Quantitative relationships between structure and cytotoxic activity of flavonoid derivatives. An application of Hirshfeld surface derived descriptors

Kupcewicz, Bogumiła; Małecka, Magdalena; Zapadka, Mariusz; Krajewska, Urszula; Różalski, Marcin; Budzisz, Elżbieta

doi:10.1016/j.bmcl.2016.05.038

Cited by 17 publications

(10 citation statements)

References 21 publications

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“…Therefore, the cytotoxic activity of a potential drug, and some of its other descriptors, such as logP, can be successfully predicted based on the fraction of contacts contributing to the Hirshfeld surface. These findings support our latest QSAR model (Kupcewicz et al, 2016) and could help future efforts towards structurebased drug design.…”

Section: Figure 14supporting

confidence: 82%

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The relationship between Hirshfeld potential and cytotoxic activity: a study along a series of flavonoid and chromanone derivatives

et al. 2020

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The present study examines a series of six biologically-active flavonoid and chromanone derivatives by X-ray crystal structure analysis: (E)-3-benzylidene-2-phenylchroman-4-one, C22H16O2, I, (E)-3-(4-methylbenzylidene)-2-phenylchroman-4-one, C23H18O2, II, (E)-3-(3-methylbenzylidene)-2-phenylchroman-4-one, C23H18O2, III, (E)-3-(4-methoxybenzylidene)-2-phenylchroman-4-one, C23H18O3, IV, (E)-3-benzylidenechroman-4-one, C16H12O2, V, and (E)-3-(4-methoxybenzylidene)chroman-4-one, C17H14O3, VI. The cytotoxic activities of the presented crystal structures have been determined, together with their intermolecular interaction preferences and Hirshfeld surface characteristics. An inverse relationship was found between the contribution of C...C close contacts to the Hirshfeld surface and cytotoxic activity against the WM-115 cancer line. Dependence was also observed between the logP value and the percentage contribution of C...H contacts to the Hirshfeld surface.

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Section: Figure 14supporting

confidence: 82%

“…A number of our previous studies have focused on the synthesis and biological activity of chromone derivatives and flavonoids (Budzisz et al, 2017;Kupcewicz et al, 2016). These heterocyclic compounds include a number of plant secondary metabolites that are widely distributed in nature (Panche et al, 2016).…”

Section: Introductionmentioning

confidence: 99%

The relationship between Hirshfeld potential and cytotoxic activity: a study along a series of flavonoid and chromanone derivatives

et al. 2020

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“…The presence of a fused pyrazoline ring may well play a key role in selective cytotoxicity. The p-methoxy-substituted analogues of 3-arylideneflavanone exhibit high cytotoxicity against four cancer cell lines [30,31]. The unsubstituted compound 6, with a phenyl ring bound to the pyrazoline ring, exhibited more than 330-fold lower cytotoxicity against HL-60 than compound 2, bearing a p-methoxy group on the phenyl ring.…”

Section: Discussionmentioning

confidence: 99%

Biological Evaluation of 3-Benzylidenechromanones and Their Spiropyrazolines-Based Analogues

et al. 2020

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A series of 3-benzylidenechrmanones 1, 3, 5, 7, 9 and their spiropyrazoline analogues 2, 4, 6, 8, 10 were synthesized. X-ray analysis confirms that compounds 2 and 8 crystallize in a monoclinic system in P21/n space groups with one and three molecules in each asymmetric unit. The crystal lattice of the analyzed compounds is enhanced by hydrogen bonds. The primary aim of the study was to evaluate the anti-proliferative potential of 3-benzylidenechromanones and their spiropyrazoline analogues towards four cancer cell lines. Our results indicate that parent compounds 1 and 9 with a phenyl ring at C2 have lower cytotoxic activity against cancer cell lines than their spiropyrazolines analogues. Analysis of IC50 values showed that the compounds 3 and 7 exhibited higher cytotoxic activity against cancer cells, being more active than the reference compound (4-chromanone or quercetin). The results of this study indicate that the incorporation of a pyrazoline ring into the 3-arylideneflavanone results in an improvement of the compounds’ activity and therefore it may be of use in the search of new anticancer agents. Further analysis allowed us to demonstrate the compounds to have a strong inhibitory effect on the cell cycle. For instance, compounds 2, 10 induced 60% of HL-60 cells to be arrested in G2/M phase. Using a DNA-cleavage protection assay we also demonstrated that tested compounds interact with DNA. All compounds at the concentrations corresponding to cytotoxic properties are not toxic towards red blood cells, and do not contribute to hemolysis of RBCs.

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“…Hirshfeld discusses the intramolecular and intermolecular interactions of molecular crystals through surfaces analyses using the Crystal Explorer program. The different shapes of the Hirshfeld surfaces characterize the degree of intermolecular bonding within the complexes, for each point isosurface d norm (standard high resolution), shape (from the outermost surface of the core to the outer surface) and d i (closest to the core of the inner surface) index reflects the bright red region of the Hirshfeld surface depression. This can be attributed to the interaction between the O atom and the H atom.…”

Section: Ir Spectramentioning

confidence: 99%

Newly synthesized homomultinuclear Co (II) and Cu (II) bissalamo‐like complexes: Structural characterizations, Hirshfeld analyses, fluorescence and antibacterial properties

Pan

Zhang

et al. 2020

Applied Organom Chemis

111

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Rare homodinuclear Co (II) complex [Co2(L)NO3] (1) and helical centrosymmetric homotetranuclear Cu (II) complex [Cu4(L)2(H2O)2]·2ClO4 (2), have been synthesized by a newly explored bis (salamo)‐like tetraoxime ligand (H3L) with Co (NO3)2·6H2O and Cu (ClO4)2·6H2O, respectively, and characterized by elemental analyses, IR, UV–Vis spectroscopy and single crystal X‐ray crystallography. X‐ray crystallographic studies indicate that the two Co (II) atoms (Co1 and Co2) in complex 1 have different N2O4 and N2O3 coordination spheres, and distorted octahedral (Co1) and slightly distorted triangular bipyramidal (Co2) geometries, while Cu (II) atoms in complex 2 have also two different N2O4 (Cu1) and N2O3 (Cu2) coordination environments, and complex 2 forms a helical centrosymmetric molecule. In addition, supramolecular interactions, Hirshfeld surfaces analyses, antibacterial and fluorescence properties were also investigated in detail.

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Quantitative relationships between structure and cytotoxic activity of flavonoid derivatives. An application of Hirshfeld surface derived descriptors

Cited by 17 publications

References 21 publications

The relationship between Hirshfeld potential and cytotoxic activity: a study along a series of flavonoid and chromanone derivatives

The relationship between Hirshfeld potential and cytotoxic activity: a study along a series of flavonoid and chromanone derivatives

Biological Evaluation of 3-Benzylidenechromanones and Their Spiropyrazolines-Based Analogues

Newly synthesized homomultinuclear Co (II) and Cu (II) bissalamo‐like complexes: Structural characterizations, Hirshfeld analyses, fluorescence and antibacterial properties

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