibitory activity assay indicated that most of the compounds showed significant activity. The in vitro antiproliferative activity of these compounds was further investigated against five human cancer cell lines (HeLa, HepG2, MCF-7, SCC-15, and A549). Several compounds exhibited evident activities. Among them, (Z)-3-(((4-bromobenzyl)sulfinyl)methylene)indolin-2-one (6j) and (Z)-3-((benzylsulfinyl)methylene)-5-bromoindolin-2-one (6o) were found to be effective tyrosine kinase inhibitors (IC50 = 1.34 and 2.69 μM, respectively) in addition to having noteworthy antitumor potential (the average IC50 value of 6j or 6o was less than 40 μM). This class of novel derivatives has promising potential for further development as anticancer agents.

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“…Cells were seeded in 96-well plates and exposed to the essential oil of A. membranacea at concentrations up to 100 µg/mL for 72 h. 1,8-cineole and doxorubicin concentrations were made up to 50 µM also for 72 h. MTT assay was then performed as previously reported [43]. Absorbances were measured using a multi-plate reader at a wavelength 550 nm.…”

Section: Cytotoxicity Assaymentioning

confidence: 99%

Proapoptotic Activity of Achillea membranacea Essential Oil and Its Major Constituent 1,8-Cineole against A2780 Ovarian Cancer Cells

et al. 2020

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Among the hundreds of reported Achillea species, A. membranacea (Labill.) DC. is one of the six that grow in Jordan. Many species of this genus are used in folk medicine to treat a variety of ailments and several biological and pharmacological activities have been ascribed to their essential oil (EO). For this study, the EO obtained from a specimen of A. membranacea grown in Jordan was analyzed by GC-MS. Ninety-six compounds were detected, of which oxygenated monoterpenes was the predominant class (47.9%), followed by non-terpene derivatives (27.9%), while sesquiterpenes represented 14.2% of the total composition. The most abundant compound in the EO was 1,8-cineole (21.7%). The cytotoxic activity of the EO was evaluated against three cancer cell lines (MCF7, A2780 and HT29), and one normal fibroblast cell line (MRC5) by MTT assay. Significant growth inhibition was observed in EO-exposed A2780 and HT29 cells (IC50 = 12.99 and 14.02 μg/mL, respectively), while MCF7 and MRC5 were less susceptible. The EO induced apoptosis and increased the preG1 events in A2780 cells. 1,8-Cineole, the major constituent of the EO, exhibited submicromolar cytotoxicity against A2780 cells, and was 42 times more selective against MRC5 cells. Its cytotoxicity against A2780 cells was comparable with that of doxorubicin, but 1,8-cineole was more selective for MRC5 normal cells. Interestingly, 1,8-cineole enhanced apoptosis in A2780, and caused a remarkable dose-dependent increase in preG1 events. Thus, 1,8-cineole has demonstrated promising cytotoxic and proapoptotic properties.

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Synthesis and biological evaluation of benzyl styrylsulfonyl derivatives as potent anticancer mitotic inhibitors

Cited by 17 publications

References 15 publications

Therapeutic Implications of Black Seed and Its Constituent Thymoquinone in the Prevention of Cancer through Inactivation and Activation of Molecular Pathways

Therapeutic Implications of Black Seed and Its Constituent Thymoquinone in the Prevention of Cancer through Inactivation and Activation of Molecular Pathways

Design, Synthesis and Preliminary Biological Evaluation of Novel Benzyl Sulfoxide 2-Indolinone Derivatives as Anticancer Agents

Proapoptotic Activity of Achillea membranacea Essential Oil and Its Major Constituent 1,8-Cineole against A2780 Ovarian Cancer Cells

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