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Effect of the Heteroaromatic Antenna on the Binding of Chiral Eu(III) Complexes to Bovine Serum Albumin
[Image: see text] The cationic enantiopure (R,R) and luminescent Eu(III) complex [Eu(bisoQcd)(H(2)O)(2)] OTf (with bisoQcd = N,N′-bis(2-isoquinolinmethyl)-trans-1,2-diaminocyclohexane N,N′-diacetate and OTf = triflate) was synthesized and characterized. At physiological pH, the 1:1 [Eu(bisoQcd)(H(2)...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American
Chemical Society
2020
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8009522/ https://www.ncbi.nlm.nih.gov/pubmed/32806003 http://dx.doi.org/10.1021/acs.inorgchem.0c01663 |
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author | De Rosa, Chiara Melchior, Andrea Sanadar, Martina Tolazzi, Marilena Giorgetti, Alejandro Ribeiro, Rui P. Nardon, Chiara Piccinelli, Fabio |
author_facet | De Rosa, Chiara Melchior, Andrea Sanadar, Martina Tolazzi, Marilena Giorgetti, Alejandro Ribeiro, Rui P. Nardon, Chiara Piccinelli, Fabio |
author_sort | De Rosa, Chiara |
collection | PubMed |
description | [Image: see text] The cationic enantiopure (R,R) and luminescent Eu(III) complex [Eu(bisoQcd)(H(2)O)(2)] OTf (with bisoQcd = N,N′-bis(2-isoquinolinmethyl)-trans-1,2-diaminocyclohexane N,N′-diacetate and OTf = triflate) was synthesized and characterized. At physiological pH, the 1:1 [Eu(bisoQcd)(H(2)O)(2)](+) species, possessing two water molecules in the inner coordination sphere, is largely dominant. The interaction with bovine serum albumin (BSA) was studied by means of several experimental techniques, such as luminescence spectroscopy, isothermal titration calorimetry (ITC), molecular docking (MD), and molecular dynamics simulations (MDS). In this direction, a ligand competition study was also performed by using three clinically established drugs (i.e., ibuprofen, warfarin, and digitoxin). The nature of this interaction is strongly affected by the type of the involved heteroaromatic antenna in the Eu(III) complexes. In fact, the presence of isoquinoline rings drives the corresponding complex toward the protein superficial area containing the tryptophan residue 134 (Trp134). As the main consequence, the metal center undergoes the loss of one water molecule upon interaction with the side chain of a glutamic acid residue. On the other hand, the similar complex containing pyridine rings ([Eu(bpcd)(H(2)O)(2)]Cl with bpcd = N,N′-bis(2-pyridylmethyl)-trans-1,2-diaminocyclohexane N,N′-diacetate) interacts more weakly with the protein in a different superficial cavity, without losing the coordinated water molecules. |
format | Online Article Text |
id | pubmed-8009522 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | American
Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-80095222021-03-31 Effect of the Heteroaromatic Antenna on the Binding of Chiral Eu(III) Complexes to Bovine Serum Albumin De Rosa, Chiara Melchior, Andrea Sanadar, Martina Tolazzi, Marilena Giorgetti, Alejandro Ribeiro, Rui P. Nardon, Chiara Piccinelli, Fabio Inorg Chem [Image: see text] The cationic enantiopure (R,R) and luminescent Eu(III) complex [Eu(bisoQcd)(H(2)O)(2)] OTf (with bisoQcd = N,N′-bis(2-isoquinolinmethyl)-trans-1,2-diaminocyclohexane N,N′-diacetate and OTf = triflate) was synthesized and characterized. At physiological pH, the 1:1 [Eu(bisoQcd)(H(2)O)(2)](+) species, possessing two water molecules in the inner coordination sphere, is largely dominant. The interaction with bovine serum albumin (BSA) was studied by means of several experimental techniques, such as luminescence spectroscopy, isothermal titration calorimetry (ITC), molecular docking (MD), and molecular dynamics simulations (MDS). In this direction, a ligand competition study was also performed by using three clinically established drugs (i.e., ibuprofen, warfarin, and digitoxin). The nature of this interaction is strongly affected by the type of the involved heteroaromatic antenna in the Eu(III) complexes. In fact, the presence of isoquinoline rings drives the corresponding complex toward the protein superficial area containing the tryptophan residue 134 (Trp134). As the main consequence, the metal center undergoes the loss of one water molecule upon interaction with the side chain of a glutamic acid residue. On the other hand, the similar complex containing pyridine rings ([Eu(bpcd)(H(2)O)(2)]Cl with bpcd = N,N′-bis(2-pyridylmethyl)-trans-1,2-diaminocyclohexane N,N′-diacetate) interacts more weakly with the protein in a different superficial cavity, without losing the coordinated water molecules. American Chemical Society 2020-08-10 2020-09-08 /pmc/articles/PMC8009522/ /pubmed/32806003 http://dx.doi.org/10.1021/acs.inorgchem.0c01663 Text en Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | De Rosa, Chiara Melchior, Andrea Sanadar, Martina Tolazzi, Marilena Giorgetti, Alejandro Ribeiro, Rui P. Nardon, Chiara Piccinelli, Fabio Effect of the Heteroaromatic Antenna on the Binding of Chiral Eu(III) Complexes to Bovine Serum Albumin |
title | Effect of the Heteroaromatic Antenna on the Binding
of Chiral Eu(III) Complexes to Bovine Serum Albumin |
title_full | Effect of the Heteroaromatic Antenna on the Binding
of Chiral Eu(III) Complexes to Bovine Serum Albumin |
title_fullStr | Effect of the Heteroaromatic Antenna on the Binding
of Chiral Eu(III) Complexes to Bovine Serum Albumin |
title_full_unstemmed | Effect of the Heteroaromatic Antenna on the Binding
of Chiral Eu(III) Complexes to Bovine Serum Albumin |
title_short | Effect of the Heteroaromatic Antenna on the Binding
of Chiral Eu(III) Complexes to Bovine Serum Albumin |
title_sort | effect of the heteroaromatic antenna on the binding
of chiral eu(iii) complexes to bovine serum albumin |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8009522/ https://www.ncbi.nlm.nih.gov/pubmed/32806003 http://dx.doi.org/10.1021/acs.inorgchem.0c01663 |
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