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Radiopharmacological characterization of 64Cu-labeled α-MSH analogs for potential use in imaging of malignant melanoma

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Abstract

The melanocortin-1 receptor (MC1R) plays an important role in melanoma growth, angiogenesis and metastasis, and is overexpressed in melanoma cells. α-Melanocyte stimulating hormone (α-MSH) and derivatives are known to bind with high affinity at this receptor that provides the potential for selective targeting of melanoma. In this study, one linear α-MSH-derived peptide Nle-Asp-His-D-Phe-Arg-Trp-Gly-NH2 (NAP-NS1) without linker and with εAhx-β-Ala linker, and a cyclic α-MSH derivative, [Lys-Glu-His-D-Phe-Arg-Trp-Glu]-Arg-Pro-Val-NH2 (NAP-NS2) with εAhx-β-Ala linker were conjugated with p-SCN-Bn-NOTA and labeled with 64Cu. Radiochemical and radiopharmacological investigations were performed with regard to transchelation, stability, lipophilicity and in vitro binding assays as well as biodistribution in healthy rats. No transchelation reactions, but high metabolic stability and water solubility were demonstrated. The linear derivatives showed higher affinity than the cyclic one. [64Cu]Cu-NOTA-εAhx-β-Ala-NAP-NS1 ([64Cu]Cu-2) displayed rapid cellular association and dissociation in murine B16F10 cell homogenate. All [64Cu]Cu-labeled conjugates exhibited affinities in the low nanomolar range in B16F10. [64Cu]Cu-2 showed also high affinity in human MeWo and TXM13 cell homogenate. In vivo studies suggested that [64Cu]Cu-2 was stable, with about 85 % of intact peptide in rat plasma at 2 h p.i. Biodistribution confirmed the renal pathway as the major elimination route. The uptake of [64Cu]Cu-2 in the kidney was 5.9 % ID/g at 5 min p.i. and decreased to 2.0 % ID/g at 60 min p.i. Due to the prospective radiochemical and radiopharmacological properties of the linear α-MSH derivative [64Cu]Cu-2, this conjugate is a promising candidate for tracer development in human melanoma imaging.

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Acknowledgments

Feng Gao thanks the German Academic Exchange Service (DAAD) for financial support (A/11/94299, 91540213). The excellent technical assistance of Regina Herrlich, Utta Herzog and Andrea Suhr is greatly acknowledged.

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Authors and Affiliations

  1. Helmholtz-Zentrum Dresden-Rossendorf, Institute of Radiopharmaceutical Cancer Research, Bautzner Landstraße 400, 01328, Dresden, Germany

    Feng Gao, Wiebke Sihver, Christoph Jurischka, Ralf Bergmann, Cathleen Haase-Kohn, Birgit Mosch, Jörg Steinbach, Jens Pietzsch & Hans-Jürgen Pietzsch

  2. Department of Chemistry and Food Chemistry, Technische Universität Dresden, 01062, Dresden, Germany

    Feng Gao, Jörg Steinbach, Jens Pietzsch & Hans-Jürgen Pietzsch

  3. Brandenburg University of Technology Cottbus-Senftenberg, Cottbus, Germany

    Christoph Jurischka

  4. Department of Pharmacological and Pharmaceutical Sciences, University of Padua, 35131, Padua, Italy

    Davide Carta

  5. IENI-CNR, Corso Stati Uniti, 35127, Padua, Italy

    Cristina Bolzati

  6. ICB-CNR, 35131, Padua, Italy

    Andrea Calderan

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  1. Feng Gao
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Correspondence to Wiebke Sihver.

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The animal experiments were performed in accordance to the guidelines of the German Regulations of Animal Welfare. The protocol was approved by the local Ethical Committee for Animal Experiments (reference number 24-9168.21-4/2004-1).

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Gao, F., Sihver, W., Jurischka, C. et al. Radiopharmacological characterization of 64Cu-labeled α-MSH analogs for potential use in imaging of malignant melanoma. Amino Acids 48, 833–847 (2016). https://doi.org/10.1007/s00726-015-2131-x

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