ABSTRACT
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.
ABSTRACT
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.Conjugated polymer nanoparticles have been applied for biological fluorescence imaging in cell culture and in small animals, but cannot readily be excreted through the renal system. Here the authors show fully conjugated polymer nanoparticles based on imidazole units that can be bio-degraded by activated macrophages.
Subject(s)
Macrophages/metabolism , Nanoparticles/chemistry , Nanoparticles/metabolism , Animals , Biocompatible Materials/chemistry , Cells, Cultured , Cysteine/chemistry , Diagnostic Imaging/methods , Fluorescence , Hydrogen Peroxide/chemistry , Imidazoles/chemistry , Macrophages/drug effects , Mice , Microscopy, Confocal/methods , Nanoparticles/therapeutic use , Polymers/chemistry , Reactive Oxygen Species/chemistry , Reactive Oxygen Species/metabolismABSTRACT
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.
Subject(s)
Indoles/chemistry , Melanins/pharmacokinetics , Photoacoustic Techniques , Polymers/chemistry , Water/chemistry , Animals , Chickens , Indoles/chemical synthesis , Injections, Subcutaneous , Melanins/administration & dosage , Melanins/chemistry , Mice , Molecular Structure , Polymers/chemical synthesis , SolubilityABSTRACT
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.
