Functional Glyco-Nanogels for Multivalent Interaction with Lectins

Tang, Jo Sing Julia; Rosencrantz, Sophia; Tepper, Lucas; Chea, Sany; Klöpzig, Stefanie; Krüger‐Genge, Anne; Storsberg, Joachim; Rosencrantz, Ruben R.

doi:10.3390/molecules24101865

Cited by 23 publications

(35 citation statements)

References 64 publications

(82 reference statements)

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“…We chose a two‐step protecting group free synthesis approach for the lactose‐based methacrylamide glycomonomer ( Scheme ) …”

Section: Resultsmentioning

confidence: 99%

“…Synthesis of Glycomonomer LacMAm : The glycomonomer LacMAm was synthesized following our published procedure …”

Section: Methodsmentioning

confidence: 99%

“…Glycopolymers synthesized from glycomonomers are highly multivalent structures and showed extraordinary high binding avidities toward lectins, even with unmodified mono‐ or disaccharides . Recently, even a green enzymatic route to yield glycomonomers and glycopolymers was reported .…”

Section: Introductionmentioning

confidence: 99%

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Glycopolymers by RAFT Polymerization as Functional Surfaces for Galectin‐3

Rosencrantz

Tang

Schulte-Osseili

et al. 2019

Macro Chemistry & Physics

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Glycan‐protein interactions are essential biological processes with many disease‐related modulations and variations. One of the key proteins involved in tumor progression and metastasis is galectin‐3 (Gal‐3). A lot of effort is put into the development of Gal‐3 inhibitors as new therapeutic agents. The avidity of glycan‐protein interactions is strongly enhanced by multivalent ligand presentation. Multivalent presentation of glycans can be accomplished by utilizing glycopolymers, which are polymers with pendent glycan groups. For the production of glycopolymers, glycomonomers are synthesized by a regioselective, microwave‐assisted approach starting from lactose. The resulting methacrylamide derivatives are polymerized by RAFT and immobilized on gold surfaces using the trithiocarbonate group of the chain transfer agent. Surface plasmon resonance spectroscopy enables the label free kinetic characterization of Gal‐3 binding to these multivalent glycopolymers. The measurements indicate oligomerization of Gal‐3 upon exposure to multivalent environments and reveal strong specific interaction with the immobilized polymers.

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“…We chose a two‐step protecting group free synthesis approach for the lactose‐based methacrylamide glycomonomer ( Scheme ) …”

Section: Resultsmentioning

confidence: 99%

“…Synthesis of Glycomonomer LacMAm : The glycomonomer LacMAm was synthesized following our published procedure …”

Section: Methodsmentioning

confidence: 99%

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Glycopolymers by RAFT Polymerization as Functional Surfaces for Galectin‐3

Rosencrantz

Tang

Schulte-Osseili

et al. 2019

Macro Chemistry & Physics

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“…Lectins are responsible for cellular recognition, adhesion, signal transduction, and metastasis. ASF is a standard glycoprotein presenting terminal galactose residues that can be bound by lectins like ECL [46].…”

Section: Real-time Monitoring Of Biomolecular Interactionsmentioning

confidence: 99%

Plasmonic biosensors fabricated by galvanic displacement reactions for monitoring biomolecular interactions in real time

Pacholski

Rosencrantz

et al. 2020

Anal Bioanal Chem

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Optical sensors are prepared by reduction of gold ions using freshly etched hydride-terminated porous silicon, and their ability to specifically detect binding between protein A/rabbit IgG and asialofetuin/Erythrina cristagalli lectin is studied. The fabrication process is simple, fast, and reproducible, and does not require complicated lab equipment. The resulting nanostructured gold layer on silicon shows an optical response in the visible range based on the excitation of localized surface plasmon resonance. Variations in the refractive index of the surrounding medium result in a color change of the sensor which can be observed by the naked eye. By monitoring the spectral position of the localized surface plasmon resonance using reflectance spectroscopy, a bulk sensitivity of 296 nm ± 3 nm/RIU is determined. Furthermore, selectivity to target analytes is conferred to the sensor through functionalization of its surface with appropriate capture probes. For this purpose, biomolecules are deposited either by physical adsorption or by covalent coupling. Both strategies are successfully tested, i.e., the optical response of the sensor is dependent on the concentration of respective target analyte in the solution facilitating the determination of equilibrium dissociation constants for protein A/rabbit IgG as well as asialofetuin/Erythrina cristagalli lectin which are in accordance with reported values in literature. These results demonstrate the potential of the developed optical sensor for cost-efficient biosensor applications.

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“…[ 11 ] For example, lectins, a class of carbohydrate binding proteins, mediate cell adhesion, communication, fertilization, or pathogen invasion. [ 12,13 ] To target carbohydrate binding pathogens or lectins directly, responsive carbohydrate ligand presenting polymers are being employed in microgels, [ 14–16 ] on nanoparticle surfaces, [ 17–19 ] 2D‐surface coatings, [ 4 ] and linear or branched polymers. [ 20–23 ]…”

Section: Introductionmentioning

confidence: 99%

Quantifying Thermoswitchable Carbohydrate‐Mediated Interactions via Soft Colloidal Probe Adhesion Studies

Strzelczyk

Paul

Schmidt

2020

Macromolecular Bioscience

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affinity of linked biomolecules, e.g., by varying their accessibility to control their specific binding. Thermoresponsive polymers with a lower critical solution temperature (LCST) between 30 and 40 °C are most frequently used for such applications, where poly(N-isopropyl acrylamide) (PNIPAM), poly(N-vinyl caprolactam) or poly(oligoethylene glycols) are well-known examples. [10] As bioligands conjugated to such LCST polymers, carbohydrates have recently gained attention since they dominate biomolecular interactions on the cellular level and drive numerous physiological processes in the healthy or diseased state. [11] For example, lectins, a class of carbohydrate binding proteins, mediate cell adhesion, communication, fertilization, or pathogen invasion. [12,13] To target carbohydrate binding pathogens or lectins directly, responsive carbohydrate ligand presenting polymers are being employed in microgels, [14-16] on nano particle surfaces, [17-19] 2D-surface coatings, [4] and linear or branched polymers. [20-23] Although many studies could show a temperature controllable affinity shift of thermoresponsive glycopolymers, the cause for this behavior and the molecular details are not well understood. For example, when increasing the temperature above the LCST, some studies found that the affinity increased, [16,17,24] whereas other studies obtained decreasing carbohydrate binding affinities. [4,20,21] The factors that may increase the binding affinities upon temperature increase are: 1) an increase of carbohydrate subunit density due to an increase of statistical rebinding or subsite binding. [25-27] 2) An increase of carbohydrate surface density due to the formation of a compact polymer globule where the hydrophilic carbohydrates enrich at the surface. [28] 3) A smoother surface upon polymer collapse leading to a reduced steric repulsion. [29,30] On the other hand, the collapse of the thermoresponsive polymer above the LCST can lead to a reduced accessibility of the carbohydrate units, e.g., due to the more compact polymer globules or aggregate formation. [21] These potentially negating mechanisms make it hard to predict the change in glycopolymer affinity upon the temperature induced coil-to-globule transition. In addition, the use of these materials is often motivated by being able to remotely "switch" the ligand-receptor interaction on and off, implying reversible ligand-receptor complex formation and dissociation. However, such reversible binding of LCST polymers was rarely shown and typically limited to Thermosensitive polymers enable externally controllable biomolecular interactions but hysteresis effects hamper the reversibility and repeated use of these materials. To quantify the temperature-dependent interactions and hysteresis effects, an optical adhesion assay based on poly(ethylene glycol) microgels (soft colloidal probes, SCPs) with mannose binding concanavalin A surfaces is used. A series of thermoresponsive glycopolymers is synthesized varying the carbohydrate type, their density, and linker type, and...

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Functional Glyco-Nanogels for Multivalent Interaction with Lectins

Cited by 23 publications

References 64 publications

Glycopolymers by RAFT Polymerization as Functional Surfaces for Galectin‐3

Glycopolymers by RAFT Polymerization as Functional Surfaces for Galectin‐3

Plasmonic biosensors fabricated by galvanic displacement reactions for monitoring biomolecular interactions in real time

Quantifying Thermoswitchable Carbohydrate‐Mediated Interactions via Soft Colloidal Probe Adhesion Studies

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