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Issue 5, 2018
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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.

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

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Publication details

The article was received on 15 Feb 2018, accepted on 13 Apr 2018 and first published on 16 Apr 2018


Article type: Paper
DOI: 10.1039/C8PP00069G
Citation: Photochem. Photobiol. Sci., 2018,17, 617-621
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    A water-soluble PEGylated RGD-functionalized bisbithiophenyl diketopyrrolopyrrole as a photoacoustic sonophore

    T. Repenko, A. Rix, B. Haehnle, W. Lederle, L. De Laporte and A. J. C. Kuehne, Photochem. Photobiol. Sci., 2018, 17, 617
    DOI: 10.1039/C8PP00069G

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