Merging Organic and Polymer Chemistries to Create Glycomaterials for Glycomics Applications

Coullerez, Géraldine; Seeberger, Peter H.; Textor, Marcus

doi:10.1002/mabi.200600090

Cited by 53 publications

(42 citation statements)

References 104 publications

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“…However, assembly of monomeric units in oligomeric lectins results in the display of an array of CRDs with a variety of topologies, which, together with the topology (relative orientation and spacing) of the glycoconjugate carbohydrate residues, critically determines the specificity and strength of lectin-carbohydrate interactions [7,10,11]. Numerous synthetic multivalent glycopolymers and dendrimers displaying this effect have been developed for the targeting of cell/organ specific lectins for drug-delivery purposes and for the inhibition of cell-cell or cell-foreign body (bacteria/virus) interactions [10,[12][13][14].…”

Section: Ln-chelate Glycoconjugates As Molecular Imaging Casmentioning

confidence: 99%

Glycoconjugate Probes and Targets for Molecular Imaging Using Magnetic Resonance

2010

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Review Molecular recognition of sugar residues applied in molecular imagingMolecular imaging aims at probing the molecular abnormalities that are the basis of diseases rather than to image their effects [1]. An important prerequisite of this approach is the selection of appropriate markers of disease and of targeting vectors to recognize them. The latter can include low-molecular weight substrates for enzymes or high-molecular weight affinity ligands, such as monoclonal antibodies, hormone analogs and recombinant proteins. Of the three major classes of biomolecules (proteins, nucleic acids and carbohydrates), the latter class is the least exploited in molecular imaging. However, a dense layer of glyco conjugates covers all cells and carbohydrate mediated cellular recognition plays an important role in nature, both in normal and malignant processes, such as cell-cell communication, infection, inflammation, metastasis and reproduction. As carriers of information, the carbohydrates have far greater potential than proteins and nucleic acids; three different nucleotides or amino acids can generate only six distinguishable structures, while over 1000 structures can be built up from three different monosaccharides [2]. This level of complexity is probably the reason for the fact that the exploration of these compounds in molecular imaging is lagging behind [3]. Recently, significant progress has been made in glycochemistry and glycobiology; for example, automated solid-phase synthesis of oligo saccharides has become possible [4], carbohydrate-based vaccines have been developed [5] and high-throughput methods have been designed for the screening of molecular interactions [6]. The exciting new developments in glycoscience are opening way for new challenges in exploring the full potential of carbohydrates in molecular imaging. Therefore, here we give an overview of the recent literature on the use of glycoconjugates either as probes or targets in molecular imaging using MRI.MRI contrast agents (CAs) are broadly described as positive or negative, depending on whether they give rise to a brightening or a darkening effect on the MR image, respectively. The positive or brightening effect predominantly relates to the longitudinal proton relaxation time (T 1 ) and the negative or darkening effect predominantly relates to the transverse proton relaxation time (T 2 ). To date, the majority of commercially available and clinically applied positive CAs are Gd 3+ complexes of the polyaminocarboxylates diethylene triamine pentacetic acid (DTPA) and 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid (DOTA) (see FiguRe 1 for some typical examples) and negative CAs are various iron oxide particles. These agents are not actively targeting. The targeted CAs for application in molecular imaging that are currently under development and described below are generally based on compounds 1 (Gd-DTPA) and 2 (Gd-DOTA), as well as iron oxide nanoparticles.Glycoconjugate probes and targets for molecular imaging using magnetic resonanceRecently...

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Section: Ln-chelate Glycoconjugates As Molecular Imaging Casmentioning

confidence: 99%

Glycoconjugate Probes and Targets for Molecular Imaging Using Magnetic Resonance

2010

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“…The resin was dried under house vacuum for 10 min and then added to 100 mL of CH 3 (6) 26 TIPNO (1.00 g, 4.54 mmol) was dissolved in 50 mL of toluene and 50 mL of EtOH followed by the addition of azide 14 (1.08 g, 6.81 mmol). Jacobsen's catalyst (R,R; 577 mg, 0.908 mmol) was added followed by sodium borohydride (515 mg, 13.6 mmol); the reaction, open to the atmosphere, was stirred overnight.…”

Section: -Azidomethyl-4-vinyl-benzene (14) 42mentioning

confidence: 99%

“…1,2 There is significant interest in hybrid constructs composed of polymers and bioactive molecules: polymers conjugated to carbohydrates, 3 peptides, 4 and small-molecule drugs. 5 These hybrid species often display enhanced permeability and stability.…”

Section: Introductionmentioning

confidence: 99%

“…This primary alcohol will allow the facile attachment of mono-or oligosaccharides to prepare hybrid glycomaterials. 3 A complementary functionality useful for both oligosaccharides and N-terminal peptide attachment would be a carboxylic acid functionalized initiator. Thus, the initiator (4-{1-[N-tert-butyl-N-(2-methyl-1-phenyl-propyl)-aminooxy]-ethyl}-benzolamino)-acetic acid tert-butyl ester (5) has been prepared, in which the tert-butyl protecting group can be easily removed by treatment with TFA following polymerization.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of arylethyl‐functionalized N‐alkoxyamine initiators and use in nitroxide‐mediated radical polymerization

Hill

Braslau

2007

J. Polym. Sci. A Polym. Chem.

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New functionalized initiators have been synthesized and evaluated for use in nitroxide‐mediated radical polymerization. Well‐defined polymers have been made of polystyrene and poly(tert‐butyl acrylate). These functionalized initiators carry convenient handles for pre‐ or post‐polymerization modification. In particular, primary alcohol, protected carboxylic acid, and amine groups are ideally suited for coupling to peptides or oligosaccharides to prepare polymer–biomolecule hybrids.

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“…Especially interesting are the so-called biohybrids, made of synthetic polymers and sugar functionalities easily available through chemical modifications and designed with a broad diversity of available synthetic oligosaccharides. [9] Fluorescent polymers presenting carbohydrates in a multivalent manner have been developed for the detection of pathogens. [10] Neoglycoproteins and mannoside clusters of different architectures were also synthesized to test their potency as inhibitors of E. coli adhesion and to reveal the factors triggering the high affinity of FimH-mannose binding.…”

Section: Introductionmentioning

confidence: 99%

An Engineered Mannoside Presenting Platform: Escherichia coli Adhesion under Static and Dynamic Conditions

Barth

Coullerez

Nilsson

et al. 2008

Adv Funct Materials

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The study of the adhesion mechanisms of pathogens to host tissues has gained increased interest as bacterial adhesion is involved in the early stages of surface colonization and infection. Here we describe a platform to study the specific binding of the bacterium Escherichia coli (E. coli) K‐12 strain to molecularly well‐defined surfaces mimicking cellular interfaces. This approach uses a poly(ethylene glycol) brush interface, which displays synthetic determinants of the high mannose N‐linked glycans in a range of densities (3.8 × 104–1.6 × 105 mannosides µm−2) for the investigation of multivalent interactions with bacteria. The bacterial attachment is mediated by specific interactions between the adhesive protein FimH located on the tip of the bacterial type 1 pili and the mannosylated surfaces. With synthetically engineered mannoses, it is found that the number of strongly adhering bacteria is co‐regulated by many structural physical parameters. Beyond the dependency on carbohydrate density, higher numbers of E. coli attach to the branched trimannose Man(α1–3)(Man(α1–6))Man compared to the monomannose, while larger oligomannoses exposing Man(α1–2) Man at their non reducing end show low binding capacity. The linker used between the mannose moiety and PEG is also affecting the binding efficacy of E. coli. The (hydrophobic) propyl linker results in higher bacteria numbers in comparison to the (hydrophilic) tri(EG), likely a consequence of additional stabilization of the binding complex by hydrophobic interactions. Furthermore, differences are observed in bacteria attachment between stagnant and flow conditions that depend on the type of mannose ligand. Finally, a photolithographic resist lift‐off combined with site‐selective assembly of the glycopolymers is used to produce micropatterns with bacteria colonies confined to defined areas and at controlled colony numbers.

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Merging Organic and Polymer Chemistries to Create Glycomaterials for Glycomics Applications

Cited by 53 publications

References 104 publications

Glycoconjugate Probes and Targets for Molecular Imaging Using Magnetic Resonance

Glycoconjugate Probes and Targets for Molecular Imaging Using Magnetic Resonance

Synthesis of arylethyl‐functionalized N‐alkoxyamine initiators and use in nitroxide‐mediated radical polymerization

An Engineered Mannoside Presenting Platform: Escherichia coli Adhesion under Static and Dynamic Conditions

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