Spectroscopic behavior of pyrrolanthrone and its derivative in aprotic and protic solvents

Abstract

Recently synthesized pyrrolanthrone, naphtho[1,2,3-cd]indole-6(2H)-one (PyAn), and its water-soluble derivative, 3(naphtho[1,2,3-cd]indole-6(2H)-one-2-yl) sodium propylsulfonate, are very promising for anticancer therapy due to both the fluorescent and cytotoxic properties. The present study is focused on the spectroscopic analysis of solvent effects in PyAn and its derivative. An increase of the solvent polarity results in the bathochromic shift in emission and absorption spectra that indicates the involvement of ππ∗-type transition. The double linear correlation of Stokes shift with bulk solvent polarity functions (in terms of Lippert's, Bakhshiev's and Chamma-Viallet's models) and microscopic solvent polarity parameter E(30)T for aprotic and protic solvents is observed. Both general and specific solvent effects are revealed for the solute-solvent systems. Fluorescence quantum yield, fluorescence lifetime and excited-state dipole moment were defined for PyAn and its derivative in different solvents for the first time. The obtained information is of a great importance for the characterization of intermolecular interactions of drugs with biomolecules for the development of new drug delivery systems.