Cocrystals of Isoniazid with Polyphenols: Mechanochemical Synthesis and Molecular Structure

González-González, Juan Saulo; Martínez-Santiago, Ana María Monserrat; Martínez‐Martínez, Francisco J.; Emparan-Legaspi, Maria Jose; Pineda-Contreras, Armando; Flores‐Álamo, Marcos; García-Ortega, Héctor

doi:10.3390/cryst10070569

Cited by 10 publications

(18 citation statements)

References 37 publications

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“…Vibrational frequencies were calculated to ensure that the optimized geometries correspond to local minima on the potential energy surface. Natural bond orbital (NBO) Fock matrix analysis at the same level of theory was performed to elucidate the electron density distribution within the molecules of the complexes, while 13 C NMR chemical shifts and magnetic shieldings were simulated using the gauge including atomic orbital (GIAO) method at B3LYP/6-31G(d,p) and referenced with the TMS HF/6-31G(d) option of the GaussView software [23].…”

Section: Theoretical Calculationsmentioning

confidence: 99%

“…Solid-state 13 C nuclear magnetic resonance spectra of CAT, TEO and the CAT-TEO cocrystal (Figure 4) were obtained to acquire information about hydrogen bonding interactions and crystallography. The 13 C NMR chemical shifts of the CAT and TEO starting products were assigned according to previous reports [8,29].…”

Section: Solid-state 13 C Nmrmentioning

confidence: 99%

“…On the other hand, catechol or 1,2-dihydroxybenzene contain hydroxyl groups, which can act as hydrogen bond donors for the synthesis of cocrystals due to their ability to form O-H•••X (X = O, N) hydrogen bonds, with the advantage that they form neutral hydrogen bonds, discarding the formation of salts. Some examples of API's that have formed cocrystals with catechol are nalidixic acid, tenoxicam, brexpiprazole, and isoniazid [10][11][12][13].…”

Section: Introductionmentioning

confidence: 99%

“…The ATR-IR spectroscopy has played an important role because it allowed to rapidly determine the formation of the powder cocrystal, discarding the hydrate formation. The characterization of the CAT-TEO cocrystal was completed using solid-state 13 C NMR, powder X-ray diffraction and DSC calorimetry. The molecular structure of the CAT-TEO cocrystal was obtained by theoretical calculations.…”

Section: Introductionmentioning

confidence: 99%

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Mechanochemical Synthesis of the Catechol-Theophylline Cocrystal: Spectroscopic Characterization and Molecular Structure

González-González¹,

Jiménez-López²,

Ortegón-Reyna³

et al. 2021

Applied Sciences

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Pharmaceutical cocrystallization offers the possibility to modify the physicochemical and biopharmaceutical properties of active pharmaceutical ingredients. The mechanochemical synthesis and spectroscopic characterization of the catechol-theophylline (CAT-TEO) cocrystal is reported. The cocrystal was prepared by the solvent-assisted grinding method. The ATR-IR spectroscopy study allowed to determine the formation of the cocrystal because the O-H and C=O stretching bands in the CAT-TEO cocrystal were shifted with respect to the starting materials, suggesting the formation of the C=O···H-O hydrogen bond interaction. Infrared spectroscopy also allowed to discard hydration of the cocrystal, and polymorphic transitions of the starting products as a consequence of the mechanochemical grinding. The X-ray powder diffraction and thermal studies confirmed the formation of a new solid phase. In the solid state 13C NMR spectra of the cocrystal, the signals were shifted with respect to the starting products. The 13C NMR chemical shifts of the CAT-TEO cocrystal were simulated by using the gauge including the atomic orbital (GIAO) method. These results showed a good correlation between the experimental and calculated 13C NMR results. Theoretical calculations and natural bonding orbital analysis (NBO) at a B3LYP/6-31G(d,p) level of theory were performed to obtain structural information of the cocrystal.

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Section: Theoretical Calculationsmentioning

confidence: 99%

Section: Solid-state 13 C Nmrmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Mechanochemical Synthesis of the Catechol-Theophylline Cocrystal: Spectroscopic Characterization and Molecular Structure

González-González¹,

Jiménez-López²,

Ortegón-Reyna³

et al. 2021

Applied Sciences

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“…In order to solve the problem of oxidative stress and low stability in tablet formulations involving INH, Mashhadi et al prepared and characterized the INH-antioxidant hydroxybenzoic acid [ 18 ] cocrystals and INH-PA cocrystal [ 19 ] by the technology of infra-red (IR) spectroscopy, XRD and DSC. In addition, there are certain studies on the cocrystals regarding polyphenols [ 20 ] and aromatic carboxylic acids [ 21 ] as co-formers.…”

Section: Introductionmentioning

confidence: 99%

Terahertz and Raman Spectroscopic Investigation of Monohydrate Cocrystal of Antitubercular Isoniazid with Protocatechuic Acid

Fang

Zhang

et al. 2021

Pharmaceutics

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Pharmaceutical cocrystal provides an alternative modification strategy for the formulation development of drugs owning to their potential ability to improve the physicochemical properties of active pharmaceutical ingredients (APIs) efficiently by changing inter-molecular interactions between raw materials. Isoniazid (INH) is an indispensable main drug for the treatment of tuberculosis, but its tablet formulation is unstable and prone to degradation. In the present study, the monohydrate cocrystal of INH and protocatechuic acid (PA) was prepared by solvent evaporation using PA as cocrystal former to optimize the properties of INH. The parent materials and corresponding 1:1 molar ratio INH-PA monohydrate cocrystal have been characterized by the terahertz time-domain (THz-TDS) and Raman spectroscopy. The THz absorption spectra displayed that there were obvious differences between the peaks of experimental cocrystal and the parent materials, and the same situation was found in Raman vibrational spectra. In addition, density functional theory (DFT) was applied to simulating and optimizing the structure of INH-PA monohydrate cocrystal and supplied corresponding vibrational modes. Our results provided a unique method to characterize the formation of INH-PA monohydrate cocrystal at the molecular-level and a lot of information about cocrystal structure and intra-molecular and/or inter-molecular hydrogen bond interactions in the emerging pharmaceutical cocrystal fields.

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Cocrystals of tuberculosis antibiotics: Challenges and missed opportunities

Salem

Khanfar

Nagy

et al. 2022

International Journal of Pharmaceutics

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Cocrystals of Isoniazid with Polyphenols: Mechanochemical Synthesis and Molecular Structure

Cited by 10 publications

References 37 publications

Mechanochemical Synthesis of the Catechol-Theophylline Cocrystal: Spectroscopic Characterization and Molecular Structure

Mechanochemical Synthesis of the Catechol-Theophylline Cocrystal: Spectroscopic Characterization and Molecular Structure

Terahertz and Raman Spectroscopic Investigation of Monohydrate Cocrystal of Antitubercular Isoniazid with Protocatechuic Acid

Cocrystals of tuberculosis antibiotics: Challenges and missed opportunities

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