Glycosyl squaramides, a new class of supramolecular gelators

Ramos, Jessica; Arufe, Santiago; Martin, Harlei; Rooney, Denise; Elmes, Robert B. P.; Erxleben, Andrea; Moreira, Ramón; Velasco‐Torrijos, Trinidad

doi:10.1039/d0sm01075h

Cited by 11 publications

(12 citation statements)

References 36 publications

(41 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The interest toward this class of compounds arises from their intrinsic features, such as the possibility to act as both H-bond donor and acceptor, the structural rigidity, aromaticity, as well as the ability to form strong bi-directional hydrogen bonds making them ideal candidates for the development of catalysts, self-complementary molecular recognition motifs and self-assembled materials. In particular, these unique properties have also been exploited in the design of squaramide-based systems for anion binding and transport [1][2][3][4] and, recently, as potential low molecular weight gelators and imaging agents [5][6][7].…”

Section: Introductionmentioning

confidence: 99%

Switching-On Fluorescence by Copper (II) and Basic Anions: A Case Study with a Pyrene-Functionalized Squaramide

et al. 2021

View full text Add to dashboard Cite

The new symmetric acyclic N,N’-bis(1-pyrenyl) squaramide (H2L) functionalized with the pyrene moiety as a fluorogenic fragment has been designed and its ability to selectively detect specific anions and metals investigated. H2L selectively binds Cl− both in solution (DMSO 0.5% H2O and MeCN) and in the solid state, and allows to selectively detect Cu2+ in MeCN with the formation of a 2:1 metal-receptor complex, with a green intense emission appreciable by naked eye under the UV lamp. The H2L copper complex preserves its emission properties in the presence of Cl−. The addition of basic anions (OH−, CN−, and F−) up to 10 equivalents caused the deprotonation of the squaramide NHs and a dramatic change of the emission properties of the H2L copper complex.

show abstract

Section: Introductionmentioning

confidence: 99%

Switching-On Fluorescence by Copper (II) and Basic Anions: A Case Study with a Pyrene-Functionalized Squaramide

et al. 2021

View full text Add to dashboard Cite

show abstract

“…The symmetrical triazole linked derivatives 28a and 28b were not very good gelators, only forming weak gels/aggregates in ethyl acetate and ethanol. On the other hand, the amphiphilic derivative 29a performed very well in ethyl acetate, acetonitrile, ethanol and 1:1 aqueous ethanol mixture with fairly low minimum gelation concentrations [63]. After the removal of the acetyl groups under basic conditions, the amphiphilic derivative 29b was found to be a supergelator in a 1:1 aqueous ethanol solution with a minimum gelation concentration of 0.1% w/v [63].…”

Section: D-mannose D-arabinose D-galactose Derivatives As Lmogsmentioning

confidence: 98%

“…On the other hand, the amphiphilic derivative 29a performed very well in ethyl acetate, acetonitrile, ethanol and 1:1 aqueous ethanol mixture with fairly low minimum gelation concentrations [63]. After the removal of the acetyl groups under basic conditions, the amphiphilic derivative 29b was found to be a supergelator in a 1:1 aqueous ethanol solution with a minimum gelation concentration of 0.1% w/v [63]. This study paved the way for the design and synthesis of a new class of supramolecular materials, which have a wide range of potential applications.…”

Section: D-mannose D-arabinose D-galactose Derivatives As Lmogsmentioning

confidence: 99%

“…Squaramides have been studied extensively in supramolecular chemistry as they contain both hydrogen bonding acceptors/donors and aromaticity. Ramos et al combined galactosyl moieties with squaramide groups, triazole linkages and long aliphatic chains to create the first examples of glycosyl squaramide based LMWGs, as shown in Figure 20 [63]. The symmetrical triazole linked derivatives 28a and 28b were not very good gelators, only forming weak gels/aggregates in ethyl acetate and ethanol.…”

Section: D-mannose D-arabinose D-galactose Derivatives As Lmogsmentioning

confidence: 99%

See 1 more Smart Citation

Recently Developed Carbohydrate Based Gelators and Their Applications

Morris

Bietsch

Bashaw

et al. 2021

Gels

View full text Add to dashboard Cite

Carbohydrate based low molecular weight gelators have been an intense subject of study over the past decade. The self-assembling systems built from natural products have high significance as biocompatible materials and renewable resources. The versatile structures available from naturally existing monosaccharides have enriched the molecular libraries that can be used for the construction of gelators. The bottom-up strategy in designing low molecular weight gelators (LMWGs) for a variety of applications has been adopted by many researchers. Rational design, along with some serendipitous discoveries, has resulted in multiple classes of molecular gelators. This review covers the literature from 2017–2020 on monosaccharide based gelators, including common hexoses, pentoses, along with some disaccharides and their derivatives. The structure-based design and structure to gelation property relationships are reviewed first, followed by stimuli-responsive gelators. The last section focuses on the applications of the sugar based gelators, including their utilization in environmental remediation, ion sensing, catalysis, drug delivery and 3D-printing. We will also review the available LMWGs and their structure correlations to the desired properties for different applications. This review aims at elucidating the design principles and structural features that are pertinent to various applications and hope to provide certain guidelines for researchers that are working at the interface of chemistry, biochemistry, and materials science.

show abstract

“…[20][21][22][23][24] In particular, squaramide synthons because of their ditopic presentation of hydrogen bond donors and acceptors on a minimal scaffold in combination with their synthetic accessibility are of interest for this aim. [25][26][27][28][29][30][31][32] We recently demonstrated their application in a tripodal hydrogelator for the culture of human induced pluripotent stem cells (hiPSCs), using the soft and self-recovering nature of the supramolecular matrix that supports cell self-assembly into spheroids driven by cell-cell contacts. [31] However, cell proliferation within these materials was found to be limited, pointing out the need to further modify this synthetic matrix with bioactive peptides to enable cell-matrix interaction.…”

mentioning

confidence: 99%

Squaramide‐Based Supramolecular Materials Drive HepG2 Spheroid Differentiation

Liu

Berk

Wondergem

et al. 2021

Adv Healthcare Materials

View full text Add to dashboard Cite

A major challenge in the use of HepG2 cell culture models for drug toxicity screening is their lack of maturity in 2D culture. 3D culture in Matrigel promotes the formation of spheroids that express liver‐relevant markers, yet they still lack various primary hepatocyte functions. Therefore, alternative matrices where chemical composition and materials properties are controlled to steer maturation of HepG2 spheroids remain desired. Herein, a modular approach is taken based on a fully synthetic and minimalistic supramolecular matrix based on squaramide synthons outfitted with a cell‐adhesive peptide, RGD for 3D HepG2 spheroid culture. Co‐assemblies of RGD‐functionalized squaramide‐based and native monomers resulted in soft and self‐recovering supramolecular hydrogels with a tunable RGD concentration. HepG2 spheroids are self‐assembled and grown (≈150 µm) within the supramolecular hydrogels with high cell viability and differentiation over 21 days of culture. Importantly, significantly higher mRNA and protein expression levels of phase I and II metabolic enzymes, drug transporters, and liver markers are found for the squaramide hydrogels in comparison to Matrigel. Overall, the fully synthetic squaramide hydrogels are proven to be synthetically accessible and effective for HepG2 differentiation showcasing the potential of this supramolecular matrix to rival and replace naturally‐derived materials classically used in high‐throughput toxicity screening.

show abstract

Glycosyl squaramides, a new class of supramolecular gelators

Abstract: First example of glycosyl squaramides that induce the efficient gelation of high polarity solvents and hydroethanolic mixtures.

Cited by 11 publications

References 36 publications

Switching-On Fluorescence by Copper (II) and Basic Anions: A Case Study with a Pyrene-Functionalized Squaramide

Switching-On Fluorescence by Copper (II) and Basic Anions: A Case Study with a Pyrene-Functionalized Squaramide

Recently Developed Carbohydrate Based Gelators and Their Applications

Squaramide‐Based Supramolecular Materials Drive HepG2 Spheroid Differentiation

Contact Info

Product

Resources

About