Fluoroaryl analogs of sulforaphane – A group of compounds of anticancer and antimicrobial activity

Cierpiał, Tomasz; Kiełbasiński, P.; Kwiatkowska, Małgorzata; Łyżwa, P.; Lubelska, Katarzyna; Kuran, Dominika; Dąbrowska, Aleksandra; Kruszewska, Hanna; Mielczarek, Lidia; Chilmończyk, Zdzisław; Wiktorska, Katarzyna

doi:10.1016/j.bioorg.2019.103454

Cited by 17 publications

(10 citation statements)

References 37 publications

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“…IC 50 for MCF-12A cell line after 48 h incubation with SFN was significantly higher (40.5 µm) than for breast cancer transformed cells, MCF-7 (27.9 µm) [115]. However, after prolonged incubation (72 h), the IC 50 value for cancer non-transformed breast cells MCF-10 was slightly higher (12.4 µm) than the value obtained in cancer transformed breast cells MCF-7 and MDA-MB-231 (11.9 µm, 11.3 µm, respectively) ( Table 4) [120]. In some studies, cells from other organs, such as dermal microvascular endothelium cells HMEC or CRL-1790, i.e., normal colon cells, were used as a model of normal cells.…”

Section: Sfn Inhibits Growth Of Breast Cancer Cellsmentioning

confidence: 85%

Breast Cancer Prevention-Is there a Future for Sulforaphane and Its Analogs?

2020

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Breast cancer is the most prevalent type of cancer among women worldwide. There are several recommended methods of breast cancer prevention, including chemoprevention. There are several approved drugs used to prevent breast cancer occurrence or recurrence and metastasizing. There are also a number of new substances undergoing clinical trials and at the stage of initial study. Studies suggest that dietary factors play a crucial role in breast cancer etiology. Epidemiological studies indicate that in particular vegetables from the Brassicaceae family are a rich source of chemopreventive substances, with sulforaphane (SFN) being one of the most widely studied and characterized. This review discusses potential applicability of SFN in breast cancer chemoprevention. A comprehensive review of the literature on the impact of SFN on molecular signalling pathways in breast cancer and breast untransformed cells is presented. The presented results of in vitro and in vivo studies show that this molecule has a potential to act as a preventive molecule either to prevent disease development or recurrence and metastasizing, and as a compound protecting normal cells against the toxic effects of cytostatics. Finally, the still scanty attempts to develop an improved analog are also presented and discussed.

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Section: Sfn Inhibits Growth Of Breast Cancer Cellsmentioning

confidence: 85%

Breast Cancer Prevention-Is there a Future for Sulforaphane and Its Analogs?

2020

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“…TEER is a nonspecific marker of the IECs barrier function [ 34 ]. Co-cultured with SFP for 24 h, the TEER of Caco-2 monolayer increased strongly, suggesting that SFP could increase the tightness of epithelial cells monolayer.…”

Section: Discussionmentioning

confidence: 99%

Sulforaphane protects intestinal epithelial cells against lipopolysaccharide-induced injury by activating the AMPK/SIRT1/PGC-1ɑ pathway

Zhang

2021

Bioengineered

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The naturally occurring isothiocyanate sulforaphane, found in vegetables, shows promising antiinflammatory, anti-apoptosis, and anti-oxidative effects. Whether sulforaphane protects against lipopolysaccharide (LPS)-induced injury in intestinal epithelial cells is unclear. The present study examines the ability of sulforaphane to protect Caco-2 cultures from LPS-induced injury, as well as the mechanism involved. Caco-2 cells were incubated for 24 h with 1 μg/mL LPS and different concentrations of sulforaphane (0.1-10 μM). Then, various indicators of oxidative stress, inflammation, apoptosis, and intestinal permeability were assayed. Sulforaphane increased cell viability and reduced lactate dehydrogenase activity in LPS-treated Caco-2 cells in a concentrationdependent manner. Sulforaphane weakened LPS-induced increases in intestinal epithelial cell permeability and oxidative stress (based on assays of reactive oxygen species, DMA, and H 2 O 2 ), and it increased levels of antioxidants (SOD, GPx, CAT and T-AOC). At the same time, sulforaphane weakened the ability of LPS to induce production of inflammatory cytokines (IL-1β, IL-6, IL-8 and TNF-α) and the pro-apoptotic caspases-3 and −9. Sulforaphane also upregulated p-AMPK, SIRT1, and PGC-1ɑ, whose inhibitors antagonized the compound's protective effects. Sulforaphane can protect intestinal epithelial cells against LPS-induced changes in intestinal permeability, oxidative stress, inflammation, and apoptosis. It appears to act by activating the AMPK/SIRT1/PGC-1ɑ pathway. The drug therefore shows potential for preventing LPS-induced intestinal injury.

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“…Recently, the same research group described synthesis and biological activity of fluoroaryl analogs of SFN with 4 and 5 carbon atoms in the unbranched alkyl chain [ 245 ]. Thus, the starting ω-aminoalk-1-yl fluoroaryl or fluoroarylmethyl sulfides 77 were converted to the final fluoroaryl or fluoroarylmethyl analogs of SFN 80a – h by two alternative pathways ( Figure 21 ).…”

Section: Synthesis Of Bifunctional Analogs Of Sulforaphane and Their ...mentioning

confidence: 99%

Sulforaphane and Its Bifunctional Analogs: Synthesis and Biological Activity

Janczewski

2022

Molecules

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For decades, various plants have been studied as sources of biologically active compounds. Compounds with anticancer and antimicrobial properties are the most frequently desired. Cruciferous plants, including Brussels sprouts, broccoli, and wasabi, have a special role in the research studies. Studies have shown that consumption of these plants reduce the risk of lung, breast, and prostate cancers. The high chemopreventive and anticancer potential of cruciferous plants results from the presence of a large amount of glucosinolates, which, under the influence of myrosinase, undergo an enzymatic transformation to biologically active isothiocyanates (ITCs). Natural isothiocyanates, such as benzyl isothiocyanate, phenethyl isothiocyanate, or the best-tested sulforaphane, possess anticancer activity at all stages of the carcinogenesis process, show antibacterial activity, and are used in organic synthesis. Methods of synthesis of sulforaphane, as well as its natural or synthetic bifunctional analogues with sulfinyl, sulfanyl, sulfonyl, phosphonate, phosphinate, phosphine oxide, carbonyl, ester, carboxamide, ether, or additional isothiocyanate functional groups, and with the unbranched alkyl chain containing 2–6 carbon atoms, are discussed in this review. The biological activity of these compounds are also reported. In the first section, glucosinolates, isothiocyanates, and mercapturic acids (their metabolites) are briefly characterized. Additionally, the most studied anticancer and antibacterial mechanisms of ITC actions are discussed.

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Fluoroaryl analogs of sulforaphane – A group of compounds of anticancer and antimicrobial activity

Cited by 17 publications

References 37 publications

Breast Cancer Prevention-Is there a Future for Sulforaphane and Its Analogs?

Breast Cancer Prevention-Is there a Future for Sulforaphane and Its Analogs?

Sulforaphane protects intestinal epithelial cells against lipopolysaccharide-induced injury by activating the AMPK/SIRT1/PGC-1ɑ pathway

Sulforaphane and Its Bifunctional Analogs: Synthesis and Biological Activity

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