7-Hydroxy-4-methyl-8-(4'-methylpiperazine-1'-yl)methyl coumarin: an efficient probe for fluorescence resonance energy transfer to a bioactive indoloquinolizine system

Abstract

Solvatochromic effects on the fluorescence behavior of 7-hydroxy-4-methyl-8-(4'-methyl-piperazine-1' yl)methylcoumarin (HMMC) was studied in different solvents. The fluorescence of HMMC was found to be highly sensitive to both the polarity and the protic character of the solvent. Exploiting the polarity-sensitive fluorescence property of HMMC, its excited-state dipole moment has been determined. Fluorescence (Förster) resonance energy transfer (FRET) process from HMMC to a potent bioactive molecule 3-acetyl-4-oxo-6,7-dihydro-12 H indolo-[2,3-a] quinolizine (AODIQ) was studied. From the determined K_SV and R₀ values, it is argued that a long-range dipole-dipole interaction is operating for the energy transfer mechanism. The energy transfer efficiency (E) and the distance between the acceptor and the donor (r₀) have been determined.