| Full text | |
| Author(s): |
Wegermann, Camila A.
[1, 2]
;
Monzani, Enrico
[3]
;
Casella, Luigi
[3]
;
Ribeiro, Marcos A.
[4]
;
Bruzeguini, Carlos E. T.
[4]
;
Vilcachagua, Janaina D.
[5]
;
Costa, Luiz Antonio S.
[6]
;
Ferreira, Ana M. Da Costa
[2]
Total Authors: 8
|
| Affiliation: | [1] Univ Fed Fluminense, Inst Quim, Niteroi, RJ - Brazil
[2] Univ Sao Paulo, Dept Quim Fundamental, Inst Quim, Sao Paulo, SP - Brazil
[3] Univ Pavia, Dipartimento Chim, Pavia - Italy
[4] Univ Fed Espirito Santo, Ctr Ciencias Exatas, Dept Quim, Vitoria, ES - Brazil
[5] Univ Sao Paulo, Inst Quim, Cent Analit, Sao Paulo, SP - Brazil
[6] Univ Fed Juiz de Fora, Dept Quim, ICE, NEQC Nucleo Estudos Quim Computac, Juiz De Fora, MG - Brazil
Total Affiliations: 6
|
| Document type: | Journal article |
| Source: | Journal of Molecular Structure; v. 1250, n. 2 FEB 15 2022. |
| Web of Science Citations: | 0 |
| Abstract | |
Molecular recognition is a crucial issue in studies on interactions between biomolecules, or potential pharmacological agents and biomolecules. Isatin-hydrazones are interesting compounds since the presence of an imine bond combined with a set of heteroatoms lead to the formation of numerous isomers whose distribution can be modulated by solvent polarity, concentration, and pH range, among other factors. Herein we report NMR spectroscopic studies, complemented by UV/Vis and IR, to characterize geometrical isomers and tautomers of two isatin-derived hydrazones, isahim and isahpy. By using different spectroscopic methods, it was possible to detect and identify among diverse possible configurations of isahim molecule the preferential species and verify its stability in solution at different temperatures. NMR spectra indicated the co-existence of diverse isomer and/or tautomer forms in solution, corroborated by UV/VIS spectra in different solvents, at varied concentrations and pHs. Further, IR spectra allowed to better identify and characterize the proposed structures. DFT simulations supported the experimental results, attesting that the most stable isomers in solution are the keto in corresponding Z forms for both hydrazone compounds. These studies provided suitable spectroscopic tools to understand and elucidate molecular interactions of such hydrazones with amyloid peptides and with essential metal ions implicated in Alzheimer disease, in subsequent studies. (c) 2021 Elsevier B.V. All rights reserved. (AU) | |
| FAPESP's process: | 13/07937-8 - Redoxome - Redox Processes in Biomedicine |
| Grantee: | Ohara Augusto |
| Support Opportunities: | Research Grants - Research, Innovation and Dissemination Centers - RIDC |