The Influence of the Amide Linkage in the FeIII-Binding Properties of Catechol-Modified Rosamine Derivatives

Giampaolo Barone, Luís Cunha-Silva, Baltazar De Castro, Andreia Leite, Ana M.G. Silva, André M.N. Silva, Carla Queirõs, Maria Rangel, Maria G.M. Couto

Risultato della ricerca: Article

5 Citazioni (Scopus)

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 FeIII center has been rationalized by mass-spectrometric analysis and semiempirical calculations. Octahedral FeIII 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.
Lingua originaleEnglish
pagine (da-a)15692-15704
Numero di pagine13
RivistaCHEMISTRY-A EUROPEAN JOURNAL
Volume21
Stato di pubblicazionePublished - 2015

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Amides
Ligands
Derivatives
Salicylates
X ray crystallography
Quantum yield
Chelation
Discrete Fourier transforms
Nuclear magnetic resonance spectroscopy
Amines
Mass spectrometry
Fluorescence
Microwaves
catechol

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cita questo

Barone, G., Cunha-Silva, L., De Castro, B., Leite, A., Silva, A. M. G., Silva, A. M. N., ... Couto, M. G. M. (2015). The Influence of the Amide Linkage in the FeIII-Binding Properties of Catechol-Modified Rosamine Derivatives. CHEMISTRY-A EUROPEAN JOURNAL, 21, 15692-15704.

The Influence of the Amide Linkage in the FeIII-Binding Properties of Catechol-Modified Rosamine Derivatives. / Barone, Giampaolo; Cunha-Silva, Luís; De Castro, Baltazar; Leite, Andreia; Silva, Ana M.G.; Silva, André M.N.; Queirõs, Carla; Rangel, Maria; Couto, Maria G.M.

In: CHEMISTRY-A EUROPEAN JOURNAL, Vol. 21, 2015, pag. 15692-15704.

Risultato della ricerca: Article

Barone, G, Cunha-Silva, L, De Castro, B, Leite, A, Silva, AMG, Silva, AMN, Queirõs, C, Rangel, M & Couto, MGM 2015, 'The Influence of the Amide Linkage in the FeIII-Binding Properties of Catechol-Modified Rosamine Derivatives', CHEMISTRY-A EUROPEAN JOURNAL, vol. 21, pagg. 15692-15704.
Barone, Giampaolo ; Cunha-Silva, Luís ; De Castro, Baltazar ; Leite, Andreia ; Silva, Ana M.G. ; Silva, André M.N. ; Queirõs, Carla ; Rangel, Maria ; Couto, Maria G.M. / The Influence of the Amide Linkage in the FeIII-Binding Properties of Catechol-Modified Rosamine Derivatives. In: CHEMISTRY-A EUROPEAN JOURNAL. 2015 ; Vol. 21. pagg. 15692-15704.
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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 FeIII center has been rationalized by mass-spectrometric analysis and semiempirical calculations. Octahedral FeIII 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.",
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AU - Barone, Giampaolo

AU - Cunha-Silva, Luís

AU - De Castro, Baltazar

AU - Leite, Andreia

AU - Silva, Ana M.G.

AU - Silva, André M.N.

AU - Queirõs, Carla

AU - Rangel, Maria

AU - Couto, Maria G.M.

PY - 2015

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N2 - 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 FeIII center has been rationalized by mass-spectrometric analysis and semiempirical calculations. Octahedral FeIII 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.

AB - 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 FeIII center has been rationalized by mass-spectrometric analysis and semiempirical calculations. Octahedral FeIII 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.

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