化学
细胞毒性T细胞
癌细胞系
细胞培养
细胞毒性
癌细胞
癌症
生物化学
体外
内科学
遗传学
医学
生物
作者
Antônio Linkoln Alves Borges Leal,Daniel Pascoalino Pinheiro,Francisco Washington Araújo Barros-Nepomuceno,Priscila T. da Silva,Cláudia Pessoa,Francisco Wagner Queiroz Almeida-Neto,Emmanuel Silva Marinho,Antônio C.H. Barreto,Murilo Sérgio da Silva Julião,Aldeneide Soares de Paiva,Paulo Nogueira Bandeira,Pedro de Lima‐Neto,Hélcio Silva dos Santos,Alexandre Magno Rodrigues Teixeira
标识
DOI:10.1016/j.molstruc.2021.131135
摘要
• Four chalcones were synthesized by Claisen-Schmidt condensation reaction. • DFT calculations presented a good agreement with the experimental data. • Spectroscopic proprieties of the chalcones depend on the substitution on the B-ring. • Anticancer activity was observed against HCT-116 and HL-60 tumor cell lines. Chalcones and their derivatives exhibit a broad spectrum of pharmacological activities, including antiproliferative activities. Accordingly, they are deemed robust anticancer candidates for cytotoxicity assays. Herein, we synthesized and characterized four chalcones using nuclear magnetic resonance ( 1 H NMR and 13 C NMR), Fourier transform Raman (FT-Raman), attenuated total reflection Fourier transform infrared (ATR-FTIR), and ultraviolet-visible (UV–vis) spectroscopy. Theoretical calculations of quantum chemistry were performed to obtain data regarding normal vibration modes, frontier molecular orbitals, molecular electrostatic potential maps, theoretical UV–vis spectra, and quantum chemical parameters expected for these chalcones. In addition, we evaluated the cytotoxic potential of these compounds. For synthesized compounds, quantum chemical calculations demonstrated excellent correlation with experimental data. The electronic properties revealed that chalcones 1 and 4 possess a higher electrophilic character, while chalcones 2 and 3 possess a higher nucleophilic character. Chalcone 3 demonstrated the highest value of HOMO energy, indicating the greatest propensity to donate electronic density among the four compounds. According to the HOMO-LUMO energy gap and global hardness, the reactivity of chalcones should follow the order 1 < 2 < 4 < 3. Regarding the cytotoxic potential, chalcones 1 and 4 exhibited superior activity against HL-60 acute promyelocytic leukemia cells (IC 50 = 14.09 ± 1.001 and 28.02 ± 1.47 µM, respectively) and HCT-116 colon cancer cells (IC 50 = 22.64 ± 0.64 and 42.74 ± 4.63 µM, respectively).
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