Thiourea‐Bridged Nanodiamond Glycoconjugates as Inhibitors of Bacterial Adhesion

Abstract

The study of bacterial adhesion is crucial to our understanding of infection processes as well as for the development of antiadhesives. Here we have investigated new nanodiamond glycoconjugates intended to inhibit adhesion of type 1 fimbriated E. coli bacteria. For conjugation of saccharides and nanodiamond, thiourea‐bridging was employed, a method that has not been used before in nanodiamond derivatization. Amino‐prefunctionalized diamond nanoparticles were prepared employing aromatic diazonium salts and reacted with different isothiocyanato‐functionalized mannose derivatives. The resulting glyconanodiamonds were characterized and then tested in bacterial binding assays. They are recognized by the bacterial protein FimH according to the structure‐activity relationships known for this lectin. Thus, owing to the particular properties of nanodiamond, a valuable material is introduced with the potential to control bacterial adhesion and colonization in a favorable way.

Affinity of Glycan‐Modified Nanodiamonds towards Lectins and Uropathogenic Escherichia Coli

“…Despite their evident potential for glycobiology, there are only few reports on glyco‐nanodiamonds (glyco‐NDs) . Krueger and co‐workers used a multistep reaction including a Diels–Alder cycloaddition of 1,2‐dimethylbromide phenol to the ND surface, followed by a classical aromatic sulfonation and reduction to thiol .…”

“…The design and preparation of sugar‐coated nanoparticles and their applications as polyvalent tools to study and intervene in carbohydrate‐mediated interactions have received sustained attention over the past years . Carbohydrates are very important components of living organisms and have been identified to play a central role in a large panel of biological processes such as cell–cell communication, viral and bacterial infection, and inflammation and immune responses.…”

“…One of the first types of multivalent nanoscaffolds developed and used as an adhesion inhibitor is gold glycoconjugates . Next to gold, carbon‐based nanomaterials have been investigated as glycan scaffolds as they comply well with several requirements needed such as easy and stable surface functionalization, good dispersibility in aqueous media, and broad availability . Next to fullerene‐based glycoclusters, nanodiamonds (NDs) are emerging as particularly well‐suited for multivalent applications .…”

Wilkinson‐Type Immobilized Catalyst on Diamond Nanoparticles for Alkene Reduction

“…NDs are moreover different from other carbon‐based materials such as fullerenes because they are completely inert, optically transparent and biocompatible. Although the production of stable colloidal solutions from ND particles produced through detonation still remains a challenge, as these particles have a strong tendency to form large aggregates, appropriate surface‐functionalization strategies were developed to overcome this drawback . Furthermore, the presence of surface hydroxyl, carboxyl, and other oxygen functions can be used, depending on their intended final application, for the attachment of other surface ligands .…”

pH‐responsive phenylboronic acid‐modified diamond particles: Switch in carbohydrate capture ability triggers modulation of physicochemical and lectin‐recognition properties

“…A). The integration of glycan functions is a general method to generate stable ND colloidal solutions . The tuning of the affinity of mannose toward the phenylboronic acid modified ND particles as a function of pH is evoked in this work to change the agglomeration state of the particles.…”