Urea-Based Low-Molecular-Weight Pseudopeptidic Organogelators for the Encapsulation and Slow Release of (R)-Limonene

Abstract

Low-molecular-weight compounds containing alkylurea fragments attached to the amino end of different miminalistic pseudopeptidic structures have been shown to be excellent organogelators in a variety of organic solvents and liquid organic compounds of different nature. The formation of gels in this work is defined through rheological measurements for those cases where G′ > G′′. Both the topology and the symmetry of the corresponding urea compounds play a role in defining their organogelator behavior. This can also be tuned by the presence of additional supramolecular guests, as is the case for suberic acid. These compounds also achieve the gelation of relevant active substances such as terpene natural oils and complex mixtures of flavors and fragrances. This provides a simple and mass-efficient supramolecular system for the quantitative encapsulation of active substances, without the need for any additional solvent or complex processes, and their consequent controlled release.

Anticancer activity of limonene: A systematic review of target signaling pathways

“…Proteins have also been described such as zein (Bidyarani & Kumar, 2019), milk proteins (Sonu, Mann, Sharma, Kumar, & Singh, 2018) or others (Ansarifar et al, 2019). Synthetic polymers (Robayo, Sierra, & Perez, 2020), solid lipid nanoparticles (Angellotti et al, 2020), liposomes (Umagiliyage, Becerra-Mora, Kohli, well reported such as encapsulation in yeast cells (Normand, Dardelle, Bouquerand, Nicolas, & Johnston, 2005), calcium carbonate microparticles (Elabbadi, Jerri, Ouali, & Erni, 2015), or pseudopeptidic organogelators (Valls et al, 2020).…”

“…Synthetic polymers (Robayo, Sierra, & Perez, 2020), solid lipid nanoparticles (Angellotti et al, 2020), liposomes (Umagiliyage, Becerra‐Mora, Kohli, Fisher, & Choudhary, 2017), metallic nanoparticles (de Barros, Cruz, Mayrink, & Tasic, 2018; Yang, Liu, & Liu, 2020), and composites with cyclodextrin derivatives (Saldanha do Carmo, Pais, Simplício, Mateus, & Duarte, 2017) have also been used to improve the pharmacological properties of the LIM. Others uncommon techniques have been as well reported such as encapsulation in yeast cells (Normand, Dardelle, Bouquerand, Nicolas, & Johnston, 2005), calcium carbonate microparticles (Elabbadi, Jerri, Ouali, & Erni, 2015), or pseudopeptidic organogelators (Valls et al, 2020).…”

Self-Assembling Oligo(2-oxazoline) Organogelators for the Encapsulation and Slow Release of Bioactive Volatiles

“…Supramolecular organogels have been attracting considerable attention over the last decades owing to their prospective and realized applications in numerous fields such as food, 1 , 2 cosmetics, 3 drug delivery, 4 − 6 encapsulation and controlled release of fragrance, 7 and advanced materials. 8 − 10 This kind of physical gel is generally formed by immobilizing organic solvents and oils in a three-dimensional network created by the entanglement of noncovalently self-assembled nanofibers.…”

Unravelling the Supramolecular Driving Forces in the Formation of CO2-Responsive Pseudopeptidic Low-Molecular-Weight Hydrogelators

“…In this regard, C 2 -symmetric pseudopeptidic compounds displaying apolar spacers have shown remarkable gelating behaviours in different solvents [ 22 ], with the presence of additional functional components, such as urea fragments, significantly increasing the stability of the resulting supramolecular gels [ 23 , 24 ]. The introduction of polarfunctionalities in such pseudopeptides with apolar spacers has shown to afford efficient hydrogelators with pH-responsive self-assembling properties [ 25 ].…”