Synthesis, physicochemical characterization, DFT calculation and biological activities of Fe(III) and Co(II)–omeprazole complexes. Potential application in the Helicobacter pylori eradication

Russo, Marcos Guillermo; Hissi, Esteban Gabriel Vega; Rizzi, Alberto Claudio; Brondino, Carlos D.; Ibáñez, Ángel Gabriel Salinas; Vega, Alba Edith; Silva, Humberto de Jesus; Mercader, R. C.; Narda, Griselda E.

doi:10.1016/j.molstruc.2013.12.073

Cited by 16 publications

(11 citation statements)

References 45 publications

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“…All of the esomeprazole molecules act as chelating ligands and coordinate the Mg centers with one oxygen as well as one nitrogen atom. This agrees with previous DFT calculations, where omeprazole was shown to favour coordination with Co(II) and Fe(III) through the sulfoxide oxygen and the benzimidazolic nitrogen [28]. All of the six water molecules that are coordinated to the magnesium center show hydrogen bonding either with other water molecules in the lattice or the nitrogen atoms in the esomeprazole ligands (Figure 5).…”

Section: Resultssupporting

confidence: 91%

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Crystallization of Esomeprazole Magnesium Water/Butanol Solvate

et al. 2016

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Abstract:The molecular structure of esomeprazole magnesium derivative in the solid-state is reported for the first time, along with a simplified crystallization pathway. The structure was determined using the single crystal X-ray diffraction technique to reveal the bonding relationships between esomeprazole heteroatoms and magnesium. The esomeprazole crystallization process was carried out in 1-butanol and water was utilized as anti-solvent. The product proved to be esomeprazole magnesium tetrahydrate with two 1-butanol molecules that crystallized in P6 3 space group, in a hexagonal unit cell. Complete characterization of a sample after drying was conducted by the use of powder X-ray diffraction (PXRD), 1 H-nuclear magnetic resonance (NMR), thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), infrared spectroscopy (IR), and dynamic vapor sorption (DVS). Investigation by 1 H-NMR and TGA has shown that the solvent content in the dried sample consists of two water molecules and 0.3 butanol molecules per esomeprazole magnesium molecule. This is different from the single crystal X-ray diffraction results and can be attributed to the loss of some water and 1-butanol molecules stabilized by intermolecular interactions. The title compound, after drying, is a true solvate in terms of water; conversely, 1-butanol fills the voids of the crystal lattice in non-stoichiometric amounts.

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Section: Resultssupporting

confidence: 91%

“…This agrees with the molecular structure determined with single crystal XRD, where esomeprazole is coordinating through benizimidazolic nitrogen and sulfoxide oxygen. The frequencies observed are in close agreement with the calculated IR spectra for omeprazole co-ordinated to different metal centers [28].…”

Section: Resultssupporting

confidence: 79%

Crystallization of Esomeprazole Magnesium Water/Butanol Solvate

et al. 2016

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“…The drug also shows good antimicrobial activity against Helicobacter pylori [7][8][9]. 8-hydroxyquinoline is well-known for its antimicrobial activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and pharmacological evaluation of mixed ligand-metal complexes containing omeprazole and 8-hydroxyquinoline

Ahmad¹,

Khan²,

Munawar³

et al. 2017

Trop. J. Pharm Res

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“…Geometry optimization of the ligand (HTTA) and the complex was carried out using DFT B3LYP/6‐31++G(d,p) level of theory using Gaussian03 package . The equilibrium geometry structures, the highest occupied molecular orbital (HOMO), and the lowest unoccupied molecular orbital (LUMO) of HTTA and its uranyl complex are shown in Figure .…”

Section: Resultsmentioning

confidence: 99%

Electrochemical Selective Determination of Uranyl Ions Using PVC Membrane Sensor

Akl

2017

Electroanalysis

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A UO22+‐PVC membrane electrode was constructed using 2‐thenoyltrifluoroacetone as ionophore and its electrochemical response performance was characterized. The effect of membrane composition on the electrode performance was studied and best results were obtained using dioctylsebacate as a mediator and potassium tetrakis(4‐chlorophenyl)borate as anion excluder. The optimized UO22+‐sensor exhibited a Nernstian response with a slope of 29.5±0.5 mV decade−1 over the concentration range 5.0×10−7−1.0×10−1 mol L−1 at 25 °C with a detection limit of 3.1×10−7 mol L−1. The optimized electrode showed very good selectivity towards UO22+ relative to a wide variety of other cations and fast response time. Surface morphology of the optimized membrane electrode at different stages of its development and use was investigated and discussed. Quantum chemical calculations for geometrical optimization of the ionophore were carried out to investigate the interaction between the ionophore and UO22+ using DFT B3LYP/6‐31++G(d,p) level of theory and the obtained data confirmed the proposed response mechanism. The developed sensor was successfully applied for UO22+ selective determination in real water samples and the obtained results were compared to those obtained by spectrophotometric method indicating no significant difference.

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Synthesis, physicochemical characterization, DFT calculation and biological activities of Fe(III) and Co(II)–omeprazole complexes. Potential application in the Helicobacter pylori eradication

Cited by 16 publications

References 45 publications

Crystallization of Esomeprazole Magnesium Water/Butanol Solvate

Crystallization of Esomeprazole Magnesium Water/Butanol Solvate

Synthesis, characterization and pharmacological evaluation of mixed ligand-metal complexes containing omeprazole and 8-hydroxyquinoline

Electrochemical Selective Determination of Uranyl Ions Using PVC Membrane Sensor

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