Desenvolvimento de um quimiodosímetro para detecção de L-cisteína em meio aquoso a partir de 2,3-dicloro-6,7-dinitroquinoxalina
Amino acids are key species in several biological processes due their role as building block for the synthesis of proteins as well as other biological functions. L-cysteine is an essential proteic amino acid, and beside other functions, acts effectively in active site of enzymes and as glutathione p...
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| Formato: | Dissertação |
| Idioma: | pt_BR |
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Universidade Federal do Rio Grande do Norte
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| Endereço do item: | https://repositorio.ufrn.br/handle/123456789/41557 |
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| Resumo: | Amino acids are key species in several biological processes due their role as building block
for the synthesis of proteins as well as other biological functions. L-cysteine is an essential
proteic amino acid, and beside other functions, acts effectively in active site of enzymes and
as glutathione precursor. Due its relevance, Cys has became an interesting target for the
development pf molecular systems able to detect it. This work reports the use of 2,3-dichloro6-7dinitroquinoxaline (DCDNQX) as a functional chemodosimeter for detection of Cys in
aqueous solution based on nucleophilic aromatic substitution (SNAr). DCDNQX was
synthetized in good overall yield (65%) via a sequential three-step protocol. UV-Vis
spectroscopy analysis indicated that DCQNQX reacts selectively with Cys over other selected
amino acids (tyrosine (Tyr), alanine (Ala), lysine (Lys), Histidine (His) and glutamic acid
(Glu)) in DMF-H2O 5:1 v/v solution in the presence of K2CO3. This behavior is justified by
the higher nucleophilicy of tiolate over phenols and amines in SNAr reactions. Selective
sensing was based on the band at 275 nm that emerges in the reaction between DCDNQX and
Cys after 20 minutes. At this moment, the products from reaction of DCQNQX and Cys are
under characterization in attempt to understand the whole mechanisms involved in the
detection of this relevant amino acid. |
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