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A water-soluble PEGylated RGD-functionalized bisbithiophenyl diketopyrrolopyrrole as a photoacoustic sonophore

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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.

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Acknowledgements

The authors wish to acknowledge support from the excellence initiative of the German federal and state governments and the Hans Hermann Voss-Stiftung through an ERS (Exploratory Research Space @ RWTH Aachen) Seedfund project. This work was performed in part at the Center for Chemical Polymer Technology CPT, which was supported by the EU and the federal state of North Rhine-Westphalia (grant no. EFRE 30 00 883 02).

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Authors and Affiliations

  1. DWI–Leibniz Institute for Interactive Materials, RWTH Aachen University, Forckenbeckstraβe 50, 52076, Aachen, Germany

    Tatjana Repenko, Bastian Haehnle, Laura De Laporte & Alexander J. C. Kuehne

  2. Institute for Experimental Molecular Imaging, University Clinic and Helmholtz Institute for Biomedical Engineering, RWTH Aachen University, Pauwelsstraβe 30, 52074, Aachen, Germany

    Anne Rix & Wiltrud Lederle

Authors
  1. Tatjana Repenko
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  2. Anne Rix
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  3. Bastian Haehnle
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  4. Wiltrud Lederle
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  5. Laura De Laporte
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  6. Alexander J. C. Kuehne
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Correspondence to Alexander J. C. Kuehne.

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Repenko, T., Rix, A., Haehnle, B. et al. A water-soluble PEGylated RGD-functionalized bisbithiophenyl diketopyrrolopyrrole as a photoacoustic sonophore. Photochem Photobiol Sci 17, 617–621 (2018). https://doi.org/10.1039/c8pp00069g

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  • DOI: https://doi.org/10.1039/c8pp00069g

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