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Synthesis and Biological Evaluation of Low Molecular Weight Fluorescent Imaging Agents for the Prostate-Specific Membrane Antigen

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    Synthesis and Biological Evaluation of Low Molecular Weight Fluorescent Imaging Agents for the Prostate-Specific Membrane Antigen
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    † †Russell H. Morgan Department of Radiology and §NeuroTranslational Drug Discovery Program, Brain Science Institute, Johns Hopkins Medical School, Baltimore, Maryland 21231, United States
    ‡ College of Pharmacy, Korea University, 2511 Sejong-ro, Jochiwon-eup, Yeongi-gun, Chungnam 339-700, South Korea
    *Phone: 410-955-2789. Fax: 443-817-0990. E-mail: [email protected]
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    Bioconjugate Chemistry

    Cite this: Bioconjugate Chem. 2012, 23, 12, 2377–2385
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    https://doi.org/10.1021/bc3003919
    Published November 19, 2012
    Copyright © 2012 American Chemical Society
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    Abstract

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    Targeted near-infrared (NIR) optical imaging can be used in vivo to detect specific tissues, including malignant cells. A series of NIR fluorescent ligands targeting the prostate-specific membrane antigen (PSMA) was synthesized and each compound was tested for its ability to image PSMA+ tissues in experimental models of prostate cancer. The agents were prepared by conjugating commercially available active esters of NIR dyes, including IRDye800CW, IRDye800RS, Cy5.5, Cy7, or a derivative of indocyanine green (ICG) to the terminal amine group of (S)-2-(3-((S)-5-amino-1-carboxypentyl)ureido)pentanedioic acid 1, (14S,18S)-1-amino-8,16-dioxo-3,6-dioxa-9,15,17-triazaicosane-14,18,20-tricarboxylic acid 2 and (3S,7S)-26-amino-5,13,20-trioxo-4,6,12,21-tetraazahexacosane-1,3,7,22-tetracarboxylic acid 3. The Ki values for the dye–inhibitor conjugates ranged from 1 to 700 pM. All compounds proved capable of imaging PSMA+ tumors selectively to varying degrees depending on the choice of fluorophore and linker. The highest tumor uptake was observed with IRDye800CW employing a poly(ethylene glycol) or lysine–suberate linker, as in 800CW-2 and 800CW-3, while the highest tumor to nontarget tissue ratios were obtained for Cy7 with these same linkers, as in Cy7-2 and Cy7-3. Compounds 2 and 3 provide useful scaffolds for targeting of PSMA+ tissues in vivo and should be useful for preparing NIR dye conjugates designed specifically for clinical intraoperative optical imaging devices.

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    HPLC conditions and traces for the final compounds, ligated to the commercial and previously reported NIR dyes used herein, are provided: 800CW-1; 800CW-2; 800CW-3; 800RS-1; 800RS-2; 800RS-3; ICG-1; ICG-2; ICG-3; Cy7-1; Cy7-2; Cy7-3; Cy5.5-1; Cy5.5-2; Cy5.5-3. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Bioconjugate Chemistry

    Cite this: Bioconjugate Chem. 2012, 23, 12, 2377–2385
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    https://doi.org/10.1021/bc3003919
    Published November 19, 2012
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