Synthesis of Intrinsically Disordered Fluorinated Peptides for Modular Design of High‐Signal <sup>19</sup>F MRI Agents

Kirberger, Steven E.; Maltseva, Sofia D.; Manulik, Joseph C.; Einstein, Samuel A.; Weegman, Bradley P.; Pomerantz, William C. K.

doi:10.1002/ange.201700426

Cited by 9 publications

(4 citation statements)

References 32 publications

(51 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Simply fluorinated molecules can also be used to construct 19 F MRI contrast agents with diverse functionality, good stability, and magnetically equivalent fluorine atoms compared to PFC-or PFPE-based nanoemulsions. 28,29 For example, our group and others have developed a number of polymeric 19 F MR contrast agents by copolymerizing 2,2,2-trifluoroethyl (meth)acrylate (TFE(M)-A) with hydrophilic monomers such as poly(ethylene glycol) methyl monoether (meth)acrylate (PEG(M)A). 30−35 By careful design, these polymeric fluorinated polymers can be prepared with excellent biocompatibility, tunable sizes, and tailored functionalities to meet the requirements of various applications.…”

Section: ■ Introductionmentioning

confidence: 99%

Enhanced Performance of Polymeric ¹⁹F MRI Contrast Agents through Incorporation of Highly Water-Soluble Monomer MSEA

Zhang

Peng

et al. 2018

Macromolecules

View full text Add to dashboard Cite

19 F magnetic resonance imaging (MRI) is a powerful non-invasive imaging technique that shows tremendous potential for the diagnosis and monitoring of human diseases. Fluorinated compounds are commonly used as 19 F MRI contrast agents to develop "hot spot" imaging. To achieve high-resolution MR images, a high density of 19 F nuclei are required in the contrast agents. However, due to the inherent hydrophobicity of fluorinated moieties, aggregation of 19 F contrast agents with high fluorine content is often observed in aqueous solution, resulting in attenuated MR signal and low sensitivity, thus significantly limiting their further biological applications. Here we report the synthesis and characterization of a series of polymeric 19 F MRI contrast agents with high fluorine content by copolymerizing the well-known fluorinated monomer 2,2,2-trifluoroethyl acrylate (TFEA) with a highly water soluble monomer 2-(methylsulfinyl)ethyl acrylate (MSEA) using RAFT polymerization. We show that these polymeric contrast agents, although with high fluorine content, display remarkable imaging performance as evidenced by preferable relaxation properties and intense in vitro/vivo MRI signals, demonstrating the huge potential for eventual clinical applications such as MRI-guided disease diagnosis and therapy.

show abstract

Section: ■ Introductionmentioning

confidence: 99%

Enhanced Performance of Polymeric ¹⁹F MRI Contrast Agents through Incorporation of Highly Water-Soluble Monomer MSEA

Zhang

Peng

et al. 2018

Macromolecules

View full text Add to dashboard Cite

show abstract

“…We conclude that quantitative MR imaging of the discrete oligoAA-CF 3 oligomers is possible, and therefore they have potential as quantitative 19 F MR tracers. 5,8,14,25,26 These observations are important as it provides useful insights into the structural design of discrete fluorinated oligomers and polymers, where a trade-off exists between structure, dynamics and MRI performance.…”

mentioning

confidence: 99%

Elucidating the Impact of Molecular Structure on the ¹⁹F NMR Dynamics and MRI Performance of Fluorinated Oligomers

et al. 2018

View full text Add to dashboard Cite

To understand molecular factors that impact the performance of polymeric 19 F magnetic resonance imaging (MRI) agents, a series of discrete fluorinated oligoacrylates with precisely-defined structure were prepared through the combination of controlled polymerization and chromatographic separation techniques. These discrete oligomers enabled thorough elucidation of the dependence of 19 F NMR and MRI properties on molecular structure e.g. the chain length. Importantly, the oligomer size and dispersity strongly influence NMR dynamics (T 1 and T 2 relaxation times) and MR imaging properties with higher signal-to-noise ratio (SNR) observed for oligomers with longer chain length and shorter T 1 . Our approach enables an effective pathway and thus opportunities to rationally design effective polymeric 19 F MR imaging agents with optimized molecular structure and NMR relaxivity.

show abstract

“…F MRI is less developed than 1 H MRI, in part due to the lack of sensitive biocompatible probes [176].…”

mentioning

confidence: 99%

Recent development of contrast agents for magnetic resonance and multimodal imaging of glioblastoma

Zhuang

Zhang

2022

J Nanobiotechnol

View full text Add to dashboard Cite

Glioblastoma (GBM) as the most common primary malignant brain tumor exhibits a high incidence and degree of malignancy as well as poor prognosis. Due to the existence of formidable blood–brain barrier (BBB) and the aggressive growth and infiltrating nature of GBM, timely diagnosis and treatment of GBM is still very challenging. Among different imaging modalities, magnetic resonance imaging (MRI) with merits including high soft tissue resolution, non-invasiveness and non-limited penetration depth has become the preferred tool for GBM diagnosis. Furthermore, multimodal imaging with combination of MRI and other imaging modalities would not only synergistically integrate the pros, but also overcome the certain limitation in each imaging modality, offering more accurate morphological and pathophysiological information of brain tumors. Since contrast agents contribute to amplify imaging signal output for unambiguous pin-pointing of tumors, tremendous efforts have been devoted to advances of contrast agents for MRI and multimodal imaging. Herein, we put special focus on summary of the most recent advances of not only MRI contrast agents including iron oxide-, manganese (Mn)-, gadolinium (Gd)-, 19F- and copper (Cu)-incorporated nanoplatforms for GBM imaging, but also dual-modal or triple-modal nanoprobes. Furthermore, potential obstacles and perspectives for future research and clinical translation of these contrast agents are discussed. We hope this review provides insights for scientists and students with interest in this area. Graphical abstract

show abstract

Synthesis of Intrinsically Disordered Fluorinated Peptides for Modular Design of High‐Signal ¹⁹F MRI Agents

Cited by 9 publications

References 32 publications

Enhanced Performance of Polymeric ¹⁹F MRI Contrast Agents through Incorporation of Highly Water-Soluble Monomer MSEA

Enhanced Performance of Polymeric ¹⁹F MRI Contrast Agents through Incorporation of Highly Water-Soluble Monomer MSEA

Elucidating the Impact of Molecular Structure on the ¹⁹F NMR Dynamics and MRI Performance of Fluorinated Oligomers

Recent development of contrast agents for magnetic resonance and multimodal imaging of glioblastoma

Contact Info

Product

Resources

About

Synthesis of Intrinsically Disordered Fluorinated Peptides for Modular Design of High‐Signal 19F MRI Agents

Cited by 9 publications

References 32 publications

Enhanced Performance of Polymeric 19F MRI Contrast Agents through Incorporation of Highly Water-Soluble Monomer MSEA

Enhanced Performance of Polymeric 19F MRI Contrast Agents through Incorporation of Highly Water-Soluble Monomer MSEA

Elucidating the Impact of Molecular Structure on the 19F NMR Dynamics and MRI Performance of Fluorinated Oligomers

Recent development of contrast agents for magnetic resonance and multimodal imaging of glioblastoma

Contact Info

Product

Resources

About

Synthesis of Intrinsically Disordered Fluorinated Peptides for Modular Design of High‐Signal ¹⁹F MRI Agents

Enhanced Performance of Polymeric ¹⁹F MRI Contrast Agents through Incorporation of Highly Water-Soluble Monomer MSEA

Enhanced Performance of Polymeric ¹⁹F MRI Contrast Agents through Incorporation of Highly Water-Soluble Monomer MSEA

Elucidating the Impact of Molecular Structure on the ¹⁹F NMR Dynamics and MRI Performance of Fluorinated Oligomers