Fluorescent probe with aggregation-induced emission characteristics for targeted labelling and imaging of cancer cells

Peng, Na; Xu, Rui; Si, Michelle; Victorious, Amanda; Ha, Emily; Chang, Chunyu; Xu, Xiaoding

doi:10.1039/c6ra25674k

Cited by 17 publications

(24 citation statements)

References 39 publications

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“…It was reported that the expression of SA on H22 tumor cells was 1.8-1.9 times that of hepatocytes 28 and the expression of SA on HepG2 tumor cells was 6 times that of normal liver tissue cells 33. To observe the cellular uptake ability of SPB NPs by the cells with different expression of SA, FITC-labeled SPB NPs were incubated with SH-SY5Y (SA-negative cells), H22 (SA-overexpressed cells) and HepG2 (SA-overexpressed cells) cell lines at 37 o C for 4 h and then observed by CLSM.…”

Section: Resultsmentioning

confidence: 97%

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Targeting and microenvironment-improving of phenylboronic acid-decorated soy protein nanoparticles with different sizes to tumor

Qian¹,

Ge²,

Yuan³

et al. 2019

Theranostics

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It is essential for nanoparticles to delivery drugs accurately and penetrate deeply to tumor. However, complicated tumor microenvironment such as elevated tumor interstitial fluid pressure (IFP) and solid stress reduces the transport efficiency of nanomedicines in tumor.Methods: We herein report a drug delivery system of phenylboronic acid-decorated soy protein nanoparticles with the size of 30 nm, 50 nm and 150 nm. In vitro examinations including cytotoxicity, cellular uptake and penetration in multicellular tumor spheroids and in vivo observations including IFP and tumor solid stress measurements and antitumor activity were performed.Results: It was found that phenylboronic acid moiety could endow the nanoparticles actively targeting affinity to sialic acid (SA) which overexpressed in tumor cells. Simultaneously soy protein could improve tumor microenvironment such as reduction of IFP and tumor stress. Among the soy protein nanoparticles with different sizes, 30 nm-sized nanoparticles showed the best cellular uptake and highest cytotoxicity in vitro after loading doxorubicin (DOX). In vivo, 30 nm-sized nanoparticles showed the best tumor microenvironment improvement efficiency, leading to the enhanced drug accumulation and antitumor efficiency when combination with DOX.Conclusion: Our study introduces a bioactive nanoparticulate design strategy to actively target and significantly improve tumor microenvironment for enhanced cancer therapy.

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Section: Resultsmentioning

confidence: 97%

“…To systematically estimate the cellular uptake ability of SPB NPs, SH-SY5Y cell lines (normal SA expression), H22 cell lines (1.8-fold SA expression 28) and HepG2 cell lines (6-fold SA expression 33) were used. FITC was used to label SPB NPs.…”

Section: Methodsmentioning

confidence: 99%

Targeting and microenvironment-improving of phenylboronic acid-decorated soy protein nanoparticles with different sizes to tumor

Qian¹,

Ge²,

Yuan³

et al. 2019

Theranostics

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“…To evaluate the capability of Py-PBA NRs on the recognition and imaging of cell surface sialylated glycans, the Py-PBA NRs were incubated with human hepatic cancer cells (HepG2), which is known to express a high level of SA on the cell membrane. 47 As shown in Figure 3A-a, clear fluorescence signals on the cell membrane was observed after incubation with Py-PBA NRs for 30 min. By co-staining with DAPI, a nucleus-specific fluorescent probe, blue fluorescence from the cell nucleus and green fluorescence from the cell membrane further indicated that most of the nanorods were bound to the cell membrane, forming a ring-shaped pattern (Figure S13).…”

Section: ■ Results and Discussionmentioning

confidence: 82%

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

Liu

2021

Anal. Chem.

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Sialic acid (SA) plays important roles in various biological and pathological processes. Methods for monitoring and detection of SA are of great significance in terms of fundamental research, cancer diagnostics, and therapeutics, which are still limited until now. Here, a phenylboronic acid (PBA)-functionalized pyrene derivative, 4-(4-(pyren-1-yl)butyramido)phenylboronic acid (Py-PBA), was synthesized and used as a building block for selfassembling into hydrophilic nanorods. The Py-PBA nanorods (Py-PBA NRs) featured highly specific and efficient imaging of SA on living cells with the advantages of excellent fluorescence stability, good biocompatibility, and unique two-photon fluorescence properties. Meanwhile, the assembled Py-PBA NRs could efficiently generate 1 O 2 under two-photon irradiation, making it an excellent candidate for photodynamic therapy. This nanoplatform realized in situ recognition and two-photon imaging of SA on the cell surface as well as effective cancer cell therapy, providing a potential method for simple and selective analysis of SA in living cells and a new prospect for image-guided therapy.

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“…This mechanism has been reported previously. 33 Furthermore, the d -ribose-induced dissociation of the nanoassembly was also evidenced by a dynamic light scattering (DLS) study to measure particle dimensions, in which the incorporation of d -ribose formed precise ensembles with smaller dimensions (from 2461 to 1081 nm), as shown in Figure 8.…”

Section: Resultsmentioning

confidence: 96%

2-(4-Boronophenyl)quinoline-4-carboxylic acid derivatives: Design and synthesis, aggregation-induced emission characteristics, and binding activity studies for D-ribose with long-wavelength emission

Fang

Wang

Bian

et al. 2019

Journal of Chemical Research

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Long-wavelength fluorescent sensors with large Stokes shifts show useful applications in chemical biology and clinical laboratory diagnosis. We have recently reported [4-(4-{[3-(4-boronobenzamido)propyl]carbamoyl}quinolin-2-yl)phenyl]boronic acid that can selectively recognize d-ribose in a buffer solution of pH 7.4. However, the short emission wavelength (395 nm) and aggregation-caused quenching effect are not conducive to applications as a sensor. Novel diboronic acid compounds are synthesized using 2-(4-boronophenyl)quinoline-4-carboxylic acid as the building block and p-phenylenediamine as the linker. These compounds show aggregation-induced emission and fluorescence emission at about 500 nm. In addition, after binding to most carbohydrates, the aggregated state of the boronic acid–containing compounds is dissociated, resulting in fluorescence quenching. Using [4-(4-{[4-(3-borono-5-methoxybenzamido)phenyl]carbamoyl}quinoline-2-yl)phenyl]boronic acid as an example, addition of 55 mM of d-ribose resulted in the strongest quenching of 83% for all the tested carbohydrates, indicating selectively recognizing d-ribose. The reciprocal of the fluorescence intensity change showed a good linear relationship with the reciprocal of d-ribose concentration ( R2 ⩾ 0.99), indicating sensor binding to d-ribose in a ratio of 1:1 to form an inclusion complex. The fluorescence emission is red-shifted compared to 2-(4-boronophenyl)quinoline-4-carboxylic acid and its common derivatives, which provides a new method for the development of long-wavelength fluorescent sensors.

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Fluorescent probe with aggregation-induced emission characteristics for targeted labelling and imaging of cancer cells

Cited by 17 publications

References 39 publications

Targeting and microenvironment-improving of phenylboronic acid-decorated soy protein nanoparticles with different sizes to tumor

Targeting and microenvironment-improving of phenylboronic acid-decorated soy protein nanoparticles with different sizes to tumor

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

2-(4-Boronophenyl)quinoline-4-carboxylic acid derivatives: Design and synthesis, aggregation-induced emission characteristics, and binding activity studies for D-ribose with long-wavelength emission

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