Turn on Fluorescent Probes for Selective Targeting of Aldehydes

Dilek, Ozlem; Bane, Susan

doi:10.3390/chemosensors4010005

Cited by 11 publications

(4 citation statements)

References 18 publications

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“…Next, we tested the selectivity of BL 660 -NO by incubating it with various biologically relevant analytes in the presence of luciferase. For instance, we evaluated its reactivity with several reactive carbonyl species (i.e., formaldehyde, glyoxal, acetaldehyde, dehydroascorbic acid) which can generate various cyclized products. − Moreover, we tested a panel of reactive oxygen species (i.e., hydrogen peroxide, tert -butyl hydrogen peroxide, hypochlorite, superoxide anion, hydroxyl radical) and reactive nitrogen species (i.e., nitrite, nitrate, nitroxyl, peroxynitrite) that could react with the substrate component or the trigger to give undesirable activation. Negligible changes (<6%) in the bioluminescent signal were observed with up to 75-fold molar excess of each species, consistent with exceptional selectivity (Figure e).…”

Section: Resultsmentioning

confidence: 99%

Activity-Based NIR Bioluminescence Probe Enables Discovery of Diet-Induced Modulation of the Tumor Microenvironment via Nitric Oxide

et al. 2022

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Nitric oxide (NO) plays a critical role in acute and chronic inflammation. NO’s contributions to cancer are of particular interest due to its context-dependent bioactivities. For example, immune cells initially produce cytotoxic quantities of NO in response to the nascent tumor. However, it is believed that this fades over time and reaches a concentration that supports the tumor microenvironment (TME). These complex dynamics are further complicated by other factors, such as diet and oxygenation, making it challenging to establish a complete picture of NO’s impact on tumor progression. Although many activity-based sensing (ABS) probes for NO have been developed, only a small fraction have been employed in vivo , and fewer yet are practical in cancer models where the NO concentration is <200 nM. To overcome this outstanding challenge, we have developed BL 660 -NO, the first ABS probe for NIR bioluminescence imaging of NO in cancer. Owing to the low intrinsic background, high sensitivity, and deep tissue imaging capabilities of our design, BL 660 -NO was successfully employed to visualize endogenous NO in cellular systems, a human liver metastasis model, and a murine breast cancer model. Importantly, its exceptional performance facilitated two dietary studies which examine the impact of fat intake on NO and the TME. BL 660 -NO provides the first direct molecular evidence that intratumoral NO becomes elevated in mice fed a high-fat diet, which became obese with larger tumors, compared to control animals on a low-fat diet. These results indicate that an inflammatory diet can increase NO production via recruitment of macrophages and overexpression of inducible nitric oxide synthase which in turn can drive tumor progression.

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Section: Resultsmentioning

confidence: 99%

Activity-Based NIR Bioluminescence Probe Enables Discovery of Diet-Induced Modulation of the Tumor Microenvironment via Nitric Oxide

et al. 2022

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“…The detection sensitivity for ß-mannanase-hydrolyzed polysaccharides is mainly limited by the background fluorescence of unbound aminooxy-bearing dye which lowers the imaging contrast but is not due to the fast oxime formation (reaction product of an aldehyde and an aminooxy group) catalyzed by aniline, which occurs in less than a minute and is therefore not rate-limiting in our case. By using non-fluorescent dyes, which turn on in fluorescence after reaction with the reducing end 41 , 42 , the sensitivity of the new visualization concept could be improved further as the background fluorescence would then be much weaker. Further limitations of our current visualization concept concern water-soluble fragments of ß-mannanase-hydrolyzed polysaccharides, which could not be detected as the labeled reducing ends were buried by the background fluorescence of the aqueous phase or were washed off later during the rinsing step in case of the ex-situ studies on soy bean seeds.…”

Section: Discussionmentioning

confidence: 99%

Spatial activity mapping of ß-mannanase on soybean seeds

Rueckel,

Janson,

Solbak

et al. 2024

Sci Rep

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For farm animals the supplementation of exogenous enzymes, like ß-mannanase, to soybean-based diets is beneficial to improve feed digestibility. In order to unravel the effect of ß-mannanase on soybean meal’s cell structure, a novel imaging concept was developed which allows visualizing the spatial activity pattern of ß-mannanase with high sensitivity by fluorescence microscopy before any visible degradation of the cellular structure occurs. It is based on fluorescence labeling of newly formed reducing ends of ß-mannanase-hydrolyzed polysaccharides after the native reducing ends of all polysaccharides present were chemically reduced. It was revealed that ß-mannanase is not only active at the cell wall but also at previously unknown sites, like the middle lamella and, most prominently, at an intracellular matrix enclosing the protein storage vacuoles. Based on these findings it can be hypothesized that the evaluated ß-mannanase can degrade the enclosing matrix of encapsulated proteins and the cell wall structure and thereby improves efficiency of feed utilization.

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“…The designed sensing mechanism was based on nucleophilic addition by the three equivalent amino groups of the dye to the carbonyl moiety of cyclohexanone in the formation of an imine species [46][47][48][49], leading to changes in the UV-vis absorption band that allows for the direct identification of low or high concentration by the naked eye (Figure 3).…”

Section: Sensor Responses Of Gaseous Cyclohexanonementioning

confidence: 99%

Nanoporous Silica-Dye Microspheres for Enhanced Colorimetric Detection of Cyclohexanone

2018

Chemosensors

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Forensic detection of non-volatile nitro explosives poses a difficult analytical challenge. A colorimetric sensor comprising of ultrasonically prepared silica-dye microspheres was developed for the sensitive gas detection of cyclohexanone, a volatile marker of explosives 1,3,5-trinitro-1,3,5-triazinane (RDX) and 1,3,5,7-tetranitro-1,3,5,7-tetrazocane (HMX). The silica-dye composites were synthesized from the hydrolysis of ultrasonically sprayed organosiloxanes under mild heating conditions (150 • C), which yielded microspherical, nanoporous structures with high surface area (~300 m 2 /g) for gas exposure. The sensor inks were deposited on cellulose paper and given sensitive colorimetric responses to trace the amount of cyclohexanone vapors even at sub-ppm levels, with a detection limit down to~150 ppb. The sensor showed high chemical specificity towards cyclohexanone against humidity and other classes of common solvents, including ethanol, acetonitrile, ether, ethyl acetate, and ammonia. Paper-based colorimetric sensors with hierarchical nanostructures could represent an alternative sensing material for practical applications in the detection of explosives.

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Turn on Fluorescent Probes for Selective Targeting of Aldehydes

Cited by 11 publications

References 18 publications

Activity-Based NIR Bioluminescence Probe Enables Discovery of Diet-Induced Modulation of the Tumor Microenvironment via Nitric Oxide

Activity-Based NIR Bioluminescence Probe Enables Discovery of Diet-Induced Modulation of the Tumor Microenvironment via Nitric Oxide

Spatial activity mapping of ß-mannanase on soybean seeds

Nanoporous Silica-Dye Microspheres for Enhanced Colorimetric Detection of Cyclohexanone

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