Thiourea‐Bridged Nanodiamond Glycoconjugates as Inhibitors of Bacterial Adhesion. Issue 25 (29th June 2015)

• Record Type: Journal Article
• Authors: Fessele, Claudia; Wachtler, Stefan; Chandrasekaran, Vijayanand; Stiller, Carina; Lindhorst, Thisbe K.; Krueger, Anke
• Is Part Of: European journal of organic chemistry. Issue 25(2015)
• Page Start: 5519
• Page End: 5525
• Publication Date: 2015-06-29
• Subjects: Nanoparticles -- Diamond -- Carbohydrates -- Conjugation -- Bioconjugation -- Surface chemistry -- Bacterial adhesion -- Sandwich assay; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201500532
• Languages: English
• ISSNs: 1434-193X

Abstract

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. Abstract : Thiourea‐bridging is a new approach to conjugating nanodiamond nanoparticles and biomolecules. This was exemplified by preparation of saccharide‐functionalized nanodiamonds (NDs) that were characterized and employed in biological studies. These studies revealed specific ND binding to E. coli bacterial cells.