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Micellar effects and analytical applications of nitro substitution in 4-Nitro-N-alkyl-1,8-naphthalimide by cysteine derivatives
The aromatic nucleophilic substitution reactions of the nitro group of 4-Nitro-N-alkyl-1,8-naphthalimides by thiolate anions produce fluorescent derivatives and their rates are strongly accelerated by micelles of hexadecyltrimethylammonium chloride even at low pH. Acceleration factors of this reacti...
Autores principales: | , , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Elsevier
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7502353/ https://www.ncbi.nlm.nih.gov/pubmed/32995623 http://dx.doi.org/10.1016/j.heliyon.2020.e04938 |
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author | Martins, V.S. Triboni, E.R. Bonilha, J.B.S. Gonçalves, L.M. Mortara, L. Carvalho, L.A.C. Manda, B.R. Lacerda, C.D. Meotti, F.C. Politi, M.J. Chaimovich, H. Cuccovia, I.M. |
author_facet | Martins, V.S. Triboni, E.R. Bonilha, J.B.S. Gonçalves, L.M. Mortara, L. Carvalho, L.A.C. Manda, B.R. Lacerda, C.D. Meotti, F.C. Politi, M.J. Chaimovich, H. Cuccovia, I.M. |
author_sort | Martins, V.S. |
collection | PubMed |
description | The aromatic nucleophilic substitution reactions of the nitro group of 4-Nitro-N-alkyl-1,8-naphthalimides by thiolate anions produce fluorescent derivatives and their rates are strongly accelerated by micelles of hexadecyltrimethylammonium chloride even at low pH. Acceleration factors of this reactions can reach million-fold. As the products are oxidant-insensible, this reaction allows the determination of SH- containing compounds such as cysteine, glutathione or proteins even in oxidative conditions. Limits of detection are as low as 5 × 10(−7) M, ten times lower than the limit for the classic 5,5′-dithiobis-(2-nitrobenzoic) acid method. Moreover, this reaction can be developed at pHs between 6.5 and 7.5 thereby diminishing the rate of spontaneous oxidation of the thiols. In addition, we demonstrated that 4-Nitro-N-alkyl-1,8-naphthalimides can be used to evidence SH groups in peptides, proteins and living cells. |
format | Online Article Text |
id | pubmed-7502353 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | Elsevier |
record_format | MEDLINE/PubMed |
spelling | pubmed-75023532020-09-28 Micellar effects and analytical applications of nitro substitution in 4-Nitro-N-alkyl-1,8-naphthalimide by cysteine derivatives Martins, V.S. Triboni, E.R. Bonilha, J.B.S. Gonçalves, L.M. Mortara, L. Carvalho, L.A.C. Manda, B.R. Lacerda, C.D. Meotti, F.C. Politi, M.J. Chaimovich, H. Cuccovia, I.M. Heliyon Research Article The aromatic nucleophilic substitution reactions of the nitro group of 4-Nitro-N-alkyl-1,8-naphthalimides by thiolate anions produce fluorescent derivatives and their rates are strongly accelerated by micelles of hexadecyltrimethylammonium chloride even at low pH. Acceleration factors of this reactions can reach million-fold. As the products are oxidant-insensible, this reaction allows the determination of SH- containing compounds such as cysteine, glutathione or proteins even in oxidative conditions. Limits of detection are as low as 5 × 10(−7) M, ten times lower than the limit for the classic 5,5′-dithiobis-(2-nitrobenzoic) acid method. Moreover, this reaction can be developed at pHs between 6.5 and 7.5 thereby diminishing the rate of spontaneous oxidation of the thiols. In addition, we demonstrated that 4-Nitro-N-alkyl-1,8-naphthalimides can be used to evidence SH groups in peptides, proteins and living cells. Elsevier 2020-09-16 /pmc/articles/PMC7502353/ /pubmed/32995623 http://dx.doi.org/10.1016/j.heliyon.2020.e04938 Text en © 2020 The Author(s) http://creativecommons.org/licenses/by-nc-nd/4.0/ This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/). |
spellingShingle | Research Article Martins, V.S. Triboni, E.R. Bonilha, J.B.S. Gonçalves, L.M. Mortara, L. Carvalho, L.A.C. Manda, B.R. Lacerda, C.D. Meotti, F.C. Politi, M.J. Chaimovich, H. Cuccovia, I.M. Micellar effects and analytical applications of nitro substitution in 4-Nitro-N-alkyl-1,8-naphthalimide by cysteine derivatives |
title | Micellar effects and analytical applications of nitro substitution in 4-Nitro-N-alkyl-1,8-naphthalimide by cysteine derivatives |
title_full | Micellar effects and analytical applications of nitro substitution in 4-Nitro-N-alkyl-1,8-naphthalimide by cysteine derivatives |
title_fullStr | Micellar effects and analytical applications of nitro substitution in 4-Nitro-N-alkyl-1,8-naphthalimide by cysteine derivatives |
title_full_unstemmed | Micellar effects and analytical applications of nitro substitution in 4-Nitro-N-alkyl-1,8-naphthalimide by cysteine derivatives |
title_short | Micellar effects and analytical applications of nitro substitution in 4-Nitro-N-alkyl-1,8-naphthalimide by cysteine derivatives |
title_sort | micellar effects and analytical applications of nitro substitution in 4-nitro-n-alkyl-1,8-naphthalimide by cysteine derivatives |
topic | Research Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7502353/ https://www.ncbi.nlm.nih.gov/pubmed/32995623 http://dx.doi.org/10.1016/j.heliyon.2020.e04938 |
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