Radiosynthesis and micro-SPECT analysis of triazole-based RGD integrin ligands as non-peptide molecular imaging probes for angiogenesis

Francesca Bianchini; Pierangelo Fabbrizzi; Gloria Menchi; Silvia Raspanti; Anna Bottoncetti; Alessandro Passeri; Elena Andreucci; Antonio Guarna; Lido Calorini; Alberto Pupi; Andrea Trabocchi

doi:10.1016/j.bmc.2014.12.065

Radiosynthesis and micro-SPECT analysis of triazole-based RGD integrin ligands as non-peptide molecular imaging probes for angiogenesis

Bioorg Med Chem. 2015 Mar 1;23(5):1112-22. doi: 10.1016/j.bmc.2014.12.065. Epub 2015 Jan 13.

Authors

Affiliations

¹ Department of Clinical and Experimental Biomedical Science 'Mario Serio', University of Florence, Viale Morgagni 50, 50134 Florence, Italy.
² Department of Chemistry 'Ugo Schiff', University of Florence, Via della Lastruccia 13, 50019 Sesto Fiorentino, Florence, Italy.
³ Department of Chemistry 'Ugo Schiff', University of Florence, Via della Lastruccia 13, 50019 Sesto Fiorentino, Florence, Italy; Interdepartmental Center for Preclinical Development of Molecular Imaging (CISPIM), University of Florence, Viale Morgagni 85, 50134 Florence, Italy.
⁴ Department of Clinical and Experimental Biomedical Science 'Mario Serio', University of Florence, Largo Brambilla 3, 50134 Florence, Italy.
⁵ Azienda Ospedaliera Universitaria Careggi (AOUC), Largo Brambilla 3, 50134 Florence, Italy.
⁶ Interdepartmental Center for Preclinical Development of Molecular Imaging (CISPIM), University of Florence, Viale Morgagni 85, 50134 Florence, Italy; Department of Clinical and Experimental Biomedical Science 'Mario Serio', University of Florence, Largo Brambilla 3, 50134 Florence, Italy.
⁷ Department of Clinical and Experimental Biomedical Science 'Mario Serio', University of Florence, Viale Morgagni 50, 50134 Florence, Italy. Electronic address: lido.calorini@unifi.it.
⁸ Interdepartmental Center for Preclinical Development of Molecular Imaging (CISPIM), University of Florence, Viale Morgagni 85, 50134 Florence, Italy; Department of Clinical and Experimental Biomedical Science 'Mario Serio', University of Florence, Largo Brambilla 3, 50134 Florence, Italy; Azienda Ospedaliera Universitaria Careggi (AOUC), Largo Brambilla 3, 50134 Florence, Italy. Electronic address: a.pupi@dfc.unifi.it.
⁹ Department of Chemistry 'Ugo Schiff', University of Florence, Via della Lastruccia 13, 50019 Sesto Fiorentino, Florence, Italy; Interdepartmental Center for Preclinical Development of Molecular Imaging (CISPIM), University of Florence, Viale Morgagni 85, 50134 Florence, Italy. Electronic address: andrea.trabocchi@unifi.it.

PMID: 25637121
DOI: 10.1016/j.bmc.2014.12.065

Abstract

Taking advantage of click chemistry, we synthesized triazole-containing RGD peptidomimetics capable of binding to αvβ3 integrin with diverse potency, and selected (125)I-labeled compounds proved to interact in vitro and in vivo with αvβ3 integrin expressed by melanoma cells. Two (125)I-compounds containing either 2-aminobenzimidazole or 2-aminopyridine groups as the arginine bioisostere with the capacity to selectively bind cells of highly expressing αvβ3 melanoma xenografts were found using micro-SPECT imaging studies.

Keywords: Amino acids; Angiogenesis; Cancer; Integrins; Molecular imaging.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Heterografts
Humans
Integrins / chemistry*
Ligands
Melanoma / diagnostic imaging
Mice
Models, Molecular
Molecular Probes*
Neovascularization, Pathologic / diagnosis*
Oligopeptides / chemical synthesis
Oligopeptides / chemistry*
Tomography, Emission-Computed, Single-Photon / methods*
Triazoles / chemistry*

Substances

Integrins
Ligands
Molecular Probes
Oligopeptides
Triazoles
arginyl-glycyl-aspartic acid