Modulation of the Prototropic Exchange Rate in pH-Responsive Yb-HPDO3A Derivatives as ParaCEST Agents
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Modulation of the Prototropic Exchange Rate in pH-Responsive Yb-HPDO3A Derivatives as ParaCEST Agents (46 visite)

Dastru W, Menchise V, Ferrauto G, Fabretto S, Carrera C, Terreno E, Aime S, Delli Castelli D

Chemistryselect (ISSN: 2365-6549), 2018 Jun; 3(22): 6035-6041.



Tipo di articolo: Journal Article,

Impact factor: 1.505, Impact factor a 5 anni: 1.505

Url: https://www.scopus.com/inward/record.uri?eid=2-s2.0-85046678126&doi=10.1002%2fslct.201800283&partnerID=40&md5=387919f42ce20c2065a370958ed75251

Parole chiave: Contrast Agents, Lanthanide Complexes, Paracest, Ph Sensitive Agents,

Affiliazioni:

*** IBB - CNR ***
Department of Molecular Biotechnology and Health Sciences, Molecular Imaging Center, University of Torino, Via Nizza 52, Torino, 10126, Italy
Istituto di Biostrutture e Bioimmagini, Consiglio Nazionale delle Ricerche, via Mezzocannone 16, Napoli, 80134, Italy


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The aim of this work was to design new pH-sensitive paramagnetic chemical exchange saturation transfer (paraCEST) agents with a more acidic pH readout window with respect to the Yb complex of the 10-(2-hydroxypropyl)-1,4,7,10- tetraazacyclododecane-1,4,7-triacetic acid (HPDO3A). In particular, three HPDO3A derivatives have been synthesized by substituting the methyl group on the 2-hydroxypropyl arm with the electron withdrawing substituents –CF3, –CH2NH2 and –CH2OH. The Yb complexes have been characterized in terms of i) number and relative abundance of isomers present and, ii) pH sensitivity range in CEST applications. The influence of the introduced substituents on the –OH proton acidity and kex has been investigated and the new agents have been compared with the parent Yb-HPDO3A. All complexes showed an increased acidity and an enhanced exchange rate of the –OH proton. As a consequence, the pH-CEST sensitivity has been shifted to more acidic values. Eventually, the –CH2OH bearing derivative has been tested to assess the intra-endosomal pH which is too acidic to be determined with Yb-HPDO3A. © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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28 Records (25 escludendo Abstract e Conferenze).
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Impact factor a 5 anni totale: 119.289 (111.295 escludendo Abstract e Conferenze).







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