Temperature-Driven Isosymmetric Reversible Phase Transition of the Hormone Estradiol 17β Valerate

Ellena, Javier; Paula, Karina de; Melo, Cristiane C. de; Silva, Cecília C. P. da; Bezerra, Beatriz Pinheiro; Venâncio, Tiago; Ayala, A. P.

doi:10.1021/cg500974r

Cited by 13 publications

(15 citation statements)

References 31 publications

(40 reference statements)

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“…Alkanes and alkyl derivatives, such as polyethylene, liquid crystals, biological membranes, and variously modified proteins are classical examples that undergo this type of isomerization, which is a major factor in the dynamics and activity of their molecular structures 15 16 17 . Recently, molecular crystals based on alkyl derivatives that exhibit conformational polymorphism have also been studied 18 19 . However, studies on converting alkyl rotation to reversible and large motion of the macroscopic crystal have never been reported.…”

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confidence: 99%

Assembling an alkyl rotor to access abrupt and reversible crystalline deformation of a cobalt(II) complex

Kamachi

Yao

et al. 2015

Nat Commun

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Harnessing molecular motion to reversibly control macroscopic properties, such as shape and size, is a fascinating and challenging subject in materials science. Here we design a crystalline cobalt(II) complex with an n-butyl group on its ligands, which exhibits a reversible crystal deformation at a structural phase transition temperature. In the low-temperature phase, the molecular motion of the n-butyl group freezes. On heating, the n-butyl group rotates ca. 100° around the C–C bond resulting in 6–7% expansion of the crystal size along the molecular packing direction. Importantly, crystal deformation is repeatedly observed without breaking the single-crystal state even though the shape change is considerable. Detailed structural analysis allows us to elucidate the underlying mechanism of this deformation. This work may mark a step towards converting the alkyl rotation to the macroscopic deformation in crystalline solids.

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confidence: 99%

Assembling an alkyl rotor to access abrupt and reversible crystalline deformation of a cobalt(II) complex

Kamachi

Yao

et al. 2015

Nat Commun

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“…With an enthalpy change limited to a few kJ mol −1 , and relative atomic positions only marginally affected by the phase transformation, the integrity of the molecular skeletons, as well as that of the primary supramolecular network (here, the extensive hydrogen-bond interactions occurring among the polar carboxyl and amino groups of ibuprofen and lysine) call for a displacive transformation, not requiring significant bond breaking. According to the very recent contribution by Ellena et al [20], isosymmetric reversible phase transitions, such as that occurring in the title compound, are rare for organic compounds, and often, but not uniquely, associated to pressure-driven processes.…”

Section: Discussionmentioning

confidence: 99%

Reversibly changing a painkiller structure: A hot topic for a cold case—Ibuprofen lysine salt

Vladiskovic

Masciocchi

2015

Journal of Pharmaceutical and Biomedical Analysis

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“…Another example shows that the vibrational frequency calculations of estradiol alone and in monohydrated form [ 165 ] has given insight into hydrogen bond formation by estradiol’s D-ring. This has been used to discuss the relationship between the stability of hydrated clusters and the estradiol conformation.…”

Section: Application Of Molecular Modelling Methods In the Study Omentioning

confidence: 99%

Application of Various Molecular Modelling Methods in the Study of Estrogens and Xenoestrogens

Mazurek

Szeleszczuk

Simonson

et al. 2020

IJMS

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In this review, applications of various molecular modelling methods in the study of estrogens and xenoestrogens are summarized. Selected biomolecules that are the most commonly chosen as molecular modelling objects in this field are presented. In most of the reviewed works, ligand docking using solely force field methods was performed, employing various molecular targets involved in metabolism and action of estrogens. Other molecular modelling methods such as molecular dynamics and combined quantum mechanics with molecular mechanics have also been successfully used to predict the properties of estrogens and xenoestrogens. Among published works, a great number also focused on the application of different types of quantitative structure–activity relationship (QSAR) analyses to examine estrogen’s structures and activities. Although the interactions between estrogens and xenoestrogens with various proteins are the most commonly studied, other aspects such as penetration of estrogens through lipid bilayers or their ability to adsorb on different materials are also explored using theoretical calculations. Apart from molecular mechanics and statistical methods, quantum mechanics calculations are also employed in the studies of estrogens and xenoestrogens. Their applications include computation of spectroscopic properties, both vibrational and Nuclear Magnetic Resonance (NMR), and also in quantum molecular dynamics simulations and crystal structure prediction. The main aim of this review is to present the great potential and versatility of various molecular modelling methods in the studies on estrogens and xenoestrogens.

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Temperature-Driven Isosymmetric Reversible Phase Transition of the Hormone Estradiol 17β Valerate

Cited by 13 publications

References 31 publications

Assembling an alkyl rotor to access abrupt and reversible crystalline deformation of a cobalt(II) complex

Assembling an alkyl rotor to access abrupt and reversible crystalline deformation of a cobalt(II) complex

Reversibly changing a painkiller structure: A hot topic for a cold case—Ibuprofen lysine salt

Application of Various Molecular Modelling Methods in the Study of Estrogens and Xenoestrogens

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