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    Phthalocyanine–Peptide Conjugates for Epidermal Growth Factor Receptor Targeting
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    † Louisiana State University, Department of Chemistry, Baton Rouge Louisiana 70803, United States
    ‡ Louisiana State University, School of Veterinary Medicine, Baton Rouge Louisiana 70803, United States
    § University of Louisiana at Monroe, College of Pharmacy, Monroe Louisiana 71201, United States
    *Phone: 225-578-7405. Fax: 225-578-3458. E-mail: [email protected]
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    Journal of Medicinal Chemistry

    Cite this: J. Med. Chem. 2012, 55, 8, 3725–3738
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    https://doi.org/10.1021/jm201544y
    Published April 2, 2012
    Copyright © 2012 American Chemical Society
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    Abstract

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    Four phthalocyanine (Pc)–peptide conjugates designed to target the epidermal growth factor receptor (EGFR) were synthesized and evaluated in vitro using four cell lines: human carcinoma A431 and HEp2, human colorectal HT-29, and kidney Vero (negative control) cells. Two peptide ligands for EGFR were investigated: EGFR-L1 and -L2, bearing 6 and 13 amino acid residues, respectively. The peptides and Pc-conjugates were shown to bind to EGFR using both theoretical (Autodock) and experimental (SPR) investigations. The Pc–EGFR-L1 conjugates 5a and 5b efficiently targeted EGFR and were internalized, in part due to their cationic charge, whereas the uncharged Pc–EGFR-L2 conjugates 4b and 6a poorly targeted EGFR maybe due to their low aqueous solubility. All conjugates were nontoxic (IC50 > 100 μM) to HT-29 cells, both in the dark and upon light activation (1 J/cm2). Intravenous (iv) administration of conjugate 5b into nude mice bearing A431 and HT-29 human tumor xenografts resulted in a near-IR fluorescence signal at ca. 700 nm, 24 h after administration. Our studies show that Pc–EGFR-L1 conjugates are promising near-IR fluorescent contrast agents for CRC and potentially other EGFR overexpressing cancers.

    Copyright © 2012 American Chemical Society

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    NMR spectra, MS, HPLC chromatograms, phototoxicity and dark toxicity plots, subcellular localization microscopy. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Cite this: J. Med. Chem. 2012, 55, 8, 3725–3738
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    https://doi.org/10.1021/jm201544y
    Published April 2, 2012
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