A cyanine-based fluorescent cassette with aggregation-induced emission for sensitive detection of pH changes in live cells

Fang, Mingxi; Xia, Shuai; Bi, Jianheng; Wigstrom, Travis; Valenzano, Loredana; Wang, Jianbo; Mazi, Wafa; Tanasova, Marina; Luo, Fen‐Tair; Liu, Haiying

doi:10.1039/c7cc08986d

Cited by 72 publications

(54 citation statements)

References 24 publications

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“…The probes show Stokes-shift fluorescence quantum yields of 12% and 9.0%, and anti-Stoke-shift fluorescence quantum yields of 2.5% and 2.1%, and have molar absorptivities of 1.3 × 10 4 and 7.0 × 10 3 M −1 cm −1 at pH 2.8, respectively. The Henderson–Hasselbach 37 equation was utilized to determine probe pK a values involving spirolactam ring opening and resulted in pK a values of 4.80 and 4.40 for probe A and B , respectively (Scheme 1, Figures 3 and S14). The probes reversibly respond to pH variance ranging from 2.4 to 7.2 for both Stokes-shift and anti-Stokes-shift fluorescence (Figures S21 and S22).…”

Section: Resultsmentioning

confidence: 99%

New Near-Infrared Fluorescent Probes with Single-Photon Anti-Stokes-Shift Fluorescence for Sensitive Determination of pH Variances in Lysosomes with a Double-Checked Capability

Chen

Zhang

Jaishi

et al. 2018

ACS Appl. Bio Mater.

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Two near-infrared luminescent probes with Stokes-shift and single-photon anti-Stokes-shift fluorescence properties for sensitive determination of pH variance in lysosomes have been synthesized. A morpholine residue in probe A which serves as a targeting group for lysosomes in viable cells was attached to the fluorophores via a spirolactam moiety while a mannose residue was ligated to probe B resulting in increased biocompatibility and solubility in water. Probes A and B contain closed spirolactam moieties, and show no Stokes-shift or anti-Stokes-shift fluorescence under neutral or alkali conditions. However, the probes incrementally react to pH

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Section: Resultsmentioning

confidence: 99%

New Near-Infrared Fluorescent Probes with Single-Photon Anti-Stokes-Shift Fluorescence for Sensitive Determination of pH Variances in Lysosomes with a Double-Checked Capability

Chen

Zhang

Jaishi

et al. 2018

ACS Appl. Bio Mater.

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“…Fang et al developed an AIE cyanine-based fluorescent cassette consisting of tetraphenylethene (TPE) donor and cyanine acceptor. 32 The cassette showed significantly strong fluorescence of both TPE donor and cyanine acceptor at pH 5.0. Conversely, fluorescence intensities of both donor and acceptor were decreased in a significant amount when intracellular pH was raised from 5.0 to 9.0.…”

Section: Discussionmentioning

confidence: 94%

“…This behavior is assigned to the restriction arising from intramolecular rotation (RIR) process; the pure polymers show very weak fluorescence alone, whereas the strong emission is observed when an interlocked network system was developed through host–guest supramolecular polymers. Fang et al developed an AIE cyanine‐based fluorescent cassette consisting of tetraphenylethene (TPE) donor and cyanine acceptor . The cassette showed significantly strong fluorescence of both TPE donor and cyanine acceptor at pH 5.0.…”

Section: Discussionmentioning

confidence: 99%

Fluorescent‐functionalized graphene oxide for selective labeling of tumor cells

Senapati

Patel

Ray

et al. 2019

J Biomedical Materials Res

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Fluorescence probe has attracted significant attention for biomedical imaging in recent years due to their high resolution at the cellular level. Organic‐based fluorescent probes with high quantum yield are widely applied in bioimaging, but most of them suffer from a serious obstacle called aggregation‐caused quenching in cellular systems. New fluorophore has been designed through functionalization of graphene oxide which emphatically exhibits aggregation‐induced emission along with pH‐responsive nanoprobe. Significantly higher emission of this material in slightly acidic media helps to detect tumor cell by creating a sharp contrast with the image of normal cells. The reason for pH‐induced enhanced emission phenomenon is revealed through aggregation of sulfonated species in acidic media. Furthermore, the biocompatible nature of the newly developed material is found to be suitable for its application in biomedical imaging for cancer detection with better accuracy at lower cost. © 2019 Wiley Periodicals, Inc. J Biomed Mater Res Part A: 107A: 1917–1924, 2019.

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“…In order to test this hypothesis, we conducted colocalization experiments by using commercial Lysosensor Green to determine the intracellular location of probe A . Intracelluar pH values were adjusted by incubating HeLa cells in different pH buffers containing 10 µM nigericine, H + ionphore, which is employed to promote equilibration between intracellular and extracellular pH values [ 7 , 9 , 29 , 41 , 42 ]. Probe A responds sensitively to intracellular pH decreases from 7.01 to 3.50 with gradual fluorescence enhancement due to acid-activated spirolactam ring opening with significantly enhanced π-conjugation, Figure 12 .…”

Section: Resultsmentioning

confidence: 99%

A Near-Infrared Fluorescent Probe Based on a FRET Rhodamine Donor Linked to a Cyanine Acceptor for Sensitive Detection of Intracellular pH Alternations

Zhang

Xia

et al. 2018

Molecules

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A fluorescence resonance energy transfer (FRET)-based near-infrared fluorescent probe (B+) for double-checked sensitive detection of intracellular pH changes has been synthesized by binding a near-infrared rhodamine donor to a near-infrared cyanine acceptor through robust C-N bonds via a nucleophilic substitution reaction. To demonstrate the double-checked advantages of probe B+, a near-infrared probe (A) was also prepared by modification of a near-infrared rhodamine dye with ethylenediamine to produce a closed spirolactam residue. Under basic conditions, probe B+ shows only weak fluorescence from the cyanine acceptor while probe A displays nonfluorescence due to retention of the closed spirolactam form of the rhodamine moiety. Upon decrease in solution pH level, probe B+ exhibits a gradual fluorescence increase from rhodamine and cyanine constituents at 623 nm and 743 nm respectively, whereas probe A displays fluorescence increase at 623 nm on the rhodamine moiety as acidic conditions leads to the rupture of the probe spirolactam rings. Probes A and B+ have successfully been used to monitor intracellular pH alternations and possess pKa values of 5.15 and 7.80, respectively.

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A cyanine-based fluorescent cassette with aggregation-induced emission for sensitive detection of pH changes in live cells

Abstract: An aggregation-induced emission (AIE) cyanine-based fluorescent cassette with a large pseudo-Stokes shift was designed and prepared to sensitively image pH changes in live cells via through-bond energy transfer (TBET) from a tetraphenylethene (TPE) donor to a cyanine acceptor.

Cited by 72 publications

References 24 publications

New Near-Infrared Fluorescent Probes with Single-Photon Anti-Stokes-Shift Fluorescence for Sensitive Determination of pH Variances in Lysosomes with a Double-Checked Capability

New Near-Infrared Fluorescent Probes with Single-Photon Anti-Stokes-Shift Fluorescence for Sensitive Determination of pH Variances in Lysosomes with a Double-Checked Capability

Fluorescent‐functionalized graphene oxide for selective labeling of tumor cells

A Near-Infrared Fluorescent Probe Based on a FRET Rhodamine Donor Linked to a Cyanine Acceptor for Sensitive Detection of Intracellular pH Alternations

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