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Anticancer gold(III) peptidomimetics: from synthesis to in vitro and ex vivo biological evaluation

Boscutti, Giulia, Nardon, Chiara, Marchiò, Luciano, Crisma, Marco, Biondi, Barbara, Dalzoppo, Daniele, Dalla Via, Lisa, Formaggio, Fernando, Casini, Angela ORCID: and Fregona, Dolores 2018. Anticancer gold(III) peptidomimetics: from synthesis to in vitro and ex vivo biological evaluation. ChemMedChem 13 (11) , pp. 1131-1145. 10.1002/cmdc.201800098

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Five new Au(III)‐peptidodithiocarbamato complexes of the type [AuIIIBr2(dtc‐AA1‐AA2‐OR] (AA1=Sar, L/D‐Pro; AA2=L/D‐Ala, Aib; R=OtBu, TEG), differing in the amino acidic sequence and/or the chiral amino acid configuration, were designed to enhance the tumor selectivity and bioavailability. The gold(III)‐based moiety was functionalized to exploit the targeting properties of the peptidomimetic ligand towards two peptide transporters (namely, PEPT1 and PEPT2), up‐regulated in several tumor cells. The compounds were synthesized and fully characterized, mainly by means of elemental analysis, mono‐ and bidimensional NMR spectroscopy, FT‐IR and UV‐Vis spectrophotometries. The crystal structures of three compounds were also solved by X‐ray diffraction. In vitro cytotoxicity studies using a panel of human tumor cell lines (A549, MCF‐7, A2780, H1975, H460 and A431) showed that the dtc‐Pro‐Aib‐OtBu derivative is very effective, with GI50 values much lower than those of Cisplatin. It was thus selected for evaluating the stability under physiological conditions and possible interaction with serum albumin as well as for PARP‐1 enzyme inhibition assays and preliminary ex vivo toxicity experiments on healthy rat tissues.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: Wiley-VCH Verlag
ISSN: 1860-7179
Funders: The University of Padova, The Cassa di Risparmio di Padova e Rovigo Foundation (, Ph.D. studies grant for G.B., L�Or�al Foundation � UNESCO (
Date of First Compliant Deposit: 27 March 2018
Date of Acceptance: 13 March 2018
Last Modified: 20 May 2024 21:07

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