Quantitative Structure–Cytotoxicity Relationship of Chalcones

doi:10.21873/anticanres.11421

Cited by 14 publications

(10 citation statements)

References 18 publications

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“…Interestingly, toxicity of 1C against non-cancerous mouse NIH/3T3 and human MRC-5 cells was markedly reduced, which is a crucial parameter to ensure safety of anticancer treatment. Such a preferential action of chalcones against cancer cells and not non-cancer cells has also been documented in other studies (26,(28)(29)(30).…”

Section: Cell Linessupporting

confidence: 77%

“…Previous studies have demonstrated inhibition of cell growth induced by methoxy chalcones in cells from various cancer types (e.g. synovial sarcoma, prostate cancer, colon cancer, bladder cancer, and human oral squamous cell carcinoma) (25,26), as well as in multidrug resistant cells (mouse T-cell lymphoma-L5178, human leukemia-CEM/ADR5000 or colon cancer-LoVo/DX) (14,24,27). Interestingly, toxicity of 1C against non-cancerous mouse NIH/3T3 and human MRC-5 cells was markedly reduced, which is a crucial parameter to ensure safety of anticancer treatment.…”

Section: Cell Linesmentioning

confidence: 99%

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New Chalcone Derivative Inhibits ABCB1 in Multidrug Resistant T-cell Lymphoma and Colon Adenocarcinoma Cells

et al. 2019

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Background/Aim: Development of new potential drugs to overcome multidrug resistance to chemotherapy is a big challenge for cancer treatment. Attention is also given to the natural compounds and their derivatives. The study aimed at evaluating the impact of a new chalcone derivative (1C) on multidrug resistant cell lines, focusing on P-glycoprotein (P-gp, ABCB1) inhibition, as well as 1C-doxorubicin interaction in vitro. Materials and Methods: Cytotoxic and antiproliferative effects of the 1C compound were assessed by thiazolyl blue tetrazolium bromide (MTT) method in mouse T-cell lymphoma and human colon adenocarcinoma cells expressing ABCB1. Alterations in ABCB1 activity were evaluated by rhodamine 123 accumulation assay using flow cytometry. Drug-drug interaction was studied using combination assay. Results: Our results confirmed antiproliferative, cytotoxic, as well as ABCB1 inhibitory potential of 1C in both tested ABCB1-expressing cancer cell lines. Furthermore, 1C displayed synergistic interaction with doxorubicin. Conclusion: Our results suggest the 1C chalcone derivative as a promising compound against resistant lymphoma and colon cancer, which could be used in monotherapy or in combination with other chemotherapeutics.

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Section: Cell Linessupporting

confidence: 77%

Section: Cell Linesmentioning

confidence: 99%

New Chalcone Derivative Inhibits ABCB1 in Multidrug Resistant T-cell Lymphoma and Colon Adenocarcinoma Cells

et al. 2019

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“…We investigated a total 291 compounds from 17 different groups ( A~Q ) of their cytotoxicity (assessed by CC 50 ) against four human OSCC (Ca9-22, HSC-2, HSC-3, and HSC-4) and three human normal mesenchymal cells (HGF, HPLF, and HPC), and then their tumor specificity (assessed by TS M , calculated as describe in Figure 2 , and potency-selectivity expression (PSE)) [ 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 ]. PSE, that reflects both tumor specificity and cytotoxicity against tumor cells, was calculated by dividing the TS M by CC 50 for tumor cells, and then multiplying by 100.…”

Section: Development Of Newly Synthesized Chromone Derivatives Witmentioning

confidence: 99%

“…This demonstrated that only limited numbers of compounds show higher tumor specificity, although their structures are very similar with each other. It is possible that such highly tumor-specific compounds show the optimal 3D structure, since the tumor specificity of chromone compounds shows the tight correlation with chemical descriptors that reflect the 3-D structure ( Table 4 ) [ 33 , 35 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 ].…”

Section: Development Of Newly Synthesized Chromone Derivatives Witmentioning

confidence: 99%

Development of Newly Synthesized Chromone Derivatives with High Tumor Specificity against Human Oral Squamous Cell Carcinoma

et al. 2020

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Since many anticancer drugs show severe adverse effects such as mucositis, peripheral neurotoxicity, and extravasation, it was crucial to explore new compounds with much reduced adverse effects. Comprehensive investigation with human malignant and nonmalignant cells demonstrated that derivatives of chromone, back-bone structure of flavonoid, showed much higher tumor specificity as compared with three major polyphenols in the natural kingdom, such as lignin-carbohydrate complex, tannin, and flavonoid. A total 291 newly synthesized compounds of 17 groups (consisting of 12 chromones, 2 esters, and 3 amides) gave a wide range of the intensity of tumor specificity, possibly reflecting the fitness for the optimal 3D structure and electric state. Among them, 7-methoxy-3-[(1E)-2-phenylethenyl]-4H-1-benzopyran-4-one (compound 22), which belongs to 3-styrylchromones, showed the highest tumor specificity. 22 induced subG1 and G2 + M cell population in human oral squamous cell carcinoma cell line, with much less keratinocyte toxicity as compared with doxorubicin and 5-FU. However, 12 active compounds selected did not necessarily induce apoptosis and mitotic arrest. This compound can be used as a lead compound to manufacture more active compound.

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“…For the last few years, chalcones, belonging to flavonoid derivatives, have attracted great interest due to their diverse bioactivities, encompassing antimalarial [ 13 , 14 ], antimicrobial [ 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 ], antioxidant [ 28 ], antitumor [ 29 , 30 , 31 ], anti-inflammatory [ 32 , 33 , 34 ], analgesic [ 34 , 35 , 36 ], to antiulcer [ 37 , 38 ]. Recent studies have also indicated the abilities of chalcones in inhibiting enzymes, including alpha-glucosidase [ 39 , 40 ], lipoxygenase [ 33 , 41 ], mammalian alpha-amylase [ 42 , 43 ], xanthine oxidase [ 44 ], monoamine oxidase (MAO) [ 45 , 46 , 47 ], especially acetylcholinesterase [ 48 , 49 , 50 , 51 , 52 ] and beta-secretase (BACE-1) [ 53 , 54 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, In Silico and In Vitro Evaluation for Acetylcholinesterase and BACE-1 Inhibitory Activity of Some N-Substituted-4-Phenothiazine-Chalcones

Thai

Nguyen

et al. 2020

Molecules

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Acetylcholinesterase (AChE) and beta-secretase (BACE-1) are two attractive targets in the discovery of novel substances that could control multiple aspects of Alzheimer’s disease (AD). Chalcones are the flavonoid derivatives with diverse bioactivities, including AChE and BACE-1 inhibition. In this study, a series of N-substituted-4-phenothiazine-chalcones was synthesized and tested for AChE and BACE-1 inhibitory activities. In silico models, including two-dimensional quantitative structure–activity relationship (2D-QSAR) for AChE and BACE-1 inhibitors, and molecular docking investigation, were developed to elucidate the experimental process. The results indicated that 13 chalcone derivatives were synthesized with relatively high yields (39–81%). The bioactivities of these substances were examined with pIC50 3.73–5.96 (AChE) and 5.20–6.81 (BACE-1). Eleven of synthesized chalcones had completely new structures. Two substances AC4 and AC12 exhibited the highest biological activities on both AChE and BACE-1. These substances could be employed for further researches. In addition to this, the present study results suggested that, by using a combination of two types of predictive models, 2D-QSAR and molecular docking, it was possible to estimate the biological activities of the prepared compounds with relatively high accuracy.

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Quantitative Structure–Cytotoxicity Relationship of Chalcones

Cited by 14 publications

References 18 publications

New Chalcone Derivative Inhibits ABCB1 in Multidrug Resistant T-cell Lymphoma and Colon Adenocarcinoma Cells

New Chalcone Derivative Inhibits ABCB1 in Multidrug Resistant T-cell Lymphoma and Colon Adenocarcinoma Cells

Development of Newly Synthesized Chromone Derivatives with High Tumor Specificity against Human Oral Squamous Cell Carcinoma

Synthesis, In Silico and In Vitro Evaluation for Acetylcholinesterase and BACE-1 Inhibitory Activity of Some N-Substituted-4-Phenothiazine-Chalcones

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