Solvent-free synthesis of novel vanillidene derivatives of Meldrum's acid: biological evaluation, DNA and BSA binding study

Janković, Nenad; Muškinja, Jovana; Ratković, Zoran; Bugarčić, Živadin D.; Ranković, Branislav; Kosanić, Marijana; Stefanović, Sofija

doi:10.1039/c6ra07711k

Cited by 20 publications

(11 citation statements)

References 51 publications

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“…However, the achieved yields were not satisfactory (29, 42 and 34% of 3a, respectively), so we tried another synthetic strategy. Inspired by the excellent application of copper(II) salt (PhNH 3 ) 2 CuCl 4 in our previous studies, [59][60][61] we decided to apply it in the synthesis of complexes 3a-e. This salt yields complexes 3a-e with ligands 2a-e in a short reaction time (∼10 min) at room temperature and the obtained yields, up to 88%, were much better than with previous copper(II) salts.…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

Synthesis, characterization, biological activity, DNA and BSA binding study: novel copper(ii) complexes with 2-hydroxy-4-aryl-4-oxo-2-butenoate

et al. 2016

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A serie of novel square pyramidal copper(ii) complexes [Cu(L)HO] (3a-d) with O,O-bidentate ligands [L = ethyl-2-hydroxy-4-aryl-4-oxo-2-butenoate; aryl = 3-methoxyphenyl-2a, (E)-2-phenylvinyl-2b, (E)-2-(4'-hydroxy-3'-methoxyphenyl)vinyl-2c, 3-nitrophenyl-2d, 2-thienyl-2e] were synthesized and characterized by spectral (UV-Vis, IR, ESI-MS and EPR), elemental and X-ray analysis. The antimicrobial activity was estimated by the determination of the minimal inhibitory concentration (MIC) using the broth microdilution method. The most active antibacterial compounds were 3c and 3d, while the best antifungal activity was showed by complexes 3b and 3e. The lowest MIC value (0.048 mg mL) was measured for 3c against Proteus mirabilis. The cytotoxic activity was tested using the MTT method on human epithelial carcinoma HeLa cells, human lung carcinoma A549 cells and human colon carcinoma LS174 cells. All complexes showed extremely better cytotoxic activity compared to cisplatin at all tested concentrations. Compound 3d expressed the best activity against all tested cell lines with IC values ranging from 7.45 to 7.91 μg mL. The type of cell death and the impact on the cell cycle for 3d and 3e were evaluated by flow cytometry. Both compounds induced apoptosis and S phase cell cycle arrest. The interactions between selected complexes (3d and 3e) and CT-DNA or bovine serum albumin (BSA) were investigated by the fluorescence spectroscopic method. Competitive experiments with ethidium bromide (EB) indicated that 3d and 3e have a propensity to displace EB from the EB-DNA complex through intercalation suggesting strong competition with EB [K = (1.4 ± 0.2) and (2.9 ± 0.1) × 10 M, respectively]. K values indicate that these complexes bind to DNA covalently and non-covalently. The achieved results in the fluorescence titration of BSA with 3d and 3e [K = (2.9 ± 0.2) × 10 and (2.5 ± 0.2) × 10 M, respectively] showed that the fluorescence quenching of BSA is a result of the formation of the 3d- and 3e-BSA complexes. The obtained K values are high enough to ensure that a significant amount of 3d and 3e gets transported and distributed through the cells.

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Section: Synthesis and Characterizationmentioning

confidence: 99%

Synthesis, characterization, biological activity, DNA and BSA binding study: novel copper(ii) complexes with 2-hydroxy-4-aryl-4-oxo-2-butenoate

et al. 2016

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“…The good antimalarial activity of vanillidene Meldrum’s acid that was comparable with chloroquine was noted against P. falciparum [ 8 ]. Some vanillidene Meldrum’s acid showed a high antimicrobial effect against B. subtilis and B. cereus [ 9 ]. Bisarylidene Meldrum’s acid possesses significant activity against S. aureus , B. cereus , E. coli , and P. aeruginosa species [ 10 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Biological Evaluation of Meldrum’s Acid Derivatives: Dual Activity and Molecular Docking Study

et al. 2023

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In the presented study, eight novel Meldrum’s acid derivatives containing various vanillic groups were synthesized. Vanillidene Meldrum’s acid compounds were tested against different cancer cell lines and microbes. Out of nine, three showed very good biological activity against E. coli, and HeLa and A549 cell lines. It is shown that the O-alkyl substituted derivatives possessed better antimicrobial and anticancer activities in comparison with the O-acyl ones. The decyl substituted molecule (3i) has the highest activity against E. coli (MIC = 12.4 μM) and cancer cell lines (HeLa, A549, and LS174 = 15.7, 21.8, and 30.5 μM, respectively). The selectivity index of 3i is 4.8 (HeLa). The molecular docking study indicates that compound 3i showed good binding affinity to DNA, E. coli Gyrase B, and topoisomerase II beta. The covalent docking showed that 3i was a Michael acceptor for the nucleophiles Lys and Ser. The best Eb was noted for the topoisomerase II beta-LYS482-3i cluster.

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“…evaluated bioactivity profiles such as in vitro antioxidant and antimalarial properties of some synthesized arylidene derivatives containing Meldrum's acid. Additionally, the syntheses, antimicrobial and antibacterial activities, DNA and BSA binding studies and biological evaluations, of some Meldrum's acid derivatives were reported in the literature [12–14] . There are the experimental and theoretical researches on structural, spectroscopic, electronic, optical, thermal, electrochemical, biological and molecular docking investigations for some Meldrum's acid derivatives in the literature [2,5,15–19] …”

Section: Introductionmentioning

confidence: 99%

Structural, Bioactivity, Molecular Docking, Spectroscopic and Electronic Properties of a Synthesized Meldrum's Acid Derivative

et al. 2021

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The molecular structure, tautomeric forms (enol and keto), spectroscopic and electronic properties of a synthesized Meldrum's acid derivative were studied by using the experimental (SCXRD, FT‐IR, NMR and UV) and computational (DFT/B3LYP/6‐311++G(d,p) level) methods. Hirshfeld surface analysis were used to investigate the presence of inter‐molecular interactions within crystal packing. The biological activity, drug‐likeness and interactions between the target protein and the ligand compound were studied by in silico ADME and molecular docking methods. The non‐linear optical (NLO) activity of the compound was determined with static computations of dipole moment, polarizability and first‐order hyperpolarizability values. Thermo‐chemical features were theoretically analyzed for both enol forms. Comparatively with the experimental vibrational frequencies, detailed assignments and interpretations of the computed harmonic vibrational wavenumbers were carried out in PED. The certain structural form at the room temperature of the compound was analyzed by 1H‐ and 13C‐NMR chemical shift studies. The UV, HOMO and LUMO analyses were studied to research electronic properties of the compound. The nature, structure and existence of the hyper‐conjugative interaction for the O−H⋅⋅⋅O intra‐molecular hydrogen bonding in two enolic forms were investigated with Natural Bond Orbital (NBO) analysis. The reactive sites were obtained from atomic charges and Molecular Electrostatic Potential (MEP) map.

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Solvent-free synthesis of novel vanillidene derivatives of Meldrum's acid: biological evaluation, DNA and BSA binding study

Abstract: A series of novel O-alkyl vanillidene derivatives containing Meldrum's acid scaffold under solvent-free conditions were synthesized.

Cited by 20 publications

References 51 publications

Synthesis, characterization, biological activity, DNA and BSA binding study: novel copper(ii) complexes with 2-hydroxy-4-aryl-4-oxo-2-butenoate

Synthesis, characterization, biological activity, DNA and BSA binding study: novel copper(ii) complexes with 2-hydroxy-4-aryl-4-oxo-2-butenoate

Synthesis, Characterization, and Biological Evaluation of Meldrum’s Acid Derivatives: Dual Activity and Molecular Docking Study

Structural, Bioactivity, Molecular Docking, Spectroscopic and Electronic Properties of a Synthesized Meldrum's Acid Derivative

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