Article In: orcid, cienciavitae

Chemical, radiochemical and biological studies of new gallium(III) complexes with hexadentate chelators

Dalton Transactions

Silva, Francisco; Campello, Maria Paula C.; Paulo, Antonio — 2015 — Royal Society of Chemistry

Key information

Authors:

Silva, Francisco; Campello, Maria Paula C. (Maria Paula Cordeiro Crespo Cabral Campello Aboim de Barros); Gano, Lurdes (Maria de Lurdes Barrela Patrício Gano); Fernandes, Celia (Célia Maria Da Cruz Fernandes); Santos, Isabel C. (Isabel Maria Fernandes Cordeiro dos Santos); Santos, Isabel; Ascenso, Jose R.; Joao Ferreira, M. (Maria João Gomes Ferreira); Paulo, Antonio (António Manuel Rocha Paulo)

Published in

2015

Abstract

New N4O2-donor acyclic chelators 2-[[2-[2-(3,5-dimethylpyrazol-1-yl)ethyl-[2-[(2-hydroxyphenyl)methylamino]ethyl]amino]ethylamino]methyl]phenol (H2Lpz*,NH) and 2-[[2-[2-[(2-hydroxyphenyl)methylamino]ethyl-(2-pyridylmethyl)amino]ethylamino]methyl]phenol (H2Lpy,NH) were obtained upon introduction of pyridyl or pyrazolyl coordinating units at the central nitrogen atom of diethylenetriamine (dien) and by functionalization of its terminal amines with phenol groups. The coordination behavior of H2Lpz*,NH and H2Lpy,NH was evaluated towards natGa/67Ga, aiming to assess their suitability to obtain Ga(III) chelates relevant for biomedical applications. Single crystal X-ray diffraction analysis of the complexes [GaLpz*,NH](ClO4) and [GaLpy,NH](ClO4) confirmed the presence of N4O2-hexadentate chelators with the phenoxide groups coordinated cis relatively to the pyridyl/pyrazolyl arms. Unlike [GaLpz*,NH](ClO4), [GaLpy,NH](ClO4) exists in solution as a mixture of isomers, as confirmed by several NMR techniques. The corresponding radiocomplex [67GaLpy,NH]+ was obtained smoothly in almost quantitative radiochemical yield, contrary to [67GaLpz*,NH]+ that seems to be (hemi)labile under the same conditions. [67GaLpy,NH]+ presents a high in vivo stability and a favourable biodistribution profile in mice. The imine congeners 2-[(E)-2-[2-(3,5-dimethylpyrazol-1-yl)ethyl-[2-[(E)-(2-hydroxyphenyl)methyleneamino]ethyl]amino]ethyliminomethyl]phenol (H2Lpz*,C[double bond, length as m-dash]N) and 2-[(E)-2-[2-[(E)-(2-hydroxyphenyl)methyleneamino]ethyl-(2-pyridylmethyl)amino]ethyliminomethyl]phenol (H2Lpy,C[double bond, length as m-dash]N) were also evaluated but they did not form complexes compatible for biomedical applications owing to their high reactivity.

Publication details

Authors in the community:

Publication version

AO - Author's Original

Publisher

Royal Society of Chemistry

Link to the publisher's version

https://pubs.rsc.org/en/journals/journal/dt

Title of the publication container

Dalton Transactions

First page or article number

3342

Last page

3355

Volume

44

Issue

7

DOI

10.1039/c4dt02274b

WoS (Web of Science)

WOS:000349403100047

Fields of Science and Technology (FOS)

health-sciences - Health sciences

Publication language (ISO code)

eng - English

Alternative identifier (URI)

http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=ORCID&SrcApp=OrcidOrg&DestLinkType=FullRecord&DestApp=WOS_CPL&KeyUT=WOS:000349403100047&KeyUID=WOS:000349403100047

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