Conjugated polymer nanoparticles exhibit strong fluorescence and have been applied for biological fluorescence imaging in cell culture and in small animals. However, conjugated polymer particles are hydrophobic and often chemically inert materials with diameters ranging from below 50 nm to several microns. As such, conjugated polymer nanoparticles cannot be excreted through the renal system. This drawback has prevented their application for clinical bio-medical imaging. Here, we present fully conjugated polymer nanoparticles based on imidazole units. These nanoparticles can be bio-degraded by activated macrophages. Reactive oxygen species induce scission of the conjugated polymer backbone at the imidazole unit, leading to complete decomposition of the particles into soluble low molecular weight fragments. Furthermore, the nanoparticles can be surface functionalized for directed targeting. The approach opens a wide range of opportunities for conjugated polymer particles in the fields of medical imaging, drug-delivery, and theranostics.
Photoacoustics is a powerful biomedical imaging and detection technique, because it is a noninvasive, nonionizing, and low‐cost method facilitating deep tissue penetration. However, suitable contrast agents need to be developed to increase the contrast for in vivo imaging. Gold nanoparticles are often discussed as potential sonophores due to their large absorption cross‐section and their tunable plasmon resonance. However, disadvantages such as toxicity and low photoacoustic efficiency in the tissue transparency window prevail, preventing their clinical application. As a result, there remains a strong need to develop colloidal photoacoustic contrast agents which absorb in the tissue transparency window, exhibit high photoacoustic signal, and are biocompatible. Here, a facile synthetic approach is presented to produce melanin shells around various gold nanoparticle geometries, from spheres to stars and rods. These hybrid particles show excellent dispersability, better biocompatibility, and augmented photoacoustic responses over the pure melanin or pristine gold particles, with a rod‐shape geometry leading to the highest performance. These experimental results are corroborated using numerical calculations and explain the improved photoacoustic performance with a thermal confinement effect. The applicability of melanin coated gold nanorods as gastrointestinal imaging probes in mouse intestine is showcased.
Here we present a facile synthetic method yielding a linear form of polydopamine via Kumada-coupling, which can be converted into water-soluble melanin, generating high contrast in photoacoustic imaging.
A solid‐state structural study on anion–π interaction in various N‐(pentafluorobenzyl)pyridinium salts accompanied by NMR spectroscopic investigations is presented. The crystal structures of 1a–1d reveal different kinds of contacts with anions, including anion–π interactions. In particular, the solid‐state structure of 1b‐I3 shows distinct evidence of anion–π interactions. Attempts to study anion–π interactions in solution were not successful, but their presence in solution could not be ruled out.
The stabilization of polyhalides in the solid state with the support of electron-deficient pentafluorophenyl groups is described. Furthermore, a synthetic approach towards the sensitive tetraiodide dianion is described and ESI mass spectrometric evidence for its presence in solution is reported.
Photoacoustic imaging presents an innocuous imaging modality with good penetration depth and resolution. To use this modality for detection and imaging of pathological sites, new imaging probes need to be developed to enhance the contrast over endogenous sonophores. These contrast agents should specifically bind to the site of interest, be non-toxic and be cleared renally if applied intravenously. Small organic dyes with absorption in the near infrared spectrum often exhibit good photoacoustic response. However, such dyes are often not water soluble or they are cytotoxic. Here, we present a novel PEGylated sonophore based on diketopyrrolopyrrole (DPP), which overcomes these limitations and can be functionalized with desired biological recognition motifs using thiol-yne click chemistry. Proof of concept is demonstrated by functionalizing the DPP-based probe with an RGD peptide, resulting in specific binding to endothelial (HUVEC) cells and an efficient photoacoustic response.
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