Biological activity tuning of antibacterial urotropine<i>via</i>co-crystallization: synthesis, biological activity evaluation and computational insight

Tabassum, Nida; Varras, Panayiotis C.; Arshad, Fiza; Choudhary, Muhammad Iqbal; Yousuf, Sammer

doi:10.1039/d0ce00226g

Cited by 8 publications

(3 citation statements)

References 27 publications

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“…Therefore, considering the availability of sufficient hydrogen-bond binding sites to match the characteristic groups on MLN molecule, SYRA and GALA can be ideal candidates as CCFs to interact with MLN. More than that, both SYRA and GALA are classic pharmaceutical property improvers, − which are conducive to simultaneously perfecting in vitro/in vivo biopharmaceutical performances of MLN. Of particular note, as nutritional phenolic acids, SYRA and GALA can serve vital influences on human daily life and health, thus displaying broad prospects of the protective roles in cardiovascular disease .…”

Section: Resultsmentioning

confidence: 99%

The First Cocrystallization of Milrinone with Nutraceuticals: The Adjusting Effects of Hydrophilicity/Hydrophobicity in Cavities on the In Vitro/In Vivo Properties of the Cocrystals

Liu

et al. 2022

Crystal Growth & Design

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To give full prominence to the superiority of phenolic acid nutraceuticals syringic acid (SYRA) and gallic acid (GALA) in perfection of in vitro and in vivo performances for cardiotonic drug milrinone (MLN), and ulteriorly attain novice insights in the development of cardiotonic drug-nutraceutical cocrystals, two new solid forms of MLN including one cocrystal with SYRA, and one cocrystal hydrate with GALAnamely, MLN-SYRA (1) and MLN-GALA- H2O (2)are first assembled and thoroughly characterized. The single-crystal X-ray diffraction showcases that both cocrystal 1 and cocrystal hydrate 2 have three-dimensional supramolecular structures controlled by hydrogen-bonding and aromatic packing interactions, where the hydrogen-bonding dimers of MLN itself still remain in 1 but are broken in 2, forming hydrophobic cavities in the former and hydrophilic ones in the latter. Such structural characteristics and aggregation motifs, because of the introduction of different phenolic acids in the crystalline lattices, have important influence on the improvements of dissolvability and permeability for the two crystalline forms, and in accordance with the theoretical studies. Intriguingly, the optimized in vitro biopharmaceutical properties can be effectually transformed to satisfactory in vivo pharmacokinetic peculiarity, performing the increased bioavailability and extended half-life. Thus, the current research not only offers promising solid-state forms for MLN with development foregrounds, but opens up new applications for nutraceutical phenolic acids in cardiotonic pharmaceutical cocrystals.

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Section: Resultsmentioning

confidence: 99%

The First Cocrystallization of Milrinone with Nutraceuticals: The Adjusting Effects of Hydrophilicity/Hydrophobicity in Cavities on the In Vitro/In Vivo Properties of the Cocrystals

Liu

et al. 2022

Crystal Growth & Design

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“…In order to select adequate coformers, we are guided by the information available in the literature on the antibacterial properties of molecules such as imidazoles, 13 piperazine, 14 3-hydroxybenzoic acid, 15 and urotropine. 16 Furthermore, it is known that 4-pyridine and 1,4diazabicyclo[2.2.2]octane (DABCO) are effective antioxidants. 4-Pyridine is also an important raw material for the synthesis of antibacterial active pyridine quaternary ammonium salts, 17 and the DABCO bis-quaternary salts also exhibit antibacterial activity.…”

Section: ■ Introductionmentioning

confidence: 99%

“…In this work we explore the possibility of preparing a series of cocrystals of kojic acid with a number of selected coformers to enrich the library of novel materials with potential antibacterial properties. In order to select adequate coformers, we are guided by the information available in the literature on the antibacterial properties of molecules such as imidazoles, piperazine, 3-hydroxybenzoic acid, and urotropine . Furthermore, it is known that 4-pyridine and 1,4-diazabicyclo[2.2.2]octane (DABCO) are effective antioxidants.…”

Section: Introductionmentioning

confidence: 99%

Searching for Suitable Kojic Acid Coformers: From Cocrystals and Salt to Eutectics

Sun

Braun

Casali

et al. 2023

Crystal Growth & Design

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The possibility of obtaining cocrystals of kojic acid with organic coformers has been investigated by both computational and experimental approaches. Cocrystallization attempts have been carried out with about 50 coformers, in different stoichiometric ratios, by solution, slurry, and mechanochemical methods. Cocrystals were obtained with 3-hydroxybenzoic acid, imidazole, 4-pyridone, DABCO, and urotropine, while piperazine yielded a salt with the kojiate anion; cocrystallization with theophylline and 4-aminopyridine resulted in stoichiometric crystalline complexes that could not be described with certainty as cocrystals or salts. In the cases of panthenol, nicotinamide, urea, and salicylic acid the eutectic systems with kojic acid were investigated via differential scanning calorimetry. In all other preparations the resulting materials were constituted of a mixture of the reactants. All compounds were investigated by powder X-ray diffraction; the five cocrystals and the salt were fully characterized via single crystal X-ray diffraction. The stability of the cocrystals and the intermolecular interactions in all characterized compounds have been investigated by computational methods based on the electronic structure and pairwise energy calculations, respectively.

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Pharmaceutical cocrystals: A review of preparations, physicochemical properties and applications

Guo

Sun

Chen

et al. 2021

Acta Pharmaceutica Sinica B

134

106

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Pharmaceutical cocrystals are multicomponent systems in which at least one component is an active pharmaceutical ingredient and the others are pharmaceutically acceptable ingredients. Cocrystallization of a drug substance with a coformer is a promising and emerging approach to improve the performance of pharmaceuticals, such as solubility, dissolution profile, pharmacokinetics and stability. This review article presents a comprehensive overview of pharmaceutical cocrystals, including preparation methods, physicochemical properties, and applications. Furthermore, some examples of drug cocrystals are highlighted to illustrate the effect of crystal structures on the various aspects of active pharmaceutical ingredients, such as physical stability, chemical stability, mechanical properties, optical properties, bioavailability, sustained release and therapeutic effect. This review will provide guidance for more efficient design and manufacture of pharmaceutical cocrystals with desired physicochemical properties and applications.

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Biological activity tuning of antibacterial urotropineviaco-crystallization: synthesis, biological activity evaluation and computational insight

Abstract: Urotropine (1) is a synthetic heterocyclic antibacterial agent.

Cited by 8 publications

References 27 publications

The First Cocrystallization of Milrinone with Nutraceuticals: The Adjusting Effects of Hydrophilicity/Hydrophobicity in Cavities on the In Vitro/In Vivo Properties of the Cocrystals

The First Cocrystallization of Milrinone with Nutraceuticals: The Adjusting Effects of Hydrophilicity/Hydrophobicity in Cavities on the In Vitro/In Vivo Properties of the Cocrystals

Searching for Suitable Kojic Acid Coformers: From Cocrystals and Salt to Eutectics

Pharmaceutical cocrystals: A review of preparations, physicochemical properties and applications

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