A highly sensitive acidic pH fluorescent probe and its application to HepG2 cells

Zhang, Wenshen; Tang, Bo; Liu, Xia; Liu, Yuanyuan; Xu, Kehua; Ma, Jian‐Ping; Tong, Lili; Yang, Guangming

doi:10.1039/b807581f

Cited by 160 publications

(69 citation statements)

References 37 publications

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“…As has been demonstrated by von Steyern et al, RhB specifically accumulates in the lysosomes of denervated skeletal muscle (Vult von Steyern et al, 1996). Novel acidic fluorescent probes based on RhB have also been described and used for the optical imaging of the intracellular H + (Zhang et al, 2009). …”

Section: Introductionmentioning

confidence: 99%

Targeting of lysosomes by liposomes modified with octadecyl-rhodamine B

Koshkaryev

Thekkedath

Pagano

et al. 2011

Journal of Drug Targeting

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The use of lysosome-targeted liposomes may significantly improve a delivery of therapeutic enzymes into lysosomes for the treatment of lysosome-associated diseases. The aim of this research was to achieve a specific intracellular targeting of lysosomes, by using liposomes modified with the lysosomotropic octadecyl-rhodamine B (RhB) and loaded with a model compound, fluorescein isothiocyanate (FITC)–dextran (FD). Plain and RhB-modified liposomes were prepared by hydration of lipid films and loaded with FD or with 5-dodecanoylaminofluorescein di-β-D-galactopyranoside (C12FDG), a specific substrate for the intralysosomal β-galactosidase. The delivery of these liposomes and their content to lysosomes in HeLa cells was investigated by confocal microscopy, flow cytometry, and subcellular fractionation. Confocal microscopy demonstrated that RhB-liposomes co-localize well with the specific lysosomal markers, unlike plain liposomes. The comparison of the FITC fluorescence of the lysosomes isolated by subcellular fractionation also showed that the efficiency of FD delivery into lysosomes by RhB-modified liposomes was significantly higher compared with plain liposomes. These results were additionally confirmed by the flow cytometry of the intact cells treated with C12FDG-loaded liposomes that also demonstrated increased lysosomal targeting by RhB-modified liposomes. The modification of the liposomal surface with a lysosomotropic ligand, such as octadecyl-RhB, can significantly increase the delivery of liposomal loads to lysosomes.

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Section: Introductionmentioning

confidence: 99%

Targeting of lysosomes by liposomes modified with octadecyl-rhodamine B

Koshkaryev

Thekkedath

Pagano

et al. 2011

Journal of Drug Targeting

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“…1 The measurement of pH by fluorescence-based techniques is well established for both imaging and sensing applications 2,3 in various fields of experimental science, such as biomedical research, 4−10 marine biology, 11,12 and biotechnology. 13,14 The most frequently used fluorescent pH indicators are 8-hydroxypyrene-1,3,6-trisulfonic acid (HPTS), carboxyfluorescein derivatives, seminaphthorhodafluors (SNARFs), and hydroxycoumarins.…”

mentioning

confidence: 99%

Highly Photostable Near-Infrared Fluorescent pH Indicators and Sensors Based on BF₂-Chelated Tetraarylazadipyrromethene Dyes

Jokic¹,

Borisov²,

Saf³

et al. 2012

Anal. Chem.

172

142

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In this study, a series of new BF2-chelated tetraarylazadipyrromethane dyes are synthesized and are shown to be suitable for the preparation of on/off photoinduced electron transfer modulated fluorescent sensors. The new indicators are noncovalently entrapped in polyurethane hydrogel D4 and feature absorption maxima in the range 660–710 nm and fluorescence emission maxima at 680–740 nm. Indicators have high molar absorption coefficients of ∼80 000 M–1 cm–1, good quantum yields (up to 20%), excellent photostability and low cross-sensitivity to the ionic strength. pKa values of indicators are determined from absorbance and fluorescence measurements and range from 7 to 11, depending on the substitution pattern of electron-donating and -withdrawing functionalities. Therefore, the new indicators are suitable for exploitation and adaptation in a diverse range of analytical applications. Apparent pKa values in sensor films derived from fluorescence data show 0.5–1 pH units lower values in comparison with those derived from the absorption data due to Förster resonance energy transfer from protonated to deprotonated form. A dual-lifetime referenced sensor is prepared, and application for monitoring of pH in corals is demonstrated.

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“…We previously reported the use of rhodamine-lactams for imaging of lysosomal acidity and lysosomal pH based tumor imaging. [13][14][15][16][17][18][19][20][21][22] Herein rhodamine-lactams were conjugated with bacterium-homing entities to envelope rhodamine-lactams within bacteria for reporting phagolysosomal acidity during bacterial phagocytosis.…”

Section: Resultsmentioning

confidence: 99%

Optical Tracking of Phagocytosis with an Activatable Profluorophore Metabolically Incorporated into Bacterial Peptidoglycan

Tian

et al. 2015

Anal. Chem.

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Phagocytosis is critical for immunity against pathogens. Prior imaging using dye-labeled synthetic beads or green fluorescent protein-expressing bacteria is limited by "always-on" signals which compromise discerning phagocytosed particles from adherent particles. Targeting cellular internalization of pathogens into acidic phagolysosomes, we herein report "turn-on" fluorescence imaging of phagocytosis with viable bacteria featuring peptidoglycans covalently modified with rhodamine-lactam responsive to acidic pH. Culturing of Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus) with d-lysine conjugated rhodamine-lactam and fluorescein isocyanate (FITC) leads to efficient metabolic incorporation of FITC and rhodamine-lactam into bacterial peptidoglycan. E. coli and S. aureus become red-emissive upon phagocytosis into Raw 264.7 macrophages. With FITC as the reference signal, the mono- and dual-color emission allow efficient in situ distinction of ingested bacteria from extracellular bacteria. Given the ease of optical peptidoglycan labeling, the prevalence of microbial peptidoglycan and preservation of microbial surface landscape, this approach would be of use for investigation on microbial pathogenesis and high-throughput screening of immunomodulators of phagocytosis.

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A highly sensitive acidic pH fluorescent probe and its application to HepG2 cells

Cited by 160 publications

References 37 publications

Targeting of lysosomes by liposomes modified with octadecyl-rhodamine B

Targeting of lysosomes by liposomes modified with octadecyl-rhodamine B

Highly Photostable Near-Infrared Fluorescent pH Indicators and Sensors Based on BF₂-Chelated Tetraarylazadipyrromethene Dyes

Optical Tracking of Phagocytosis with an Activatable Profluorophore Metabolically Incorporated into Bacterial Peptidoglycan

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A highly sensitive acidic pH fluorescent probe and its application to HepG2 cells

Cited by 160 publications

References 37 publications

Targeting of lysosomes by liposomes modified with octadecyl-rhodamine B

Targeting of lysosomes by liposomes modified with octadecyl-rhodamine B

Highly Photostable Near-Infrared Fluorescent pH Indicators and Sensors Based on BF2-Chelated Tetraarylazadipyrromethene Dyes

Optical Tracking of Phagocytosis with an Activatable Profluorophore Metabolically Incorporated into Bacterial Peptidoglycan

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Resources

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Highly Photostable Near-Infrared Fluorescent pH Indicators and Sensors Based on BF₂-Chelated Tetraarylazadipyrromethene Dyes