Sugar Recognition: Designing Artificial Receptors for Applications in Biological Diagnostics and Imaging

Miron, Caitlin E.; Petitjean, Anne

doi:10.1002/cbic.201402549

Cited by 48 publications

(26 citation statements)

References 100 publications

(119 reference statements)

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“…[15,16] Although in recent decades significant efforts have been dedicatedt ot he design of biomimetic receptors for carbohydrates, [17][18][19][20] at present, only af ew examples of structures effective in the competitive aqueous environmenth ave been reported. [21] Although good affinities toward charged sugars have been reported, [22,23] the recognition of neutralc arbohydrates is generally more challenging, so effective recognition has only been achieved toward all-equatorial carbohydrates, such as glucose and related sugars. [24][25][26][27][28] Because many biologically relevant carbohydratesp resent a-glycosidic linkages and/ora xial hydroxy groups in their structures, it is of paramount importance to expand the realm of biomimetic receptorst od ifferent classes of saccharides, such as galactose, fucose, mannose, and N-acetylgalactosamine.…”

Section: Introductionmentioning

confidence: 99%

A Biomimetic Synthetic Receptor Selectively Recognising Fucose in Water

Francesconi

Martinucci

Badii

et al. 2018

Chemistry A European J

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Carbohydrate recognition in water by biomimetic receptors is an attractive, but very challenging goal. Despite advances achieved in glucose recognition, little or no success has been obtained in the recognition of other saccharidic epitopes of paramount importance in biological processes. Herein, the unprecedented recognition of fucose in water by an artificial receptor that shows affinities closely comparable to those of several lectins is reported. The receptor has been constructed by assembling a hydrogen-bonding element (carbazole), a hydrophobic aromatic moiety (anthracene), and a water-solubilising function (phosphonate) into a macrocyclic structure to provide the appropriate binding geometry. The described receptor binds fucose with sub-millimolar affinity in water at physiological pH; this shows that enthalpic binding can be ascribed to hydrogen bonding to saccharidic hydroxy groups and to CH-π interactions between the sugar backbone and aromatic moieties. Experimental NOE contacts coupled to conformational search calculations return a picture of a binding site in which fucose assumes a staggered orientation reminiscent of that shown by fucose when bound to the Ralstonia solanacearum lectin (RSL).

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Section: Introductionmentioning

confidence: 99%

A Biomimetic Synthetic Receptor Selectively Recognising Fucose in Water

Francesconi

Martinucci

Badii

et al. 2018

Chemistry A European J

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“…Moreover, as proteins, their therapeutic potential is limited by issues such as immunogenicity . There is consequently much interest in small‐molecule receptors, which could complement lectins and perhaps be developed for new types of application . However, the design of such molecules has proved difficult, especially for biomimetic systems based on noncovalent bonding .…”

Section: Figurementioning

confidence: 99%

Platform Synthetic Lectins for Divalent Carbohydrate Recognition in Water

et al. 2016

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Biomimetic carbohydrate receptors ("synthetic lectins") have potential as agents for biological researcha nd medicine.H owever,a lthough effective strategies are available for "all-equatorial" carbohydrates (glucose,e tc.), the recognition of other types of saccharide under natural (aqueous) conditions is less well developed. Herein we report an ew approach based on ap yrene platform with polar arches extending from aryl substituents.The receptors are compatible with axially substituted carbohydrates,a nd also feature two identical binding sites,t hus mimicking the multivalency observed for natural lectins.Avariant with negative charges forms 1:2h ost/guest complexes with aminosugars,w ith K 1 > 3000 m À1 for axially substituted mannosamine,w hereas ap ositively charged version binds the important a-sialyl unit with K 1 % 1300 m À1 .

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“…Despite the great efforts dedicated to addressing this challenging task, biomimetic CBAs have only recently been successfully employed in a biological context, opening the way to further preclinical investigations. Although valuable reviews have been published on nonproteic CBAs, as well as on specific diagnostic and therapeutic applications, several significant biological studies carried out on biomimetic CBAs have recently been reported but, to the best of our knowledge, have not yet been covered by a general review in the current literature.…”

Section: Introductionmentioning

confidence: 99%

Biomimetic Carbohydrate‐Binding Agents (CBAs): Binding Affinities and Biological Activities

Francesconi

Roelens

2019

ChemBioChem

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Mimicking nature in carbohydrate recognition—that is, by using noncovalent interactions exclusively—is a hot topic that has attracted the interest of many scientists in the last 30 years. Carbohydrates are challenging ligands of high biological relevance, playing central roles in several physiological and pathological processes. Carbohydrate‐binding agents (CBAs) of proteic nature, such as lectins, have been extensively used in glycobiology to target carbohydrates, but intrinsic drawbacks conferred on them by their proteic nature limit their therapeutic development. Biomimetic CBAs, artificial small molecules designed for molecular recognition of carbohydrates through noncovalent interactions, have been shown to be effective alternatives in recognising carbohydrates in physiological media, opening the way to biological applications. Herein, we describe the recent achievements in this continually developing field, focusing on those biomimetic CBAs for which biological investigations have been carried out.

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Sugar Recognition: Designing Artificial Receptors for Applications in Biological Diagnostics and Imaging

Cited by 48 publications

References 100 publications

A Biomimetic Synthetic Receptor Selectively Recognising Fucose in Water

A Biomimetic Synthetic Receptor Selectively Recognising Fucose in Water

Platform Synthetic Lectins for Divalent Carbohydrate Recognition in Water

Biomimetic Carbohydrate‐Binding Agents (CBAs): Binding Affinities and Biological Activities

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