A 1:1 pharmaceutical cocrystal of myricetin in combination with uncommon piracetam conformer: X-ray single crystal analysis and mechanochemical synthesis

Sowa, Michał; Ślepokura, Katarzyna; Matczak-Jon, Ewa

doi:10.1016/j.molstruc.2013.10.071

Cited by 47 publications

(22 citation statements)

References 32 publications

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“…1 (detailed structural data and harmonic vibrational wavenumbers are provided as S1). This is consistent with the calculational results of Álvarez-Diduk et al [16] and with the results of X-ray single crystal and powder diffraction experiments [27]. Starting with a planar geometry (C s symmetry), a planar molecular structure is predicted with no imaginary frequencies, indicating a true equilibrium structure (S1).…”

Section: Calculationssupporting

confidence: 90%

Electronic states of Myricetin. UV–Vis polarization spectroscopy and quantum chemical calculations

Vojta

Karlsen

Spanget‐Larsen

2017

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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Myricetin (3,3',4',5,5',7'-hexahydroxyflavone) was investigated by linear dichroism spectroscopy on molecular samples partially aligned in stretched poly(vinyl alcohol) (PVA). At least five electronic transitions in the range 40,000-20,000cm were characterized with respect to their wavenumbers, relative intensities, and transition moment directions. The observed bands were assigned to electronic transitions predicted with TD-B3LYP/6-31+G(d,p).

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Section: Calculationssupporting

confidence: 90%

Electronic states of Myricetin. UV–Vis polarization spectroscopy and quantum chemical calculations

Vojta

Karlsen

Spanget‐Larsen

2017

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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“…Differences in crystal structures of cocrystals could be observed and evaluated by lots of research technologies. Traditional techniques that could be employed include powder X-ray diffractormetry (PXRD) [5,[18][19][20], thermal analysis(such as differential scanning calorimetry, DSC), and also solid-state nuclear magnetic resonance spectroscopy (ss-NMR) [20][21][22][23][24]. These established techniques are sometimes time-consuming or lack specific structural information about crystals and/or molecules-especially the effect from the intra-molecular and weak inter-molecular interactions.…”

Section: Raman Spectral Characterization Of Nf 4aba and Its Correspmentioning

confidence: 99%

Raman and Terahertz Spectroscopic Investigation of Cocrystal Formation Involving Antibiotic Nitrofurantoin Drug and Coformer 4-aminobenzoic Acid

Cai

Xue

et al. 2016

Crystals

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Cocrystallization could improve most physicochemical properties of specific active pharmaceutical ingredients, which has great potential in pharmaceutical development. In this study, the cocrystal of nitrofurantoin and 4-aminobenzoic acid was prepared with solid-state (solvent-free or green-chemistry) grinding approach, and the above cocrystal has been characterized by Raman and terahertz vibrational spectroscopic techniques. Spectral results show that the vibrational modes of the cocrystal within the whole spectral region are different from those of the corresponding parent materials. The dynamic process of such pharmaceutical cocrystal formation has also been monitored directly with Raman spectra. These results offer us unique means for characterizing the cocrystal conformation from the molecule-level, and provides us with rich information about the reaction dynamic of cocrystal formation within pharmaceutical fields.

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“…Such delivery systems include complexation with β-cyclodextrins (11,12), a microemulsion (13), and the development of a 1:1 cocrystal with piracetam (14). The aim of this study is to further investigate the solution and solid-state properties of MYR.…”

Section: Myricetin (Myrmentioning

confidence: 99%

Solid-State and Solution Characterization of Myricetin

Franklin

Myrdal

2015

AAPS PharmSciTech

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Abstract. Myricetin (MYR) is a natural compound that has been investigated as a chemopreventative agent. MYR has been shown to suppresses ultraviolet B (UVB)-induced cyclooxygenase-2 (COX-2) protein expression and reduce the incidence of UVB-induced skin tumors in mice. Despite MYR's promise as a therapeutic agent, minimal information is available to guide the progression of formulations designed for future drug development. Here, data is presented describing the solid-state and solution characterization of MYR. Investigation into the solid-state properties of MYR identified four different crystal forms, two hydrates (MYR I and MYR II) and two metastable forms (MYR IA and MYR IIA). From solubility studies, it was evident that all forms are very insoluble (<5 μg/ml) in pure water. MYR I was found to be the most stable form at 23, 35, and 56°C. Stability determination indicated that MYR undergoes rapid apparent first-order degradation under basic pH conditions, and that degradation was influenced by buffer species. Apparent first-order degradation was also seen when MYR was introduced to an oxidizing solution. Improved stability was achieved after introducing 0.1% antioxidants to the solution. MYR was found to have good stability following exposure to ultraviolet radiation (UVR), which is a consideration for topical applications. Finally, a partitioning study indicated that MYR possess a log P of 2.94 which, along with its solid-state properties, contributes to its poor aqueous solubility. Both the solid-state properties and solution stability of MYR are important to consider when developing future formulations.

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A 1:1 pharmaceutical cocrystal of myricetin in combination with uncommon piracetam conformer: X-ray single crystal analysis and mechanochemical synthesis

Cited by 47 publications

References 32 publications

Electronic states of Myricetin. UV–Vis polarization spectroscopy and quantum chemical calculations

Electronic states of Myricetin. UV–Vis polarization spectroscopy and quantum chemical calculations

Raman and Terahertz Spectroscopic Investigation of Cocrystal Formation Involving Antibiotic Nitrofurantoin Drug and Coformer 4-aminobenzoic Acid

Solid-State and Solution Characterization of Myricetin

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