Bottom-up Synthesis of Water-Soluble Gold Nanoparticles Stabilized by N-Heterocyclic Carbenes: From Structural Characterization to Applications

Overview

Journal Chemistry

Specialty Chemistry

Date 2022 Jul 8

PMID 35801389

Authors

Sophie R Thomas

Wenjie Yang

David J Morgan

Thomas E Davies

Jiao Jiao Li

Roland A Fischer

Jun Huang

Nikolaos Dimitratos

Angela Casini

Affiliations

Soon will be listed here.

Abstract

N-heterocyclic carbenes (NHCs) have become attractive ligands for functionalizing gold nanoparticle surfaces with applications ranging from catalysis to biomedicine. Despite their great potential, NHC stabilized gold colloids (NHC@AuNPs) are still scarcely explored and further efforts should be conducted to improve their design and functionalization. Here, the 'bottom-up' synthesis of two water-soluble gold nanoparticles (AuNP-1 and AuNP-2) stabilized by hydrophilic mono- and bidentate NHC ligands is reported together with their characterization by various spectroscopic and analytical methods. The NPs showed key differences likely to be due to the selected NHC ligand systems. Transmission electron microscopy (TEM) images showed small quasi-spherical and faceted NHC@AuNPs of similar particle size (ca. 2.3-2.6 nm) and narrow particle size distribution, but the colloids featured different ratios of Au(I)/Au(0) by X-ray photoelectron spectroscopy (XPS). Furthermore, the NHC@AuNPs were supported on titania and fully characterized. The new NPs were studied for their catalytic activity towards the reduction of nitrophenol substrates, the reduction of resazurin and for their photothermal efficiency. Initial results on their application in photothermal therapy (PTT) were obtained in human cancer cells in vitro. The aforementioned reactions represent important model reactions towards wastewater remediation, bioorthogonal transformations and cancer treatment.

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Bottom-up Synthesis of Water-Soluble Gold Nanoparticles Stabilized by N-Heterocyclic Carbenes: From Structural Characterization to Applications.

Thomas S, Yang W, Morgan D, Davies T, Li J, Fischer R Chemistry. 2022; 28(56):e202201575.

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References

Young A, Sauer M, Rubio G, Sato A, Foelske A, Serpell C . One-step synthesis and XPS investigations of chiral NHC-Au(0)/Au(i) nanoparticles. Nanoscale. 2019; 11(17):8327-8333. DOI: 10.1039/c9nr00905a. View

Fu Q, Saltsburg H, Flytzani-Stephanopoulos M . Active nonmetallic Au and Pt species on ceria-based water-gas shift catalysts. Science. 2003; 301(5635):935-8. DOI: 10.1126/science.1085721. View

Liu X, Li B, Fu F, Xu K, Zou R, Wang Q . Facile synthesis of biocompatible cysteine-coated CuS nanoparticles with high photothermal conversion efficiency for cancer therapy. Dalton Trans. 2014; 43(30):11709-15. DOI: 10.1039/c4dt00424h. View

Feng Y, Chang Y, Sun X, Cheng Y, Zheng R, Wu X . Differential photothermal and photodynamic performance behaviors of gold nanorods, nanoshells and nanocages under identical energy conditions. Biomater Sci. 2019; 7(4):1448-1462. DOI: 10.1039/c8bm01122b. View

Prati L, Villa A . Gold colloids: from quasi-homogeneous to heterogeneous catalytic systems. Acc Chem Res. 2013; 47(3):855-63. DOI: 10.1021/ar400170j. View

Schaper L, Hock S, Herrmann W, Kuhn F . Synthesis and application of water-soluble NHC transition-metal complexes. Angew Chem Int Ed Engl. 2012; 52(1):270-89. DOI: 10.1002/anie.201205119. View

Jakob C, Dominelli B, Hahn E, Berghausen T, Pinheiro T, Marques F . Antiproliferative Activity of Functionalized Histidine-derived Au(I) bis-NHC Complexes for Bioconjugation. Chem Asian J. 2020; 15(17):2754-2762. PMC: 7689731. DOI: 10.1002/asia.202000620. View

Thomas S, Yang W, Morgan D, Davies T, Li J, Fischer R . Bottom-up Synthesis of Water-Soluble Gold Nanoparticles Stabilized by N-Heterocyclic Carbenes: From Structural Characterization to Applications. Chemistry. 2022; 28(56):e202201575. PMC: 9804724. DOI: 10.1002/chem.202201575. View

Sun M, Liu F, Zhu Y, Wang W, Hu J, Liu J . Salt-induced aggregation of gold nanoparticles for photoacoustic imaging and photothermal therapy of cancer. Nanoscale. 2016; 8(8):4452-7. DOI: 10.1039/c6nr00056h. View

10.

Baquero E, Tricard S, Flores J, de Jesus E, Chaudret B . Highly stable water-soluble platinum nanoparticles stabilized by hydrophilic N-heterocyclic carbenes. Angew Chem Int Ed Engl. 2014; 53(48):13220-4. DOI: 10.1002/anie.201407758. View

11.

Grzelczak M, Perez-Juste J, Mulvaney P, Liz-Marzan L . Shape control in gold nanoparticle synthesis. Chem Soc Rev. 2008; 37(9):1783-91. DOI: 10.1039/b711490g. View

12.

Zhou X, Xu W, Liu G, Panda D, Chen P . Size-dependent catalytic activity and dynamics of gold nanoparticles at the single-molecule level. J Am Chem Soc. 2009; 132(1):138-46. DOI: 10.1021/ja904307n. View

13.

MacLeod M, Johnson J . PEGylated N-Heterocyclic Carbene Anchors Designed To Stabilize Gold Nanoparticles in Biologically Relevant Media. J Am Chem Soc. 2015; 137(25):7974-7. DOI: 10.1021/jacs.5b02452. View

14.

Young A, Eisen C, Rubio G, Chin J, Reithofer M . pH responsive histidin-2-ylidene stabilized gold nanoparticles. J Inorg Biochem. 2019; 199:110707. DOI: 10.1016/j.jinorgbio.2019.110707. View

15.

MacLeod M, Goodman A, Ye H, Nguyen H, Van Voorhis T, Johnson J . Robust gold nanorods stabilized by bidentate N-heterocyclic-carbene-thiolate ligands. Nat Chem. 2018; 11(1):57-63. DOI: 10.1038/s41557-018-0159-8. View

16.

Karaca O, Scalcon V, Meier-Menches S, Bonsignore R, Brouwer J, Tonolo F . Characterization of Hydrophilic Gold(I) N-Heterocyclic Carbene (NHC) Complexes as Potent TrxR Inhibitors Using Biochemical and Mass Spectrometric Approaches. Inorg Chem. 2017; 56(22):14237-14250. DOI: 10.1021/acs.inorgchem.7b02345. View

17.

Man R, Li C, MacLean M, Zenkina O, Zamora M, Saunders L . Ultrastable Gold Nanoparticles Modified by Bidentate N-Heterocyclic Carbene Ligands. J Am Chem Soc. 2017; 140(5):1576-1579. DOI: 10.1021/jacs.7b08516. View

18.

Wang G, Ruhling A, Amirjalayer S, Knor M, Ernst J, Richter C . Ballbot-type motion of N-heterocyclic carbenes on gold surfaces. Nat Chem. 2017; 9(2):152-156. DOI: 10.1038/nchem.2622. View

19.

Smith C, Narouz M, Lummis P, Singh I, Nazemi A, Li C . N-Heterocyclic Carbenes in Materials Chemistry. Chem Rev. 2019; 119(8):4986-5056. DOI: 10.1021/acs.chemrev.8b00514. View

20.

Slablab A, Le Xuan L, Zielinski M, De Wilde Y, Jacques V, Chauvat D . Second-harmonic generation from coupled plasmon modes in a single dimer of gold nanospheres. Opt Express. 2012; 20(1):220-7. DOI: 10.1364/OE.20.000220. View