Synthesis, Characterization, and Retinol Stabilization of Fatty Amide-β-cyclodextrin Conjugates

Abstract

Amphiphilic cyclodextrin (CD) has been the object of growing scientific attention because of its two recognition sites, the cavity and the apolar heart, formed by self-assembly. In the present study, mono[6-deoxy-6-(octadecanamido)]-β-CD and mono[6-deoxy-6-(octadecenamido)]-β-CD were successfully synthesized by reacting mono-6-amino-6-deoxy-β-CD with N-hydroxysuccinimide esters of corresponding fatty acids in DMF. The structures were analyzed using nuclear magnetic resonance spectroscopy and mass spectrometry. The amphiphilic β-CDs were able to form self-assembled nano-vesicles in water, and the supramolecular architectures were characterized using fluorescence spectroscopy, dynamic light scattering, and transmission electron microscopy. Using the cavity-type nano-vesicles, all-trans-retinol was efficiently encapsulated; it was then stabilized against the photo-degradation. Therefore, the present fatty amide-β-CD conjugate will be a potential molecule for carrier systems in cosmetic and pharmaceutical applications.

Improvement of mild photoaged facial skin in middle‐aged Chinese females by a supramolecular retinol plus acetyl hexapeptide‐1 containing essence

“…The 24‐h patch test results presented here have shown that there are two cases of (±) doubtful reactions in the 0.1% supramolecular retinol group and eight cases of (±) doubtful reactions in the 0.1% non‐encapsulated retinol group respectively, with significant differences between the two groups. Other studies have shown that retinol can be efficiently encapsulated by cyclodextrins with the benefit of increasing the stability of retinol to light and heat 18,19 . In this study, supramolecular retinol, formed through the hydrophobic/hydrophilic action of cyclodextrin and the inter‐molecular association of supramolecular association agent, improves the stability and reduces irritation in retinol application.…”

“…Other studies have shown that retinol can be efficiently encapsulated by cyclodextrins with the benefit of increasing the stability of retinol to light and heat. 18,19 In this study, supramolecular retinol, formed through the hydrophobic/hydrophilic action of cyclodextrin and the inter-molecular association of supramolecular association agent, improves the stability and reduces irritation in retinol application. Taken together, our patch test data indicate that the general safe retinol concentration is less than or equal to 0.1%.…”

Triple-target stimuli-responsive anti-COVID-19 face mask with physiological virus-inactivating agents

“…4.II ). Tretinoin which was added in some series of experiments had the published spectrum, 47 with OH signal at 3245 cm −1 , with C 2 H at 2945 cm −1 and 2868 cm −1 , C C at 1623 cm −1 , with CH 2 at 1438 cm −1 and 1363 cm −1 and with H–C C–H at 960 cm −1 . In addition, the pattern for PCL is added in order to allow a mapping of the spun fibers, prepared from PCL, tretinoin and “Ca-polyP-NP”, the complex “PCL/Ca-polyP-NP/Treti” material.…”

Silica Microparticles from Sugarcane By-Products as an Encapsulation System for Retinoids Aimed at Topical Sustained Release

“…[8,13] Cyclodextrins Solubilization of poorly soluble molecules and protection from chemical degradation. Nanometric diameters (<100 nm) and encapsulation efficiencies ranging from 20-50% [14] Polymeric micelles…”