Versatile “click” synthesis of 1-hydroxy-1,1-methylenebisphosphonic acids with thioalkoxy substituents for the preparation of stable gold nanoparticles

Aufaure, Romain; Buendia, R.; Motte, Laurence; Hardouin, Julie; Lalatonne, Yoann; Guénin, Erwann

doi:10.1039/c7nj02773g

Cited by 7 publications

(6 citation statements)

References 57 publications

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“…The obtained hydrogels showed good biocompatibility, showing no effect on cell adhesion. In addition, the presence of HMBP-CCH on the NP surface can be easily used for further functionalization such as for coupling fluorophores, catalysts, drugs, and peptides. ,− Interestingly, we showed the successful acquisition of NP-derived properties such as antibacterial, magnetic activity, and MRI potency. Further investigation can be extended to in vivo tests to assess the ability of these materials to be used as tissue replacements or to induce regeneration.…”

Section: Discussionmentioning

confidence: 85%

“…Hydrogen tetrachloroaurate (III) (HAuCl 4 ·3H 2 O, ≥99.9%), silver nitrate (AgNO 3 , ≥99.9% Alfa Aesar), sodium ascorbate, iron (II) chloride tetrahidrate (FeCl 2 ·4H 2 O, ≥99.9%), iron (III) chloride hexahydrate (FeCl 3 ·6H 2 O, ≥99.9%), sodium carbonate (Na 2 CO 3 , 99.8%, anhydrous), hydrogen peroxide (H 2 O 2 , 35 wt %), and Nunc Thermanox plastic coverslips (174934) were purchased from Fisher Scientific. HMBP-CCH (1-hydroxy-1-phosphonohept-6-ynyl) phosphonic acid was synthesized as previously reported …”

Section: Methodsmentioning

confidence: 99%

“…HMBP-CCH (1-hydroxy-1phosphonohept-6-ynyl) phosphonic acid was synthesized as previously reported. 50 Lithium bromide (LiBr, reagent plus ≥99.9%), horseradish peroxidase type VI (HRP, P8375), poly(dimethylsiloxane) (PDMS) (Sylgard 184), 2,2′-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS), Muller−Hilton and Luria−Broth culture media, and AC agar for microbiology, acridine orange (A6014), phosphate-buffered saline (PBS) solution, 4′,6-diamidino-2-phenylindole (DAPI) (28718-90-3), phalloidin sulfo-rhodamine SR101 (FP-033991), and MTS reagent (CellTiter 96 AQueous One Solution Cell Proliferation Assay (MTS), Promega) were purchased from Sigma-Aldrich.…”

Section: Introductionmentioning

confidence: 99%

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Gold, Silver, and Iron Oxide Nanoparticle Incorporation into Silk Hydrogels for Biomedical Applications: Elaboration, Structure, and Properties

Marín

Egles

Humblot

et al. 2021

ACS Biomater. Sci. Eng.

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Silk fibroin (SF) is a versatile material with biodegradable and biocompatible properties, which make it fit for broad biomedical applications. In this context, the incorporation of nanosized objects into SF allows the development of a variety of bionanocomposites with tailored properties and functions. Herein, we report a thorough investigation on the design, characterization, and biological evaluation of SF hydrogels incorporating gold, silver, or iron oxide nanoparticles. The latter are synthesized in aqueous media using a biocompatible ligand allowing their utilization in various biomedical applications. This ligand seems to play a pivotal role in nanoparticle dispersion within the hydrogel. Results show that the incorporation of nanoparticles does not greatly influence the mechanism of SF gelation and has a minor impact on the mechanical properties of the so-obtained bionanocomposites. By contrast, significant changes are observed in the swelling behavior of these materials, depending on the nanoparticle used. Interestingly, the main characteristics of these bionanocomposites, related to their potential use for biomedical purposes, show the successful input of nanoparticles, including antibacterial properties for gold and silver nanoparticles and magnetic properties for iron oxide ones.

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Section: Discussionmentioning

confidence: 85%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Gold, Silver, and Iron Oxide Nanoparticle Incorporation into Silk Hydrogels for Biomedical Applications: Elaboration, Structure, and Properties

Marín

Egles

Humblot

et al. 2021

ACS Biomater. Sci. Eng.

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“…Free alendronate and Au@alendronate gold NPs reduced cell viability in a concentration-dependent manner ( Fig. 3 ) with an IC 50 equal to 100 µM for both systems whereas Au@HMBP-PEG NPs [ 39 ] do not exhibit any cytotoxicity ( Supporting Information File 1 , Figure S3). Under similar cell-treatment conditions, this IC 50 value is consistent with values obtained for free alendronate with other cancer cell lines [ 10 ].…”

Section: Resultsmentioning

confidence: 99%

Hybrid Au@alendronate nanoparticles as dual chemo-photothermal agent for combined cancer treatment

Sangnier¹,

Aufaure²,

Motte³

et al. 2018

Beilstein J. Nanotechnol.

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A gold therapeutic nanoplatform with the same molecule used as reductant, coating and therapeutic agent has been developed in a one-pot, one-phase process using alendronate, a drug from the bisphosphonate family known for its antitumor effects. In addition, the core made of gold nanoparticles (NPs) brings thermal functionalities under irradiation within the first biological window (650–900 nm). The Au@alendronate nanoplatform thus provided a combined antitumor activity through drug delivery and photothermal therapy. Au@alendronate NPs inhibited in vitro the proliferation of prostate cancer cells (PC3) in a dose-dependent manner, with an IC50 value of 100 µM. Under NIR irradiation a temperature increase was observed leading to a reduction of the IC50 value to 1 µM, with total tumor cell death at 100 µM.

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“…The Mattoussi group has been very successful in designing and synthesizing polymeric ligands based on carboxylic acid, catechol, thiol, phosphonic acid, etc . In the realm of small molecules, there are multidentate carboxylate ligands derived from citric acid or EDTA. , One can also classify the zwitterionic ligands for CsPbBr 3 nanocrystals as multidentate. , The bisphosphonate ligand class has been successful in stabilizing various nanocrystals in water. − In our recent work, we focused on multidentate phosphates. The first generation comprised 10-R-anthracene-1,8-diphosphoric acid (R = octyl, 2-hexyldecyl, phenyl) derivatives; see Figure A.…”

Section: Ligand Design Toward High Binding Affinitymentioning

confidence: 99%

The Surface Chemistry of Colloidal Nanocrystals Capped by Organic Ligands

Roo

2023

Chem. Mater.

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Nanocrystal surface chemistry is a pivotal element in the synthesis and application of nanocrystals. This perspective focuses on colloidal nanocrystals, capped with organic ligands. We start with insights into a workhorse characterization technique: solution nuclear magnetic resonance (NMR) spectroscopy. We then discuss the different models used to conceptualize nanocrystal surface chemistry and how the classification of binding motifs helps in the prediction of surface reactions. The thermodynamics and kinetics of these surface reactions are analyzed, and we arrive at the deciding factors for a high binding affinity: sterics, pK a/pK b, and solubility/solvent. Finally, we discuss recent ligand designs; most notably we introduce a new ligand class: monoalkyl phosphinic acids.

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Versatile “click” synthesis of 1-hydroxy-1,1-methylenebisphosphonic acids with thioalkoxy substituents for the preparation of stable gold nanoparticles

Abstract: Click synthesis of pegylated bisphosphonates for one pot preparation of stable gold nanoparticles.

Cited by 7 publications

References 57 publications

Gold, Silver, and Iron Oxide Nanoparticle Incorporation into Silk Hydrogels for Biomedical Applications: Elaboration, Structure, and Properties

Gold, Silver, and Iron Oxide Nanoparticle Incorporation into Silk Hydrogels for Biomedical Applications: Elaboration, Structure, and Properties

Hybrid Au@alendronate nanoparticles as dual chemo-photothermal agent for combined cancer treatment

The Surface Chemistry of Colloidal Nanocrystals Capped by Organic Ligands

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