Fluorescent photoremovable precursor (acridin-9-ylmethyl)ester: synthesis, photophysical, photochemical and biological applications

Abstract

A series of carboxylic acids including amino acids were protected as their corresponding fluorescent ester conjugates by coupling with an environment sensitive fluorophore 9-methylacridine. Photophysical properties of all the ester conjugates along with the protecting group have been investigated. Interestingly, the emission properties of the ester conjugates and 9-methylacridine were found to be highly sensitive to polarity, H-bonding and pH of the environment. Photolysis of all the ester conjugates was carried out using UV light above 360 nm and it was found that in every case the corresponding carboxylic acids were released in high chemical yield. Further, intercalation and the preferred binding mode of acridine-9-methanol and its ester conjugates with DNA were studied. In vitro biological studies revealed that acridine-9-methanol has good biocompatibility, cellular uptake property and cell imaging ability.