Both F-19 MRI and optical imaging are powerful noninvasive molecular imaging modalities in biomedical applications. To integrate these two complementary imaging modalities, the design and synthesis of a novel F-19 MRI/fluorescence dual-modal imaging agent is reported herein. Through Sonogashira coupling reaction between the fluorinated phenylacetylene and 1,2,4,5-tetraiodobenzene, a fluorophore with 48 symmetrical fluorines at its periphery was constructed with high efficacy. High aqueous solubility was achieved by PEGylation of the fluorophore with monodisperse PEGs. However, an unexpected self-assembly of the PEGylated amphiphilic fluorophore in water "turned off" the F-19 NMR signal. However, hydrogenation of the triple bonds or introduction of branched monodisperse PEGs was able to efficiently tune the self-assembly, resulting in the "turning on" of the F-19 NMR signal. One of these amphiphiles combines the advantages of label-free fluorescence, high F-19 MRI sensitivity, biocompatibility, and excellent aqueous solubility. The results demonstrate the great potential of such amphiphiles for real-time F-19 MRI and fluorescence dual-modality imaging.

Design and Synthesis of Fluorinated Amphiphile as F-19 MRI/Fluorescence Dual-Imaging Agent by Tuning the Self-Assembly

Convenient strategies to transform regular liposomes or nano-micelles into multifunctional theranostics would be highly valuable in cancer therapy. Herein, we developed an amphiphilic fluorinated porphyrin dendrimer as a multifunctional “add-on” module which would self-assemble onto liposomal drug delivery systems and conveniently transform the liposomes into novel theranostics. Through cancer cells and murine xenograft tumor model assays, the theranostics showed valuable fluorescence/19F magnetic resonance dual modal imaging and highly efficient chemo-photodynamic therapy. The modular strategy facilitates the convenient and standardized preparation of multifunctional theranostics.

Fluorinated porphyrin-based theranostics for dual imaging and chemo-photodynamic therapy.

Developing a theranostic system that integrates multimodal imaging, synergistic therapeutic, and formulation entities is a promising strategy for efficient cancer treatment. However, the complexity and safety concerns of multiple functional entities hinder their clinical translation. Herein, versatile "all-in-one" heptamethine cyanine amphiphiles (PEG-Cy-Fs) with multiple favorable capabilities, including fluorine-19 magnetic resonance imaging (19 F MRI), near-infrared fluorescence imaging (NIR FLI), photodynamic therapy (PDT), photothermal therapy (PTT), polyethylene glycolation (PEGylation) and high biocompatibility, are developed for the convenient construction of theranostic platforms. Amphiphiles PEG-Cy-Fs were synthesized on a multi-hundred-milligram scale with high efficacy, which self-assembled with a chemotherapy drug tamoxifen (TAM) into monodisperse and stable nanoparticles (SoFoTm/PEG-Cy-F18 ) with "turned on" FLI, sensitive 19 F MRI, mitochondria-targeting ability, high PDT and PTT efficacy, and PEGylation-optimized pharmacokinetics. The selective accumulation of SoFoTm/PEG-Cy-F18 in xenograft MCF-7 tumor with a long retention time (>10 days) enabled 19 F MRI-NIR FLI-guided chemo-PDT-PTT of breast cancer with high therapeutical index in mice. The "all-in-one" heptamethine cyanine amphiphile may facilitate the convenient and standardized preparation of high-performance theranostics systems for clinical translation. This article is protected by copyright. All rights reserved.

All-in-One Heptamethine Cyanine Amphiphiles for Dual Imaging-Guided Chemo-Photodynamic-Photothermal Therapy of Breast Cancer.

The concentration dependences of self-diffusion coefficient for irregular-shaped fibrinogen, for globular, spheroidal trypsin and α-chymotrypsin were studied by pulsed field gradient nuclear magnetic resonance. The experimental data were analyzed in a view of two known theoretical approaches—the hydrodynamic model of rigid spheres by Tokuyama and Oppenheim and the phenomenological approach based on the frictional formalism of non-equilibrium thermodynamics by Vink. The detailed discussion of their merits and drawbacks is presented. Our results testify that the Vink’s approach is quite universal, providing a satisfactory description of experimental data for proteins of complicated structure and different shape while the model of Tokuyama and Oppenheim is applicable only to proteins of more regular shape.

The Effect of Shape and Concentration on Translational Diffusion of Proteins Measured by PFG NMR

The capability of ring-opening metathesis polymerization (ROMP) to efficiently incorporate bulky monomers and conserve olefin bonds during polymerization was exploited to design water-soluble fluor...

Polymeric 19F MRI Contrast Agents Prepared by Ring-Opening Metathesis Polymerization/Dihydroxylation

Amphiphiles comprise a hydrophobic moiety and a hydrophilic moiety. A common property of many amphiphiles is to self-associate in aqueous solutions, driven by the need to shield the hydrophobic moiety from water. This feature has been utilized extensively to create various nano-scale architectures from amphiphiles. However, to effectively control amphiphile behavior, one should have the ability to both promote and prevent self-association. Fluorinated amphiphiles are especially prone to self-association, thus presenting a big challenge in developing non-associative amphiphiles. In this work, we solve this challenge by creating steric hindrance to association. The resulting fluorinated asymmetric amphiphile remains monomeric well above its apparent critical micelle concentration and up to its solubility limit, as demonstrated by small-angle X-ray and neutron scattering, dynamic light scattering and NMR diffusometry techniques. Not being able to associate intermolecularly, the amphiphile undergoes an intramolecular conformational transition, akin to protein folding, to wrap its hydrophilic moiety around its hydrophobic fluorocarbon moiety to shield it from water. This work demonstrates that steric hindrance is an effective tool in creating non-associative amphiphiles.

Conformational transition of a non-associative fluorinated amphiphile in aqueous solution

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Conformational transition of a non-associative fluorinated amphiphile in aqueous solution