Unusual hydrogen bond patterns contributing to supramolecular assembly: conformational study, Hirshfeld surface analysis and density functional calculations of a new steroid derivative

Ruíz, Alexis Lorenzo; Pérez, Hiram; Morera-Boado, Cercis; Almagro, Luis; Silva, Cecília C. P. da; Ellena, Javier; Vega, José Manuel García de la; Martínez‐Álvarez, Roberto; Suárez, Margarita; Martı́n, Nazario

doi:10.1039/c4ce00709c

Cited by 19 publications

(14 citation statements)

References 68 publications

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“…Hence, by gathering these results, it can be seen a tendency to a close trans disposition of the carbonyl groups when the fullerene aggre- gate is present at the ethylmalonate functionality, and other tendency to a close cis configuration when it is not. [49] These results show that the pres-ence of a hydrogen bond, in all cases, has a major role in the final geometry of the ethylmalonate fragment together with the presence or not of the fullerene moiety, previously noted. [22] Moreover, theoretical calculations predict that the relative disposition of hydrogens H3 and H17 of the corresponding rings A and D of the steroid moiety and the closest carbonyl groups to each one is nearly similar in all cases.…”

Section: Resultssupporting

confidence: 62%

Steroid–Fullerene Hybrids from Epiandrosterone: Synthesis, Characterization and Theoretical Study

et al. 2018

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New hybrid fullerene–steroid derivatives were prepared by using the Bingel–Hirsch protocol, by treatment of [60]fullerene with malonates bearing the appropriate steroid moieties obtained, in turn, from the functionalization of epiandrosterone, an important naturally occurring steroid hormone. Monocycloadduct C60‐steroid conjugates were obtained by functionalization of ring A or ring D of the steroid moiety. We have also described the multistep preparation of a [60]fullerene hybrid dumbbell endowed with two fullerene units connected through an epiandrosterone molecule by a cyclopropanation reaction. The new compounds have been spectroscopically characterized and their redox potentials, determined by cyclic voltammetry, reveal three reversible reduction waves for monocycloadducts (8, 9 and 11, 12), whereas dumbbell‐type derivative 10 exhibits the best electron‐accepting abilities of the Bingel‐type fullerene–steroid series. Theoretical calculations at semiempirical (AM1) and single point B3LYP‐D3/6‐31G+(d,p) levels have predicted the most stable conformations for the hybrid compounds and allow explaining the observed regioselectivity in the cyclopropanation reaction with dimalonate 7 during the synthesis of the dumbbell derivative.

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Section: Resultssupporting

confidence: 62%

Steroid–Fullerene Hybrids from Epiandrosterone: Synthesis, Characterization and Theoretical Study

et al. 2018

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“…This affinity can simply be an association or a certain bond formation which could result owing to unsatisfied coordination sites within the Schiff base. [ 17–19 ] A number of weak associations like secondary bonding within the Schiff base which itself helps to form an even stronger association with the BSA moiety is another arena for study. However, quantitative estimation with respect to affinity factor, bond energies, and so forth, needs to be stuided and correlated with the spectroscopic analysis.…”

Section: Methodsmentioning

confidence: 99%

Probing the binding interaction of zinc (II) Schiff bases with bovine serum albumin: A spectroscopic and molecular docking study

Chowdhury

Sarkar

Raj

et al. 2021

Applied Organom Chemis

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Entrapping of potent Schiff base with biomimetic environment using fluorescence properties enables better understanding of their interaction for drug‐based application. A detailed photophysical study of zinc (II) Schiff bases, 2,6‐bis((E)‐((2‐(dimethylamino) ethyl)imino)methyl)‐4‐R‐phenol, where R = methyl/tertiary butyl/chloro is reported by utilizing bovine serum albumin (BSA) as the bio membrane. Steady state absorption and emission studies of Schiff base‐protein system have been found to get altered by change in the compartmental ligand. Alternation of polarity caused by such compartmental ligands is reported by comparing the fluorescence behavior of the probes in microheterogeneous environment in a mixture of dioxane and water of varying composition. Hildebrand equation accounts for negative binding constants among BSA with Schiff base with Cl (‐I) group as the compartmental ligand in contrast to the positive magnitudes with ligands exhibiting +I effect. Functionality of such compartmental ligands (intra interactions studied using Hirshfeld analyses) upon binding with the protein is also studied in terms of quenching and denaturation studies. Schiff base with Me is found to be the most favorable ligand that bound to BSA as corroborated from the binding, quenching, micropolarity, and docking studies. Molecular docking studies predict the affinity energies for suitable binding conformations to be ~ − 6 kcal mol−1 for BSA‐Schiff base (with Me ligand).

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“…Low values (ρ(r) and ∇ 2 (ρ(r) > 0) also represent the Closed‐shell interaction, in which case the charge dissipation is seen between the nuclei, which is related to ionic, hydrogen, and van der Waals bonds. [ 76,77 ] However, further research shows that energy parameters including kinetic energy density ( G(r) ), potential energy density ( V(r) ), and total electron energy density ( H(r) ) at the critical point can be more appropriate criteria for better identification of interactions. In this case, open‐shell interaction (((

\frac{(||, (V (r)))}{((), G ((), r))}

) > 2) and H(r) < 0 ) and also (((

\frac{(||, (V (normalr)))}{((), normalG ((), r))}

) < 1) and H(r) > 0 ) a closed‐shell interaction are detected.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, characterization, spectral studies two new transition metal complexes derived from pyrazolone by theoretical studies, and investigate anti‐proliferative activity

Parvarinezhad

Salehi

Malekshah

et al. 2022

Applied Organom Chemis

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Metal (II) complexes of Cu (II) (1), and Ni (II) (2) with Schiff base derived from 4‐amino‐antipyrine were synthesized. These complexes were fully characterized by FTIR, and UV–Vis spectroscopies, crystallography, and cyclic voltammetry. Crystal structures of these two complexes were mononuclear. Furthermore, complex Cu (II) (1), of [CuII(H2L1)(NO3)] composition, is 4‐coordinated in a square‐planar environment. Complex Ni (II) (2) is six‐coordinated in an octahedral geometry and can be described as [NiII (H2L2)2]; this crystal structure additionally contains solvent—DMSO molecule. The experimental structural models are interpreted by Hirshfeld surface analysis, density functional theory calculations, Molecular Electrostatic Potential, and the atoms in molecules method. Density functional theory calculations support all experimental results, as well as predict the correct structure of complexes. In addition, the types of interactions in the structure of the complexes were identified by Hirshfeld surface analysis, and molecular electrostatic potential was used to confirm the formation of these interactions, and the results of these studies are consistent. Then the theory of atom in molecule was performed, which predicts the type of interaction of the ligand metal non‐covalently with ionic nature. To determine the mechanism of adsorption of complexes on chitosan, a Monte Carlo adsorption locator was utilized. The adsorption process of complex [CuII (H2L1)NO3]and [NiII(H2L2)2(C2H6SO)] in the aqueous phase on CS was calculated by Monte Carlo adsorption locator. The results showed complex [NiII(H2L2)2(C2H6SO)] had a high binding efficiency on CS compared with complex [CuII (H2L1)NO3]. Moreover, the anticancer effects of ligands and complexes toward MTT assay against SW480 cancer cell lines were investigated. The biological activity results illustrate that the ligands and complexes have anticancer activity. Molecular docking studies were also carried out for both complexes to find their binding affinity with protein B‐cell lymphorna (BCL‐2, PDB ID: 4LXD).

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Unusual hydrogen bond patterns contributing to supramolecular assembly: conformational study, Hirshfeld surface analysis and density functional calculations of a new steroid derivative

Abstract: Structural and conformational study of a new steroid derivative using X-ray and density functional calculations.

Cited by 19 publications

References 68 publications

Steroid–Fullerene Hybrids from Epiandrosterone: Synthesis, Characterization and Theoretical Study

Steroid–Fullerene Hybrids from Epiandrosterone: Synthesis, Characterization and Theoretical Study

Probing the binding interaction of zinc (II) Schiff bases with bovine serum albumin: A spectroscopic and molecular docking study

Synthesis, characterization, spectral studies two new transition metal complexes derived from pyrazolone by theoretical studies, and investigate anti‐proliferative activity

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