Synthesis of 2-(2,4-dihydroxyphenyl)thieno-1,3-thiazin-4-ones, their lipophilicity and anticancer activity in vitro

Matysiak, Joanna; Juszczak, Małgorzata; Karpińska, Monika; Langner, Ewa; Walczak, Katarzyna; Lemieszek, Marta Kinga; Skrzypek, Alicja; Niewiadomy, Andrzej; Rzeski, Wojciech

doi:10.1007/s11030-015-9599-x

Cited by 15 publications

(7 citation statements)

References 39 publications

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“…The compounds with the additional Et substituent in the benzenediol residue show higher antiproliferative potency compared to the unsubstituted ones (4b, 5b). That effect is similar to that found for other heterocyclic benzenediols prepared by us 24,26 . LNcaP cells are the most sensitive to the studied compounds and the potency of the most active compounds is similar to that of cisplatin (compounds 4 and 5).…”

Section: Resultssupporting

confidence: 90%

“…This is a continuation of our studies on design and synthesis of biologically active compounds with the resorcinol moiety 22,23 . A lot of benzenediol heterocyclic derivatives display a substantial antiproliferative potency, and some of them were studied as potential anticancer agents [24][25][26] . These properties prompted our further studies in this area.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and antiproliferative activity of some N′-substituted 2,4-dihydroxybenzothiohydrazides

Matysiak

Skrzypek

Karpińska

et al. 2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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The paper shows that new N'-substituted 2,4-dihydroxybenzocarbothiohydrazides are able to inhibit the in vitro proliferation of human tumor cell lines. The compounds were prepared by the reaction of sulfinylbis[(2,4-dihydroxyphenyl)methanethione] (STB) or its analogs with the hydrazines. The panel of N'-substitution included aryl, pyridinyl and pyrimidinyl rings. The highest antiproliferative activity for N'-(4-(4-chlorophenyl)-6-(trifluoromethyl)pyrimidin-2-yl)-5-ethyl-2,4-dihydroxybenzothiohydrazide (5b) was found. The antiproliferative potency of some compounds was similar to that of cisplatin. Analogs with the Et substituent on benzenediol moiety displayed higher potency than with the unsubstituted one. The influence of N'-substitution on antiproliferative activity of compounds was discussed.

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Section: Resultssupporting

confidence: 90%

Section: Introductionmentioning

confidence: 99%

Synthesis and antiproliferative activity of some N′-substituted 2,4-dihydroxybenzothiohydrazides

Matysiak

Skrzypek

Karpińska

et al. 2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…IC 50 was calculated using the computerized linear regression analysis of quantal log dose-probit functions, according to the method of Litchfield and Wilcoxon. Cell proliferation (%) was expressed as a percentage relative to the untreated control cells [22].…”

Section: Objectivesmentioning

confidence: 99%

Evaluation of anticancer activity of water and juice extracts of young <i>Hordeum vulgare</i> in human cancer cell lines HT-29 and A549

Czerwonka¹,

Kawka²,

Cykier³

et al. 2017

Ann Agric Environ Med.

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Introduction and objective. Barley (Hordeum vulgare L.) is known as a rich source of different bioactive compounds. At present, considerable attention of researchers is focused on young barley grass. It can be a good source of dietary minerals, vitamins, carbohydrates, amino acids, phenolic compounds and proteins. It is possible that the composition of chemical ingredients beneficial for health may induce an anticancer potential of young barley in human colon adenocarcinoma (HT-29) and human lung adenocarcinoma (A549) cell lines. Materials and method. Hordeum vulgare water extract (HWE) and Hordeum vulgare juice extract (HJE) were prepared. Cell proliferation and viability were examined with the use of MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) and NR (neutral red) methods. Induction of necrosis was assessed by propidium iodide/Hoechst staining. Progress of the cell cycle involved in cell proliferation, apoptosis, and regulation of transcription was estimated using flow cytometry analysis. Additionally, the capability of free radical scavenging was evaluated with the DPPH assay. Results. The study revealed that extracts inhibited the proliferation of cancer cells. The NR study confirmed the low cytotoxic activity of the tested extracts to normal human colon epithelial cells (CCD 841 CoTr) and human skin fibroblasts (HSF). Furthermore, a dose-dependent cytotoxicity against HT-29 cells, but not A549 cells, has been reported. The free radical scavenging activity was observed in the case of the HWE but not the HJE. Conclusions. The obtained results indicate a cancer chemopreventive potential of young barley as a safe dietary agent in colon carcinoma.

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“…Recently, we have revealed high activity of DPBT against bladder cancer cells HCV29T (the IC 50 value was 20.37 µM for sulforhodamine B assay) and some anti-proliferative features of benzofuro-1,3-thiazinone resorcinol hybrids against the A549 (human non-small cell lung carcinoma), T47D (human breast cancer), and SW707 (human rectal adenocarcinoma) cell lines (Matysiak et al 2015b ). We also detected comparable anticancer activity of some thieno-1,3-thiazin-4-one derivatives against lung cancer A549, colon adenocarcinoma HT-29, and glioma C6 cells (Matysiak et al 2015a ). As can be seen, 1,3-thiazine derivatives exhibit significant anti-proliferative potency in a broad range of cancer cells.…”

Section: Discussionmentioning

confidence: 61%

Evaluation of the effect of 2-(2,4-dihydroxyphenyl)-4H-benzofuro[3,2-d][1,3]thiazin-4-one on colon cells and its anticancer potential

et al. 2018

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In this paper, we present the biological effect of the newly synthesized 2-(2,4-dihydroxyphenyl)-4H-benzofuro[3,2-d][1,3]thiazin-4-one (DPBT) on human colon adenocarcinoma cell lines (HT-29 and LS180). Additionally, DPBT cytotoxicity was examined in human colon epithelial cells (CCD 841 CoTr) and human skin fibroblasts (HSF). The studies revealed a significant decrease in the proliferation of cancer cells after exposure to DPBT at concentrations in the range of 10–100 µM. Additionally, DPBT was not toxic to normal CCD 841 CoTr and HSF cells at concentrations that induced inhibition of cancer cell proliferation. The nature of the anti-proliferative action of DPBT in the cell cycle progression in colon cancer cells and the expression of proteins involved in this process were examined by flow cytometry and western blotting, respectively. The investigations demonstrated higher sensitivity of LS180 than HT-29 to the DPBT treatment. The anti-proliferative action of DPBT in LS180 was attributed to cell cycle arrest in the G1 phase via up-regulation of p27KIP1 and down-regulation of cyclin D1 and CDK4 proteins.

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Synthesis of 2-(2,4-dihydroxyphenyl)thieno-1,3-thiazin-4-ones, their lipophilicity and anticancer activity in vitro

Cited by 15 publications

References 39 publications

Synthesis and antiproliferative activity of some N′-substituted 2,4-dihydroxybenzothiohydrazides

Synthesis and antiproliferative activity of some N′-substituted 2,4-dihydroxybenzothiohydrazides

Evaluation of anticancer activity of water and juice extracts of young <i>Hordeum vulgare</i> in human cancer cell lines HT-29 and A549

Evaluation of the effect of 2-(2,4-dihydroxyphenyl)-4H-benzofuro[3,2-d][1,3]thiazin-4-one on colon cells and its anticancer potential

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