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Thiourea‐Bridged Nanodiamond Glycoconjugates as Inhibitors of Bacterial Adhesion
Author(s) -
Fessele Claudia,
Wachtler Stefan,
Chandrasekaran Vijayanand,
Stiller Carina,
Lindhorst Thisbe K.,
Krueger Anke
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500532
Subject(s) - nanodiamond , chemistry , glycoconjugate , adhesion , thiourea , derivatization , bacteria , combinatorial chemistry , biochemistry , organic chemistry , diamond , biology , high performance liquid chromatography , genetics
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.