Structure-mutagenicity relationships of chalcones and their oxides in the Salmonella assay

Rashid, Kamal A.; Mullin, Christopher A.; Mumma, Ralph O.

doi:10.1016/0165-1218(86)90086-8

Cited by 17 publications

(15 citation statements)

References 14 publications

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“…A similar condition was found in other studies with the Ames test using substituted chalcones with other different groups [38][39][40][41]. Furthermore, Rashid et al [42] analyzed the mutagenicity of several ρ-monosubstituted chalcones, by the Ames test, and using multiple factorial analysis revealed that the increase in hydrophilicity and resonance electronic were the most important factors associated with mutagenicity. Thus, the low hydrophilicity may be associated with absence of mutagenicity in S. typhimurium of 4-CL and DMF.…”

Section: Discussionsupporting

confidence: 74%

“…On the other hand, high concentrations of some hydrophobic compounds can result in microcrystallization [42], increasing the generation of ROS during biotransformation from hydrophobic to a hydrophilic compound to improve clearance and therefore an increase in mutagenicity [66], such as occurred with the highest concentration of 4-CL co-treated with SA, in the Ames test.…”

Section: Discussionmentioning

confidence: 99%

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In vitro and in vivo evaluation of genotoxicity, cytotoxicity, and protective effects of synthetic chalcones (E)-3-(4-chlorophenyl)-1-phenyl-2-propen-1-one (4-CL) and (E)-3-(3,4-dimethoxyphenyl)-1- phenyl-2-propen-1-one (DMF)

Nunes

Melo

Barbosa

et al. 2022

J Pharm Biopharm Res

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The chalcones (E)-3-(4-chlorophenyl)-1-phenyl-2-propen-1-one (4-CL) and (E)-3-(3,4-dimethoxyphenyl)-1-phenyl-2 -propen-1-one (DMF) are versatile and easily synthesized into low-cost compounds that have a wide spectrum of biological activities. In this study, the cytotoxic, genotoxic and modulatory activities of 4-CL and DMF were evaluated using the Ames test and the mouse micronucleus assay. The results of the Ames test revealed that both chalcones did not show mutagenic activity in Salmonella typhimurium strains TA98 and TA100, and demonstrated significant antimutagenicity (p< 0.05) when co-administered with sodium azide (SA) in strain TA100. In the micronucleus assay, both showed a significant increase in the frequency of micronucleated polychromatic erythrocytes (MNPCE) at 24 h and 48 h, revealing a genotoxic effect. In the co-treatment with mitomycin C (MMC) there was a significant decrease (p< 0.05) in the frequency of MNPCE both in chalcones at 24h and in the less concentrated dose of DMF at 48h, demonstrating its antigenotoxic activity. 4-CL showed a significant decrease in the polychromatic/ normochromatic erythrocyte (PCE/ NCE) ratio at 24 and 48 h (p< 0.05), indicating cytotoxicity. However, 4-CL and DMF when co-administered with MMC showed a significant increase in the PCE/NCE ratio within 24 hours, demonstrating anticytotoxicity. Furthermore, a biphasic dose-response behavior was observed in both chalcones, 4-CL in the co-administration with SA, in the Ames Test and DMF in the co-treatment with MMC, at 48 hours of exposure, in the micronucleus assay. In this study, 4-CL and DMF showed genotoxic, cytotoxic, antigenotoxic, anticytotoxic and no mutagenic properties.

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Section: Discussionsupporting

confidence: 74%

Section: Discussionmentioning

confidence: 99%

In vitro and in vivo evaluation of genotoxicity, cytotoxicity, and protective effects of synthetic chalcones (E)-3-(4-chlorophenyl)-1-phenyl-2-propen-1-one (4-CL) and (E)-3-(3,4-dimethoxyphenyl)-1- phenyl-2-propen-1-one (DMF)

Nunes

Melo

Barbosa

et al. 2022

J Pharm Biopharm Res

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“…In our study, 2HMC did not exhibit mutagenic effect by Ames test, since none of the doses reached MI ≥ 2 on either tester strains ( Table 1 ). Several studies have reported the lack of mutagenic action for many classes of chalconas [ 38 , 39 ]. Furthemore, in a study using diferent hydroxychalcones, 4’5’-dimethyl-2’,3,4-trihydroxylchalcone, 6 methyl-2’,3,4-trihydroxychalcone, and 3,3’,4’,7-tetrahydroxyflavone, none of them presented mutagenic effect by the Ames test [ 40 ].…”

Section: Discussionmentioning

confidence: 99%

Absence of genotoxic effects of the chalcone (E)-1-(2-hydroxyphenyl)-3-(4-methylphenyl)-prop-2-en-1-one) and its potential chemoprevention against DNA damage using in vitro and in vivo assays

et al. 2017

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The chalcone (E)-1-(2-hydroxyphenyl)-3-(4-methylphenyl)-prop-2-en-1-one), or 2HMC, displays antileishmanial, antimalarial, and antioxidant activities. The aim of this study was to investigate the cytotoxic, genotoxic, mutagenic, and protective effects of 2HMC using the Ames mutagenicity test, the mouse bone marrow micronucleus test, and the comet assay in mice. In the assessment using the Ames test, 2HMC did not increase the number of His+ revertants in Salmonella typhimurium strains, demonstrating lack of mutagenicity. 2HMC showed no significant increase in micronucleated polychromatic erythrocyte frequency (MNPCE) in the micronucleus test, or in DNA strand breaks using the comet assay, evidencing absence of genotoxicity. Regarding cytotoxicity, 2HMC exhibited moderate cytotoxicity in mouse bone marrow cells by micronucleus test. 2HMC showed antimutagenic action in co-administration with the positive controls, sodium azide (SA) and 4-nitroquinoline-1-oxide (4NQO), in the Ames test. Co-administered and mainly pre-administered with cyclophosphamide (CPA), 2HMC caused a decrease in the frequency of MNPCE using the micronucleus test and in DNA strand breaks using the comet assay. Thus, 2HMC exhibited antimutagenic and antigenotoxic effects, displaying a DNA-protective effect against CPA, SA, and 4NQO carcinogens. In conclusion, 2HMC presented antimutagenic, antigenotoxic and moderate cytotoxic effects; therefore it is a promising molecule for cancer prevention.

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“…Since the displacement of electron density of this system coupled to substituent group, in the position B, decreases the reactivity of the amino group, in ring A, thus likely decreasing toxicity. Regarding the nitrochalcones, it is interesting to note that the nitro group may suggest a possible toxic [ 23 ] , and mutagenic actions [ 24 ] , but in our results, no toxicity against Artemia salina was observed (CL 50 > 1 000 μg/mL). It is important to mention that some clinically used drugs contain a nitroaromatic moiety, e. g. nimesulide, fl utamide, tolcapone, nitrofurantoin and others.…”

mentioning

confidence: 48%

Antimicrobial and Cytotoxicity Potential of Acetamido, Amino and Nitrochalcones

Tristão

Buzzi

Corrêa

et al. 2012

Arzneimittelforschung

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Chalcones constitute one of the major classes of natural products belonging to the flavonoid family, and they have been reported as having a range of important therapeutic activities, including some chalcones are effective as antimicrobial agents. Currently, the search for new structures with antimicrobial activity has been intensified due to the emergence of many strains resistant to antibiotics currently used to treat infectious diseases.3 chalcone series (amino, acetamido and nitrochalcones) were prepared (23 compounds) and evaluated for their antimicrobial and cytotoxic potential. The effects of substituents on their respective activities also was evaluated.The results showed that 4 aminochalcones (2, 4, 8, 9), 3 acetoamidochalcones (10, 14, 18) and 3 nitrochalcones (20, 22, 23), exhibited antifungal effects. The aminochalcones were more toxic than the acetamidochalcones, while the nitrochalcones did not present any toxic effect. It was verified that there seems to be structure-activity correlation in some electron-donating and withdrawing substituents groups in rings A and B of the synthetized chalcone analogues and its antifungal and cytotoxic activity.

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Structure-mutagenicity relationships of chalcones and their oxides in the Salmonella assay

Cited by 17 publications

References 14 publications

In vitro and in vivo evaluation of genotoxicity, cytotoxicity, and protective effects of synthetic chalcones (E)-3-(4-chlorophenyl)-1-phenyl-2-propen-1-one (4-CL) and (E)-3-(3,4-dimethoxyphenyl)-1- phenyl-2-propen-1-one (DMF)

In vitro and in vivo evaluation of genotoxicity, cytotoxicity, and protective effects of synthetic chalcones (E)-3-(4-chlorophenyl)-1-phenyl-2-propen-1-one (4-CL) and (E)-3-(3,4-dimethoxyphenyl)-1- phenyl-2-propen-1-one (DMF)

Absence of genotoxic effects of the chalcone (E)-1-(2-hydroxyphenyl)-3-(4-methylphenyl)-prop-2-en-1-one) and its potential chemoprevention against DNA damage using in vitro and in vivo assays

Antimicrobial and Cytotoxicity Potential of Acetamido, Amino and Nitrochalcones

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