Molecular recognition of caffeine in solution and solid state

Sahoo, Prithidipa

doi:10.1016/j.bioorg.2014.11.002

Cited by 18 publications

(7 citation statements)

References 182 publications

(195 reference statements)

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“…In this study, caffeine (C8H10N4O2) was used as an API model. Caffeine is one of the most widely used psychoactive drug in the world and it is cheap and readily available (Sahoo, 2015). This common molecule is well known for polymorphism studies (Pirttimäki et al, 1993;Lehto and Laine, 1998;Manduva et al, 2008;Mazel et al, 2011) which presents a simple enantiotropic behaviour.…”

Section: Introductionmentioning

confidence: 99%

Processing-induced-transformations (PITs) during direct compression: Impact of tablet composition and compression load on phase transition of caffeine

Juban

Briançon

Puel

2016

International Journal of Pharmaceutics

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In the pharmaceutical field, solid-state transitions that may occur during manufacturing of pharmaceuticals are of great importance. The phase transition of a model API, caffeine Form I (CFI), was studied during direct compression process by analysing the impacts of the operating conditions (process and formulation). This work is focused on two formulation parameters: nature of the diluent and impact of the caffeine dilution, and one process parameter: the compression pressure that may impact the phase transition of CFI. Tablets were made from pure CFI and from binary mixture of CFI/diluent (microcrystalline cellulose or anhydrous dicalcium phosphate). A kinetic study performed during six months helped to highlight the influence of these parameters on the CFI transition degree. Results showed a triggering effect of the direct compression process, transformation was higher in tablets than in uncompressed powders. Whatever the pressure applied, CFI transition degree was almost constant and uniformly occurring throughout the tablet volume. Nevertheless, several differences on the evolution of the CFI transition degree were observed between binary mixtures of CFI/diluent. An analysis of the transition mechanism with a stretched exponential law of the Johnson-Mehl-Avrami model shows that tableting accelerates the polymorphic transition without modifying its mechanism controlled by nucleation only.

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Section: Introductionmentioning

confidence: 99%

Processing-induced-transformations (PITs) during direct compression: Impact of tablet composition and compression load on phase transition of caffeine

Juban

Briançon

Puel

2016

International Journal of Pharmaceutics

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“…5 The use of artificial receptors that effectively recognize caffeine in water can therefore find a wide range of applications in biomedical, technological, and analytical fields. 6,7 In a recent paper we reported that the diaminocarbazole tweezer-shaped receptor 1 (Figure 1, left) recognizes caffeine in chloroform with a 26 μM affinity, showing a sixfold selectivity versus theobromine and a nearly fivefold selectivity versus theophylline, the natural-occurring metabolites of caffeine. 8 The X-ray structure of the complex between 1 and caffeine (Figure 1, right) shows that the binding ability of the receptor mainly relies on the hydrogen-bonding interaction established between the tridentate diaminocarbazole unit of the receptor 9 and the O-6 of caffeine, which is reinforced by CH−π interactions between the methyl groups of the xanthine and the two anthracene units of the receptor as well as πstacking between caffeine and the anthracene rings.…”

Section: ■ Introductionmentioning

confidence: 96%

“… 5 The use of artificial receptors that effectively recognize caffeine in water can therefore find a wide range of applications in biomedical, technological, and analytical fields. 6 , 7 …”

Section: Introductionmentioning

confidence: 99%

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A Sulfonated Tweezer-Shaped Receptor Selectively Recognizes Caffeine in Water

et al. 2022

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The selective recognition of caffeine in water among structurally related xanthines and purine or pyrimidine bases was achieved by a simple tweezer-shaped receptor featuring sulfonate hydrosolubilizing groups. The remarkable affinity for caffeine, among the highest reported thus far in the literature and larger than that shown by adenosine receptors of all subtypes, stems from a synergistic combination of hydrogen bonding, CH−π, and π-stacking interactions.

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“…Thus, a natural substrate should not be considered as a set of isolated molecules but as an entity consisting of species generated from continuous processes of molecular interaction, in a situation of equilibrium dependent on thermodynamic conditions, following the rules of supramolecular chemistry [25]. As an example, in the case of caffeine, its complexation with polyphenolic substrates has been found and described in detail [26][27][28].…”

Section: Introductionmentioning

confidence: 99%

An investigation on [5 fluorouracil and epigallocatechin-3-gallate] complex activity on HT-29 cell death and its stability in gastrointestinal fluid

et al. 2022

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Recently an enhancement of the sensitivity of colorectal cancer (CRC) cells by 5-fluorouracil (5FU) due to the concurrent treatment with epigallocatechin-3gallate (EGCG) has been found. In the present paper, to investigate on this aspect, adenocarcinoma cells HT29 were treated with 5FU, EGCG and an equimolar mixture of 5FU and EGCG ([5FU+EGCG]) and cell viability was determined. While 5FU exhibits a clear activity, EGCG alone does not express any activity. However by treating the cells with [5FU+EGCG] a strong effect of EGCG is evidenced: the sensitivity of HT29 cells to 5FU was increased by 12-fold. A simulation of the behavior of [5FU+EGCG] in different compartments of the gastrointestinal digestion model was also performed. 5FU and EGCG solubilized into a mixture of digestive fluids analyzed by mass spectrometry did not lead to signals of 5FU, EGCG and the related complex, while by diluting the solution they become detectable. On the contrary, when 5FU and EGCG are submitted to the step-by-step digestion model procedure, the analysis did not show the presence of 5FU, EGCG and [5FU+EGCG]. This behaviour could be ascribed to the instability of these compounds due to the too severe digestion conditions and/or to the complexity of the matrix which could lead in ESI conditions to the suppression of the signals of the analytes of interest.

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Molecular recognition of caffeine in solution and solid state

Cited by 18 publications

References 182 publications

Processing-induced-transformations (PITs) during direct compression: Impact of tablet composition and compression load on phase transition of caffeine

Processing-induced-transformations (PITs) during direct compression: Impact of tablet composition and compression load on phase transition of caffeine

A Sulfonated Tweezer-Shaped Receptor Selectively Recognizes Caffeine in Water

An investigation on [5 fluorouracil and epigallocatechin-3-gallate] complex activity on HT-29 cell death and its stability in gastrointestinal fluid

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