4.7 Article

Transformation of L-DOPA and Dopamine on the Surface of Gold Nanoparticles: An NMR and Computational Study

Journal

INORGANIC CHEMISTRY
Volume 61, Issue 28, Pages 10781-10791

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.inorgchem.2c00996

Keywords

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Funding

  1. Program of the Croatian Science Foundation - European Union from the European Social Fund under the Operational Programme Efficient Human Resources [HRZZ-PZS-2019-02-4323]

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Gold nanoparticles have potential applications in biomedicine as diagnostic tools and drug delivery agents. The research findings show that the final form of catechol on the nanosurface of gold nanoparticles depends on the molar ratio of gold used for preparation. The study highlights the importance of a combined experimental and computational approach for reliable characterization of binding events on the surface of gold nanoparticles.
Gold nanoparticles (AuNPs) have found applica-tions in biomedicine as diagnostic tools, but extensive research efforts have been also directed toward their development as more efficient drug delivery agents. The high specific surface area of AuNPs may provide dense loading of molecules like catechols (L-DOPA and dopamine) on nanosurfaces, enabling functionalization strategies for advancing conventional therapy and diagnostic approaches of neurodegenerative diseases. Despite numerous well-described procedures in the literature for preparation of different AuNPs, possible transformation and structural changes of surface functionalization agents have not been considered thoroughly. As a case in point, the catechols L-DOPA and dopamine were selected because of their susceptibi l i t y to oxidation, cyclization, and polymerization. To assess the fate of coating and functionalization agents during the preparation of AuNPs or interaction at the nano-bio interface, a combination of spectroscopy, light scattering , and microscopy techniques was used while structural information and reaction mechanism were obtained by NMR in combination with computational tools. The results revealed that the final form of catechol on the AuNP nanosurface depends on the molar ratio of Au used for AuNP preparation. A large molar excess of L-DOPA or dopamine is needed to prepare AuNPs funtionalized with fully reduced catechols. In the case of molar excess of Au, the oxidation of catechols to dopamine quinone and dopaquinone was promoted, and dopaquinone underwent intramolecular cyclization in which additional oxidation products, leukodopachrome, dopachrome, or its tautomer, were formed because of the larger intrinsic acidity of the more nucleophilic amino group in dopaquinone. MD simulations showed that, of the oxidation products, dopachrome had the highest affinity for binding to the AuNPs surface. The results highlight how a more versatile methodological approach, combining experimental and in silico techniques, allows more reliable characterization of binding events at the surface of AuNPs for possible applications in biomedicine.

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