Structures of isothiocyanates attributed to reactive oxygen species generation and microtubule depolymerization in HepG2 cells

Pocasap, Piman; Weerapreeyakul, Natthida; Thumanu, Kanjana

doi:10.1016/j.biopha.2018.02.132

Cited by 26 publications

(28 citation statements)

References 44 publications

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“…Determination of cell phase and tubulin polymerization was performed as previously described (Pocasap et al ., 2018). HepG2 cells were treated with 10, 20, and 40 μM ITCs for 12 h. The cells were collected and washed with cold 0.9% NaCl, then fixed with cold ethanol (80%, for 15 min).…”

Section: Methodsmentioning

confidence: 99%

“…Intracellular ROS levels were measure by 2′,7′-dichlorodihydrofluorescein diacetate (DCFH-DA), as previously reported (Pocasap et al ., 2018). DCFH-DA is oxidized by intracellular ROS to 2′,7′-dichlorofluorescein (DCF)—a fluorescent compound detected by flow cytometer.…”

Section: Methodsmentioning

confidence: 99%

“…DNA and microtubule morphological changes were examined using fluorescent microscopy as in a previous study (Pocasap et al ., 2018). HepG2 cells were seeded into 96-well plates for 24 h prior to be treated with 40 μM ITCs for 12 h. The cells were then washed with cold 0.9% NaCl, then fixed with cold ethanol (80%, 15 min).…”

Section: Methodsmentioning

confidence: 99%

“…Sulforaphane was tested in all experiments as an ITC standard. Our previous study reported the correlation between structural alteration at the ITC side chain (including oxidation state of sulfur atom, number of double bond, and number of aromatic ring) and anticancer activity (Pocasap et al ., 2018). Since structural alteration on the chain length was also noticed between the studied ITCs (iberin (3C), sulforaphane (4C), and alyssin (5C)), the influences of chemical structure correlation on activity were also analyzed and discussed.…”

Section: Introductionmentioning

confidence: 99%

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Alyssin and Iberin in Cruciferous Vegetables Exert Anticancer Activity in HepG2 by Increasing Intracellular Reactive Oxygen Species and Tubulin Depolymerization

Pocasap

Weerapreeyakul

Thumanu

2019

Biomolecules & Therapeutics

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To determine the chemopreventive potential of alyssin and iberin, the in vitro anticancer activities and molecular targets of isothiocyanates (ITCs) were measured and compared to sulforaphane in hepatocellular carcinoma cell HepG2. The SR-FTIR spectra observed a similar pattern vis-à-vis the biomolecular alteration amongst the ITCs-treated cells suggesting a similar mode of action. All of the ITCs in this study cause cancer cell death through both apoptosis and necrosis in concentration dependent manner (20–80 μM). We found no interactions of any of the ITCs studied with DNA. Notwithstanding, all of the ITCs studied increased intracellular reactive oxygen species (ROS) and suppressed tubulin polymerization, which led to cell-cycle arrest in the S and G2/M phase. Alyssin possessed the most potent anticancer ability; possibly due to its ability to increase intracellular ROS rather than tubulin depolymerization. Nevertheless, the structural influence of alkyl chain length on anticancer capabilities of ITCs remains inconclusive. The results of this study indicate an optional, potent ITC (viz., alyssin) because of its underlying mechanisms against hepatic cancer. As a consequence, further selection and development of effective chemotherapeutic ITCs is recommended.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Alyssin and Iberin in Cruciferous Vegetables Exert Anticancer Activity in HepG2 by Increasing Intracellular Reactive Oxygen Species and Tubulin Depolymerization

Pocasap

Weerapreeyakul

Thumanu

2019

Biomolecules & Therapeutics

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“…The antiproliferation of sesamol was performed using a neutral red assay, as previously described, with minor optimization [29]. Briefly, SK-MEL-2 cells were seeded in 96-well plates at 5 × 10 4 cells per well and incubated for 48 h. Then the cells were treated with sesamol for 24 h. The medium was discarded and incubated with freshly prepared neutral red in medium (final concentration of 50 µg/mL) for 2 h at 37 °C.…”

Section: Methodsmentioning

confidence: 99%

Validation of Cell-Based Assay for Quantification of Sesamol Uptake and Its Application for Measuring Target Exposure

Srisongkram

Weerapreeyakul

2019

Molecules

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The intracellular drug concentration is needed for determination of target exposure at the site of action regarding its pharmacological action and adverse effects. Sesamol is an antiproliferative molecule from Sesamum indicum with promising health benefits. We present a method for measuring the intracellular sesamol content using reverse-phase HPLC with a UV diode array in melanoma cells. Sesamol was completely resolved by isocratic elution (4.152 ± 0.008 min) with methanol/water (70%, v/v) through a 30 °C, 5-µm C-18 column and detection at 297 nm. The present assay offers high sensitivity, fast elution, and an accurate and linear nominal concentration range of 10–1000 ng/mL (R2 = 0.9972). The % accuracy of the sesamol quality control sample was −3.36% to 1.50% (bias) with a 0.84% to 5.28% relative standard deviation (RSD), representing high repeatability and high reproducibility. The % recovery was 94.80% to 99.29%, which determined that there was no loss of sesamol content during the sample preparation. The validated method was applied to monitor intracellular sesamol concentration after treatment from 5 min to 24 h. The remaining intracellular sesamol content was correlated with its antiproliferative effect (R2 = 0.9483). In conclusion, this assay demonstrated low manipulation, quick elution, and high sensitivity, precision, accuracy, and recovery, and it was successfully applied to the quantification of sesamol in target cells.

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Sulforaphane and ophthalmic diseases

Zhang,

Zhao,

Liu

et al. 2024

Food Science & Nutrition

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Sulforaphane (SFN) is an organosulfur compound categorized as an isothiocyanate (ITC), primarily extracted from cruciferous vegetables like broccoli and cabbage. The molecular formula of sulforaphane (SFN) is C6H11NOS2. SFN is generated by the hydrolysis of glucoraphanin (GRP) through the enzyme myrosinase, showing notable properties including anti‐diabetic, anti‐inflammatory, antimicrobial, anti‐angiogenic, and anticancer attributes. Ongoing clinical trials are investigating its potential in diseases such as cancer, neurodegenerative diseases, diabetes‐related complications, chronic kidney disease, cardiovascular disease, and liver diseases. Several animal carcinogenesis models and cell culture models have shown it to be a very effective chemopreventive agent, and the protective effects of SFN in ophthalmic diseases have been linked to multiple mechanisms. In murine models of diabetic retinopathy and age‐related macular degeneration, SFN delays retinal photoreceptor cell degeneration through the Nrf2 antioxidative pathway, NF‐κB pathway, AMPK pathway, and Txnip/mTOR pathway. In rabbit models of keratoconus and cataract, SFN has been shown to protect corneal and lens epithelial cells from oxidative stress injury by activating the Keap1‐Nrf2‐ARE pathway and the Nrf‐2/HO‐1 antioxidant pathway. Oral delivery or intraperitoneal injection at varying concentrations are the primary strategies for SFN intake in current preclinical studies. Challenges remain in the application of SFN in eye disorders due to its weak solubility in water and limited bioavailability because of the presence of blood–ocular barrier systems. This review comprehensively outlines recent research on SFN, elucidates its mechanisms of action, and discusses potential therapeutic benefits for eye disorders such as age‐related macular degeneration (AMD), diabetic retinopathy (DR), cataracts, and other ophthalmic diseases, while also indicating directions for future clinical research to achieve efficient SFN treatment for ophthalmic diseases.

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Structures of isothiocyanates attributed to reactive oxygen species generation and microtubule depolymerization in HepG2 cells

Cited by 26 publications

References 44 publications

Alyssin and Iberin in Cruciferous Vegetables Exert Anticancer Activity in HepG2 by Increasing Intracellular Reactive Oxygen Species and Tubulin Depolymerization

Alyssin and Iberin in Cruciferous Vegetables Exert Anticancer Activity in HepG2 by Increasing Intracellular Reactive Oxygen Species and Tubulin Depolymerization

Validation of Cell-Based Assay for Quantification of Sesamol Uptake and Its Application for Measuring Target Exposure

Sulforaphane and ophthalmic diseases

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