FLUORESCENCE HISTOCHEMISTRY OF BIOGENIC MONOAMINES A STUDY OF THE CAPACITY OF VARIOUS CARBONYL COMPOUNDS TO FORM FLUOROPHORES WITH BIOGENIC MONOAMINES IN GAS PHASE REACTIONS

Abstract

The capacity of biogenic amines to form fluorophores in histochemical gas phase reactions has been tested with 20 compounds having a carbonyl group (> C = O) as a common characteristic. Significant visible fluorescence was induced from catecholamines and indolamines with aldehydes, ketones, α-keto acids and carboxylic acids, suggesting that all of these compounds can enter fluorophore-forming cyclization reactions under the histochemical gas phase conditions. The most "reactive" reagents are found among the low molecular aldehydes, and formaldehyde and glyoxylic acid seem to be the most suitable reagents, combining high reactivity with good selectivity. Fluorescence, interesting for the histochemical demonstration of N-acetylated indolamines, was obtained from melatonin and N-acetyl-5-hydroxytryptamine with some acid reagents (glyoxylic acid, formic acid, acetic acid and pyruvic acid). A direct cyclodehydration according to the classical Bischler-Napieralski reaction is the most likely mechanism underlying this fluorophore formation. The usefulness of the various carbonyl reagents for the fluorescence histochemical demonstration of other biologically interesting amines, such as histamine, p-tyramine and octopamine, has been specially investigated.