Comparison of thermal and elastic properties of glassy racemic and enantiomorphic ibuprofen studied by Brillouin light scattering and modulated differential scanning calorimetry

Kim, Tae Hyun; Shibata, Tomohiko; Kojima, Seiji; Shin, Dong‐Myeong; Hwang, Yoon‐Hwae; Ko, Jae‐Hyeon

doi:10.1016/j.cap.2014.05.001

Cited by 16 publications

(10 citation statements)

References 24 publications

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“…3It was demonstrated that, (Coquerel and Tamura, 2016). Many experimental confirmations have been reported in literature: limonene (Gallis et al, 2000), diprophylline (Viel et al, 2017) or ibuprofen (Kim et al, 2014). For the same cooling or heating conditions, Tg value was not impacted by the asymmetric property of chirality.…”

Section: Thermal Lag and Glass Transitionmentioning

confidence: 75%

Impact of chirality on the Glass Forming Ability and the crystallization from the amorphous state of 5-ethyl-5-methylhydantoin, a chiral poor glass former

Atawa

Couvrat

Coquerel

et al. 2018

International Journal of Pharmaceutics

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The investigation of the glassy state of 5-ethyl-5-methylhydantoin (i.e. 12H, a chiral Active Pharmaceutical Ingredient) was attempted by Differential Scanning Calorimetry (DSC) and Fast Scanning Calorimetry (FSC). This compound exhibits a high crystallization propensity for every enantiomeric composition. Nevertheless, glassy states of pure enantiomer or mixtures between enantiomers were successfully reached by FSC at cooling rates of: 1000 °C/s and 300 °C/s respectively, even though limitations on the sampling reproducibility were evidenced due to FSC sample size. The Glass Forming Ability (GFA) was proven to increase with the counter-enantiomer content. From the glassy state, pure enantiomer displayed a more pronounced crystallogenic character (with a crystallization occurring 36 °C below Tg during ageing) than that of the mixture between enantiomers. Ageing of amorphous 12H promotes a strong nucleation behavior in both samples but enantiopure 12H crystallizes upon ageing while scalemic 12H evolves towards the metastable equilibrium. Finally, potential new phase equilibria (previously not reported) in the enantiomeric phase diagram could have been highlighted by FSC by recrystallization from the amorphous state.

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Section: Thermal Lag and Glass Transitionmentioning

confidence: 75%

Impact of chirality on the Glass Forming Ability and the crystallization from the amorphous state of 5-ethyl-5-methylhydantoin, a chiral poor glass former

Atawa

Couvrat

Coquerel

et al. 2018

International Journal of Pharmaceutics

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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%

“…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%

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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“…Since nonequilibrium glassy/amorphous states have a solubility and dissolution rate that is higher than the equilibrium crystalline states, the presence of the glassy/amorphous states have the advantage in pharmaceutical materials. The liquid, glassy, and crystalline states of various drug materials, such as aspirin [ 88 , 89 ], ibuprofen [ 90 , 91 ], ketoprofen [ 92 ], and indomethacin [ 34 , 93 ] were studied by Brillouin scattering.…”

Section: Brillouin Scattering Spectroscopy In Materials Sciencementioning

confidence: 99%

100th Anniversary of Brillouin Scattering: Impact on Materials Science

Kojima

2022

Materials

Self Cite

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L. Brillouin predicted inelastic light scattering by thermally excited sound waves in 1922. Brillouin scattering is a non-contact and non-destructive method to measure sound velocity and attenuation. It is possible to investigate the elastic properties of gases, liquids, glasses, and crystals. Various kinds of phase transitions, i.e., liquid–glass transitions, crystallization, polymorphism, and denaturation have been studied by changing the temperature, pressure, time, and external fields such as the electric, magnetic, and stress fields. Nowadays, Brillouin scattering is extensively used to measure various elementary excitations and quasi-elastic scattering in the gigahertz range between 0.1 and 1000 GHz. A brief history, spectroscopic methods, and Brillouin scattering studies in materials science on ferroelectric materials, glasses, and proteins are reviewed.

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Comparison of thermal and elastic properties of glassy racemic and enantiomorphic ibuprofen studied by Brillouin light scattering and modulated differential scanning calorimetry

Cited by 16 publications

References 24 publications

Impact of chirality on the Glass Forming Ability and the crystallization from the amorphous state of 5-ethyl-5-methylhydantoin, a chiral poor glass former

Impact of chirality on the Glass Forming Ability and the crystallization from the amorphous state of 5-ethyl-5-methylhydantoin, a chiral poor glass former

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

100th Anniversary of Brillouin Scattering: Impact on Materials Science

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