In silico and in vitro analysis of coumarin derivative induced anticancer effects by undergoing intrinsic pathway mediated apoptosis in human stomach cancer

Perumalsamy, Haribalan; Sankarapandian, Karuppasamy; Veerappan, Karpagam; Natarajan, Sathishkumar; Kandaswamy, Narendran; Thangavelu, Lakshmi; Balusamy, Sri Renukadevi

doi:10.1016/j.phymed.2018.04.021

Cited by 49 publications

(39 citation statements)

References 35 publications

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“…e cell cytotoxicity of citral toward the human prostate cancer cells (PC3 and PC-3M) was evaluated using an MTT assay performed as described previously [25,26]. 10x MTT stock solution (5 mg/mL) was dissolved in phosphate-buffered saline (PBS) (pH 7.4), filter sterilized, and stored at −20°C.…”

Section: Cell Viability Assaymentioning

confidence: 99%

Citral Induced Apoptosis through Modulation of Key Genes Involved in Fatty Acid Biosynthesis in Human Prostate Cancer Cells: In Silico and In Vitro Study

Balusamy

Perumalsamy

Veerappan

et al. 2020

BioMed Research International

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The isomers of citral (cis-citral and trans-citral) were isolated from the Cymbopogon citratus (DC.) Stapf oil demonstrates many therapeutic properties including anticancer properties. However, the effects of citral on suppressing human prostate cancer and its underlying molecular mechanism have yet to be elucidated. The citral was isolated from lemongrass oil using various spectroscopic analyses, such as electron ionized mass spectrometry (EI-MS) and nuclear magnetic resonance (NMR) spectroscopy respectively. We carried out 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay to evaluate the cell viability of citral in prostate cancer cells (PC-3 and PC3M). Furthermore, to confirm that PC3 undergoes apoptosis by inhibiting lipogenesis, we used several detection methods including flow cytometry, DNA fragmentation, Hoechst staining, PI staining, oil staining, qPCR, and Western blotting. Citral impaired the clonogenic property of the cancer cells and altered the morphology of cancer cells. Molecular interaction studies and the PASS biological program predicted that citral isomers tend to interact with proteins involved in lipogenesis and the apoptosis pathway. Furthermore, citral suppressed lipogenesis of prostate cancer cells through the activation of AMPK phosphorylation and downregulation of fatty acid synthase (FASN), acetyl coA carboxylase (ACC), 3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMGR), and sterol regulatory element-binding protein (SREBP1) and apoptosis of PC3 cells by upregulating BAX and downregulating Bcl-2 expression. In addition, in silico studies such as ADMET predicted that citral can be used as a safe potent drug for the treatment of prostate cancer. Our results indicate that citral may serve as a potential candidate against human prostate cancer and warrants in vivo studies.

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Section: Cell Viability Assaymentioning

confidence: 99%

Citral Induced Apoptosis through Modulation of Key Genes Involved in Fatty Acid Biosynthesis in Human Prostate Cancer Cells: In Silico and In Vitro Study

Balusamy

Perumalsamy

Veerappan

et al. 2020

BioMed Research International

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“…Perumalsamy et al . reported the anti‐cancer activity of styrene substituted biscoumarin (SSBC) against stomach cell lines (AGS).…”

Section: Biological Activity Of Biscoumarinmentioning

confidence: 99%

An Insight View on Synthetic Protocol, Mechanistic and Biological Aspects of Biscoumarin Derivatives

2019

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Biscoumarin has emerged as one of the most unique and valuable moiety in the field of synthetic as well as in medicinal chemistry. This moiety has been examined for the designing of potent derivatives and hybrids with other moieties and substituents exhibiting a myriad of medicinal properties. These far‐flung characteristics enthralled the researchers to discover various methods for the synthesis of biscoumarin nucleus and its derivatives from 4‐hydroxycoumarin and varieties of aldehydes using different types of catalysts to improve the selectivity, purity and yield of the products. Moreover, liberal scope is available for this structural unit which needs to be explored by chemists for the advancement of new potential drug candidates. This article summarizes the current eco‐benign pathways for the synthetic strategies of biscoumarins under various reaction conditions viz. solid supported catalyst, ionic liquid, nanoparticles, Lewis acid, heteropolyacids, nanocomposites etc.

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“…Synthetic and naturally occurring biscoumarin derivatives are of considerable interest in synthetic and medicinal chemistry (Figure 1). They are highly potent due to their hydrogen bonding property via two OH groups and also exhibit various biological activities like anticoagulant, urease inhibitory, antioxidant, anti‐leshmanial, α‐glucosidase inhibitor, anti‐inflammatory, antifungal, antibacterial, enzymatic inhibition activity, HIV integrase, anticancer, and so on 1–12 . Furthermore, they have varied applications such as fluorescent brighteners, agrochemicals, effective laser dyes, polymer synthesis, WLED display, additives in food and cosmetics, and so on 13–17 …”

Section: Introductionmentioning

confidence: 99%

Click chemistry‐inspired design, synthesis, and molecular docking studies of biscoumarin derivatives using carbon‐based acid catalyst

Agarwal¹,

Sethiya

Teli

et al. 2020

Journal of Heterocyclic Chem

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A green and eco‐benign synthesis of biscoumarin derivatives using carbon sulfonic acid, a solid support catalyst has been described. The reaction involved a one‐pot two‐component reaction of 4‐hydroxycoumarin and aldehyde using carbon sulfonic acid involving Knoevenegal‐Michael condensation. A series of aromatic (bearing electron withdrawing and releasing group) and heteroaromatic aldehydes has been converted to biscoumarins with excellent isolated yields. The reaction is in compliance with green principles, that is, inexpensive catalyst, easy to prepare, nontoxic, easy handling, reusable up to five recycle runs, easy separation, short reaction time, no need of time consuming column purification, high yielding, and so on. The synthesized catalyst and biscoumarin derivatives were well characterized by spectral analysis. The molecular modeling studies showed that the designed molecular scaffolds (3a‐j) showed outstanding interaction with methylenetetrahydrofolate reductase (MTHFR) and cytochrome P450 3A4 (CYP3A4) proteins. It was noticed that 3f (−17.55 kJ/mol) and 3d (−26.23 kJ/mol) showed the highest docking score against CYP3A4 and MTHFR proteins, respectively.

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In silico and in vitro analysis of coumarin derivative induced anticancer effects by undergoing intrinsic pathway mediated apoptosis in human stomach cancer

Cited by 49 publications

References 35 publications

Citral Induced Apoptosis through Modulation of Key Genes Involved in Fatty Acid Biosynthesis in Human Prostate Cancer Cells: In Silico and In Vitro Study

Citral Induced Apoptosis through Modulation of Key Genes Involved in Fatty Acid Biosynthesis in Human Prostate Cancer Cells: In Silico and In Vitro Study

An Insight View on Synthetic Protocol, Mechanistic and Biological Aspects of Biscoumarin Derivatives

Click chemistry‐inspired design, synthesis, and molecular docking studies of biscoumarin derivatives using carbon‐based acid catalyst

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