Inhibition of carcinogen-induced pulmonary and mammary carcinogenesis by chalcone administered subsequent to carcinogen exposure

Wattenberg, Lee W.; Coccia, Judith B.; Galbraith, Arthur R.

doi:10.1016/0304-3835(94)90314-x

Cited by 83 publications

(47 citation statements)

References 9 publications

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“…5 In particular, chalcone systems usually show different levels of inhibition during proliferative processes of a plethora of cancer cell lines. 6 The presence of hydroxyl, allyl and prenyl groups in their structures commonly potentiates their activities. 7 For instance, the inclusion of two hydroxyl groups (dihydroxychalcones) enhanced both the antitumor and lipidic antiperoxidation activities.…”

Section: Introductionmentioning

confidence: 99%

Biological and structure-activity evaluation of chalcone derivatives against bacteria and fungi

Silva¹,

Andrade²,

Napolitano³

et al. 2013

J. Braz. Chem. Soc.

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O presente trabalho descreve as atividades antibacterianas e antifúngicas de diversas chalconas obtidas diretamente através da condensação aldólica tipo Claisen-Schmidt das quais se determinou a concentração inibitória mínima frente a diferentes microrganismos (bactérias Gram-positivas e Gram-negativas e fungos). Estruturas no estado sólido cristalino de sete chalconas foram determinadas por análise de difração de raios X (XRD). Estudos quimiométricos foram realizados com intuito de identificar uma potencial relação entre estrutura e atividade.The present work describes the antibacterial and antifungal activities of several chalcones obtained by a straight Claisen-Schmidt aldol condensation determined by the minimal inhibitory concentration against different microorganisms (Gram-positive and Gram-negative bacteria and fungi). Solid state crystal structures of seven chalcones were determined by X-ray diffraction (XRD) analysis. Chemometric studies were carried out in order to identify a potential structureactivity relationship.

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Section: Introductionmentioning

confidence: 99%

Biological and structure-activity evaluation of chalcone derivatives against bacteria and fungi

Silva¹,

Andrade²,

Napolitano³

et al. 2013

J. Braz. Chem. Soc.

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“…Hydroxyl chalcones and isoliquiritigenin have been shown to be potent inhibitors of skin carcinogenesis in vivo (Yamamoto et al, 1991;Satomi, 1993). Several studies have demonstrated that chalcones act as chemopreventive agents, capable of inhibiting carcinogenesis induced by chemical agents through enhancement of reduced glutathione levels (Wattenberg et al, 1994;Makita et al, 1996). However, the exact mechanisms of action of chalcones in tumor cells remain to be elucidated.…”

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confidence: 99%

A Boronic-Chalcone Derivative Exhibits Potent Anticancer Activity through Inhibition of the Proteasome

et al. 2006

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Chalcones and their derivatives have been shown to have potent anticancer activity. However, the exact mechanisms of cytotoxic activity remain to be established. In this study, we have evaluated a series of boronic chalcones for their anticancer activity and mechanisms of action. Among the eight chalcone derivatives tested, 3,5-bis-(4-boronic acid-benzylidene)-1-methyl-piperidin-4-one (AM114) exhibited most potent growth inhibitory activity with IC 50 values of 1.5 and 0.6 M in 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay and colony formation assay, respectively. The cytotoxic activity of AM114 was shown to be associated with the accumulation of p53 and p21 proteins and induction of apoptosis. Mechanistic studies showed that AM114 treatment inhibited the chymotrypsin-like activity of the 20S proteasome in vitro, leading to a significant accumulation of ubiquitinated p53 and other cellular proteins in whole cells. In vitro studies showed that AM114 did not significantly disrupt the interaction of p53 and murine double minute 2 protein. It is noteworthy that AM114 as a single agent was preferentially toxic to cells with wild-type p53 expression, whereas combination of this compound with ionizing radiation (IR) significantly enhanced the cell-killing activity of IR in both wild-type p53 and p53-null cells. Together, these results indicate that the boronic chalcone derivative AM114 induces significant cytotoxic effect in cancer cells through the inhibition of the cellular proteasome and provide a rationale for the further development of this class of compounds as novel cancer chemotherapeutic agents.Chalcones and their derivatives are a group of compounds reported to exhibit promising anticancer activity. These compounds are precursors of flavonoids and isoflavonoids, which are abundant in edible plants. The chemical structure of chalcones (1,3-diphenyl-2-propen-1-

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“…Isoliquiritigenin also exhibits significant anticancer activity such as induction of cell cycle arrest and up-regulation of p21 expression in a lung cancer cell line (Ii et al, 2004), suppression of pulmonary metastasis of mouse renal cell carcinoma through activation of the immune system , and induction of apoptosis in human gastric cancer cells (Ma et al, 2001). As a chemopreventive agent, isoliquiritigenin has been shown in vivo to prevent colon and mammary cancer in several rat carcinogenesis models (Wattenberg et al, 1994;Baba et al, 2002). Another mechanism of chemoprevention by isoliquiritigenin is induction of phase 2 enzymes, such as quinone reductase, that protect cells against reactive, toxic, and potentially carcinogenic species (Ross et al, 2000;Cuendet et al, 2006).…”

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confidence: 99%

In Vitro Metabolism of Isoliquiritigenin by Human Liver Microsomes

Guo¹,

Liu²,

Nikolić³

et al. 2007

Drug Metab Dispos

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ABSTRACT:Isoliquiritigenin (2,4,4-trihydroxychalcone), a chalcone found in licorice root and other plants, has shown potent antitumor, antioxidant, and phytoestrogenic activity in vitro. In preparation for in vivo studies, the metabolism of isoliquiritigenin by human liver microsomes was investigated, and seven phase 1 metabolites were identified. In addition to aromatic hydroxylation that occurred on the A or B ring to form 2,4,4,5-tetrahydroxychalcone or butein, respectively, reduction of the carbon-carbon double bond of an ␣,␤-unsaturated ketone and cyclization occurred to form 2,4,4-trihydroxydihydrochalcone and (Z/E)-6,4-dihydroxyaurone. All metabolites were characterized and identified by using liquid chromatography-tandem mass spectrometry with comparison to authenticated compounds. Finally, monoclonal antibody inhibitors of specific human cytochrome P450 (P450) enzymes and recombinant human P450 enzymes were used to identify the enzymes responsible for the formation of the major mono-oxygenated metabolites, and P450 2C19 was found to be a significant enzyme in the formation of butein from isoliquiritigenin, which also has anticancer activity. Cytochromes P450, reactive oxygen species, and peroxidases can all contribute to the formation of (Z/E)-6,4-dihydroxyaurone in human liver microsomes.

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Inhibition of carcinogen-induced pulmonary and mammary carcinogenesis by chalcone administered subsequent to carcinogen exposure

Cited by 83 publications

References 9 publications

Biological and structure-activity evaluation of chalcone derivatives against bacteria and fungi

Biological and structure-activity evaluation of chalcone derivatives against bacteria and fungi

A Boronic-Chalcone Derivative Exhibits Potent Anticancer Activity through Inhibition of the Proteasome

In Vitro Metabolism of Isoliquiritigenin by Human Liver Microsomes

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