Synthesis of short and long-wavelength functionalised probes: amino acids' labelling and photophysical studies

Fluorescent labelling of alpha-amino acids at their N or C terminals in the main and lateral chains at short and long wavelengths was carried out in different ways. The N-[3-(naphthalen-1-ylamino)propanoyl I amino acid methyl esters synthesised showed strong fluorescence in the visible region (similar to 415 nm) of the electromagnetic spectrum. Condensation of these compounds with 5-diethylamino-2-nitrosophenol or 5-ethylamino-4-methyl-2-nitrosophenol produced the benzo[a]phenoxazine derivatives, with maximum emission wavelengths shifted to values higher than 644 nm. The synthesis of novel functionalised 5,9-diaminobenzo[a]phenoxazinium salts, by reaction of 5-ethylamino-4-methyl-2-nitrosophenol and N-substituted 1-naphthylamine and their use in the covalent labelling of the N or C terminals of valine, produced derivatives with long-wavelength emissions (644-653 nm). Photophysical studies using the synthesised compounds both in different solvents and in controlled pH were undertaken. Preliminary evaluation of photostability of the cationic polycyclic heterocycles in ethanol and water at physiological pH was also performed. (c) 2007 Elsevier Ltd. All rights reserved.