Electronic Effects of the Substituents on Relaxometric and CEST Behaviour of Ln(III)-DOTA-Tetraanilides

Three different 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetamide (DOTAM) derivatives bearing as amide N-substituents phenyl, p-methoxyphenyl and p-ethylbenzoate groups were synthesized and the 1H and 17&...

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Main Authors:	Valeria Lagostina, Loredana Leone, Fabio Carniato, Giuseppe Digilio, Lorenzo Tei, Mauro Botta
Format:	Article
Language:	English
Published:	MDPI AG 2019-03-01
Series:	Inorganics
Subjects:	macrocyclic ligands lanthanide complexes relaxometry CEST electronic effects
Online Access:	https://www.mdpi.com/2304-6740/7/4/43

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spelling	doaj-5aaf56a715084b05ad47ef6ebc15beee2020-11-24T20:42:10ZengMDPI AGInorganics2304-67402019-03-01744310.3390/inorganics7040043inorganics7040043Electronic Effects of the Substituents on Relaxometric and CEST Behaviour of Ln(III)-DOTA-TetraanilidesValeria Lagostina0Loredana Leone1Fabio Carniato2Giuseppe Digilio3Lorenzo Tei4Mauro Botta5Dipartimento of Scienze e Innovazione Tecnologica, Università del Piemonte Orientale, Viale T. Michel 11, 15121 Alessandria, ItalyDipartimento of Scienze e Innovazione Tecnologica, Università del Piemonte Orientale, Viale T. Michel 11, 15121 Alessandria, ItalyDipartimento of Scienze e Innovazione Tecnologica, Università del Piemonte Orientale, Viale T. Michel 11, 15121 Alessandria, ItalyDipartimento of Scienze e Innovazione Tecnologica, Università del Piemonte Orientale, Viale T. Michel 11, 15121 Alessandria, ItalyDipartimento of Scienze e Innovazione Tecnologica, Università del Piemonte Orientale, Viale T. Michel 11, 15121 Alessandria, ItalyDipartimento of Scienze e Innovazione Tecnologica, Università del Piemonte Orientale, Viale T. Michel 11, 15121 Alessandria, ItalyThree different 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetamide (DOTAM) derivatives bearing as amide <i>N</i>-substituents phenyl, <i>p</i>-methoxyphenyl and <i>p</i>-ethylbenzoate groups were synthesized and the <sup>1</sup>H and <sup>17</sup>O NMR relaxometric behaviour of the Gd(III)-chelates and chemical exchange saturation transfer (CEST) effect of the Eu(III) complexes were evaluated. The electronic properties of the substituents were shown to strongly influence the coordinated water exchange rate (<i>k</i><sub>ex</sub>), resulting in five times faster <i>k</i><sub>ex</sub> for the electron donating phenylmethoxy group compared to the electron withdrawing ethylbenzoate group.https://www.mdpi.com/2304-6740/7/4/43macrocyclic ligandslanthanide complexesrelaxometryCESTelectronic effects
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Valeria Lagostina Loredana Leone Fabio Carniato Giuseppe Digilio Lorenzo Tei Mauro Botta
spellingShingle	Valeria Lagostina Loredana Leone Fabio Carniato Giuseppe Digilio Lorenzo Tei Mauro Botta Electronic Effects of the Substituents on Relaxometric and CEST Behaviour of Ln(III)-DOTA-Tetraanilides Inorganics macrocyclic ligands lanthanide complexes relaxometry CEST electronic effects
author_facet	Valeria Lagostina Loredana Leone Fabio Carniato Giuseppe Digilio Lorenzo Tei Mauro Botta
author_sort	Valeria Lagostina
title	Electronic Effects of the Substituents on Relaxometric and CEST Behaviour of Ln(III)-DOTA-Tetraanilides
title_short	Electronic Effects of the Substituents on Relaxometric and CEST Behaviour of Ln(III)-DOTA-Tetraanilides
title_full	Electronic Effects of the Substituents on Relaxometric and CEST Behaviour of Ln(III)-DOTA-Tetraanilides
title_fullStr	Electronic Effects of the Substituents on Relaxometric and CEST Behaviour of Ln(III)-DOTA-Tetraanilides
title_full_unstemmed	Electronic Effects of the Substituents on Relaxometric and CEST Behaviour of Ln(III)-DOTA-Tetraanilides
title_sort	electronic effects of the substituents on relaxometric and cest behaviour of ln(iii)-dota-tetraanilides
publisher	MDPI AG
series	Inorganics
issn	2304-6740
publishDate	2019-03-01
description	Three different 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetamide (DOTAM) derivatives bearing as amide <i>N</i>-substituents phenyl, <i>p</i>-methoxyphenyl and <i>p</i>-ethylbenzoate groups were synthesized and the <sup>1</sup>H and <sup>17</sup>O NMR relaxometric behaviour of the Gd(III)-chelates and chemical exchange saturation transfer (CEST) effect of the Eu(III) complexes were evaluated. The electronic properties of the substituents were shown to strongly influence the coordinated water exchange rate (<i>k</i><sub>ex</sub>), resulting in five times faster <i>k</i><sub>ex</sub> for the electron donating phenylmethoxy group compared to the electron withdrawing ethylbenzoate group.
topic	macrocyclic ligands lanthanide complexes relaxometry CEST electronic effects
url	https://www.mdpi.com/2304-6740/7/4/43
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Electronic Effects of the Substituents on Relaxometric and CEST Behaviour of Ln(III)-DOTA-Tetraanilides

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