Smart supramolecular gels of enolizable amphiphilic glycosylfuran

Thamizhanban, Ayyapillai; Lalitha, Krishnamoorthy; Sarvepalli, Guru Prasanth; Maheswari, C. Uma; Sridharan, Vellaisamy; Rayappan, John Bosco Balaguru; Nagarajan, Subbiah

doi:10.1039/c9tb01480b

Cited by 10 publications

(22 citation statements)

References 46 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…On the other hand, gels are interesting soft materials owing to their functional properties, leading to potential applications (Yao et al, 2017). Using gels as drug carriers has attracted tremendous attention for their numerous advantages in medical treatments, including prolonged drug release time, reduced side effects of drugs, and maintained effective plasma concentration (Nishimura et al, 2019;Teng et al, 2019;Thamizhanban et al, 2019). For example, Prof. Yao and co-workers prepared a soft gel based on pillar[5]arene by using a carbazone reaction and found that dyes such as TPP or TPPE can be incorporated into this gel and then released in a sustained way in water due to solvent exchange (Yao et al, 2017).…”

Section: Introductionmentioning

confidence: 99%

A p-tert-Butyldihomooxacalix[4]arene Based Soft Gel for Sustained Drug Release in Water

et al. 2020

View full text Add to dashboard Cite

P -tert-butyldihomooxacalix[4]arene is a well-known calix [4]arene analog in which one CH 2 bridge is replaced by one -O-group. Thus, dihomooxacalix[4]arene has a slightly larger cavity than that of calix[4]arene and usually possesses a more flexible cone conformation, and the bridged oxygen atom might provide additional binding sites. Here, we synthesized a new functional p-tert-butyldihomooxacalix[4]arene 1 through Ugi reaction with good yield (70%), starting from condensed p-tert-butyldihomooxacalix [4]arene O-alkoxy-substituted benzaldehydes, benzoic acid, benzylamine, and cyclohexyl isocyanide. Proton nuclear magnetic resonance spectroscopy ( 1 H NMR), 13 C NMR, IR, and diffusion-ordered 1 H NMR spectroscopy (DOSY) methods were used to characterize the structure of 1. Then soft gel was prepared by adding 1 into cyclohexane directly. It shows remarkable thermoreversibility and can be demonstrated for several cycles. As is revealed by scanning electron microscopy (SEM) images, xerogel showed highly interconnected and homogeneous porous network structures, and hence, the gel is suitable for storage and controlled release. . (2019). Enzyme-mediated dynamic combinatorial chemistry allows out-of-equilibrium template-directed synthesis of macrocyclic oligosaccharides. Chem. Sci. 10, 9981-9987.

show abstract

Section: Introductionmentioning

confidence: 99%

A p-tert-Butyldihomooxacalix[4]arene Based Soft Gel for Sustained Drug Release in Water

et al. 2020

View full text Add to dashboard Cite

show abstract

“…Both functionalized furans hold promise as precursors for platform chemicals, value-added chemicals, pharmaceutical intermediates, and materials. To date, these functionalized furans have been used to access a variety of anticancer agents, 9 antimicrobials, 10 antifungals, 10 glyco-mimetics, 11 biological probes, 12 hydrogels, 13 and fuel precursor molecules. 14 Despite this promise, scalability issues have limited the reaction's broader utility.…”

Section: ■ Introductionmentioning

confidence: 99%

“…For example, using 2-nitroterephthalic acid instead of terephthalic acid in the synthesis of UiO-66 has led to a more Lewis acidic zirconium node for Lewis acid catalyzed reactions. 45 The Garcia Gonzalez product is of increased interest, due to acting as a precursor in biologically active molecules, 9−12 materials, 13 various synthetic motifs, and fuel applications. 14 Due to this understudied reaction being catalyzed primarily by homogeneous catalysts, we have focused on developing a wellcharacterized, truly heterogeneous catalyst in the form of a zirconium MOF.…”

Section: ■ Introductionmentioning

confidence: 99%

Modulation and Tuning of UiO-66 for Lewis Acid Catalyzed Carbohydrate Conversion: Conversion of Unprotected Aldose Sugars to Polyhydroxyalkyl and C-Glycosyl Furans

Ronaghi

Shade

Moon

et al. 2021

ACS Sustainable Chem. Eng.

View full text Add to dashboard Cite

Trifluoroacetic acid-modulated UiO-66 metal–organic frameworks (MOFs) are used to catalyze the reaction of unprotected aldose sugars with acetylacetone to polyhydroxyalkyl and C-glycosyl furans, known as the Garcia Gonzalez reaction. The effects of trifluoroacetic acid (TFA) modulation, linker substitution, and MOF activation temperature on the pore structure and catalytic activity are evaluated. Differing trends in activity and thermal stability are observed for MOFs with ligand substitutions vs ones without. Optimal MOF activation temperatures vary based on linker substitution, though both substituted and unsubstituted linkers give rise to catalysts with high activity. Catalytic tests using sugars of different sizes suggest catalysis occurs in the micropores and/or mesopores of the MOF, though deposition of carbonaceous species on the MOF limits catalyst recyclability. The MOF system leads to improved product yields and different ratios of cyclized to uncyclized products compared to a homogeneous zirconium salt catalyst under similar conditions, suggesting the MOF catalysts may offer synthetic utility.

show abstract

“…In recent years, the design and study of sugar based gelators have attracted much attention. They have been explored for applications in several research fields ranging from drug delivery [ 5 , 6 , 7 , 8 ], to environmental applications [ 9 , 10 , 11 , 12 , 13 , 14 ], enzyme immobilization, ion sensing [ 15 , 16 , 17 ], and supramolecular gel catalysts [ 18 , 19 , 20 ].…”

Section: Introductionmentioning

confidence: 99%

Fine-Tuning of Molecular Structures to Generate Carbohydrate Based Super Gelators and Their Applications for Drug Delivery and Dye Absorption

Bietsch

Olson

Wang

2021

Gels

View full text Add to dashboard Cite

Carbohydrate-based low molecular weight gelators (LMWGs) exhibit many desirable properties making them useful in various fields including applications as drug delivery carriers. In order to further understand the structural connection to gelation properties, especially the influence of halide substitutions, we have designed and synthesized a series of para-chlorobenzylidene acetal protected D-glucosamine amide derivatives. Fifteen different amides were synthesized, and their self-assembling properties were assessed in multiple organic solvents, as well as mixtures of organic solvents with water. All derivatives were found to be gelators for at least one solvent and majority formed gels in multiple solvents at concentrations lower than 2 wt%. A few derivatives rendered remarkably stable gels in aqueous solutions at concentrations below 0.1 wt%. The benzamide 13 formed gels in water and in EtOH/H2O (v/v 1:2) at 0.36 mg/mL. The gels were characterized using optical microscopy and atomic force microscopy, and the self-assembly mechanism was probed using variable temperature 1H-NMR spectroscopy. Gel extrusion studies using H2O/DMSO gels successfully printed lines of gels on glass slides, which retained viscoelasticity based on rheology. Gels formed by the benzamide 13 were used for encapsulation and the controlled release of chloramphenicol and naproxen, as well as for dye removal for toluidine blue aqueous solutions.

show abstract

Smart supramolecular gels of enolizable amphiphilic glycosylfuran

Abstract: In this report, bio-based amphiphilic glycosylfurans were synthesized using a biocatalyst. For the first time, we are reporting on hydrogelation via in situ molecular tuning of amphiphilic glycosylfurans followed by a self-sorting mechanism.

Cited by 10 publications

References 46 publications

A p-tert-Butyldihomooxacalix[4]arene Based Soft Gel for Sustained Drug Release in Water

A p-tert-Butyldihomooxacalix[4]arene Based Soft Gel for Sustained Drug Release in Water

Modulation and Tuning of UiO-66 for Lewis Acid Catalyzed Carbohydrate Conversion: Conversion of Unprotected Aldose Sugars to Polyhydroxyalkyl and C-Glycosyl Furans

Fine-Tuning of Molecular Structures to Generate Carbohydrate Based Super Gelators and Their Applications for Drug Delivery and Dye Absorption

Contact Info

Product

Resources

About