| Autor: |
Rigby EL; Department of Chemistry and Biochemistry, Oberlin College, Oberlin, Ohio 44074, United States., Saylor RA; Department of Chemistry and Biochemistry, Oberlin College, Oberlin, Ohio 44074, United States. |
| Jazyk: |
angličtina |
| Zdroj: |
Analytical chemistry [Anal Chem] 2023 Oct 10; Vol. 95 (40), pp. 14889-14897. Date of Electronic Publication: 2023 Sep 28. |
| DOI: |
10.1021/acs.analchem.3c01900 |
| Abstrakt: |
Dopamine (DA) and serotonin (5-HT) are neurotransmitters that are vital for proper brain function and are implicated in a wide variety of diseases and disorders. Unfortunately, quantitative analysis of DA and 5-HT is difficult, as they are present at low concentrations in complex biological matrices. The fluorogenic reaction of napththalene-2,3-dicarboxaldehyde (NDA) with a primary amine in the presence of cyanide (CN) creates an N-substituted 1-cyanobenz[ f ]isoindole (CBI) derivative, whose fluorescence can be sensitively monitored in biological matrices. Given their biological importance, there are surprisingly few reports showing fluorescence of CBI-DA and no prior publications concerning CBI-5-HT. In this work, nuclear magnetic resonance spectroscopy (NMR) was employed to determine the atom connectivity of over 10 CBI-products, including CBI-DA and CBI-5-HT. NMR and fluorescence spectroscopy were applied to CBI-DA, CBI-5-HT, and select structural analogs to determine structural correlations with the observed lack of fluorescence. Experiments with CBI-DA and structural analogs indicated fluorescence was rapidly quenched due to both complexation with the historically employed buffer and oxidation in solution. Fluorescence of CBI-DA was recovered by modifying the derivatization background to prevent complexation and oxidation. In contrast, fluorescence characterization of CBI-5-HT and its structural analogs indicated that 5-HT was acting as a quencher of the CBI-ring. The addition of acid to protonate 5-HT was found to disrupt this interaction and enable the first reported fluorescence detection of CBI-5-HT. In the future, this work will be applied to detect DA and 5-HT in biological systems to gain insight into neurobiological disease states and disorders. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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