Synthesis and characterization of monosaccharide lipids as novel hydrogelators

Wang, Guijun; Cheuk, Sherwin; Williams, Kristopher; Sharma, Vibha; Dakessian, Lousi; Thorton, Zeus

doi:10.1016/j.carres.2006.01.023

Cited by 32 publications

(33 citation statements)

References 35 publications

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“…The selection of the R groups used in this series was based on our previous results [34–36]. We synthesized the terminal acetylenes 9–11 , saturated hydrocarbons 12–14 , aryl derivatives 15 , 16 , and two long chain diacetylene containing glycolipids 17 , 18 .…”

Section: Resultsmentioning

confidence: 99%

“…Glucose, in particular, is a versatile building block for the preparation of various small molecule gelators [30–37], as it is relatively easy to obtain substituted products by selective functionalization of the anomeric position and the 4- and 6-hydroxy groups. We have found that further derivatization of the glucose headgroup to form different glycolipids can result in organogelators [34–37]. …”

Section: Introductionmentioning

confidence: 99%

“…1), including esters and carbamates with different functional groups. Several of these compounds proved to be effective gelators for organic solvents and aqueous solutions [34–37]. We found that the structures of the acyl chains of diester 2 , and monoesters 3 and 4, are important for gelation.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and self-assembly of 1-deoxyglucose derivatives as low molecular weight organogelators

Wang¹,

Yang²,

Cheuk³

et al. 2011

Beilstein J. Org. Chem.

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SummaryLow molecular weight gelators are an important class of molecules. The supramolecular gels formed by carbohydrate derived low molecular weight gelators are interesting soft materials that show great potential for many applications. Previously, we have synthesized a series of methyl 4,6-O-benzylidene-α-D-glucopyranoside derivatives and found that several of them are good gelators for water, aqueous mixtures of DMSO, or aqueous mixtures of ethanol. The gelation efficiency of these glycolipid derivatives is dependent upon the structures of their acyl chains. In order to understand the influence of the anomeric position of the sugar headgroup towards self-assembly, we synthesized a series of 1-deoxyglucose analogs, and examined their gelation properties in several solvents. Several long chain esters, including diacetylene containing esters, and aryl esters exhibited gelation in ethanol, aqueous ethanol, or aqueous DMSO. The synthesis and characterization of these novel analogs are reported.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis and self-assembly of 1-deoxyglucose derivatives as low molecular weight organogelators

Wang¹,

Yang²,

Cheuk³

et al. 2011

Beilstein J. Org. Chem.

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“…Most of them are excellent hydrogelators, which are able to form varies self-assembled structures, including birefringent fibers and tubules. [218] Wang and coworkers also reported hydrogelators based on 4,6-O-benzylidenea-D-methyl-glucopyranoside. [219] By clicking different saccharides as the polar heads onto a hydrophobic chain via copper(I)-catalyzed azide-alkyne [3 + 2] cycloaddition, Oriol et al developed several glycolipid hydrogelators (Figure 12B), which, at room temperature, self-assembled to form fibrillar supramolecular structures as the matrices of stable hydrogels.…”

Section: Supramolecular Hydrogels Made Of the Basic Biological Buimentioning

confidence: 99%

Supramolecular biofunctional materials

et al. 2017

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This review discusses supramolecular biofunctional materials, a novel class of biomaterials formed by small molecules that are held together via noncovalent interactions. The complexity of biology and relevant biomedical problems not only inspire, but also demand effective molecular design for functional materials. Supramolecular biofunctional materials offer (almost) unlimited possibilities and opportunities to address challenging biomedical problems. Rational molecular design of supramolecular biofunctional materials exploit powerful and versatile noncovalent interactions, which offer many advantages, such as responsiveness, reversibility, tunability, biomimicry, modularity, predictability, and, most importantly, adaptiveness. In this review, besides elaborating on the merits of supramolecular biofunctional materials (mainly in the form of hydrogels and/or nanoscale assemblies) resulting from noncovalent interactions, we also discuss the advantages of small peptides as a prevalent molecular platform to generate a wide range of supramolecular biofunctional materials for the applications in drug delivery, tissue engineering, immunology, cancer therapy, fluorescent imaging, and stem cell regulation. This review aims to provide a brief synopsis of recent achievements at the intersection of supramolecular chemistry and biomedical science in hope of contributing to the multidisciplinary research on supramolecular biofunctional materials for a wide range of applications. We envision that supramolecular biofunctional materials will contribute to the development of new therapies that will ultimately lead to a paradigm shift for developing next generation biomaterials for medicine.

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“…For example, the N-linked carbamates ( 83 , 84) , in which the nitrogen atom of the carbamate group is directly attached to the sugar ring, self-assemble to form gels in pure water with long, narrow, uniform fibrous networks at the mgc about 0.5 wt%. [139] The replacement of N-linked to the O-linked carbamates or change in the position of the side chains on the sugar ring still affords excellent hydrogelators (e.g., 85 , 86 , 87 , and 88 ), [140] which form self-assembled network structures. Although the gelation properties depend on the acyl chain length and the structures of the head groups, these results indicate that the aromatic-aromatic interactions among the gelators and intermolecular hydrophobic interactions contribute to the hydrogelation.…”

Section: Supramolecular Hydrogels Made Of Saccharidesmentioning

confidence: 99%

Supramolecular Hydrogels Made of Basic Biological Building Blocks

Zhou

2014

Chemistry An Asian Journal

113

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As a consequence of the self-assembly of small organic molecules in water, supramolecular hydrogels are evolving from serendipitous events during organic synthesis to become a new type of materials that promise increased applications in biomedicine. In this focus review, we describe the recent development on the use of basic biological building blocks for creating molecules that act as hydrogelators and the potential applications of the corresponding hydrogels. After introducing the concept of supramolecular hydrogels and defining the scope of this review, we briefly describe the methods for making and characterizing supramolecular hydrogels. Then, we discuss representative hydrogelators according to the categories of their building blocks, such as amino acids, nucleobases, and saccharides, and highlight the applications of the hydrogels when necessary. Finally, we offer our perspectives and outlooks on this fast-growing field at the interface of organic chemistry, materials, biology, and medicine. By providing a snapshot for chemists, engineers, and medical scientists, we hope that this focus review will contribute to the development of multidisciplinary research on supramolecular hydrogels for a wide range of applications in different fields.

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Synthesis and characterization of monosaccharide lipids as novel hydrogelators

Cited by 32 publications

References 35 publications

Synthesis and self-assembly of 1-deoxyglucose derivatives as low molecular weight organogelators

Synthesis and self-assembly of 1-deoxyglucose derivatives as low molecular weight organogelators

Supramolecular biofunctional materials

Supramolecular Hydrogels Made of Basic Biological Building Blocks

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