Synthesis of novel fluorescent 1,3,5-trisubstituted triazine derivatives and photophysical property evaluation of fluorophores and their BSA conjugates

摘要

Cyanuric chloride was allowed to react with N,N - diethylaniline to obtain 4-(4,6-dichloro-1,3,5-triazin-2-yl)- N,N -diethylaniline, which was converted into six novel 1,3,5-trisubstituted triazine derivatives on reaction with different amino acids. These compounds had UV absorption in the range 352 - 379 nm, accompanied by intense single emission in the range 420 - 497 nm with fairly good quantum yield (0.106 - 0.383). The new compounds were characterized by FT-IR, ~1H NMR, ~(13)C NMR, mass spectral, and elemental analyses. These fluorophor es were conjugated with protein bovine serum albumin through carbodiimide chemistry between the negatively charged carboxylate groups (-COO-) of the fluorophore and the surface terminated positively charged amino groups (-NH _3 ~+) of the protein. The interaction between functionalized amino acids with protein molecules was investigated using fluorescence spectroscopy showing fluorescence enhancement or quenching of the fluorophore after conjugation.