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An innovative and efficient route to the synthesis of metal-based glycoconjugates: proof-of-concept and potential applications
Pettenuzzo, Andrea; Montagner, Diego; McArdle, Patrick; Ronconi, Luca
With a view to developing more efficient strategies to the functionalization of metallodrugs with carbohydrates, we here report on an innovative and efficient synthetic route to generate gold(III) glycoconjugates in high yields and purity. The method is based on the initial synthesis of the zinc(II)-dithiocarbamato intermediate [ZnII(SSC-Inp-GlcN)2] (Inp = isonipecotic moiety; GlcN = amino-glucose) followed by the transfer of the glucoseisonipecoticdithiocarbamato ligand to the gold(III) center via transmetallation reaction between the zinc(II) intermediate and K[AuIIIBr4] in 1 : 2 stoichiometric ratio, yielding the corresponding glucose-functionalized gold(III)-dithiocarbamato derivative [AuIIIBr2(SSC-Inp-GlcN)]. No protection/deprotection of the amino-glucose scaffold and no chromatographic purification were needed. The synthetic protocol was optimized for glucose precursors bearing the amino function at either the C2 or the C6 position, and works in the case of both α and β anomers. The application of the synthetic strategy was also successfully extended to other metal ions of biomedical interest, such as gold(I) and platinum(II), to obtain [AuI(SSC-Inp-GlcN)(PPh3)] and [PtII(SSC-Inp-GlcN)2], respectively. All compounds were fully characterized by elemental analysis, mid- and far-IR, mono- and multidimensional NMR spectroscopy, and, where possible, X-ray crystallography. Results and potential applications are here discussed.
Keyword(s): Anticancer-Agents; In-Vitro; Dithiocatbamate Derivatives; Glucose Transporters; Model Biomolecules; Hydrogen-Peroxide; Crystal Structure; Thermal Behavior; Amino-Sugars; Complexes
Publication Date:
Type: Journal article
Peer-Reviewed: Yes
Institution: Maynooth University
Citation(s): Pettenuzzo, Andrea and Montagner, Diego and McArdle, Patrick and Ronconi, Luca (2018) An innovative and efficient route to the synthesis of metal-based glycoconjugates: proof-of-concept and potential applications. Dalton Transactions, 47 (31). pp. 10721-10736. ISSN 1477-9226
Publisher(s): Royal Society of Chemistry
File Format(s): other
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First Indexed: 2020-04-02 06:00:26 Last Updated: 2020-04-02 06:00:26