Exploring the inclusion interaction of estradiol with β-CD and HP-β-CD with the help of molecular dynamics simulation as well as multi-spectroscopic approaches

Lin, Zhen‐Yi; Wang, Xiao-Xuan; Kou, Song‐Bo; Shi, Jie‐Hua

doi:10.1016/j.saa.2021.120764

Cited by 9 publications

(4 citation statements)

References 40 publications

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“…The current state of knowledge regarding the stoichiometry of the complexes indicates a 1:1 [98][99][100] value for HP-β-CD and β-CD or a 2:1 [99,100] for β-CD in the form of polymer-based materials. The 1:1 stoichiometry with β-CD was also shown to be stable in a molecular modeling study [101]. Both native and modified β-CDs are more effective in forming complexes with E2 in aqueous solutions than α-CD or γ-CD [102].…”

Section: Estradiol (E2) 421 Complex Preparation Methodsmentioning

confidence: 87%

“…The in silico study showed that the aromatic ring was located closer to the wider rim and the cyclopentyl to the narrow rim of the CD. The association constants of β-CD/E2 and HP-β-CD/E2 were established at 298 K [101]. Another paper also showed the association constants of E2/β-CD and E2/γ-CD fluorometrically measured in methanol/water (20/80 v/v) at 35 • C. Then, the values were compared to values from an HPLC study.…”

Section: Complex Structure Analysismentioning

confidence: 99%

“…The thermodynamic parameters of the complex formation were also measured and analyzed. This determined that the dominating interaction forces are the hydrophobic and hydrogen-bonding interactions, which stabilize the β-CD/E2 complex, as well as the hydrogen bonding interaction and van der Waals forces for the HP-β-CD/E2 complex [101].…”

Section: Complex Structure Analysismentioning

confidence: 99%

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A Review on Cyclodextrins/Estrogens Inclusion Complexes

Araj,

Szeleszczuk

2023

IJMS

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This review focuses on the methods of preparation and biological, physiochemical, and theoretical analysis of the inclusion complexes formed between estrogens and cyclodextrins (CDs). Because estrogens have a low polarity, they can interact with some cyclodextrins’ hydrophobic cavities to create inclusion complexes, if their geometric properties are compatible. For the last forty years, estrogen-CD complexes have been widely applied in several fields for various objectives. For example, CDs have been used as estrogen solubilizers and absorption boosters in pharmaceutical formulations, as well as in chromatographic and electrophoretic procedures for their separation and quantification. Other applications include the removal of the endocrine disruptors from environmental materials, the preparation of the samples for mass spectrometric analysis, or solid-phase extractions based on complex formation with CDs. The aim of this review is to gather the most important outcomes from the works related to this topic, presenting the results of synthesis, in silico, in vitro, and in vivo analysis.

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Section: Estradiol (E2) 421 Complex Preparation Methodsmentioning

confidence: 87%

Section: Complex Structure Analysismentioning

confidence: 99%

Section: Complex Structure Analysismentioning

confidence: 99%

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A Review on Cyclodextrins/Estrogens Inclusion Complexes

Araj,

Szeleszczuk

2023

IJMS

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“…The properties and structures of the complexes of EST with various CDs have been studied extensively for the last 30 years [20][21][22][23][24][25][26][27]. For example, in a recent work [28], single-crystal X-ray diffraction (SCXRD) results of the EST/ß-CD complex were presented, determining the unit cell and the crystallographic space group of the crystal structure.…”

Section: 28 3747mentioning

confidence: 99%

17-β-Estradiol—β-Cyclodextrin Complex as Solid: Synthesis, Structural and Physicochemical Characterization

et al. 2023

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17-β-estradiol (EST) is the most potent form of naturally occurring estrogens; therefore, it has found a wide pharmaceutical application. The major problem associated with the use of EST is its very low water solubility, resulting in poor oral bioavailability. To overcome this drawback, a complexation with cyclodextrins (CD) has been suggested as a solution. In this work, the host–guest inclusion complex between the ß-CD and EST has been prepared using four different methods. The obtained samples have been deeply characterized using 13C CP MAS solid state NMR, PXRD, FT-IR, TGA, DSC, and SEM. Using SCXRD, the crystal structure of the complex has been determined, being to the best of our knowledge the first solved crystal structure of an estrogen/CD complex. The periodic DFT calculations of NMR properties using GIPAW were found to be particularly helpful in the analysis of disorder in the solid state and interpretation of experimental NMR results. This work highlights the importance of a combined ssNMR/SCXRD approach to studying the structure of the inclusion complexes formed by cyclodextrins.

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