Antimicrobial and Cytotoxicity Potential of Acetamido, Amino and Nitrochalcones

Tristão, Taline Canto; Buzzi, Fátima de Campos; Corrêa, Rogério; Cruz, Ramón; Filho, Valdir Cechinel; Cruz, Alexandre Bella

doi:10.1055/s-0032-1327610

Cited by 7 publications

(4 citation statements)

References 16 publications

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“…The literature describes chalcones containing a single amino group as promising agents with antitumor [10], antimicrobial [11,12] and antioxidant activity [13]. The DPPH assay performed on 2′-amino- and 4′-aminochalcones proved their ability to scavenge free radicals.…”

Section: Introductionmentioning

confidence: 99%

“…Lin et al described the high potential of 3′-amino-2-iodochalcone to inhibit the growth of Mycobacterium tuberculosis , a Gram-positive pathogenic bacterium which is an tuberculosis agent [24]. Moreover, 4′-aminochalcones, especially those with methoxy substituents attached to the ring B, exhibited antimicrobial activity against Escherichia coli , Staphylococcus aureus , Candida albicans and Trichophyton mentagrophytes [11,25]. Furthermore, the presence of a -NO 2 group attached to the C-4 position enhances by 2–3 times the antifungal activity against Microsporum canis , Trichophyton rubrum and Epidermophyton floccosum in comparison to unsubstituted chalcone [26].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Biological Evaluation of Novel Aminochalcones as Potential Anticancer and Antimicrobial Agents

et al. 2019

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A series of 18 aminochalcone derivatives were obtained in yields of 21.5–88.6% by applying the classical Claisen-Schmidt reaction. Compounds 4–9, 14 and 16–18 with 4-ethyl, 4-carboxy-, 4-benzyloxy- and 4-benzyloxy-3-methoxy groups were novel, not previously described in the scientific literature. To determine the biological properties of the synthesized compounds, anticancer and antimicrobial activity assays were performed. Antiproliferative potential was evaluated on four different human colon cancer cell lines—HT-29, LS180, LoVo and LoVo/DX —using the SRB assay and compared with green monkey kidney fibroblasts COS7. Anticancer activity was described as the IC50 value. The best results were observed for 2′-aminochalcone (1), 3′-aminochalcone (2) and 4′-aminochalcone (3) (IC50 = 1.43–1.98 µg·mL−1) against the HT-29 cell line and for amino-nitrochalcones 10–12 (IC50 = 2.77–3.42 µg·mL−1) against the LoVo and LoVo/DX cell lines. Moreover, the antimicrobial activity of all derivatives was evaluated on two strains of bacteria: Escherichia coli ATCC10536 and Staphylococcus aureus DSM799, the yeast strain Candida albicans DSM1386 and three strains of fungi: Alternaria alternata CBS1526, Fusarium linii KB-F1 and Aspergillus niger DSM1957. In the case of E. coli ATCC10536 almost all derivatives hindered the bacterial growth (∆OD = 0). Furthermore, the best results were observed in the presence of 4′-aminochalcone (3), that completely limited the growth of all tested strains at the concentration range of 0.25–0.5 mg·mL−1. The strongest bacteriostatic activity was exhibited by novel 3′-amino-4-benzyloxychalcone (14), that prevented the growth of E. coli ATCC10536 with MIC = 0.0625 mg·mL−1.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of Novel Aminochalcones as Potential Anticancer and Antimicrobial Agents

et al. 2019

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“…It should be mentioned that the ability to fluoresce via 3PE has not been reported so far for similar compounds, as far as we know. Additionally, the low toxicity of compounds similar to ChN(CH3)2 was already reported [ 43 , 44 ], which is essential for biological applications. Thus, the fluorescence was collected by an optical fiber for different excitation pulse energies, and plotted in a log-log scale, revealing an angular coefficient equal to 2 (for 2PE) and 3 (for 3PE), thus confirming that the fluorescence emission was triggered by 2PE and 3PE.…”

Section: Resultsmentioning

confidence: 99%

Two-Photon Absorption and Multiphoton Excited Fluorescence of Acetamide-Chalcone Derivatives: The Role of Dimethylamine Group on the Nonlinear Optical and Photophysical Properties

et al. 2023

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This work studied the effect of different electron-withdrawing and electron-donating groups on the linear and nonlinear optical properties of acetamide-chalcone derivatives. The results showed that the addition of the dimethylamine group led to a large fluorescence emission (71% of fluorescence quantum yield in DMSO solution) that can be triggered by two and three-photon excitations, which is essential for biological applications. Furthermore, dimethylamine also red-shifts the lower energy state by approximately 90 nm, increasing the two-photon absorption cross-section of the lower energy band by more than 100% compared with the other studied compounds. All compounds presented two-electronic states observed through one and two-photon absorption spectroscopy and confirmed by Quantum Chemistry Calculations (QCCs). QCC results were also used to model the experimental two-photon absorption cross-sectional spectrum by the Sum-Over-States (SOS) approach, revealing a dependence between the coupling of the ground state with the first excited state and the transition dipole moment between these states.

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“…The purity was determined as the percentage ratio of the area of the compound's peak and the total area. 4.3 Antimicrobial assays of the synthesized compounds against C. albicans, E. coli and S. aureus via the diffusion method [73][74][75] 4.3.1 Biological assaymicroorganisms, media and inocula. For the antimicrobial evaluation, strains from the American Type Culture Collection (ATCC), Rockville, MD, USA, were used.…”

Section: Chemistrymentioning

confidence: 99%

Novel one-pot synthesis of a library of 2-aryloxy-1,4-naphthoquinone derivatives. Determination of antifungal and antibacterial activity

et al. 2022

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Antimicrobial and Cytotoxicity Potential of Acetamido, Amino and Nitrochalcones

Cited by 7 publications

References 16 publications

Synthesis and Biological Evaluation of Novel Aminochalcones as Potential Anticancer and Antimicrobial Agents

Synthesis and Biological Evaluation of Novel Aminochalcones as Potential Anticancer and Antimicrobial Agents

Two-Photon Absorption and Multiphoton Excited Fluorescence of Acetamide-Chalcone Derivatives: The Role of Dimethylamine Group on the Nonlinear Optical and Photophysical Properties

Novel one-pot synthesis of a library of 2-aryloxy-1,4-naphthoquinone derivatives. Determination of antifungal and antibacterial activity

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