Dissipation of Pyrene‐Based Phenylboronic Acid‐Anchored Vesicular Self‐Assemblies: A Motif for Neurotransmitter Recognition

Abstract

The present article delineates an elegant strategy to develop vesicular self-assembly based bio-molecule recognition motif to sense particular class of neuro-chemicals. Pyrene based phenylboronic acid (PBA) tailored amphiphiles were synthesized that formed vesicular self-assemblies in aqueous solution. Molecular aggregation patterns and various non-covalent forces involved in the vesiculation process were analysed through microscopybased and spectroscopic techniques. The incorporation of PBA functionality in the amphiphilic backbone rendered di-ol sensitivity within the vesicular structures owing to its high affinity to bind reversibly with di-ol (catechol) moieties. Interestingly, the vesicular self-assemblies exhibited enhanced fluorescence signals in response to miniscule amounts of catecholamine-class neurotransmitters (dopamine, adrenaline, and noradrenaline) including L-3,4-dihydroxyphenylalanine (L-DOPA). Moreover, the vesicular aggregates underwent dissipation in presence of L-DOPA. This dissolution of well-ordered molecular arrangement along with fluorescence enhancement took place due to the probable formation of boronate-diol adduct. The soft materials failed to exhibit any physicochemical change in the presence of other neuro-chemicals devoid of a catechol moiety. Thus, the di-ol induced dissipation and fluorescent augmentation feature of the PBA tethered vesicular aggregates hoisted the soft-material as proficient biomarker for catecholamine class neurotransmitters.[a] Dr.

Biosensors with Boronic Acid-Based Materials as the Recognition Elements and Signal Labels

“…According to the principle of signal change, boronic acid-based fluorescent methods can be mainly divided into three categories: binding-induced fluorescent enhancement, aggregation-induced quenching or emission, and sandwich boronate-affinity biosensors ( Table 2 ). In addition, boronic acid-based fluorescent hydrogelators have been elaborately synthesized to prepare cis -diol-responsive hydrogel-based soft sensors for fluorescent sensing and controlled drug release [ 66 , 146 , 147 ]. Fluorescence boronic acid derivatives have been combined with non-invasive techniques to design novel devices for continuous physiological monitoring and bioimaging of cis -diol-containing species because of their advantages of high-resolution and real-time detection [ 148 ].…”

Self-Assembled Nanorods of Phenylboronic Acid Functionalized Pyrene for In Situ Two-Photon Imaging of Cell Surface Sialic Acids and Photodynamic Therapy

“…These complex and elegant molecular assemblies are inspiring for creating superior artificial nanosystems that can dramatically increase the biocompatibility, enhance the targeting specificity, and improve the therapeutic efficacy, thus being widely exploited in numerous applications including biosensors, cell imaging, and drug delivery. 37,38 In this work, we reported a self-assembled nanorod bearing PBA tags for in situ imaging and evaluation of SA expression on the surface of living cells. As shown in Scheme 1, the unit block molecule of 4-(4-(pyren-1-yl)butyramido) phenylboronic acid (Py-PBA) that is composed of a hydrophilic tail of PBA and a hydrophobic head of pyrene, was synthesized first.…”

“…Molecular self-assembly is the spontaneous organization of molecules into stable and well-defined structures through noncovalent interactions such as π–π stacking, hydrophobic interactions and hydrogen bonding, which is a burgeoning and powerful way for bottom-up fabrication of functional nanoscale materials for bioimaging and therapy applications. , Moreover, the assembled nanostructured materials can be precisely tuned in both shape and function by regulating the composite of the molecular building blocks and the self-assembly processes. , In addition, self-assembly can provide a platform for combining various functionalities into one system. These complex and elegant molecular assemblies are inspiring for creating superior artificial nanosystems that can dramatically increase the biocompatibility, enhance the targeting specificity, and improve the therapeutic efficacy, thus being widely exploited in numerous applications including biosensors, cell imaging, and drug delivery. , …”