Antimicrobial Activities and In silico Analysis of Methoxy Amino Chalcone Derivatives

Two chalcone derivatives i.e. (E)-1-(4-aminophenyl)-3-(2,3dimethoxyphenyl)-prop-2-en-1-one (Compound-1), and (E)-1-(4-aminophenyl)-3-phenylprop-2-en-1-one) (Compound-2), has been proven to have potential cytotoxic activity. The aim of this study was to evaluate the effect of these compounds on PI3K/Akt signalling pathway in K562 cell lines. After incubation with the tested compounds, AKT, caspase-3, STAT3 and cyclin D1 concentrations were measured using ELISA. Furthermore, cell cycle was analysed using flowcytometry. Imatinib and isotretinoin were used as positive control, whereas cell culture without treatment was used as negative control. The AKT concentration after treatment with Compound-1 and -2 was significantly lower than that control, imatinib and isotretinoin (p<0.05). The apoptotic indices after treatment with Compound-1 and -2 were significantly higher than control, however they were lower than imatinib and isotretinoin (p<0.05). The caspase-3 concentration after treatment with Compound-1 at 5 and 10 µg/mL and Compound-2 at 10 µg/mL was significantly higher than that control and imatinib, however it was lower than isotretinoin (p<0.05). The STAT3 concentration after treatment with Compound-1 and -2 was significantly lower than that control and isotretinoin at 50 µg/mL (p<0.05) and similar with imatinib (p>0.05). The cyclin D1 concentration after treatment with Compound-1 and -2 was significantly lower than that control, imatinib and isotretinoin (p<0.05). In addition, Compound-1 and -2 arrested G 0 / G 1 and G 2 /M phase in K562 cell lines, with comparable results to imatinib and isotretinoin. In conclusion, the mechanism of cytotoxic activity of Compound-1 and -2 are through the PI3K/Akt signalling pathway inhibition, apoptosis induction by upregulation of apoptotic markers, and inhibition of cell cycle progression by regulating cell cycle-related factors. ABSTRAKDua turunan kalcon yaitu (E)-1-(4-aminofenil)-3-(2,3dimetoksifenil)-prop-2-en-1-one (Senyawa-1), and (E)-1-(4-aminofenil)-3-fenilprop-2-en-1-one) (Senyawa-2), terbukti mempunyai aktivitas sitotoksik yang potensial. Tujuan penelitian ini adalah untuk mengkaji efek kedua senyawa tersebut pada jalur sinyal PI3K/Akt pada sel K562. Setelah J Med Sci, Volume 49, No. 4, 2017 October: 153-164 154 diinkubasikan dengan senyawa uji, kadar AKT, caspase-3, STAT3 dan siklin D1 diukur dengan ELISA. Selanjutnya siklus sel dianalisis dengan flowcyometry. Imatinib dan isotretinoin digunakan sebagai kontrol positif dan kultur sel tanpa perlakuan sebagai kontrol negatif. Kadar AKT setelah perlakuan dengn Senyawa-1 dan -2 lebah rendah secara nyata dibaningkan dengan kontrol, imatiib dan isotretinoin (p<0.05). Indeks apoptosis setelah perlakuan dengan Senyawa-1 dan -2 lebih tinggi secara nyata dibandingkan kontrol, tetapi lebih rendah dibandingkan imatinib dan isotretinoin (p<0.05). Kadar caspase-3 setelah perlakuan Senyawa-1 dengan kadar 5 dan 10 µg/mL dan Senyawa-2 dengan kadar 10 µg/mL lebih tinggi secara nyata dibandingkan kontrol dan imatinib, tet...

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“…The methoxy amino chalcone derivatives were synthesized by Suwito et al 14 The structure of these compounds is presented in FIGURE 1. …”

Section: Tested Compoundsmentioning

confidence: 99%

Mechanism of cytotoxic activity of chalcone derivatives against K562 leukemia cell lines

et al. 2017

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“…. Nowadays several chalcones are used to treat the inflammatory conditions 6,7 , cancer 8 viral infections 9,10 , cardiovascular diseases, parasitic infections, gastritis, microbial infections 11,12 and convulsions 13 . In addition, they are also used as food additives and cosmetic formulation ingredients.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Antibacterial, Antifungal Antitubercular Activities and Molecular Docking Studies of Nitrophenyl Derivatives

BABU

Prasad

Nissankararao³

et al. 2019

Int J Life Sci Pharm Res

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Infectious diseases are one of the common problems encountered globally. Even though there are a number of drugs available in the market for the treatment of infectious diseases, still many new molecules are required due to the problems with the existing drugs. Hence we prepared a series of chalcones (A1-A10) containing nitrophenyl moieties by Claisen-Schmidt condensation reaction. All the ten compounds were characterized by IR, NMR, Mass spectroscopy and elemental analysis. The compounds were further screened for antitubercular activity employing MABA assay and antibacterial and antifungal activities by cup plate method against selected tubercular, bacterial and fungal organisms. The compound A9 displayed potent antitubercular activity with MIC 11.02±0.030, whereas the compound A3 showed superior antibacterial and antifungal activities. Further, molecular docking studies were performed on Thymidine Kinase (TMP) of Mycobacterium tuberculosis by employing AU autodocker. The docking scores were in association with the in vitro MABA results and also identified the potent nature of A9 with the docking score-6.7. This study helped to identify novel nitrophenyl derivatives against thymidylate kinase.

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“…Chalcone scaffold represents a core unit that exhibits various biological activities especially highlighting antimicrobial activity. In addition, they present a combinatorial assembly for the synthesis of heterocyclic scaffolds 12–14 . Molecular hybridisation is a new concept in drug design and development based on the combination of pharmacophoric moieties of different bioactive substances to produce a new hybrid compound with improved affinity and efficacy when compared to the parent drugs.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, antimicrobial, anti-biofilm evaluation, and molecular modelling study of new chalcone linked amines derivatives

El‐Messery

Habib

Al-Rashood

et al. 2018

Journal of Enzyme Inhibition and Medicinal Chemistry

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A series of amide chalcones conjugated with different secondary amines were synthesised and characterised by different spectroscopic techniques 1H NMR, 13C NMR, and ESI-MS. They were screened for in vitro antibacterial activity. Compounds 36, 37, 38, 42, and 44 are the most active among the synthesised series exhibiting MIC value of 2.0–10.0 µg/ml against different bacterial strains. Compound 36 was equipotent to the standard drug Ampicillin displaying MBC value of 2.0 µg/ml against the bacterial strain Staphylococcus aureus. The products were screened for anti-biofilm activity. Compounds 36, 37, and 38 exhibited promising anti-biofilm activity with IC50 value ranges from 2.4 to 8.6 µg. Molecular modelling was performed suggesting parameters of signalling anti-biofilm mechanism. AspB327 HisB340 (arene–arene interaction) and IleB328 amino acid residues seemed of higher importance to inhibit c-di-GMP. Hydrophobicity may be crucial for activity. ADME calculations suggested that compounds 36, 37, and 38 could be used as good orally absorbed anti-biofilm agents.

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Antimicrobial Activities and In silico Analysis of Methoxy Amino Chalcone Derivatives

Cited by 21 publications

References 12 publications

Mechanism of cytotoxic activity of chalcone derivatives against K562 leukemia cell lines

Mechanism of cytotoxic activity of chalcone derivatives against K562 leukemia cell lines

Synthesis, Antibacterial, Antifungal Antitubercular Activities and Molecular Docking Studies of Nitrophenyl Derivatives

Synthesis, antimicrobial, anti-biofilm evaluation, and molecular modelling study of new chalcone linked amines derivatives

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