Urea based low molecular weight pseudopeptidic organogelators for the encapsulation and slow release of (R)-limonene.

Low molecular weight compound containing alkylurea fragments attached to the amino end of different miminalistic pseudopeptidic structures have 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 of suberic acid. They also achieve the gelation of relevant active substances like 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 of any additional solvent or complex processes, and their consequent controlled release.

[1]  S. Luis,et al.  Synthesis of second-generation self-assembling Gemini Amphiphilic Pseudopeptides. , 2019, Journal of colloid and interface science.

[2]  M. Mishra Applications of Encapsulation and Controlled Release , 2019 .

[3]  M. Dusselier,et al.  Sustainable Chemistry Considerations for the Encapsulation of Volatile Compounds in Laundry-Type Applications , 2019, ACS Sustainable Chemistry & Engineering.

[4]  Christopher D. Jones,et al.  Braiding, branching and chiral amplification of nanofibres in supramolecular gels , 2019, Nature Chemistry.

[5]  Zhuxian Zhou,et al.  Encapsulation and controlled release of fragrances from functionalized porous metal-organic frameworks , 2018, AIChE Journal.

[6]  Hiroharu Ajiro,et al.  Cationic Moieties in Polystyrene Gels Swollen with d-Limonene Improved Transdermal Delivery System , 2018, Polymers.

[7]  Hiroharu Ajiro,et al.  The electrostatic advantages of cross-linked polystyrene organogels swollen with limonene for selective adsorption and storage of hydrophobic drugs , 2018, Polymer Journal.

[8]  Anya Kwan,et al.  Controlled release of flavor oil nanoemulsions encapsulated in filled soluble hydrogels. , 2018, Food chemistry.

[9]  Masamichi Yamanaka,et al.  Synthesis of a Bis-Urea Dimer and Its Effects on the Physical Properties of an Amphiphilic Tris-Urea Supramolecular Hydrogel. , 2018, Chemistry, an Asian journal.

[10]  Qi Kang,et al.  Supramolecular gels: using an amide-functionalized imidazolium-based surfactant. , 2018, Journal of colloid and interface science.

[11]  D. Adams,et al.  Low-Molecular-Weight Gels: The State of the Art , 2017 .

[12]  W. Yokoyama,et al.  Development of β-Carotene-Loaded Organogel-Based Nanoemulsion with Improved In Vitro and In Vivo Bioaccessibility. , 2017, Journal of agricultural and food chemistry.

[13]  Vasiliki Evageliou,et al.  Limonene encapsulation in freeze dried gellan systems. , 2017, Food chemistry.

[14]  A. Allafchian,et al.  Development and characterization of electrosprayed Alyssum homolocarpum seed gum nanoparticles for encapsulation of d-limonene. , 2017, Journal of colloid and interface science.

[15]  Wei-min Liu,et al.  Supramolecular ionogel lubricants with imidazolium-based ionic liquids bearing the urea group as gelator. , 2017, Journal of colloid and interface science.

[16]  P. Fischer,et al.  The effects of intermolecular interactions on the physical properties of organogels in edible oils. , 2016, Journal of colloid and interface science.

[17]  S. Luis,et al.  Structure - membrane activity relationship in a family of peptide-based gemini amphiphiles: An insight from experimental and theoretical model systems. , 2016, Colloids and surfaces. B, Biointerfaces.

[18]  Zeynep Aytac,et al.  Fast-Dissolving, Prolonged Release, and Antibacterial Cyclodextrin/Limonene-Inclusion Complex Nanofibrous Webs via Polymer-Free Electrospinning. , 2016, Journal of agricultural and food chemistry.

[19]  Chi-Tang Ho,et al.  Development of Organogel-Derived Capsaicin Nanoemulsion with Improved Bioaccessibility and Reduced Gastric Mucosa Irritation. , 2016, Journal of agricultural and food chemistry.

[20]  V. Jaitak,et al.  Polymeric Encapsulates of Essential Oils and Their Constituents: A Review of Preparation Techniques, Characterization, and Sustainable Release Mechanisms , 2016 .

[21]  Isabel T Carvalho,et al.  Application of microencapsulated essential oils in cosmetic and personal healthcare products – a review , 2016, International journal of cosmetic science.

[22]  Masamichi Yamanaka Development of C3-Symmetric Tris-Urea Low-Molecular-Weight Gelators. , 2016, Chemical record.

[23]  Marco Caggioni,et al.  Encapsulation and Enhanced Retention of Fragrance in Polymer Microcapsules. , 2016, ACS applied materials & interfaces.

[24]  M. Mishra Handbook of Encapsulation and Controlled Release , 2015 .

[25]  Philip A. Gale,et al.  Acyclic Pseudopeptidic Hosts as Molecular Receptors and Transporters for Anions , 2015 .

[26]  N. Basarić,et al.  Anion binding with urea and thiourea derivatives , 2015 .

[27]  S. Armes,et al.  Colloidosomes: synthesis, properties and applications. , 2015, Journal of colloid and interface science.

[28]  D. Mcclements,et al.  Nutraceutical delivery systems: resveratrol encapsulation in grape seed oil nanoemulsions formed by spontaneous emulsification. , 2015, Food chemistry.

[29]  Qipeng Yuan,et al.  Formation and stability of D-limonene organogel-based nanoemulsion prepared by a high-pressure homogenizer. , 2014, Journal of agricultural and food chemistry.

[30]  Alírio E. Rodrigues,et al.  Microencapsulation of essential oils with biodegradable polymeric carriers for cosmetic applications , 2014 .

[31]  S. Luis,et al.  Bioinspired chemistry based on minimalistic pseudopeptides. , 2014, Accounts of chemical research.

[32]  K. Aissat,et al.  Tetraclinis articulata (Vahl) Masters essential oils: chemical composition and biological activities , 2013 .

[33]  S. Luis,et al.  Synthesis and organogelating ability of bis-urea pseudopeptidic compounds , 2013 .

[34]  Masamichi Yamanaka Urea derivatives as low-molecular-weight gelators , 2013, Journal of Inclusion Phenomena and Macrocyclic Chemistry.

[35]  S. Luis,et al.  Photoluminescence enhancement of CdSe quantum dots: a case of organogel-nanoparticle symbiosis. , 2012, Journal of the American Chemical Society.

[36]  D. Peressini,et al.  Release behavior and stability of encapsulated D-limonene from emulsion-based edible films. , 2012, Journal of agricultural and food chemistry.

[37]  G. Moschetti,et al.  Inhibition of foodborne pathogen bacteria by essential oils extracted from citrus fruits cultivated in Sicily , 2012 .

[38]  F. Zhong,et al.  Physical and antimicrobial properties of peppermint oil nanoemulsions. , 2012, Journal of agricultural and food chemistry.

[39]  S. Luis,et al.  Organogel–quantum dots hybrid materials displaying fluorescence sensitivity and structural stability towards nitric oxide , 2012 .

[40]  S. Luis,et al.  Interplay between hydrophilic and hydrophobic interactions in the self-assembly of a gemini amphiphilic pseudopeptide: from nano-spheres to hydrogels. , 2012, Chemical communications.

[41]  A. Herrmann,et al.  Release of bioactive volatiles from supramolecular hydrogels: influence of reversible acylhydrazone formation on gel stability and volatile compound evaporation. , 2011, Organic & biomolecular chemistry.

[42]  Murray B. Isman,et al.  Commercial opportunities for pesticides based on plant essential oils in agriculture, industry and consumer products , 2011, Phytochemistry Reviews.

[43]  Jonathan W. Steed,et al.  Anion-tuned supramolecular gels: a natural evolution from urea supramolecular chemistry. , 2010, Chemical Society reviews.

[44]  Hiromitsu Fujii,et al.  Chloroalkane gel formations by tris-urea low molecular weight gelator under various conditions. , 2009, The Journal of organic chemistry.

[45]  G. Reineccius,et al.  Encapsulation performance of proteins and traditional materials for spray dried flavors. , 2009, Journal of agricultural and food chemistry.

[46]  Tomohiko Nakamura,et al.  Synthesis and estimation of gelation ability of C3-symmetry tris-urea compounds , 2008 .

[47]  P. Dastidar,et al.  Supramolecular gelling agents: can they be designed? , 2008, Chemical Society reviews.

[48]  B. Escuder,et al.  Molecular recognition through divalent interactions with a self-assembled fibrillar network of a supramolecular organogel. , 2008, Organic & biomolecular chemistry.

[49]  David K Smith,et al.  High-tech applications of self-assembling supramolecular nanostructured gel-phase materials: from regenerative medicine to electronic devices. , 2008, Angewandte Chemie.

[50]  R. Negri,et al.  Correlation between rheological properties and limonene release in pectin gels using an electronic nose , 2008 .

[51]  A. Viljoen,et al.  Antimicrobial activity of limonene enantiomers and 1,8-cineole alone and in combination , 2007 .

[52]  B. Feringa,et al.  C3-Symmetric, amino acid based organogelators and thickeners: a systematic study of structure–property relations , 2007 .

[53]  Claire E. Stanley,et al.  Anion binding inhibition of the formation of a helical organogel. , 2006, Chemical communications.

[54]  Ali Hossain Khan,et al.  Solubilization and location of phenethylalcohol, benzaldehyde, and limonene in lamellar liquid crystal formed with block copolymer and water. , 2006, Journal of colloid and interface science.

[55]  V. John,et al.  Urea and thiourea derivatives as low molecular-mass organogelators. , 2005, Chemistry.

[56]  S. Luis,et al.  Understanding the Expression of Molecular Chirality in the Self-Assembly of a Peptidomimetic Organogelator , 2005 .

[57]  S. Luis,et al.  Self-assembly of small peptidomimetic cyclophanes. , 2004, Chemistry.

[58]  A. Hamilton,et al.  Water gelation by small organic molecules. , 2004, Chemical reviews.

[59]  E. Garcı́a-España,et al.  Efficient macrocyclization of U-turn preorganized peptidomimetics: the role of intramolecular H-bond and solvophobic effects. , 2003, Journal of the American Chemical Society.

[60]  E. W. Meijer,et al.  C3-symmetrical supramolecular architectures: fibers and organic gels from discotic trisamides and trisureas. , 2002, Journal of the American Chemical Society.

[61]  M. Querol,et al.  Minimalist peptidomimetic cyclophanes as strong organogelators. , 2002, Chemical communications.

[62]  A. Siani,et al.  Stability of monoterpenes encapsulated in gum Arabic by spray-drying. , 2001, Journal of agricultural and food chemistry.

[63]  Richard G. Weiss,et al.  Low Molecular Mass Gelators of Organic Liquids and the Properties of Their Gels. , 1997, Chemical reviews.

[64]  H. Cutler,et al.  Antimicrobial, insecticidal, and medicinal properties of natural product flavors and fragrances , 1996 .

[65]  M. Gould,et al.  Chemoprevention of mammary carcinogenesis by hydroxylated derivatives of d-limonene. , 1992, Carcinogenesis.