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Pregled bibliografske jedinice broj: 1204057

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


Kalčec, Nikolina; Ljulj, Antonio; Božičević, Lucija; Vrček, Valerije; Marson, Domenico; Pricl, Sabrina; Separovic, Frances; Vinković Vrček, Ivana
Transformation of L-DOPA and Dopamine on the Surface of Gold Nanoparticles: An NMR and Computational Study // Inorganic chemistry, 61 (2022), 28; 10781-10791 doi:10.1021/acs.inorgchem.2c00996 (međunarodna recenzija, članak, znanstveni)


CROSBI ID: 1204057 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

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

Autori
Kalčec, Nikolina ; Ljulj, Antonio ; Božičević, Lucija ; Vrček, Valerije ; Marson, Domenico ; Pricl, Sabrina ; Separovic, Frances ; Vinković Vrček, Ivana

Izvornik
Inorganic chemistry (0020-1669) 61 (2022), 28; 10781-10791

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Amines, Cyclization, Gold, Metal nanoparticles, Quinones

Sažetak
Gold nanoparticles (AuNPs) have found applications 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 susceptibility 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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Farmacija



POVEZANOST RADA


Projekti:
HRZZ-PZS-2019-02-4323 - Siguran pristup za razvoj nano-sustava za ciljanu isporuku lijekova u mozak (SENDER) (Vinković Vrček, Ivana, HRZZ - 2019-02) ( CroRIS)
EK-EFRR-KK.01.1.1.02.0021 - Jačanje znanstveno-istraživačkih i inovacijskih kapaciteta Farmaceutsko-biokemijskog fakulteta Sveučilišta u Zagrebu (FarmInova) (Lovrić, Jasmina, EK - Ulaganje u organizacijsku reformu i infrastrukturu u sektoru istraživanja, razvoja i inovacija) ( CroRIS)

Ustanove:
Farmaceutsko-biokemijski fakultet, Zagreb,
Institut za medicinska istraživanja i medicinu rada, Zagreb

Poveznice na cjeloviti tekst rada:

doi pubs.acs.org

Citiraj ovu publikaciju:

Kalčec, Nikolina; Ljulj, Antonio; Božičević, Lucija; Vrček, Valerije; Marson, Domenico; Pricl, Sabrina; Separovic, Frances; Vinković Vrček, Ivana
Transformation of L-DOPA and Dopamine on the Surface of Gold Nanoparticles: An NMR and Computational Study // Inorganic chemistry, 61 (2022), 28; 10781-10791 doi:10.1021/acs.inorgchem.2c00996 (međunarodna recenzija, članak, znanstveni)
Kalčec, N., Ljulj, A., Božičević, L., Vrček, V., Marson, D., Pricl, S., Separovic, F. & Vinković Vrček, I. (2022) Transformation of L-DOPA and Dopamine on the Surface of Gold Nanoparticles: An NMR and Computational Study. Inorganic chemistry, 61 (28), 10781-10791 doi:10.1021/acs.inorgchem.2c00996.
@article{article, author = {Kal\v{c}ec, Nikolina and Ljulj, Antonio and Bo\v{z}i\v{c}evi\'{c}, Lucija and Vr\v{c}ek, Valerije and Marson, Domenico and Pricl, Sabrina and Separovic, Frances and Vinkovi\'{c} Vr\v{c}ek, Ivana}, year = {2022}, pages = {10781-10791}, DOI = {10.1021/acs.inorgchem.2c00996}, keywords = {Amines, Cyclization, Gold, Metal nanoparticles, Quinones}, journal = {Inorganic chemistry}, doi = {10.1021/acs.inorgchem.2c00996}, volume = {61}, number = {28}, issn = {0020-1669}, title = {Transformation of L-DOPA and Dopamine on the Surface of Gold Nanoparticles: An NMR and Computational Study}, keyword = {Amines, Cyclization, Gold, Metal nanoparticles, Quinones} }
@article{article, author = {Kal\v{c}ec, Nikolina and Ljulj, Antonio and Bo\v{z}i\v{c}evi\'{c}, Lucija and Vr\v{c}ek, Valerije and Marson, Domenico and Pricl, Sabrina and Separovic, Frances and Vinkovi\'{c} Vr\v{c}ek, Ivana}, year = {2022}, pages = {10781-10791}, DOI = {10.1021/acs.inorgchem.2c00996}, keywords = {Amines, Cyclization, Gold, Metal nanoparticles, Quinones}, journal = {Inorganic chemistry}, doi = {10.1021/acs.inorgchem.2c00996}, volume = {61}, number = {28}, issn = {0020-1669}, title = {Transformation of L-DOPA and Dopamine on the Surface of Gold Nanoparticles: An NMR and Computational Study}, keyword = {Amines, Cyclization, Gold, Metal nanoparticles, Quinones} }

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus
  • MEDLINE


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