NDLI: The Influence of the Amide Linkage in the $Fe^{III}-Binding$ Properties of Catechol-Modified Rosamine Derivatives

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The Influence of the Amide Linkage in the $Fe^{III}-Binding$ Properties of Catechol-Modified Rosamine Derivatives

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Couto, Maria G. M. Cunha-silva, Luís Silva, Ana M. G. Queirós, Carla De Castro, Baltazar Barone, Giampaolo Leite, Andreia Silva, André M. N. Rangel, Maria
Description	Author Affiliation: Queirós C ( LAQV-REQUIMTE, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, 4169-007 Porto (Portugal).); Leite A ( UCIBIO-REQUIMTE, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, 4169-007 Porto (Portugal).); G M Couto M ( UCIBIO-REQUIMTE, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, 4169-007 Porto (Portugal).); Cunha-Silva L ( LAQV-REQUIMTE, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, 4169-007 Porto (Portugal).); Barone G ( Dipartimento di Scienze e Tecnologie Biologiche, Chimiche e Farmaceutiche (STEBICEF), Università di Palermo, Vialle delle Scienze, Edifício 17, 90128 Palermo (Italy).); de Castro B ( LAQV-REQUIMTE, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, 4169-007 Porto (Portugal).); Rangel M ( UCIBIO-REQUIMTE, Instituto de Ciências Biomédicas de Abel Salazar, Universidade do Porto, 4050-313 Porto (Portugal).); M N Silva A ( UCIBIO-REQUIMTE, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, 4169-007 Porto (Portugal). ana.silva@fc.up.pt.); M G Silva A ( UCIBIO-REQUIMTE, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, 4169-007 Porto (Portugal). andre.silva@fc.up.pt.)
Abstract	The two new fluorescent ligands RosCat1 and RosCat2 contain catechol receptors connected to rosamine platforms through an amide linkage and were synthesized by using microwave-assisted coupling reactions of carboxyl- or amine-substituted rosamines with the corresponding catechol units and subsequent deprotection. RosCat1 possesses a reverse amide, whereas RosCat2 has the usual oriented amide bond (HNCO vs. CONH, respectively). The ligands were characterized by means of NMR spectroscopy, mass-spectrometry, and DFT calculations and X-ray crystallography studies for RosCat1. The influence of the amide linkage on the photophysical properties of the fluorescent ligands was assessed in different solvents and showed a higher fluorescence quantum yield for RosCat1. The coordination chemistry of these ligands with a $Fe^{III}$ center has been rationalized by mass-spectrometric analysis and semiempirical calculations. Octahedral $Fe^{III}$ complexes were obtained by the chelation of three RosCat1 or RosCat2 ligands. Interestingly, the unconventional amide connectivity in RosCat1 imposes the formation of an eight-membered ring on the chelate complex through a “salicylate-type” mode of coordination.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	44
Volume Number	21
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2015-10-26
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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