Amino acid recognition by a fluorescent chemosensor based on cucurbit[8]uril and acridine hydrochloride

Abstract

A new fluorescent chemosensor comprised of cucurbit[8]uril (Q[8]) and acridine hydrochloride (AC) has been designed and utilized for the recognition of amino acids. The AC was encapsulated by the Q[8] cavity and formed a 1:2 host-guest inclusion complex both in solution (aqueous) and in the solid-state. Whilst free AC is known to be strongly fluorescent, this strong fluorescence was quenched in the inclusion complex Q [8]-AC. This non-fluorescent complex Q[8]-AC was capable of serving as a fluorescence "off-on" probe, and was able to recognize either L-Phe or L-Trp via the competitive interaction between L-Phe or L-Trp. Moreover, the pH responsive nature of the probe allowed for the detection of basic amino acids, namely L-Arg, L-His, or L-Lys). As a result, a fluorescence method for the detection of five amino acids using a single system has been developed.

Keywords: Chemosensor; Recognition; cucurbit[8]uril; pH-responsive; “Off-on” probe.