Synthesis, molecular docking and cytotoxicity evaluation of novel 2-(4-amino-benzosulfonyl)-5H-benzo[b]carbazole-6,11-dione derivatives as histone deacetylase (HDAC8) inhibitors

Ravichandiran, Palanisamy; Jegan, A.; Premnath, D.; Periasamy, Vaiyapuri Subbarayan; Muthusubramanian, Shanmugam; Vasanthkumar, Samuel

doi:10.1016/j.bioorg.2014.01.002

Cited by 30 publications

(9 citation statements)

References 26 publications

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“…Compounds 28 , 29a,b (Figure 36) exhibited a good cytotoxicity with IC 50 values of 52.2, 53.8 and 33.5 µM, respectively. The interaction between all compounds and HDAC8 was also carried out by performing molecular docking studies with the use of the GLIDE program 67 .…”

Section: Tetracyclic Fused Carbazolesmentioning

confidence: 99%

Carbazole scaffolds in cancer therapy: a review from 2012 to 2018

Issa

Prandina

Bedel

et al. 2019

Journal of Enzyme Inhibition and Medicinal Chemistry

114

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For over half a century, the carbazole skeleton has been the key structural motif of many biologically active compounds including natural and synthetic products. Carbazoles have taken an important part in all the existing anti-cancer drugs because of their discovery from a large variety of organisms, including bacteria, fungi, plants, and animals. In this article, we specifically explored the literature from 2012 to 2018 on the anti-tumour activities reported to carbazole derivatives and we have critically collected the most significant data. The most described carbazole anti-tumour agents were classified according to their structure, starting from the tricyclic–carbazole motif to fused tetra-, penta-, hexa- and heptacyclic carbazoles. To date, three derivatives are available on the market and approved in cancer therapy.

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Section: Tetracyclic Fused Carbazolesmentioning

confidence: 99%

Carbazole scaffolds in cancer therapy: a review from 2012 to 2018

Issa

Prandina

Bedel

et al. 2019

Journal of Enzyme Inhibition and Medicinal Chemistry

114

View full text Add to dashboard Cite

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“…We recently reported the synthesis and biological evaluation of new naphthoquinone derivatives as potential anticancer and antimicrobial agents [14,15]. The molecules were previously studied for anticancer activity, and an apoptotic mechanism in cancer cells was reported [16].…”

Section: Introductionmentioning

confidence: 99%

1,4-Naphthoquinone Analogues: Potent Antibacterial Agents and Mode of Action Evaluation

et al. 2019

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1,4-Naphthoquinones have antibacterial activity and are a promising new class of compound that can be used to treat bacterial infections. The goal was to improve effective antibacterial agents; therefore, we synthesized a new class of naphthoquinone hybrids, which contain phenylamino-phenylthio moieties as significant counterparts. Compound 4 was modified as a substituted aryl amide moiety, which enhanced the antibacterial activity of earlier compounds 3 and 4. In this study, five bacterial strains Staphylococcus aureus (S. aureus), Listeria monocytogenes (L. monocytogenes), Escherichia coli (E. coli), Pseudomonas aeruginosa (P. aeruginosa) and Klebsiella pneumoniae (K. pneumoniae) were used to evaluate the antibacterial potency of synthesized naphthoquinones using the minimal inhibitory concentration (MIC) method. Most of the studied naphthoquinones demonstrated major antibacterial activity with a MIC of 15.6 µg/mL–500 µg/mL. Selected compounds (5a, 5f and 5x) were studied for the mode of action, using intracellular ROS generation, determination of apoptosis by the Annexin V-FITC/PI assay, a bactericidal kinetic study and in silico molecular modelling. Additionally, the redox potentials of the specified compounds were confirmed by cyclic voltammetry (CV).

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“…Naphthoquinones are quinone derivatives that are widely distributed in plants and exhibit excellent biological properties, including pro-inflammatory, anti-inflammatory, anti-bacterial and anti-cancer properties [17][18][19][20]. Plumbagin (PL) is a 5-hydroxy-2-methyl-1,4-naphthoquinone that has a variety of pharmacological properties such as anti-cancer, anti-microbial, anti-fertility and antioxidative properties [21].…”

Section: Introductionmentioning

confidence: 99%

Plumbagin triggers redox-mediated autophagy through the LC3B protein in human papillomavirus-positive cervical cancer cells

Periasamy

Athinarayanan

Girija³

et al. 2020

Arch Med Sci

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IntroductionIn this study, we analyzed the effect of plumbagin (PL) on cultured SiHa cervical cancer cells using fluorescence microscopy and flow cytometry techniques to identify the mode of cell death and to elucidate whether cells die through apoptosis or non-apoptosis.Material and methodsThe cell death was analyzed using MTT assay. The cellular morphological changes were assessed using acridine orange/ethidium bromide dual staining. DNA damage and cell cycle progression were analyzed using a comet assay and flow cytometry respectively.ResultsMorphological and cytological features revealed that PL induced autophagic cell death in cancer cells. The results of a cell cycle analysis indicated that the proportion of cells in sub-G0 phase increased. Translocation of LC-3B protein from the cytoplasm to the autophagosome was found in 31% of PL-treated cells, suggesting that PL provoked autophagic cell death. In this study, it was observed that plumbagin treatment caused cleavage of DNA in SiHa cancer cells, and morphological analysis provided very strong evidence supporting the occurrence of autophagic cell death as a result of plumbagin treatment.ConclusionsIn addition, a Cytoscape-based protein-PL interaction network analysis provided very strong evidence in support of the specific mode of cell death in the context of autophagy, which has also been one of the desired endpoints in human papillomavirus-positive cervical cancer therapy and apoptotic cell death-resistant cancer treatment. Thus, this study is the first to test PL against the SiHa cervical cancer cell line, providing leads for further testing on non-apoptotic cell death for application in cervical cancer management.

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Synthesis, molecular docking and cytotoxicity evaluation of novel 2-(4-amino-benzosulfonyl)-5H-benzo[b]carbazole-6,11-dione derivatives as histone deacetylase (HDAC8) inhibitors

Cited by 30 publications

References 26 publications

Carbazole scaffolds in cancer therapy: a review from 2012 to 2018

Carbazole scaffolds in cancer therapy: a review from 2012 to 2018

1,4-Naphthoquinone Analogues: Potent Antibacterial Agents and Mode of Action Evaluation

Plumbagin triggers redox-mediated autophagy through the LC3B protein in human papillomavirus-positive cervical cancer cells

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