Synthesis and characterization of water-soluble polythiophene derivatives for cell imaging.

Abstract

In this work, four water-soluble polythiophene derivatives (PT, PT-DDA, PT-ADA, and PT-ADA-PPR) with different pendant moieties were synthesized via oxidative copolymerization by FeCl3. By increasing the hydrophobic ability of side chain moieties, there is a gradually blue shift for the maximum absorption wavelength and red shift for the maximum emission wavelength, a reducing trend for fluorescence quantum yields, a growing trend for Stokes shift, and an increasing trend for the mean sizes in the order of PT, PT-ADA, and PT-DDA. All the synthesized polymers show low toxicity and good photostability and accumulate in the lysosomes of A549 cells. Furthermore, the introduction of porphyrin group to PT-ADA side chain (PT-ADA-PPR) broadens the absorption and emission ranges of PT-ADA. PT-ADA-PPR could be excited at two different excitation wavelengths (488 nm and 559 nm) and exhibits two emission pathways, and dual-color fluorescence images (orange and red) of PT-ADA-PPR accumulated in A549 cells are observed. Thus, PT-ADA-PPR could be used as an excellent dual-color fluorescent and lysosome-specific imaging material.