Progress in biomimetic carbohydrate recognition

Walker, D. Barney; Joshi, Gururaj; Davis, Anthony P.

doi:10.1007/s00018-009-0081-8

Cited by 109 publications

(67 citation statements)

References 109 publications

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“…Cell surface carbohydrates and their endogenous biological receptors are therefore of interest, and a number of tools have been developed to investigate this interaction. The progress of these has recently been reviewed by Walker et al [76].…”

Section: Detection Of Gram-positive Bacteriamentioning

confidence: 99%

Molecular recognition with boronic acids—applications in chemical biology

2013

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Small molecules have long been used for the selective recognition of a wide range of analytes. The ability of these chemical receptors to recognise and bind to specific targets mimics certain biological processes (such as proteinsubstrate interactions) and has therefore attracted recent interest. Due to the abundance of biological molecules possessing polyhydroxy motifs, boronic acids-which form fivemembered boronate esters with diols-have become increasingly popular in the synthesis of small chemical receptors. Their targets include biological materials and natural products including phosphatidylinositol bisphosphate, saccharides and polysaccharides, nucleic acids, metal ions and the neurotransmitter dopamine. This review will focus on the many ways in which small chemical receptors based on boronic acids have been used as biochemical tools for various purposes, including sensing and detection of analytes, interference in signalling pathways, enzyme inhibition and cell delivery systems. The most recent developments in each area will be highlighted.

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Section: Detection Of Gram-positive Bacteriamentioning

confidence: 99%

Molecular recognition with boronic acids—applications in chemical biology

2013

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“…Although the focus of the present work is on covalently linked porphyrin-sugar systems, the possibility for noncovalently bound systems exists [94,95] . For example, boronic acid porphyrins have been used for sugar sensing [96][97][98][99][100][101][102][103][104][105] , discrimination of sugars [106,107] , and have been used to control sugar-DNA interactions [108] .…”

Section: Porphyrin Carbohydrate Interactionsmentioning

confidence: 99%

Chemical Synthesis and Medicinal Applications of Glycoporphyrins

Moylan¹,

Scanlan²,

Senge

2015

CMC

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Abstract:This review presents an in-depth overview of the modification of porphyrins with bioconjugates and their applications in medicine today. Porphyrin bioconjugates ranging from nucleotides to steroids are under active scrutiny. However, carbohydrates have been at the forefront of such research in recent years and offer significant potential. This is attributed to their own selectivity to lectins on the surface of cancer cells and their influence on the amphiphilicity of the porphyrin macrocycle. These characteristics and the tendency of porphyrin photosensitizers to accumulate in tumor tissues make glycoporphyrins promising candidates for use as photosensitizers. Thus, a detailed overview of the synthesis and biological evaluation of glycoporphyrins is given with a particular focus on their applications in photodynamic therapy and their future prospects as drug candidates have been reported.

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“…The branched alkyl groups in 4 and 5 largely contribute to their binding capacity probably through van der Waals interaction with carbohydrates. The most effective CBM for n-octyl β-D-galactoside reported to date is the 8-hydroxyquinoline-based compound (6), which displayed more than 20 times higher affinity for n-octyl β-Dgalactoside compared to n-octyl α-and β-D-glucosides (9). In addition to these CBMs for monosaccharides, Mazik and coworkers have developed synthetic CBMs for disaccharides (7, 8) using the dimesitylmethane as an arene spacer (20).…”

Section: B Tripod-type Synthetic Cbmsmentioning

confidence: 99%

“…Small-size CBMs of synthetic origin have been progressively developed in the field of supramolecular chemistry (6,(9)(10)(11)(12)(13). On the basis of molecular design principles, these CBMs are roughly classified into two groups, boronic acid-dependent and boronic acid-independent CBMs.…”

Section: A Introductionmentioning

confidence: 99%

Carbohydrate-Binding Molecules with Non-Peptidic Skeletons

Nakagawa

Ito

2012

TIGG

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Emerging biological significance of carbohydrates has increased the importance of carbohydrate-binding molecules (CBMs) as diagnostic and therapeutic agents as well as research tools in glycobiology. Especially, there are rapidly growing interests in small molecules with a carbohydratebinding property due to the ease of preparation and chemical modification. This minireview focuses on small-size CBMs that bind carbohydrates through non-covalent interactions. Small-size CBMs of synthetic origin have been progressively developed in the field of supramolecular chemistry. The representative architectures of the synthetic CBMs are briefly reviewed mainly focusing on recent examples. We also highlight naturally-occurring CBMs, pradimicins and its congeners. They are the only class of natural products with a lectin-like ability to recognize D-mannosides (Man) in the presence of Ca 2+ ion. Our recent findings on molecular basis of their Man recognition are also described.

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Progress in biomimetic carbohydrate recognition

Cited by 109 publications

References 109 publications

Molecular recognition with boronic acids—applications in chemical biology

Molecular recognition with boronic acids—applications in chemical biology

Chemical Synthesis and Medicinal Applications of Glycoporphyrins

Carbohydrate-Binding Molecules with Non-Peptidic Skeletons

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