Direct Functionalization of Nanodiamond Particles Using Dopamine Derivatives

Abstract

The article reports on the strong linking of dopamine derivatives as a simple and a versatile strategy for the surface functionalization of hydroxyl-terminated nanodiamond (ND-OH) particles. Azide- (ND-N(3)) or poly-N-isopropylacrylamide-terminated (ND-PNIPAM) particles were obtained from ND-OH particles through the reaction with the corresponding dopamine derivatives. The azide-terminated ND particles were further derivatized with a fluorescent probe, alkynyl-pyrene, via copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition. The modified ND particles were characterized using transmission Fourier transform infrared (FTIR) spectroscopy, UV-vis spectroscopy, electrochemical measurements, thermogravimetric analysis (TGA), and particle size measurements. The surface loading of ND particles with dopamine was estimated from TGA and UV-vis spectroscopy and was found to be around 0.27 mmol g(-1). Because of its simple, gentle nature and versatility, the chemistry developed in this work can be used as an avenue for the preparation of functional nanodiamond particles for various applications.

Surface Modifications of Nanodiamonds and Current Issues for Their Biomedical Applications

“…Efficient surface treatments also permit to conjugate ND surfaces with fluorescent molecules [202][203][204][205], with DNA [206], siRNA [27], proteins [207,208], lysozymes [208], growth hormones [209], antibodies [210,211], anti-cancer drugs [30][31][32], as well as with dopamine derivatives [212].…”

Inhibition of type 1 fimbriae-mediated Escherichia coli adhesion and biofilm formation by trimeric cluster thiomannosides conjugated to diamond nanoparticles

“…[40][41][42]72 ND particles are completely inert, optically transparent, biocompatible and moreover, easily functionalizable via a variety of strategies depending on their intended application. [43][44][45][46][47][48][49][50] Although their in vivo toxicity depends in particular on their surface characteristics (as well as the nature of the ligands they carry on their surface), 51 ND particles have thus far been reported not to induce significant cytotoxicity in a variety of cell types. [51][52][53][54] The demonstration that our 1 st -generation sugar-conjugated NDs do show marked anti-adhesive activity in cell-based assays without displaying toxicity against eukaryotic cells conforted us in our choice of particle and convinced us that sugar-NDs should indeed be further pursued as biomaterials.…”

Antimicrobial activity of menthol modified nanodiamond particles

“…One of the advantages of NDs over other carbon-based materials such as fullerenes and carbon nanotubes is that they are completely inert, optically transparent, biocompatible and can be functionalized in many ways depending on their intended ultimate application [24], [25], [26], [27], [28], [29], [30] and [31]. Although their in vivo toxicity depends on their particular surface characteristics [32], ND particles do not induce significant cytotoxicity in a variety of cell types [32], [33], [34] and [35] and have been used in a variety of biomedical applications.…”