Relaxation behaviors of enantiomorphic S-ibuprofen as revealed by dielectric and photon correlation spectroscopies

Shin, Dong‐Myeong; Hwang, Yoon‐Hwae; Ko, Jae‐Hyeon; Kojima, Seiji

doi:10.1016/j.cap.2015.05.012

Cited by 7 publications

(10 citation statements)

References 20 publications

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“…Consistent with previous reports, the dynamics of S - and R S -ibuprofen are similar. 22 , 68 Taking this fact into account, we decided to fit the same VFT equation for both materials at a given pressure. Additionally, comparison between the results of our dielectric measurement performed for S - (see Supporting Information ) and those published for R S -ibuprofen 25 , 38 revealed that both systems exhibit a very similar temperature dependence of the structural relaxation time at constant ambient and elevated pressure.…”

Section: Discussionmentioning

confidence: 99%

“…Additionally, comparison between the results of our dielectric measurement performed for S - (see Supporting Information ) and those published for R S -ibuprofen 25 , 38 revealed that both systems exhibit a very similar temperature dependence of the structural relaxation time at constant ambient and elevated pressure. 22 Finally, we estimated the overall crystallization rate k using eqs 3 , 4 , and 5 . The results are shown in the upper panel of Figure 7 .…”

Section: Discussionmentioning

confidence: 99%

“…Therefore, thermodynamic aspects of the crystallization process should be examined in detail. 22 , 68 Consequently, in Figure 8 we present Δ G and γ for both substances.…”

Section: Discussionmentioning

confidence: 99%

“… 21 Interestingly, the dynamics of the enantiomeric systems does not strongly differ, and therefore their effect on the crystallization process might be excluded. 22 Consequently, enantiomers and their mixture seem to be interesting candidates to examine the role of thermodynamics on the crystallization process. One of the popular and commonly used examples of a pharmaceutical existing in two enantiomeric forms is ibuprofen.…”

Section: Introductionmentioning

confidence: 99%

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Pressure Dependence of the Crystallization Rate for the S-Enantiomer and a Racemic Mixture of Ibuprofen

Koperwas

Affouard

et al. 2021

Crystal Growth & Design

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This paper examines the pressure effect on the crystallization rate of the pharmaceutically active enantiomerically pure S-enantiomer and the racemic mixture of the well-known drug ibuprofen. Performed experimental studies revealed that at ambient pressure S -ibuprofen crystallizes faster than the racemic mixture. When the pressure increases, the crystallization rate slows down for both systems, but interestingly it is more apparent in the case of the S-enantiomer. It is found that this experimentally observed trend can be understood based on the predictions of the classical nucleation theory. We suggest that the solid–liquid interfacial free energy is the main reason for the observed variations in S - and RS -ibuprofen’s stability behaviors. Employing a special method of computational studies, i.e., the capillary fluctuation method, we show that the increase in pressure affects the solid–liquid interfacial free energy for S - and RS -ibuprofen in an entirely different way. Importantly, the detected differences correspond to the experimentally observed variations in the overall crystallization rates.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

“…Therefore, thermodynamic aspects of the crystallization process should be examined in detail. 22 , 68 Consequently, in Figure 8 we present Δ G and γ for both substances.…”

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Pressure Dependence of the Crystallization Rate for the S-Enantiomer and a Racemic Mixture of Ibuprofen

Koperwas

Affouard

et al. 2021

Crystal Growth & Design

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“…Moreover, these acoustic waves can couple to fast relaxation dynamics, the characteristic frequency of which is in the GHz~THz range. Previous Brillouin scattering studies on aspirin [ 17 , 18 , 19 ], ibuprofen [ 20 , 21 , 22 ], acetaminophen [ 23 ], and other pharmaceuticals [ 24 , 25 , 26 ] revealed clear anomalies near the glass transition temperatures ( T g ) and fast relaxation processes that coupled to the longitudinal acoustic waves. The present study is aimed at investigating and comparing acoustic properties of progesterone in its glassy, ultraviscous, crystalline, and liquid states.…”

Section: Introductionmentioning

confidence: 99%

Acoustic Anomalies and Fast Relaxation Dynamics of Amorphous Progesterone as Revealed by Brillouin Light Scattering

Kim

Yoo

2017

Materials

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The amorphous state of pharmaceuticals has attracted much attention due to its high bioavailability and other advantages. The stability of the amorphous state in relation with the local molecular mobility is important from both fundamental and practical points of view. The acoustic properties of amorphous progesterone, one of the representative steroid hormones, were investigated by using a Brillouin inelastic light scattering technique. The Brillouin spectrum of the longitudinal acoustic mode exhibited distinct changes at the glass transition and the cold-crystallization temperatures. The acoustic dispersions of the longitudinal sound velocity and the acoustic absorption coefficient were attributed to the fast and possibly the secondary relaxation processes in the glassy and supercooled liquid states, while the structural relaxation process was considered as the dominant origin for the significant acoustic damping observed even in the liquid phase. The persisting acoustic dispersion in the liquid state was attributed to the single-molecule nature of the progesterone which does not exhibit hydrogen bonds in the condensed states.

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Chiral Recognition of Amino Acids Using CC2 Porous Organic Cages

et al. 2023

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Enantiomers have the same physical properties but different chemical properties due to the difference in the orientation of groups in space and thus Chiral discrimination is quite necessary, as an enantiomer of drug can have lethal effects. In this study, we used the CC2 cage for chiral discrimination of amino acids using density functional theory. The results indicated the physisorption of amino acids in the central cavity of the cage. Among the four selected amino acids, proline showed maximum interactions with the cage and maximum chiral discrimination energy is also observed in the case of proline that is 2.78 kcal/mol. Quantum theory of atoms in molecules and noncovalent interaction index analyses showed that the S enantiomer in each case has maximum interactions. The charge transfer between the analyte and surface is further studied through natural bond orbital analysis. It showed sensitivity of cage for both enantiomers, but a more pronounced effect is seen for S enantiomers. In frontier molecular orbital analysis, the least EH‑L gap is observed in the case of R proline with a maximum charge transfer of −0.24 e–. Electron density difference analysis is carried out to analyze the pattern of the charge distribution. The partial density of state analysis is computed to understand the contribution of each enantiomer in overall density of the complexes. Our results show that S-CC2 porous organic cages have a good ability to differentiate between two enantiomers. S-CC2 porous organic cages efficiently differentiated the S enantiomer from the R enantiomers of selected amino acids.

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Relaxation behaviors of enantiomorphic S-ibuprofen as revealed by dielectric and photon correlation spectroscopies

Cited by 7 publications

References 20 publications

Pressure Dependence of the Crystallization Rate for the S-Enantiomer and a Racemic Mixture of Ibuprofen

Pressure Dependence of the Crystallization Rate for the S-Enantiomer and a Racemic Mixture of Ibuprofen

Acoustic Anomalies and Fast Relaxation Dynamics of Amorphous Progesterone as Revealed by Brillouin Light Scattering

Chiral Recognition of Amino Acids Using CC2 Porous Organic Cages

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