Polydiacetylenyl beta-cyclodextrin based smart vesicles for colorimetric assay of arginine and lysine

Abstract

Selective visualization of arginine and lysine has been explored among 20 amino acids using the hybrid conjugate of beta-cyclodextrin (beta-CD) and polydiacetylene (PDA). The mono pentacosa-10,12-diynyl aminomethyl group was successfully coupled to either the primary or the secondary face of beta-CD, where mono-6-amino-6-deoxy-beta-CD or mono-3-amino-3-deoxy-beta-CD reacted with the N-hydroxysuccinimide ester of 10,12-pentacosadiynoic acid. In this combinatorial system, the cylindrical beta-cyclodextrin functions as a channel for the introduction of the cationic amino acids to the artificial membrane. The membrane perturbation and aggregation by the target amino acids could be exclusively visualized as a blue to red color change based on the responsive polydiacetylene domain. These interesting findings demonstrated that the developed beta-CD conjugated PDA system may offer a new method of cell-penetrating mechanism, a promising vector system, as well as impact the production industry of arginine or lysine.