Micellar effects and analytical applications of nitro substitution in 4-Nitro-N-alkyl-1,8-naphthalimide by cysteine derivatives

Author(s):Show less -

Martins, V. S. ; Triboni, E. R. ; Bonilha, J. B. S. ; Goncalves, 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.

• Document type: Journal article
• Source: HELIYON; v. 6, n. 9, p. 14-pg., 2020-09-01.

Abstract

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 x 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. (AU)

• FAPESP's process: 18/15214-0 - Polysilsesquioxane gels and assembly of organic crystals based on diimides and anions
• Grantee: Eduardo Rezende Triboni
• Support Opportunities: Scholarships abroad - Research
• FAPESP's process: 18/14898-2 - Investigations of the redox processes in inflammatory response and associated pathologies
• Grantee: Flavia Carla Meotti
• Support Opportunities: Research Grants - Young Investigators Grants - Phase 2
• FAPESP's process: 16/00709-8 - Interfacial chemistry: drugs, peptides and ezymes interactions with membrane models
• Grantee: Bhaskar Manda
• Support Opportunities: Scholarships in Brazil - Post-Doctoral
• FAPESP's process: 18/19838-8 - Decisive forces for the structure and stability of aggregates composed by synthetic surfactants: ion association selectivity to interfaces and vesicle formation
• Grantee: Laura Mortara
• Support Opportunities: Scholarships in Brazil - Doctorate (Direct)
• FAPESP's process: 11/18106-4 - Oxidation of uric acid by myeloperoxidase in inflammatory processes and the implications for cardiovascular disease
• Grantee: Flavia Carla Meotti
• Support Opportunities: Research Grants - Young Investigators Grants
• FAPESP's process: 15/10411-3 - Multi-User Equipment, previously approved in grant 2015/08166-5: stopped-flow
• Grantee: Iolanda Midea Cuccovia
• Support Opportunities: Multi-user Equipment Program
• FAPESP's process: 13/02195-3 - Analysis of the pro-inflammatory mechanisms of urate hydroperoxide in innate immunity: the participation of redox modulated proteins and the inflammassome pathway
• Grantee: Larissa Anastacio da Costa Carvalho
• Support Opportunities: Scholarships in Brazil - Doctorate