Charge density analysis of abiraterone acetate

Korlyukov, Alexander A.; Вологжанина, Анна В.; Trzybiński, Damian; Malińska, Maura; Woźniak, Krzysztof

doi:10.1107/s2052520620013244

Cited by 6 publications

(6 citation statements)

References 55 publications

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“…The S-C bonds in 3TC have the least values (∇ 2 ρ(r) comparable with the other bonds. A similar result was obtained in the charge density study of bicalutamide [ 33 ] and abiraterone acetate [ 34 ], published earlier.…”

Section: Resultssupporting

confidence: 87%

“…The faces of atomic Voronoi polyhedra form the molecular Voronoi surface, and a pair of atoms that shares a molecular surface is supposed to form an intermolecular interaction. The MVP represents well molecular volumes and networks of intermolecular interactions in crystals of small molecules [ 34 , 57 , 58 , 59 , 60 , 61 ], compared with the AIM approach. It has also been applied to compare Imatinib interactions in small molecules and ligand–receptor complexes [ 32 ] and for analysis of protein volumes and packing [ 62 , 63 , 64 ], and for interactions between macromolecules [ 65 , 66 ].…”

Section: Resultsmentioning

confidence: 99%

“…The usage of Voronoi tessellation to the crystal structures of polymorphs, salts, solvatomorphs and ligand–receptor complexes of 3TC and 3TC-TP and the comparison with charge density and quantum chemical studies allowed us to verify how the results obtained for small molecules are applicable for biomolecules. The methods mentioned above were successfully applied for the study of intermolecular interactions in the crystal structures of the drug and ligand–receptor complexes of the imatinib salts [ 32 ], bicalutamide [ 33 ], and abiraterone acetate [ 34 ].…”

Section: Introductionmentioning

confidence: 99%

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Ligand-Receptor Interactions of Lamivudine: A View from Charge Density Study and QM/MM Calculations

et al. 2023

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The nature and strength of interactions for an anti-HIV drug, Lamivudine, were studied in a pure crystal form of the drug and the ligand–receptor complexes. High-resolution single-crystal X-ray diffraction studies of the tetragonal polymorph allowed the drug’s experimental charge density distribution in the solid state to be obtained. The QM/MM calculations were performed for a simplified model of the Lamivudine complex with deoxycytidine kinase (two complexes with different binding modes) to reconstruct the theoretical charge density distribution. The peculiarities of intramolecular interactions were compared with previously reported data for an isolated molecule. Intermolecular interactions were revealed within the quantum theory of ‘Atoms in Molecules’, and their contributions to the total crystal energy or ligand–receptor binding energy were evaluated. It was demonstrated that the crystal field effect weakened the intramolecular interactions. Overall, the energies of intermolecular interactions in ligand–receptor complexes (320.1–394.8 kJ/mol) were higher than the energies of interactions in the crystal (276.9 kJ/mol) due to the larger number of hydrophilic interactions. In contrast, the sum of the energies of hydrophobic interactions was found to be unchanged. It was demonstrated by means of the Voronoi tessellation that molecular volume remained constant for different molecular conformations (250(13) Å3) and increased up to 399 Å3 and 521(30) Å3 for the Lamivudine phosphate and triphosphate.

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Section: Resultssupporting

confidence: 87%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Ligand-Receptor Interactions of Lamivudine: A View from Charge Density Study and QM/MM Calculations

et al. 2023

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“…Common themes across recent cocrystal studies have investigated the physical property enhancement of cocrystallization but the chemical explanation for the property alteration has largely not been identified. Charge density studies may provide the necessary tools to highlight weak interaction patterns across organic structures; − future coformer selection requires a strong understanding of how the physical properties are influenced by these interactions. ,, …”

Section: Introductionmentioning

confidence: 99%

Understanding Hygroscopicity of Theophyllineviaa Novel Cocrystal Polymorph: A Charge Density Study

Stanton

Lai

et al. 2021

J. Phys. Chem. A

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The charge density distribution in a novel cocrystal (1) complex of 1,3-dimethylxanthine (theophylline) and propanedioic acid (malonic acid) has been determined. The molecules crystallize in the triclinic, centrosymmetric space group P1̅, with four independent molecules (Z = 4) in the asymmetric unit (two molecules each of theophylline and malonic acid). Theophylline has a notably high hygroscopic nature, and numerous cocrystals have shown a significant improvement in stability to humidity. A charge density study of the novel polymorph has identified interesting theoretical results correlating the stability enhancement of theophylline via cocrystallization. Topological analysis of the electron density highlighted key differences (up to 17.8) in Laplacian (∇2ρ) between the experimental (EXP) and single-point (SP) models, mainly around intermolecular-bonded carbonyls. Further investigation via molecular electrostatic potential maps reaffirmed that the charge redistribution enhanced intramolecular hydrogen bonding, predominantly for N(2′) and N(2) (61.2 and 61.8 kJ mol–1, respectively). An overall weaker lattice energy of the triclinic form (−126.1 kJ mol–1) compared to that of the monoclinic form (−133.8 kJ mol–1) suggests a lower energy threshold to overcome to initiate dissociation. Future work via physical testing of the novel cocrystal in both dissolution and solubility will further solidify the correlation between theoretical and experimental results.

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“…Indeed, an amount of the different types of such intermolecular interactions can be quantitively estimated using various approaches, which are based on analysis of their contributions to the corresponding molecular surfaces. Molecular Voronoi polyhedra [ 24 ] can be successfully used for analysis of the intermolecular interactions in molecular crystals (in particular, those in the crystals of pharmaceutically active compounds and their complexes with various bioreceptors [ 25 ] ). Within this method of a crystal space analysis, an atomic domain is constructed of all points which are closer to a given atom than to any external one, while a…”

Section: Resultsmentioning

confidence: 99%

Monoribbed‐Functionalized Macrobicyclic Iron(II) Complexes Decorated with Terminal Reactive and Vector Groups: Synthetic Strategy, Chemical Transformations and Structural Characterization

et al. 2022

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General and straightforward synthetic strategy towards the iron(II) clathrochelates with functionalizing substituents in their apical capping and one of the three chelate ribbed fragments was developed. Their hexachloroclathrochelate precursors were prepared by the direct template condensation of dichloroglyoxime with a suitable boronic acid on the Fe 2+ ion as a matrix and underwent a stepwise nucleophilic substitution with S 2 -, N 2 -or O 2 -bis-nucleophiles, forming the alicyclic or aromatic N 2 -, S 2 -or O 2 -six-membered fragments. Depending on the reaction conditions and precursor-to-dinucleophile molar ratios, iron(II) clathrochelates with one (S, O and N), two (S, O and N) or three (S and O) X 2 -six-membered ribbed substituent(s) were obtained. Their reactivity substantially decreases in a row: Cl 6 -Cage > Cl 4 X 2 -Cage (where X = S, O or, especially, N) > Cl 2 X 4 -Cage (where X = S or O). The reactive monoribbed-functionalized clathrochelates underwent further chemical transformations giving the target macrobicyclic complexes with terminal vector groups. As follows from the single crystal XRD data, their FeN 6 -coordination polyhedra possess the geometry intermediate between a trigonal prism and a trigonal antiprism ( = 21.3°-25.20°). Fe-N distances vary from 1.887(6) to 1.933(8) Å. Their 3D-molecules, the hydrophobic-hydrophilic balance in which can be tuned using a ribbed functionalization, form in the crystals the intermolecular specific halogen bonds and/or hydrophobic interactions.

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Charge density analysis of abiraterone acetate

Cited by 6 publications

References 55 publications

Ligand-Receptor Interactions of Lamivudine: A View from Charge Density Study and QM/MM Calculations

Ligand-Receptor Interactions of Lamivudine: A View from Charge Density Study and QM/MM Calculations

Understanding Hygroscopicity of Theophyllineviaa Novel Cocrystal Polymorph: A Charge Density Study

Monoribbed‐Functionalized Macrobicyclic Iron(II) Complexes Decorated with Terminal Reactive and Vector Groups: Synthetic Strategy, Chemical Transformations and Structural Characterization

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