Schiff and pseudo-Schiff reagents: the reactions and reagents of Hugo Schiff, including a classification of various kinds of histochemical reagents used to detect aldehydes
| Autor: | RW Dapson |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
0301 basic medicine
Models Molecular Reaction mechanism Histology Imine Rosaniline Dyes Aldehyde Adduct 03 medical and health sciences chemistry.chemical_compound Organic chemistry Coloring Agents chemistry.chemical_classification Aldehydes 030102 biochemistry & molecular biology Staining and Labeling Histocytochemistry General Medicine Medical Laboratory Technology 030104 developmental biology chemistry Reagent Aminal Schiff test Indicators and Reagents |
| Zdroj: | Biotechnichistochemistry : official publication of the Biological Stain Commission. 91(8) |
| ISSN: | 1473-7760 |
| Popis: | During the 1860's, Hugo Schiff studied many reactions between amines and aldehydes, some of which have been used in histochemistry, at times without credit to Schiff. Much controversy has surrounded the chemical structures and reaction mechanisms of the compounds involved, but modern analytical techniques have clarified the picture. I review these reactions here. I used molecular modeling software to investigate dyes that contain primary amines representing eight chemical families. All dyes were known to perform satisfactorily for detecting aldehydes in tissue sections. The models verified the correct chemical structures at various points in their reactions and also determined how decolorization occurred in those with "leuco" forms. Decolorization in the presence of sulfurous acid can occur by either adduction or reduction depending on the dye. The final condensation product with aldehyde was determined to be either a C-sulfonic acid adduct on the carbonyl carbon atom or an aminal at the same atom. Based on the various outcomes, I have placed the dyes and their reactions into five categories. Because Hugo Schiff studied the reactions between aldehydes and amines with and without various acids or alcohol, it is only proper to call each of them Schiff reactions that used various types of Schiff reagents. |
| Databáze: | OpenAIRE |
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