Theoretical and Experimental Study of Inclusion Complexes Formed by Isoniazid and Modified β-Cyclodextrins: <sup>1</sup>H NMR Structural Determination and Antibacterial Activity Evaluation

Teixeira, Milena Galdino; Assis, João Vitor de; Soares, Cássia G. P.; Venâncio, Mateus F.; Lopes, Juliana Fedoce; Nascimento, Clébio S.; Anconi, Cléber P. A.; Carvalho, Guilherme S. L.; Lourenço, Cristina; Almeida, Mauro Vieira de; Fernandes, Sérgio Antônio; Almeida, Wagner B. De

doi:10.1021/jp409579m

Cited by 33 publications

(13 citation statements)

References 50 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The dramatic morphological change attribute to the host-guest interaction between didymin and HP-b-CD. Similar results were also found in the didymin/b-CD inclusion complex (Figure 1 NMR is a technique that provides evidence for the inclusion of a guest molecule into the cyclodextrin cavity (Teixeira et al, 2014). Insoluble particles will not show up in a solution NMR spectrum.…”

Section: Characterization Of Didymin Inclusion Complexessupporting

confidence: 73%

In vitro and in vivo evaluation of didymin cyclodextrin inclusion complexes: characterization and chemosensitization activity

et al. 2019

View full text Add to dashboard Cite

Didymin is a dietary flavonoid that first found in citrus fruits, and possesses antioxidant properties.Our preliminary experiments first discovered that didymin was able to sensitize the resistant cancer cells against chemotherapeutics and combat multidrug resistance. However, its poor aqueous solubility and resultant low bioavailability limit its potentials as an adjuvant phytochemical drug for chemotherapy. Thus, this study prepared the inclusion complex of didymin with b-cyclodextrin and 2-hydroxypropyl-b-cyclodextrin to improve its bioavailability and then evaluate their chemosensitization effects. The didymin inclusion complexes formulation was prepared and their host-guest structure was characterized by FT-IR, PXRD, DSC, and SEM techniques. In vitro/in vivo results demonstrated that didymin inclusion complex enhanced its water solubility and orally bioavailability. Furthermore, didymin inclusion complex exerted considerable chemosensitivity potency, and improve the anti-tumor effects of chemotherapeutics in vivo. Therefore, didymin inclusion complex could provide a safe, effective, economical, and adjuvant drug for future treatment of chemoresistant cancers.

show abstract

Section: Characterization Of Didymin Inclusion Complexessupporting

confidence: 73%

In vitro and in vivo evaluation of didymin cyclodextrin inclusion complexes: characterization and chemosensitization activity

et al. 2019

View full text Add to dashboard Cite

show abstract

“…Another useful technique in the structural description of organic molecules is nuclear magnetic resonance spectroscopy (NMR). Detailed analysis of NMR chemical shifts may provide specific information regarding molecular structure . Molecular modeling associated with density functional theory (DFT) has been widely employed by our group in studies at the molecular level of the action mechanism of potential drugs candidates for the treatment of cancer and other diseases.…”

Section: Introductionmentioning

confidence: 99%

Structural Determination of Antioxidant and Anticancer Flavonoid Rutin in Solution through DFT Calculations of ¹H NMR Chemical Shifts

Souza

Silva

2018

ChemistryOpen

View full text Add to dashboard Cite

As the knowledge of the predominant molecular structure of antioxidant and anticancer flavonoid rutin in solution is very important for understanding the mechanism of action, a quantum chemical investigation of plausible rutin structures including solvent effects is of relevance. In this work, DFT calculations were performed to find possible minimum energy structures for the rutin molecule. 1H NMR chemical shift DFT calculations were carried out in DMSO solution using the polarizable continuum model (PCM) to simulate the solvent effect. Analysis of the experimental and theoretical 1H NMR chemical shift profiles offers a powerful fingerprint criterion to determine the predominant molecular structure in solution. Therefore, our aim is to find the best match between experimental (in DMSO‐d) and theoretical (PCM–DMSO) 1H NMR spectrum profiles. Among 34 optimized structures located on the potential energy surface, we found that structure 32, with a B‐ring deviated 30° from a planar configuration (geometry usually assumed for polyphenols), showed an almost perfect agreement with experimental the 1H NMR pattern when compared to the corresponding fully optimized planar geometry. This structure is also predicted as the global minimum based on room‐temperature Gibbs free energy calculations in solution and, therefore, should be experimentally observed. This is new and valuable structural information regarding structure–activity relationship studies, and such information is hard to obtain by experimentalists without the aid of the X‐ray diffraction technique.

show abstract

“…Nuclear resonance magnetic (NMR) spectroscopy have largely been used in conformational analysis studies and also as a useful guide for structural determination, in particular in the area of supramolecular chemistry involving inclusion compounds with biological activity. − The NMR measurements are conducted for a macroscopic sample in a given solvent, usually deuterated water (D 2 O), and the NMR assignments are made based on pre-established criteria. The theoretical calculations are made for selected local minima equilibrium structures obtained from geometry optimization for a single molecule in the vacuum using a wisely chosen level of theory.…”

Section: Introductionmentioning

confidence: 99%

Water Solvent Effect on Theoretical Evaluation of ¹H NMR Chemical Shifts: o-Methyl-Inositol Isomer

Santos¹,

Chagas

Souza

et al. 2017

J. Phys. Chem. A

Self Cite

View full text Add to dashboard Cite

In this paper, density functional theory calculations of nuclear magnetic resonance (NMR) chemical shifts for l-quebrachitol isomer, previously studied in our group, are reported with the aim of investigating in more detail the water solvent effect on the prediction of H NMR spectra. In order to include explicit water molecules, 20 water-l-quebrachitol configurations obtained from Monte Carlo simulation were selected to perform geometry optimizations using the effective fragment potential method encompassing 60 water molecules around the solute. The solvated solute optimized geometries were then used in B3LYP/6-311+G(2d,p) NMR calculations with PCM-water. The inclusion of explicit solvent in the B3LYP NMR calculations resulted in large changes in theH NMR profiles. We found a remarkable improvement in the agreement with experimental NMR profiles when the explicit hydrated l-quebrachitol structure is used in B3LYP H NMR calculations, yielding a mean absolute error (MAE) of only 0.07 ppm, much lower than reported previously for the gas phase optimized structure (MAE = 0.11 ppm). In addition, a very improved match between theoretical and experimentalH NMR spectrum measured in DO was achieved with the new hydrated optimized l-quebrachitol structure, showing that a fine-tuning of the theoretical NMR spectra can be accomplished once solvent effects are properly considered.

show abstract

Theoretical and Experimental Study of Inclusion Complexes Formed by Isoniazid and Modified β-Cyclodextrins: ¹H NMR Structural Determination and Antibacterial Activity Evaluation

Cited by 33 publications

References 50 publications

In vitro and in vivo evaluation of didymin cyclodextrin inclusion complexes: characterization and chemosensitization activity

In vitro and in vivo evaluation of didymin cyclodextrin inclusion complexes: characterization and chemosensitization activity

Structural Determination of Antioxidant and Anticancer Flavonoid Rutin in Solution through DFT Calculations of ¹H NMR Chemical Shifts

Water Solvent Effect on Theoretical Evaluation of ¹H NMR Chemical Shifts: o-Methyl-Inositol Isomer

Contact Info

Product

Resources

About

Theoretical and Experimental Study of Inclusion Complexes Formed by Isoniazid and Modified β-Cyclodextrins: 1H NMR Structural Determination and Antibacterial Activity Evaluation

Cited by 33 publications

References 50 publications

In vitro and in vivo evaluation of didymin cyclodextrin inclusion complexes: characterization and chemosensitization activity

In vitro and in vivo evaluation of didymin cyclodextrin inclusion complexes: characterization and chemosensitization activity

Structural Determination of Antioxidant and Anticancer Flavonoid Rutin in Solution through DFT Calculations of 1H NMR Chemical Shifts

Water Solvent Effect on Theoretical Evaluation of 1H NMR Chemical Shifts: o-Methyl-Inositol Isomer

Contact Info

Product

Resources

About

Theoretical and Experimental Study of Inclusion Complexes Formed by Isoniazid and Modified β-Cyclodextrins: ¹H NMR Structural Determination and Antibacterial Activity Evaluation

Structural Determination of Antioxidant and Anticancer Flavonoid Rutin in Solution through DFT Calculations of ¹H NMR Chemical Shifts

Water Solvent Effect on Theoretical Evaluation of ¹H NMR Chemical Shifts: o-Methyl-Inositol Isomer