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...
| Main Authors: | , , , , , , , , , , , |
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| Format: | Article |
| Language: | English |
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Elsevier
2020-09-01
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| Series: | Heliyon |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2405844020317813 |
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| author | V.S. Martins E.R. Triboni J.B.S. Bonilha L.M. Gonçalves L. Mortara L.A.C. Carvalho B.R. Manda C.D. Lacerda F.C. Meotti M.J. Politi H. Chaimovich I.M. Cuccovia |
| author_facet | V.S. Martins E.R. Triboni J.B.S. Bonilha L.M. Gonçalves L. Mortara L.A.C. Carvalho B.R. Manda C.D. Lacerda F.C. Meotti M.J. Politi H. Chaimovich I.M. Cuccovia |
| author_sort | V.S. Martins |
| collection | DOAJ |
| 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. |
| first_indexed | 2024-12-19T19:39:09Z |
| format | Article |
| id | doaj.art-19d831eb1c83465bad8c0dd6ce61a17c |
| institution | Directory Open Access Journal |
| issn | 2405-8440 |
| language | English |
| last_indexed | 2024-12-19T19:39:09Z |
| publishDate | 2020-09-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Heliyon |
| spelling | doaj.art-19d831eb1c83465bad8c0dd6ce61a17c2022-12-21T20:08:18ZengElsevierHeliyon2405-84402020-09-0169e04938Micellar effects and analytical applications of nitro substitution in 4-Nitro-N-alkyl-1,8-naphthalimide by cysteine derivativesV.S. Martins0E.R. Triboni1J.B.S. Bonilha2L.M. Gonçalves3L. Mortara4L.A.C. Carvalho5B.R. Manda6C.D. Lacerda7F.C. Meotti8M.J. Politi9H. Chaimovich10I.M. Cuccovia11Departamento de Bioquímica, Instituto de Química, Universidade de São Paulo, BrazilEscola de Engenharia de Lorena da Universidade de São Paulo, Departamento de Engenharia Química (DEQUI), Lorena, SP, BrazilFaculdade de Filosofia Ciências e Letras da Universidade de São Paulo, FFCLRP, Ribeirão Preto, SP, BrazilDepartamento de Bioquímica, Instituto de Química, Universidade de São Paulo, BrazilDepartamento de Bioquímica, Instituto de Química, Universidade de São Paulo, BrazilDepartamento de Bioquímica, Instituto de Química, Universidade de São Paulo, BrazilDepartamento de Bioquímica, Instituto de Química, Universidade de São Paulo, BrazilDepartamento de Bioquímica, Instituto de Química, Universidade de São Paulo, BrazilDepartamento de Bioquímica, Instituto de Química, Universidade de São Paulo, BrazilDepartamento de Bioquímica, Instituto de Química, Universidade de São Paulo, BrazilDepartamento de Bioquímica, Instituto de Química, Universidade de São Paulo, BrazilDepartamento de Bioquímica, Instituto de Química, Universidade de São Paulo, Brazil; Corresponding author.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.http://www.sciencedirect.com/science/article/pii/S2405844020317813Analytical chemistryOrganic chemistryThiol levelsMicellar solutionsFluorescence assayProtein thiols |
| spellingShingle | V.S. Martins E.R. Triboni J.B.S. Bonilha L.M. Gonçalves L. Mortara L.A.C. Carvalho B.R. Manda C.D. Lacerda F.C. Meotti M.J. Politi H. Chaimovich I.M. Cuccovia Micellar effects and analytical applications of nitro substitution in 4-Nitro-N-alkyl-1,8-naphthalimide by cysteine derivatives Heliyon Analytical chemistry Organic chemistry Thiol levels Micellar solutions Fluorescence assay Protein thiols |
| 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 | Analytical chemistry Organic chemistry Thiol levels Micellar solutions Fluorescence assay Protein thiols |
| url | http://www.sciencedirect.com/science/article/pii/S2405844020317813 |
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