Hydroxyl containing benzo[b]thiophene analogs mitigates the acrylamide induced oxidative stress in the zebrafish larvae by stabilizing the glutathione redox cycle

Muthu, B. Hari Deva; Manjunathan, Tamilvelan; Guru, Ajay; Kumar, Rajendran Saravana; Rajakrishnan, R.; Kuppusamy, Palaniselvam; Juliet, Annie; Gopinath, Pushparathinam; Arockiaraj, Jesu

doi:10.1016/j.lfs.2022.120507

Cited by 41 publications

(14 citation statements)

References 46 publications

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“…It has already been stated that the presence of a hydroxyl group in the third or fifth positions of a structural element is responsible for free radical scavenging [ 25 ] and is also associated with anticancer potential [ 26 ]. While examining the antioxidant potential in our previous study [ 22 ], BP, which possesses the ketone group in the 2nd position, shows better activity compared to that of EP, which possesses the ester group in the 2nd position; the better activity profile of BP is due to the resonance stability of the keto-enol form, where the ketone group has lower pKa value compared to that of the ester group, since this is more acetic than EP is [ 22 ]. BP has better stability in keto-enol tautomerism and shows better activity compared to that of EP ( Figure 2 ) [ 22 , 27 ].…”

Section: Resultsmentioning

confidence: 99%

“…Researchers also found that cyanide and imidazolinyl-substituted benzothiophene analogs showed specificity toward the inhibition of HeLa cells [ 20 ]. Here, we have followed a one-pot strategy starting with 2,2 dithio dibenzoylchloride to synthesize two hydroxyl-containing analogues, 1-(3-hydroxybenzo[b]thiophen-2-yl) ethanone (BP) and 1-(3-hydroxybenzo[b]thiophen-2-yl) propan-1-one hydrate (EP), and further mask the hydroxyl group with acetyl chloride and methyl iodide to obtain 2-acetylbenzo[b]thiophene-3-yl acetate (BN) and 1-(3-methoxybenzo[b]thiophene-2-yl) propan-1-one (EN) [ 21 , 22 ]. Hydroxyl-containing analogs BP and EP were predicted to be CYP1A2 inhibitors in our previous report [ 22 ].…”

Section: Introductionmentioning

confidence: 99%

“…Here, we have followed a one-pot strategy starting with 2,2 dithio dibenzoylchloride to synthesize two hydroxyl-containing analogues, 1-(3-hydroxybenzo[b]thiophen-2-yl) ethanone (BP) and 1-(3-hydroxybenzo[b]thiophen-2-yl) propan-1-one hydrate (EP), and further mask the hydroxyl group with acetyl chloride and methyl iodide to obtain 2-acetylbenzo[b]thiophene-3-yl acetate (BN) and 1-(3-methoxybenzo[b]thiophene-2-yl) propan-1-one (EN) [ 21 , 22 ]. Hydroxyl-containing analogs BP and EP were predicted to be CYP1A2 inhibitors in our previous report [ 22 ]. Therefore, we speculate that the synthesized benzo[b]thiophene analogs with a hydroxyl moiety might possess an anticancer effect.…”

Section: Introductionmentioning

confidence: 99%

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Functionalized Sulfur-Containing Heterocyclic Analogs Induce Sub-G1 Arrest and Apoptotic Cell Death of Laryngeal Carcinoma In Vitro

et al. 2023

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In this study, we speculate that the hydroxyl-containing benzo[b]thiophene analogs, 1-(3-hydroxybenzo[b]thiophen-2-yl) ethanone (BP) and 1-(3-hydroxybenzo[b]thiophen-2-yl) propan-1-one hydrate (EP), might possess antiproliferative activity against cancer cells. Hydroxyl-containing BP and EP show selectivity towards laryngeal cancer cells (HEp2), with IC50 values of 27.02 ± 1.23 and 35.26 ± 2.15 µM, respectively. The hydroxyl group present in the third position is responsible for the anticancer activity and is completely abrogated when the hydroxyl group is masked. BP and EP enhance the antioxidant enzyme activity and reduce the ROS production, which are correlated with the antiproliferative effect in HEp-2 cells. An increase in the BAX/BCL-2 ratio occurs during the BP and EP treatment and activates the caspase cascade, resulting in apoptosis stimulation. It also arrests the cells in the Sub-G1 phase, indicating the induction of apoptosis. The molecular docking and simulation studies predicted a strong interaction between BP and the CYP1A2 protein, which could aid in combinational therapy by enhancing the bioavailability of the drugs. BP and EP possess an antioxidant property with low antiproliferative effects (~5.18 µg/mL and ~7.8 µg/mL) as a standalone drug, therefore, they can be combined with other drugs for effective chemotherapy that might trigger the effect of pro-oxidant drug on healthy cells.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Functionalized Sulfur-Containing Heterocyclic Analogs Induce Sub-G1 Arrest and Apoptotic Cell Death of Laryngeal Carcinoma In Vitro

et al. 2023

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“…An extremely complex interplay exists between the innate and specific mechanisms of teleost that must be taken into consideration. The innate immune system gets activated by effector molecules resulting from the cellular stress and tissue damage, which in‐turn triggers the co‐stimulatory sequences that are required for the activation of a specific immune system 39,40 . However, the non‐specific immune system of teleost is highly sophisticated and, may be supreme to that of the other mammals 6 .…”

Section: Immune and Lncrna In Teleostmentioning

confidence: 99%

“…The innate immune system gets activated by effector molecules resulting from the cellular stress and tissue damage, which in-turn triggers the co-stimulatory sequences that are required for the activation of a specific immune system. 39,40 However, the non-specific immune system of teleost is highly sophisticated and, may be supreme to that of the other mammals. 6 Although the pathways engendering such a response appear simpler than those in higher vertebrates, synthesis of antibodies that protect against diverse bacterial pathogens is a critical component of disease prevention in the aquaculture industry.…”

Section: Immune and Lncrna In Teleostmentioning

confidence: 99%

Long non‐coding RNA, a supreme post‐transcriptional immune regulator of bacterial or virus‐driven immune evolution in teleost

Haridevamuthu

Guru

Velayutham

et al. 2022

Reviews in Aquaculture

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The global aquaculture boom, fuelled by a reduction in wild population and detection of novel viruses, has created a demanding market, hence, there is a pressing need to investigate the immune system of fish, further. As the most diverse community of vertebrates and a central contributor to the progressing global aquaculture market, teleost continues to draw vast scientific interest. Recent breakthroughs in multiomics technologies have provided a platform to understand the role of long noncoding RNA (lncRNA) in the host immune system during infection. Emerging evidence shows that teleost lncRNA might have a regulatory role in immune responses, mostly through lncRNA-microRNA (miRNA) sponging. Teleost lncRNA shares a functionally active short sequence complement to target the miRNA which is conserved among the several fish species. Recent report suggests that rhabdovirus exploits a lncRNA in teleost and, to dodge the host immune mechanism and negatively regulate the immune system. This observation reveals the essentiality of lncRNA in pathogendriven immunity in teleost. Reports available on the function of teleost lncRNA are still in early stages and experimental verifications are a limiting factor. Unravelling the lncRNA-mediated immune regulation in fishes could be used against the invading pathogens to strengthen the aquaculture production. This review elaborates on the experimentally identified and functionally characterized lncRNA and its regulatory role in the teleost immune response during infection and pathogen-driven host immune evolution, which could eventually lead to achieving high standards in aquaculture productivity.

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6‐Gingerdione Reduces Apoptotic Conditions in HepG2 Cells and Inhibits Inflammatory Cytokine Gene Expression in Alcoholic Liver Injured Zebrafish Larvae

Guru

Manjunathan

Sudhakaran

et al. 2022

Chemistry & Biodiversity

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Antioxidant natural products and their analogs especially phenolic compounds, exhibit diverse biological properties, including anti‐inflammatory, antioxidant, and anticancer activities. Ginger which is widely used worldwide for various beneficial effects also contains several phenolic antioxidants, and 6‐gingerol is one of the natural products studied extensively. However, the molecular mechanism of synthetically synthesized 6‐gingerdione (compound 1) from 6‐gingerol was not known. In this study, compound 1 and methylated 6‐gingerdione (compound 2) were obtained semi synthetically from 6‐gingerol. Compound 1 and 2 are subjected to SwissADME prediction. Then the protective effect of compound 1 was analyzed in 2 % EtOH induced HepG2 cells and zebrafish larvae. Hydroxyl and nitric oxide scavenging assays reveal that compound 1 showed more antioxidant activity than compound 2 at 50 μM. Moreover, compound 1 exhibited good anti‐inflammatory activity via lipoxygenase inhibition and proteinase inhibition. Apoptosis and oxidative stress in HepG2 cells were induced by 2 % EtOH and treated with compound 1. Compound 1 significantly inhibited the EtOH induced nitric oxide production, apoptosis, and ROS generation in HepG2 cells. Encouraged by the in‐vitro antioxidant and anti‐inflammatory activities, compound 1 was then investigated for its protective effect in 2 % EtOH induced ALD zebrafish larva. Compound 1 protected the zebrafish larvae from liver injury by suppressing inflammatory (COX‐2, TNF‐α, and IL‐1β) and lipogenic genes (C/EBP‐α, SREBP1, and IL‐1β) while upregulating the antioxidant gene. Our findings indicate that compound 1 synthesized from 6‐gingerol ameliorated liver injury that likely, contributes to its potential antioxidant and anti‐inflammatory properties.

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Hydroxyl containing benzo[b]thiophene analogs mitigates the acrylamide induced oxidative stress in the zebrafish larvae by stabilizing the glutathione redox cycle

Cited by 41 publications

References 46 publications

Functionalized Sulfur-Containing Heterocyclic Analogs Induce Sub-G1 Arrest and Apoptotic Cell Death of Laryngeal Carcinoma In Vitro

Functionalized Sulfur-Containing Heterocyclic Analogs Induce Sub-G1 Arrest and Apoptotic Cell Death of Laryngeal Carcinoma In Vitro

Long non‐coding RNA, a supreme post‐transcriptional immune regulator of bacterial or virus‐driven immune evolution in teleost

6‐Gingerdione Reduces Apoptotic Conditions in HepG2 Cells and Inhibits Inflammatory Cytokine Gene Expression in Alcoholic Liver Injured Zebrafish Larvae

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