Huge solubility increase of poorly water-soluble pharmaceuticals by sulfobutylether-β-cyclodextrin complexation in a low-melting mixture

Petitprez, Justine; Legrand, François-Xavier; Tams, Catherine; Pipkin, J.D.; Antle, Vince; Kfoury, Miriana; Fourmentin, Sophie

doi:10.1007/s10311-022-01415-y

Cited by 12 publications

(7 citation statements)

References 44 publications

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“…The enhanced bioactivity of bioactive compounds after supramolecular inclusion can be attributed to the improved water solubility and thereby the enhanced bioavailability. − To verify if it applies to the insecticide@C4A complexes, water solubilities of the complexes were measured and compared with the guest insecticides. Results showed that complexation with C4A can significantly enhance the water solubility of insecticides (Figure ), possibly due to the presence of hydroxyl groups on C4A that contribute to the hydrophilicity.…”

Section: Resultsmentioning

confidence: 99%

“…The improved efficacy of bioactive compounds after inclusion by supramolecular hosts can also be attributed to the prevention of degradation during the delivery process. 47,52 It can be the reason for the enhanced bioactivity of Ind@C4A and Aba@C4A and explains the low synergic effect of C4A on Chl: as a typical pro-insecticide, Chl needs to be metabolized in the digestive system of insect to show insecticidal activity, so a reduced degradation rate would lead to reduced bioactivity. The insecticidal activity of Chl@C4A at 0.25 mg/L against third-instar larvae of P. xylostella after 24 h of treatment was even lower than that of Chl (Table S5).…”

Section: Discussionmentioning

confidence: 99%

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Preparation and Characterization of Insecticide/Calix[4]arene Complexes and Their Enhanced Insecticidal Activities againstPlutella xylostella

Jia

Pan

Song

et al. 2023

J. Agric. Food Chem.

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Applications of supramolecular materials in plant protection have attracted significant interest in recent years. To develop a feasible method to improve the efficacy and reduce the usage of chemical pesticides, the effect of calix[4]arene (C4A) inclusion on enhancing the insecticidal activity of commercial insecticides was investigated. Results showed that all three tested insecticides (chlorfenapyr, indoxacarb, and abamectin) with distinct molecular sizes and modes of action were able to form stable 1:1 host–guest complexes with C4A through simple preparation steps. The insecticidal activities of the complexes against Plutella xylostella were effectively enhanced compared to the guest molecule, with the synergism ratio being up to 3.05 (for indoxacarb). An obvious correlation was found between the enhanced insecticidal activity and the high binding affinity between insecticide and C4A, while the improvement in water solubility may not be a determining factor. The work would provide hints for the further development of functional supramolecular hosts as synergists in pesticide formulations.

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Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Preparation and Characterization of Insecticide/Calix[4]arene Complexes and Their Enhanced Insecticidal Activities againstPlutella xylostella

Jia

Pan

Song

et al. 2023

J. Agric. Food Chem.

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“…In medicinal science, increasing the solubility of active pharmaceutical ingredients (APIs) to improve their bioavailability is a core objective. Several methods have been established to address this concern, including the use of prodrugs [ 1 , 2 , 3 , 4 , 5 ], nanosuspensions, [ 6 , 7 , 8 , 9 ] or complexation of APIs [ 10 , 11 , 12 , 13 , 14 ], and modification of the solid API phase itself. The latter approach can be achieved through the formation of API salts, co-crystals, or amorphous systems to enhance the targeted drug’s solubility properties [ 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 ].…”

Section: Introductionmentioning

confidence: 99%

Maleic Acid as a Co-Former for Pharmaceutically Active GABA Derivatives: Mechanochemistry or Solvent Crystallization?

2023

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In this study, we compare the mechanochemical and classical solvent crystallization methods for forming maleates of GABA and its pharmaceutically active derivatives: Pregabalin, Gabapentin, Phenibut, and Baclofen. Common characterization techniques, like powder and single crystal X-ray diffraction, IR-spectroscopy, differential scanning calorimetry, thermogravimetric analysis and 1H-NMR spectroscopy, are used for the evaluation of structural and physicochemical properties. Our work shows that maleate formation is possible with all investigated target compounds. Large increases in solubility can be achieved, especially for Pregabalin, where up to twentyfold higher solubility in its maleate compared to the pure form can be reached. We furthermore compare the mechanochemical and solvent crystallization regarding quickness, reliability of phase production, and overall product quality. A synthetic route is shown to have an impact on certain properties such as melting point or solubility of the same obtained products, e.g., for Gabapentin and Pregabalin, or lead to the formation of hydrates vs. anhydrous forms. For the GABA and Baclofen maleates, the method of crystallization is not important, and similarly, good results can be obtained by either route. In contrast, Phenibut maleate cannot be obtained pure and single-phase by either method. Our work aims to elucidate promising candidates for the multicomponent crystal formation of blockbuster GABA pharmaceuticals and highlight the usefulness of mechanochemical production routes.

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“…SUPRA-DES ability to improve the solubility of bioactive compounds was shown, and it was demonstrated that, while being part of the solvent, CDs retained their complexing ability. ,, Still in their infancy, SUPRA-DES impact begins to be appreciated: Guo et al exploited their association with polyoxometalates to develop functional supramolecular materials for energy and electronic applications; applications for extraction, absorption, and adhesive have been recently reported and reviewed. ,, Considering the high SUPRA-DES compliance with the requirements of green chemistry, the observations collected so far are pointing toward new exciting applications of these CD-based solvents. Accordingly, a more profound comprehension of the interaction mechanism between the different components as well as the guest encapsulation process is necessary.…”

Section: Introductionmentioning

confidence: 99%

Liquid Structure Scenario of the Archetypal Supramolecular Deep Eutectic Solvent: Heptakis(2,6-di-O-methyl)-β-cyclodextrin/levulinic Acid

Triolo

Celso

Fourmentin

et al. 2023

ACS Sustainable Chem. Eng.

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The concept of supramolecular solvents has been recently introduced, and the extended liquid-state window accessible for mixtures of functionalized cyclodextrins (CDs) with hydrogen bond (HB) donor species, e.g., levulinic acid, led to the debut of supramolecular deep eutectic solvents (SUPRA-DES). These solvents retain CD's inclusion ability and complement it with enhanced solvation effectiveness due to an extended HB network. However, so far, these promising features were not rationalized in terms of a microscopic description, thus hindering a more complete capitalization. This is the first joint experimental and computational study on the archetypal SUPRA-DES: heptakis-(2,6-di-O-methyl)-β-CD/levulinic acid (1:27). We used X-ray scattering to probe CD's aggregation level and molecular dynamics simulation to determine the nature of interactions between SUPRA-DES components. We discover that CDs are homogeneously distributed in bulk and that HB interactions, together with the electrostatic ones, play a major role in determining mutual interaction between components. However, dispersive forces act in synergy with HB to accomplish a fundamental task in hindering hydrophobic interactions between neighbor CDs and maintaining the system homogeneity. The mechanism of mutual solvation of CD and levulinic acid is fully described, providing fundamental indications on how to extend the spectrum of SUPRA-DES combinations. Overall, this study provides the key to interpreting structural organization and solvation tunability in SUPRA-DES to extend the range of sustainable applications for these new, unique solvents.

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Huge solubility increase of poorly water-soluble pharmaceuticals by sulfobutylether-β-cyclodextrin complexation in a low-melting mixture

Cited by 12 publications

References 44 publications

Preparation and Characterization of Insecticide/Calix[4]arene Complexes and Their Enhanced Insecticidal Activities againstPlutella xylostella

Preparation and Characterization of Insecticide/Calix[4]arene Complexes and Their Enhanced Insecticidal Activities againstPlutella xylostella

Maleic Acid as a Co-Former for Pharmaceutically Active GABA Derivatives: Mechanochemistry or Solvent Crystallization?

Liquid Structure Scenario of the Archetypal Supramolecular Deep Eutectic Solvent: Heptakis(2,6-di-O-methyl)-β-cyclodextrin/levulinic Acid

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