Rational tuning of binding properties of pillar [5] arene-based sensing material by synergistic effect and its application for fluorescent turn-on detection of isoniazid and controlled reversible morphology.

ABSTRACT

Isoniazid (INH) is crucial in the treatment of tuberculosis; however, its overuse may induce significant gastrointestinal and hepatic side effects. On October 27, 2017, the International Agency for Research on Cancer, under the auspices of the World Health Organization, published a list of carcinogens for preliminary collation and reference. Isoniazid was categorized as a Group 3 carcinogen. The efficient detection of INH poses an important and challenging task. In this study, a "synergistic effect" is incorporated into the pillar (Yamagishi and Ogoshi, 2018) [5] arene-based macrocyclic host (DPA) by strategically attaching bis-p-hydroxybenzoic acid groups to the opposite ends of the pillar (Yamagishi and Ogoshi, 2018) [5] arene. This combination endows DPA with a reversible and selective fluorescence response to isoniazid. Additionally, DPA exhibits excellent analytical capabilities for isoniazid, including speed and selectivity, with a detection limit as low as 4.85 nM. Concurrently, DPA can self-assemble into a microsphere structure, which is convertible into micrometer-sized tubular structures through host-guest interactions with isoniazid. The introduction of a competitive guest, trimethylamine, enables the reversion to its microsphere structure. Consequently, this study presents an innovative and straightforward synthetic approach for smart materials that facilitates the reversible morphological transition between microspheres and microtubes in response to external chemical stimuli. This discovery provides a valuable strategy for designing "synergistic effects" in constructing trace-level isoniazid-responsive interfaces, with potential applications across various fields, such as controlled drug delivery.