Maleimide-Modified Gold Nanoparticles (AuNPs): A Versatile ­Platform for Interfacial Click Reactions Leading to Chemically Modified AuNPs

Abstract

The maleimide moiety can undergo a wide variety of organic reactions, including Diels-Alder reactions, dipolar cycloadditions, and Michael-type additions, making it a suitable moiety for further elaboration of the functionality at the interface of gold nanoparticles (AuNPs) through key reactions that are useful in a host of applications. This account will cover: (1) our approach to prepare maleimide-AuNPs, (2) our survey of the scope of the reactivity of organic-solvent-soluble maleimide-AuNPs, which are very slow, impractical, and required the development of high-pressure techniques in AuNP chemistry yielding dramatic results, and (3) the extension of these ideas to prepare water-soluble small AuNPs to expand the scope of the organic transformation to aqueous environments. Within each of these sections there were challenges that had to be overcome, and we will describe the evolution of the ideas so that readers can get a glimpse of our thinking and problem solving as we proceeded. 1 Introduction 2 Maleimide-AuNPs: The Synthetic Strategy 3 Reactivity of the Organic-Solvent-Soluble Maleimide-AuNP Template 4 Synthesis of the Water-Soluble Maleimide-AuNP Template 5 Reactivity of the Water-Soluble Maleimide-AuNP Template 6 Concluding Remarks

Dimeric Drug Polymeric Micelles with Acid‐Active Tumor Targeting and FRET‐Traceable Drug Release

“…The signals of hydrogen protons adjacent to difsulfide bond in (CPT) 2 ‐ss appeared at 2.83 and 4.02 ppm, while transferred to 3.08 and 4.41 ppm after reaction with 2,3‐dibromomaleimide (Figure S2d,e, Supporting Information). This change in chemical shift is caused by the electron‐withdrawing inductive effect of maleimide …”

“…This change in chemical shift is caused by the electron-withdrawing inductive effect of maleimide. [25] The average size of DA-TAT-PECL micelles was 43.9 nm with low polydispersity index (PDI) of 0.135, indicating a narrow distribution of diameters ( Figure 1a). The transmission electron microscopy (TEM) image showed that the DA-TAT-PECL micelles exhibited a spherical shape and a nearly uniform distribution.…”

“…This change in chemical shift is caused by the electron-withdrawing inductive effect of maleimide. [25] …”

Bombesin‐functionalized water‐soluble gold nanoparticles for targeting prostate cancer

“…Most importantly, the interfacial chemistry between the two reaction moieties is orthogonal to the surface chemistry of the nanomaterial and leads to the desired (bio)conjugate with no effects on the nanomaterial stability. This approach to conjugation has demonstrated that nanomaterials can potentially be functionalized with any molecular system of interest through easy and reliable chemical reactions (Gobbo et al, ; Gobbo et al, ; Gobbo & Workentin, ; Gobbo et al, ).…”