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, 4 (21), 19106-19115
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Nitrone-Modified Gold Nanoparticles: Synthesis, Characterization, and Their Potential as 18 F-Labeled Positron Emission Tomography Probes via I-SPANC

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Nitrone-Modified Gold Nanoparticles: Synthesis, Characterization, and Their Potential as 18 F-Labeled Positron Emission Tomography Probes via I-SPANC

Sara Ghiassian et al. ACS Omega.

Abstract

A novel bioorthogonal gold nanoparticle (AuNP) template displaying interfacial nitrone functional groups for bioorthogonal interfacial strain-promoted alkyne-nitrone cycloaddition reactions has been synthesized. These nitrone-AuNPs were characterized in detail using 1H nuclear magnetic resonance spectroscopy, transmission electron microscopy, thermogravimetric analysis, and X-ray photoelectron spectroscopy, and a nanoparticle raw formula was calculated. The ability to control the conjugation of molecules of interest at the molecular level onto the nitrone-AuNP template allowed us to create a novel methodology for the synthesis of AuNP-based radiolabeled probes.

Conflict of interest statement

The authors declare no competing financial interest.

Figures

Scheme 1
Scheme 1. Synthesis of Nitrone–AuNPs; Top: Synthetic Strategy for the Preparation of the Nitrone-Terminated Thiol Ligand 4
Reaction conditions: (a) Ph3CSH, NaOH, EtOH/benzene; (b) P2O5, DMSO, Et3N, CH2Cl2; (c) CH3NHOH, Et3N, CH3CN; (d) TFA/CH2Cl2, iPr3SiH.
Figure 1
Figure 1
Characterization of nitrone–AuNPs. (A) 1H NMR spectra recorded in D2O and referenced against residual water (*) of nitrone–AuNP (top) and TEG–AuNP starting material (bottom). The peaks corresponding to the protons of the nitrone moiety are labeled with alphabetical letters and correspond to the protons highlighted in Scheme 1. (B) TGA of nitrone-AuNPs recorded under a stream of nitrogen gas. (C) nitrone–AuNP’s high-resolution XPS scan of the N 1s peak. (D) Typical TEM image of nitrone–AuNPs (scale bar 20 nm).
Scheme 2
Scheme 2. Synthesis of [19F]AuNPs; Top: Synthetic Strategy for the Preparation of the 19F-Containing Prosthetic Group Compound [19F]13
Reaction conditions: (a) CsF, tBuOH, 60 °C, 5 h; (b) H2N–NH2·H2O, 95% EtOH, reflux, 5 h; (c) compound 12, Et3N, DMF, 0 °C, 20 min. Bottom: characterization of [19F]AuNPs.
Figure 2
Figure 2
Characterization of [19F]AuNPs. (A) 1H and 19F NMR spectra recorded in D2O and CDCl3 for [19F]AuNPs (top) and model compound 14 (bottom) and referenced against residual solvents (*); (B) typical TEM image of [19F]AuNPs (scale bar 20 nm); (C) high-resolution XPS scan of C 1s and F 1s peaks for [19F]AuNPs.
Figure 3
Figure 3
Top: PET image of [18F]AuNPs at 40–60 min after intravenous injection in C57/B6 mouse, coronal image (left) sagittal image (right). Bottom: SUV curves at 1 h postinjection, n = 2.
Scheme 3
Scheme 3. Synthesis of [18F]AuNPs
Reaction conditions: (a) 18F, K2CO3, Krypofix222, CH3CN, 90 °C, 5 min; (b) hydrazine, CH3CN/36% H2O/0.1% TFA, 60 °C, 5 min; (c) Compound 12, Et3N, CH3CN, room temperature, 20 min; followed by 60 °C, 5 min

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