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  • Royal Society of Chemistry (RSC)  (6)
  • Zhang, Gang  (6)
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  • Royal Society of Chemistry (RSC)  (6)
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  • 1
    Online Resource
    Online Resource
    Conjugated structures based on quinazolinones and their application in fluorescent labeling
    Royal Society of Chemistry (RSC) ; 2023
    In:  Organic & Biomolecular Chemistry Vol. 21, No. 9 ( 2023), p. 1992-2000
    Details
    In: Organic & Biomolecular Chemistry, Royal Society of Chemistry (RSC), Vol. 21, No. 9 ( 2023), p. 1992-2000
    Abstract: As an alkaloid, quinazolinone exhibits excellent biological properties; structurally, it also has the potential to construct fluorescent probes with conjugated structures. In this work, probes 5a–c and 6b were obtained by introducing quinazolone into aldehydes with different numbers of double bonds. Their absorption maxima were located at 420–540 nm and their emission maxima were at 500–600 nm in solvents of different polarities. In particular, probe 5c showed significant fluorescence enhancement with the increase in viscosity due to the limited intramolecular rotation, and its fluorescence intensity in glycerol was 37.8 times higher than that in water. Moreover, probes 5a–c and 6b containing the N H structure showed sensitive response to pH, and their fluorescence intensity in alkaline solution (pH 9–11) was suddenly enhanced, which was elucidated with the help of theoretical calculation. In addition, the cell experiments showed that probes 5a and 5b had the ability to target mitochondria and probes 5c and 6b targeted lysosomes in HeLa cells. Furthermore, the viscosity-sensitive probe 5c could be used for monitoring changes in lysosomal viscosity in HeLa cells, which had important guiding significance for designing multi-response fluorogenic probes and promoting the advancement of cancer diagnosis.
    Type of Medium: Online Resource
    ISSN: 1477-0520 , 1477-0539
    URL: Article
    DOI: 10.1039/D2OB02293A
    Language: English
    Publisher: Royal Society of Chemistry (RSC)
    Publication Date: 2023
    detail.hit.zdb_id: 2097583-1
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  • 2
    Online Resource
    Online Resource
    Fluorescent probes based on acridine derivatives and their application in dynamic monitoring of cell polarity variation
    Royal Society of Chemistry (RSC) ; 2022
    In:  The Analyst Vol. 147, No. 22 ( 2022), p. 5231-5238
    Details
    In: The Analyst, Royal Society of Chemistry (RSC), Vol. 147, No. 22 ( 2022), p. 5231-5238
    Abstract: Polarity and viscosity, as important microenvironment parameters, play an essential role in cell metabolism. Therefore, 9-acridine carboxaldehyde reacted with cyano compounds to obtain polarity-sensitive probes 1a–b and viscosity-sensitive probes 1c–d. Among them, with the increase in solvent polarity, the maximum emission wavelength of acridine-dicyanoisophorone-based probe 1a red-shifted from 553 nm to 594 nm, the fluorescence quantum yield increased from 0.5% to 35.6%, and the fluorescence intensity enhanced 38 fold. The acridine-cyanofuranone based probe 1b also has a polarity response similar to 1a. Nevertheless, when the solution viscosity increased from 0.89 cP (100% water) to 856 cP (1% water), the fluorescence intensity of the acridine-tricyanodihydrofuran based probe 1c at 430 nm enhanced 5.6 times. The acridine-cyanobenzothiazole based probe 1d also had a viscosity response similar to 1c. In addition, probes 1a–b were used for further HeLa cell imaging experiments due to their good photostability and the results suggested that probe 1a could locate lipid droplets and probes 1b–c could stain lysosomes. Moreover, probes 1a–b could dynamically monitor the changes in intracellular polarity.
    Type of Medium: Online Resource
    ISSN: 0003-2654 , 1364-5528
    URL: Article
    DOI: 10.1039/D2AN01449A
    Language: English
    Publisher: Royal Society of Chemistry (RSC)
    Publication Date: 2022
    detail.hit.zdb_id: 1472713-4
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  • 3
    Online Resource
    Online Resource
    Distinguishing cancer cells from normal cells with an organelle-targeted fluorescent marker
    Royal Society of Chemistry (RSC) ; 2022
    In:  Journal of Materials Chemistry B Vol. 10, No. 30 ( 2022), p. 5796-5803
    Details
    In: Journal of Materials Chemistry B, Royal Society of Chemistry (RSC), Vol. 10, No. 30 ( 2022), p. 5796-5803
    Abstract: In this paper we report a hemicyanine dye that is used to distinguish cancer cells from normal cells with its ability to target different organelles. Probe 1, a red emission hemicyanine functional dye, was connected to oxazolo[4,5- b ]pyridine and diethylaminobenzene with a double bond. The maximum absorption peaks of probe 1 were located in the 509–552 nm range in organic solvents. Meanwhile, the probe possessed a high molar extinction coefficient (5.50 × 10 4 M −1 cm −1 in DMSO) with high photostability. The maximum emission wavelength of the probe ranged from 572 nm to 644 nm, and it also had a large Stokes shift (126 nm in DMSO). In particular, the probe showed weak fluorescence in water ( Φ = 0.016), whereas it displayed strong fluorescence at 595 nm in β-cyclodextrin (β-CD) solution ( Φ = 0.13). In addition, cell colocalization experiments showed that probe 1 (3 μM) was located in the endoplasmic reticulum in cancer cells, while it could target lysosomes in normal cells. What's more, further cell imaging experiments demonstrated that the average fluorescence intensity of probe 1 (0.3 μM) in cancer cells increased with the addition of β-CD, but it did not occur in normal cells. The study provides a convenient way to distinguish cancer cells from normal ones, which has potential for application in the early detection of cancer.
    Type of Medium: Online Resource
    ISSN: 2050-750X , 2050-7518
    URL: Article
    DOI: 10.1039/D2TB01351G
    Language: English
    Publisher: Royal Society of Chemistry (RSC)
    Publication Date: 2022
    detail.hit.zdb_id: 2702241-9
    detail.hit.zdb_id: 2705149-3
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  • 4
    Online Resource
    Online Resource
    Viscosity probes towards different organelles with red emission based on an identical hemicyanine structure
    Royal Society of Chemistry (RSC) ; 2023
    In:  The Analyst Vol. 148, No. 18 ( 2023), p. 4463-4469
    Details
    In: The Analyst, Royal Society of Chemistry (RSC), Vol. 148, No. 18 ( 2023), p. 4463-4469
    Abstract: A series of viscosity probes targeting different organelles were obtained using a single hemicyanine dye as the matrix structure. Specifically, probes 1a–d were obtained by introducing four amines (6-amino-2 H -chromen-2-one, N -(2-aminoethyl)-4-methylbenzenesulfonamide, dodecan-1-amine and N , N diphenylbenzene-1,4-diamine) into the indole hemicyanine dye of the carboxylic acid with a D–π-A structure. Their maximum absorption wavelengths were in the range 570–586 nm and they had relatively large molar absorption coefficients, while their maximum emission wavelengths in the red light region were in the range 596–611 nm. Moreover, their fluorescence intensity in glycerol was 35–184 times higher than that in phosphate buffer solution (PBS). The lg(Fl) and lg  η of probes 1a–d showed good linearity with high correlation coefficients according to the Förster–Hoffman equation. In addition, cell staining experiments demonstrated that 1a–c could target lysosomes, endoplasmic reticulum and mitochondria, respectively. They could also undergo viscosity-detectable changes in the corresponding organelles under the action of the corresponding ion carriers.
    Type of Medium: Online Resource
    ISSN: 0003-2654 , 1364-5528
    URL: Article
    DOI: 10.1039/D3AN00550J
    Language: English
    Publisher: Royal Society of Chemistry (RSC)
    Publication Date: 2023
    detail.hit.zdb_id: 1472713-4
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  • 5
    Online Resource
    Online Resource
    Near-infrared fluorescent probes based on a quinoxaline skeleton for imaging nucleic acids in mitochondria
    Royal Society of Chemistry (RSC) ; 2022
    In:  Organic & Biomolecular Chemistry Vol. 20, No. 28 ( 2022), p. 5558-5565
    Details
    In: Organic & Biomolecular Chemistry, Royal Society of Chemistry (RSC), Vol. 20, No. 28 ( 2022), p. 5558-5565
    Abstract: In this paper, two cationic probes 1a and 1b and a neutral dye 1c were successfully designed and synthesized according to the Knoevenagel condensation reaction, which combines the good optical properties of hemocyanine and the biocompatibility of nitrogen-containing heterocyclic rings based on a quinoxaline skeleton. Probes 1a and 1b showed an OFF–ON fluorescence response to nucleic acids with excellent selectivity. Specifically, the fluorescence intensity of probe 1a was enhanced by 18 and 133 times, respectively, along with the increase of DNA or RNA concentrations (0–600 μg mL −1 ). Furthermore, a good linear correlation between the fluorescence intensity of probes 1a and 1b and the concentrations of DNA or RNA (0–350 μg mL −1 ) was obtained. In particular, the maximum emission wavelengths of probes 1a and 1b reached the near-infrared region (660–664 nm) when DNA or RNA was detected, which might reduce the light damage to cells and facilitate cell experiments. Fluorescence imaging revealed that all three dyes could be localized in the mitochondria of HeLa cells. The difference was that probes 1a and 1b could stain the nucleic acid in the mitochondria, while dye 1c was only a neutral mitochondrial biomarker. The results indicated that probes 1a and 1b are promising in the development of low toxicity mitochondrial nucleic acid probes and are expected to be used in monitoring the normal state of mitochondrial nucleic acids for living cells, which will help improve the situation in that currently reported studies of fluorescent probes are mainly focused on the nucleic acids in the nucleus, but less so on DNA in the mitochondria.
    Type of Medium: Online Resource
    ISSN: 1477-0520 , 1477-0539
    URL: Article
    DOI: 10.1039/D2OB01095J
    Language: English
    Publisher: Royal Society of Chemistry (RSC)
    Publication Date: 2022
    detail.hit.zdb_id: 2097583-1
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  • 6
    Online Resource
    Online Resource
    Multiple organelle-targeted 1,8-naphthyridine derivatives for detecting the polarity of organelles
    Royal Society of Chemistry (RSC) ; 2023
    In:  Journal of Materials Chemistry B Vol. 11, No. 30 ( 2023), p. 7134-7143
    Details
    In: Journal of Materials Chemistry B, Royal Society of Chemistry (RSC), Vol. 11, No. 30 ( 2023), p. 7134-7143
    Abstract: Four 1,8-naphthyridine derivatives (1a–1d) with different organelle targeting abilities were obtained using the Knoevenagel condensation reaction of 1,8-naphthyridine with 4-( N , N -diethylamino)benzaldehyde (2a), 4-( N , N -diphenylamino)benzaldehyde (2b), 4-(piperazin-1-yl)benzaldehyde (2c) and 4-(ethyl(4-formylphenyl)amino)- N -(2-((4-methylphenyl)sulfonamido)ethyl)butanamide (2d), respectively. The maximal absorption bands of dyes 1a–1d were observed at 375–447 nm, while their maximum emission peaks were situated at 495–605 nm. The optical properties showed that the fluorescence emission of dyes 1a–1d is shifted toward greater wavelengths as the system polarity (Δ f ) increased. Meanwhile, with increasing polarity of the mixed 1,4-dioxane/H 2 O system, the fluorescence intensity of dyes 1a–1d gradually decreased. Furthermore, the fluorescence intensity of 1a–1d enhanced by 12–239 fold as the polarity of 1,4-dioxane/H 2 O mixtures declined. 1a–1d had a large Stokes shift (up to 229 nm) in polar solvents in comparison to nonpolar solvents. The colocalization imaging experiments demonstrated that dyes 1a–1d (3–10 μM) were located in mitochondria, lipid droplets, lysosomes and the endoplasmic reticulum in living HeLa cells, respectively; and they could monitor the polarity fluctuation of the corresponding organelles. Consequently, this work proposes a molecular design idea with different organelle targeting capabilities based on the same new fluorophore, and this molecular design idea may provide more alternatives for polarity-sensitive fluorescent probes with organelle targeting.
    Type of Medium: Online Resource
    ISSN: 2050-750X , 2050-7518
    URL: Article
    DOI: 10.1039/D3TB00601H
    Language: English
    Publisher: Royal Society of Chemistry (RSC)
    Publication Date: 2023
    detail.hit.zdb_id: 2702241-9
    detail.hit.zdb_id: 2705149-3
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