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

Li, Ting; Liu, Yang

doi:10.1021/acs.analchem.1c00118

Cited by 22 publications

(21 citation statements)

References 62 publications

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“…In aqueous basic media, sp 2 -hybridized trigonal planar PBA groups can be converted into sp 3 -hybridized tetrahedral phenylborates, , with which the reaction of the cis -1,2 and 1,3-diol sites of saccharides generates the covalent five- or six-membered rings, respectively. , That is, the covalent coupling between the PBA groups and the cis -diol sites can be greatly facilitated by a basic medium with a pH above the p K a of the PBA group . Accordingly, the boronate affinity-based site-specific labeling of target glycoproteins is pH-dependent.…”

Section: Resultsmentioning

confidence: 99%

Boronate Affinity-Based Electrochemical Aptasensor for Point-of-Care Glycoprotein Detection

et al. 2022

Anal. Chem.

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As a class of oligosaccharide chain-containing proteins, glycoproteins are of great value in screening and early diagnosis of malignant tumors and other major diseases. Herein, we report a universal boronate affinity-based electrochemical aptasensor for point-of-care glycoprotein detection. Aptasensing of glycoproteins involves the specific recognition and capture of target glycoproteins by end-tethered nucleic acid aptamers and the site-specific labeling of ferrocene tags via the phenylboronic acid (PBA)-based boronate affinity interactions because the cis-diol sites of oligosaccharide chains on glycoproteins can selectively react with the PBA receptor groups to form cyclic phenylborates in aqueous basic media. Due to the presence of hundreds to thousands of cis-diol sites on a glycoprotein, a large number of ferrocene tags can be recruited for the signal-on aptasensing of glycoproteins at a low-abundance level, eliminating the need for extra amplification strategies. As a result, the boronate affinity-based electrochemical aptasensor is highly sensitive and selective for glycoprotein detection and tolerant to the false-positive results. The detection limit for α-fetoprotein (AFP) is 0.037 ng/mL, with a linear response ranging from 0.1 to 100 ng/mL. In addition to the merits of simple operation, short assay time, and low detection cost, the aptasensor is applicable to the detection of glycoproteins in serum samples and the point-of-care detection using disposable flexible electrodes. Overall, this work provides a universal and promising platform for the point-of-care detection of glycoproteins, holding great potential in screening and early diagnosis of glycoprotein-related malignant tumors and other major diseases.

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Section: Resultsmentioning

confidence: 99%

Boronate Affinity-Based Electrochemical Aptasensor for Point-of-Care Glycoprotein Detection

et al. 2022

Anal. Chem.

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“…Li et al demonstrated self-assembly of the amphiphilic 4-(4-(pyren-1-yl)butyramido)phenylboronic acid ( Py-PBA ) in a nanorod (NR) shape in DMSO-water mixture and applied in intracellular two-photon imaging of the sialic acid (SA; plays vital role in many biological and pathological processes) [ 92 ]. The monomer emission of the Py-PBA was at 400 nm.…”

Section: Aie Active Pyrene Conjugates For Bioimagingmentioning

confidence: 99%

Pyrene-Based AIE Active Materials for Bioimaging and Theranostics Applications

Shellaiah

Sun

2022

Biosensors

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Aggregation-induced emission (AIE) is a unique research topic and property that can lead to a wide range of applications, including cellular imaging, theranostics, analyte quantitation and the specific detection of biologically important species. Towards the development of the AIE-active materials, many aromatic moieties composed of tetraphenylethylene, anthracene, pyrene, etc., have been developed. Among these aromatic moieties, pyrene is an aromatic hydrocarbon with a polycyclic flat structure containing four fused benzene rings to provide an unusual electron delocalization feature that is important in the AIE property. Numerous pyrene-based AIE-active materials have been reported with the AIE property towards sensing, imaging and theranostics applications. Most importantly, these AIE-active pyrene moieties exist as small molecules, Schiff bases, polymers, supramolecules, metal-organic frameworks, etc. This comprehensive review outlines utilizations of AIE-active pyrene-based materials on the imaging and theranostics studies. Moreover, the design and synthesis of these pyrene-based molecules are delivered with discussions on their future scopes.

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“…The above contents demonstrated the imaging ability of PBA-functionalized polymers to glycoprotein-overexpressing cancer cells and developed a controllable imaging system for biological applications. To improve the selectivity of PBA-functionalized small molecules, Li et al designed and synthesized PBA-functionalized pyrene derivatives (Py-PBA) and formed nanorods through self-assembly (Py-PBA NRs) . (Figure B) Py-PBA NRs could bind specifically to SA, which could help Py-PBA NRs locate and image on the cell membrane.…”

Section: Fluorescence Imagingmentioning

confidence: 99%

Section: Fluorescence Imagingmentioning

confidence: 99%

Phenylboronic-acid-based Functional Chemical Materials for Fluorescence Imaging and Tumor Therapy

Hou

et al. 2022

ACS Omega

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Various functional chemical materials have been widely used in imaging and tumor therapy. Targeted ligands such as antibodies, peptides, and small molecules have been combined with functional materials to enhance cellular uptake and are used for active targeting of cancer cells and tumors. Among them, phenylboronic acid (PBA), as a small molecular ligand, has the characteristics of low cytotoxicity and easy modification. PBA improves the cancer cell imaging and tumor treatment effect by binding to glycans on the surface of cancer cells. In this Mini-Review, we introduced the modification strategy and targeting strategy of PBA. We focused on the applications of PBA-based functional materials in fluorescence imaging and tumor therapy. For fluorescence imaging, the potential of PBA-based functional chemical materials in cancer diagnosis and tumor targeting was proved by cell imaging and in vivo imaging. For tumor therapy, we mainly discussed the applications of PBA-based functional chemical materials in chemotherapy, gene therapy, phototherapy, and immunotherapy. PBA-based functional chemical materials provide a useful method for cancer diagnosis and treatment.

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

Cited by 22 publications

References 62 publications

Boronate Affinity-Based Electrochemical Aptasensor for Point-of-Care Glycoprotein Detection

Boronate Affinity-Based Electrochemical Aptasensor for Point-of-Care Glycoprotein Detection

Pyrene-Based AIE Active Materials for Bioimaging and Theranostics Applications

Phenylboronic-acid-based Functional Chemical Materials for Fluorescence Imaging and Tumor Therapy

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