Fluorescence mechanism switching from ICT to PET by substituent chemical manipulation: Macrophage cytoplasm imaging probes

Fueyo-González, Francisco; González‐Vera, Juan A.; Alkorta, Ibón; Infantes, Lourdes; Jimeno, María Luisa; Fernández-Gutiérrez, Mar; González-García, Mary-Paz; Orte, Angel; Herranz, Rosario

doi:10.1016/j.dyepig.2019.108172

Cited by 11 publications

(5 citation statements)

References 42 publications

(56 reference statements)

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“…The enhancement of fluorescence of LysoPB Yellow in lysosomes is due to neither the aggregation of the probe in lysosomes 20 nor the change of the electronic structure induced by protonation of the amino groups (Figures S4 and S5 in the Supporting Information). 21 Importantly, the high lysosome selectivity observed for LysoPB Yellow is general; even in other cell lines, including HepG2 and 3T3-L1, LysoPB Yellow selectively stains lysosomes, which indicates promising potential in this application (Figure S6 in the Supporting Information). Subsequently, we evaluated the working concentration range of LysoPB Yellow for lysosomal staining.…”

supporting

confidence: 66%

“…(2) The phosphole oxide skeleton more effectively suppresses nonspecific interactions than the phosphole sulfide skeleton, probably due to its higher hydrophilicity. The enhancement of fluorescence of LysoPB Yellow in lysosomes is due to neither the aggregation of the probe in lysosomes nor the change of the electronic structure induced by protonation of the amino groups (Figures S4 and S5 in the Supporting Information) . Importantly, the high lysosome selectivity observed for LysoPB Yellow is general; even in other cell lines, including HepG2 and 3T3-L1, LysoPB Yellow selectively stains lysosomes, which indicates promising potential in this application (Figure S6 in the Supporting Information).…”

supporting

confidence: 65%

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Phosphole-Oxide-Based Fluorescent Probe for Super-resolution Stimulated Emission Depletion Live Imaging of the Lysosome Membrane

Wang

Taki

Kajiwara

et al. 2020

ACS Materials Lett.

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Super-resolution imaging techniques have become increasingly important tools to visualize suborganelle structures and dynamic processes in living cells on the nanoscale. However, the utility of these imaging techniques is currently limited by the availability of advanced fluorescent probes that enable the specific labeling of the organelle of interest and provide the absorption/emission properties required for super-resolution imaging techniques. Herein, LysoPB Yellow is presented as a new small-molecule fluorescent probe that can selectivity stain the lysosomal membrane. Its outstandingly high photostability and long fluorescence lifetime are beneficial for its use in super-resolution stimulated emission depletion (STED) microscopy. A lysosomal membrane stained with LysoPB Yellow was successfully visualized by STED imaging in living cells with a full width at half maximum (FWHM) of 70 nm, which is substantially below the diffraction limit of light. Additionally, LysoPB Yellow displayed excellent retention ability and negligible cytotoxicity. Consequently, long-term time-lapse confocal imaging of living cells was successfully conducted, which demonstrates the practical utility of LysoPB Yellow in fluorescence imaging.

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supporting

confidence: 66%

supporting

confidence: 65%

Phosphole-Oxide-Based Fluorescent Probe for Super-resolution Stimulated Emission Depletion Live Imaging of the Lysosome Membrane

Wang

Taki

Kajiwara

et al. 2020

ACS Materials Lett.

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“…[145] To achieve the sensing of hazardous chemicals using noncovalent interactions, features such as structural architecture, presence of electron-rich or electron-deficient sites, nature or mode of light absorption and emission have been modified. [146,147] For example, a MOF linked with 1,3,5-triazine as the central aromatic ring bearing -NO 2 and -NH 2 functional groups showed good luminescent properties and provided electron-rich and electron-deficient sites for feasible electrostatic interactions with guest analytes. [148] In another example, the existence of electron-rich functionalities in the MOF cavity led to the formation of suitable hydrogen bonding and good sensing properties that allowed the easy detection of analytes in aqueous solutions.…”

Section: Noncovalent Interactions and Sensor Featuresmentioning

confidence: 99%

“…[162] However, the whole optical sensing process, involving different transitions and energy or charge transfer from donor to acceptor through photophysical changes, might result from PET, PCT, CHEF, RET, FRET, coupled transitions, radiative transitions, radiationless transitions, TBET, DTBET, and ET (Figure 1). [147,[163][164][165][166][167][168] Among these, PET and RET are found most commonly in MOF sensors owing to electron transfer and overlap of the analyte absorption spectrum with the MOF emission spectrum. [169] Different sensors follow different mechanisms during the sensing or recognition process.…”

Section: Mechanisms For Altering Luminescence Signalsmentioning

confidence: 99%

Mechanistic Insight into Charge and Energy Transfers of Luminescent Metal–Organic Frameworks Based Sensors for Toxic Chemicals

Mohan

Kumar

et al. 2021

Advanced Sustainable Systems

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The success of MOFs has driven their development as a new tool for sensing analytes including toxic chemicals. [19][20][21] The MOF sensors can be applied in both environmental and biological systems. [22] The MOF sensor field has been established with the development of sensors for different metal ions, anions, and molecules. [23,24] The potential application of MOF sensors to the detection of heavy metal ions, toxic anions, and other hazardous species is of great interest. [25,26] Specifically, luminescence technology has allowed the roles of various MOF sites in analyte capture to be easily studied. [27][28][29] The precise use of MOFs is potentially a good tool for analyte detection. Furthermore, MOFs have been established as potential materials for selective, fast, and portable tools for sensing toxic chemicals, with the advantage of light-emitting properties. [30,31] Interestingly, these sensing models can operate in water and are pH stable with high efficiency. [32] Furthermore, MOFs are wellknown materials for the degradation of toxic chemicals. [33,34] Several reports have been published on MOF sensors for toxicant chemicals, such as metal ions, anions, organic solvents, pesticides, nitroaromatic compounds (NACs), chemical warfare agents, [35] and others. [36][37][38] Some reviews have summarized applications of MOFs in sensing and detection probes for ions and volatile organic compounds, [39] and MOF sensors in pesticide detection and absorption with their classification. [40] Others have summarized and analyzed interactions between hazardous compound adsorbates and MOFs. [41,42] The stability and applications of MOFs have been summarized by the research groups of Ding and coworkers. [43] Pehlivan and et al. summarized the role of fluorescence resonance energy transfer in elucidating molecular interactions utilized in biosensing tools. [44,45] Besides luminescence sensing, the reviewers summarized the progress of MOFs relevance in the various area including environment and medical science. [46] Recently, Liu and coworkers summarized the progress of MOFs and discussed the remaining challenges in drug delivery, [47] Garcia and coworkers studied and compared the MOFs as photocatalysts with common inorganic photocatalysts, [48] and Manos and coworkers studied and summarized MOFs challenges and prospects for ion-exchange and sorption applications. [49] Despite these meaningful reviews, the factors responsible for signal changes, mechanisms, and limits of detection have Mechanistic studies of materials able to detect hazardous and toxic chemicals, such as common organic solvents, pesticides, and nitroaromatic compounds (NACs), are critically important owing to the threat they pose to humans and the environment. Recently, porous luminescent metal-organic frameworks (MOFs) with multifunctional sites, high surface areas, and structural tunability have emerged as sensory devices for the detection of hazardous and toxic chemicals. Herein, recent progress regarding the mechanistic behavior of MOF sensors in the det...

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“…We have recently described the switching from naphthalimide and quinolimide-based (ICT) fluorophores 1 (Figure 1) to PET fluorophores by the simple substituent manipulation of a hydroxyl to an N-dimethylamino group in analogues 2 [11]. This switch transformed the "on-off" polarity sensors N-(2-hydroxyethyl)-substituted derivatives 1a and 1b into the "off-on" polarity sensors N- (2-(dimethyl)aminoethyl)substituted analogues 2a and 2b.…”

Section: Introductionmentioning

confidence: 99%

Naphthalimide-based macrophage nucleus imaging probes

Fueyo-González

Fernández-Gutiérrez

García-Puentes

et al. 2020

European Journal of Medicinal Chemistry

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Fluorescence mechanism switching from ICT to PET by substituent chemical manipulation: Macrophage cytoplasm imaging probes

Cited by 11 publications

References 42 publications

Phosphole-Oxide-Based Fluorescent Probe for Super-resolution Stimulated Emission Depletion Live Imaging of the Lysosome Membrane

Phosphole-Oxide-Based Fluorescent Probe for Super-resolution Stimulated Emission Depletion Live Imaging of the Lysosome Membrane

Mechanistic Insight into Charge and Energy Transfers of Luminescent Metal–Organic Frameworks Based Sensors for Toxic Chemicals

Naphthalimide-based macrophage nucleus imaging probes

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