Abstract
Selective visualization of arginine and lysine has been explored among 20 amino acids using the hybrid conjugate of β-cyclodextrin (β-CD) and polydiacetylene (PDA). The mono pentacosa-10,12-diynyl aminomethyl group was successfully coupled to either the primary or the secondary face of β-CD, where mono-6-amino-6-deoxy-β-CD or mono-3-amino-3-deoxy-β-CD reacted with the N-hydroxysuccinimide ester of 10,12-pentacosadiynoic acid. In this combinatorial system, the cylindrical β-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 β-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.
Highlights
Selective visualization of arginine and lysine has been explored among 20 amino acids using the hybrid conjugate of β-cyclodextrin (β-CD) and polydiacetylene (PDA)
PDA has been utilized as a fascinating sensor platform for interesting target molecules such as antimicrobial peptides, oligonucleotides, and volatile organic acids[11,12,13]; here, we have designed a novel functionalized PDA with β-CD having inclusion capability, and it is evaluated as smart PDA vesicles showing selective colorimetric response targeting amino acids
The determination of certain amino acids has been reported based on liquid chromatography[23], ampherometry[24], and gold nanoparticles[25], it is still of great interest to develop a rapid, selective, inexpensive and simple handling methods
Summary
In the β-CD conjugated PDA vesicles in this study, β-CD might offer a promising path of the cationic amino acids into the membrane surface, facilitating the ionic interactions and hydrogen bonds with the carboxylic head groups. Upon the addition of arginine, the blue to red color transition was observed, and the average size could not be detectable in DLS (Fig. 7B) This result represents aggregation or disruption of β-CD conjugated PDA vesicles in the presence of arginine. Following the addition of adamantane carboxylate, the spherical morphology was retained, but the larger size and a more concerted state were observed in the vesicle solution (Fig. 8C). Since bulky PDA chain occupies primary rim space of β-CD, the arginine/6 PCD β-CD complexes are able to interact with each other by their secondary face This secondary face interaction between 6 PCD-β-CDs can be stabilized by extra hydrogen bonding between guest arginine molecules (Fig. 9A). It would provide a new platform for antimicrobial activity, a promising delivery system as well as a novel method for the production industry of arginine or lysine
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