Melanoma targeting with alpha-melanocyte stimulating hormone analogs labeled with fac-[99mTc(CO)3]+: effect of cyclization on tumor-seeking properties

Journal of Biological Inorganic Chemistry : JBIC : a Publication of the Society of Biological Inorganic Chemistry
Paula D RaposinhoIsabel Santos

Abstract

Early detection of primary melanoma tumors is essential because there is no effective treatment for metastatic melanoma. Several linear and cyclic radiolabeled alpha-melanocyte stimulating hormone (alpha-MSH) analogs have been proposed to target the melanocortin type 1 receptor (MC1R) overexpressed in melanoma. The compact structure of a rhenium-cyclized alpha-MSH analog (Re-CCMSH) significantly enhanced its in vivo tumor uptake and retention. Melanotan II (MT-II), a cyclic lactam analog of alpha-MSH (Ac-Nle-cyclo[Asp-His-DPhe-Arg-Trp-Lys]-NH2]), is a very potent and stable agonist peptide largely used in the characterization of melanocortin receptors. Taking advantage of the superior biological features associated with the MT-II cyclic peptide, we assessed the effect of lactam-based cyclization on the tumor-seeking properties of alpha-MSH analogs by comparing the pharmacokinetics profile of the 99mTc-labeled cyclic peptide betaAla-Nle-cyclo[Asp-His-D-Phe-Arg-Trp-Lys]-NH2 with that of the linear analog betaAla-Nle-Asp-His-DPhe-Arg-Trp-Lys-NH2 in melanoma-bearing mice. We have synthesized and coupled the linear and cyclic peptides to a bifunctional chelator containing a pyrazolyl-diamine backbone (pz) through the amino group of ...Continue Reading

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Citations

Feb 13, 2010·Journal of Nuclear Medicine : Official Publication, Society of Nuclear Medicine·Haixun GuoYubin Miao
Jan 31, 2012·Journal of Biological Inorganic Chemistry : JBIC : a Publication of the Society of Biological Inorganic Chemistry·Maurício MoraisIsabel Santos
Jul 26, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Oxana V KharissovaPerla Elizondo Martínez
Mar 26, 2016·Nanomedicine : Nanotechnology, Biology, and Medicine·Kristof ZarschlerKenneth A Dawson
Apr 12, 2014·Chembiochem : a European Journal of Chemical Biology·Ali BarandovPeter H Seeberger
Feb 26, 2016·Natural Product Reports·C L CharronL G Luyt
Nov 29, 2017·Molecular Imaging·Chengcheng ZhangFrançois Bénard
Sep 9, 2008·Journal of Biological Inorganic Chemistry : JBIC : a Publication of the Society of Biological Inorganic Chemistry·Catarina XavierIsabel Santos
Nov 11, 2009·Current Opinion in Endocrinology, Diabetes, and Obesity·Prasant K NandaCharles Jeffrey Smith
May 14, 2011·The British Journal of Dermatology·D PauroballyA F Nikkels
Jun 26, 2012·The Australasian Journal of Dermatology·Suyin Ong, Jonathan Bowling
Feb 26, 2011·Dalton Transactions : an International Journal of Inorganic Chemistry·João D G CorreiaIsabel Santos
Feb 21, 2021·The Journal of Investigative Dermatology·Leonid KoikovZalfa A Abdel-Malek
Dec 3, 2014·Journal of Nuclear Medicine : Official Publication, Society of Nuclear Medicine·Haixun Guo, Yubin Miao

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