Chemiluminescent Probes for Activity‐Based Sensing of Formaldehyde Released from Folate Degradation in Living Mice

Bruemmer, Kevin J.; Green, Ori; Su, Timothy A.; Shabat, Doron; Chang, Christopher J.

doi:10.1002/anie.201802143

Cited by 171 publications

(152 citation statements)

References 52 publications

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“…In aqueous media, these next‐generation phenoxy‐dioxetane chemiluminescent luminophores exhibit up to 3000‐fold greater light emission than the original Schaap's dioxetanes . This discovery has already been exploited in a number of applications that require rapid and sensitive detection of various enzymes and analytes . In addition, the intense light emitted from the probe can be used to effectively image transfected and native enzymatic activity in live cells .…”

Section: Introductionmentioning

confidence: 99%

Chemiluminescent Carbapenem‐Based Molecular Probe for Detection of Carbapenemase Activity in Live Bacteria

Das

Ihssen²,

Wick³

et al. 2020

Chemistry A European J

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Carbapenemase‐producing organisms (CPOs) pose a severe threat to antibacterial treatment due to the acquisition of antibiotic resistance. This resistance can be largely attributed to the antibiotic‐hydrolyzing enzymes that the bacteria produce. Current carbapenem “wonder drugs”, such as doripenem, ertapenem, meropenem, imipenem, and so on, are resistant to regular β‐lactamases, but susceptible to carbapenemases. Even worse, extended exposure of bacteria to these drugs accelerates the spread of resistance genes. In order to preserve the clinical efficacy of antibacterial treatment, carbapenem drugs should be carefully regulated and deployed only in cases of a CPO infection. Early diagnosis is therefore of paramount importance. Herein, we report the design, synthesis, and activity of the first carbapenemase‐sensitive chemiluminescent probe, CPCL, which may be used to monitor CPO activity. The design of our probe enables enzymatic cleavage of the carbapenem core, which is followed by a facile 1,8‐elimination process and the emission of green light through rapid chemical excitation. We have demonstrated the ability of the probe to detect a number of clinically relevant carbapenemases and the successful identification of CPO present in bacterial cultures, such as those used for clinical diagnosis. We believe that our use of “turn‐on” chemiluminescence activation will find significant application in future diagnostic assays and improve antibacterial treatment.

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Section: Introductionmentioning

confidence: 99%

Chemiluminescent Carbapenem‐Based Molecular Probe for Detection of Carbapenemase Activity in Live Bacteria

Das

Ihssen²,

Wick³

et al. 2020

Chemistry A European J

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“…Presumptive colonies have to be confirmed after the initial isolation. [25][26][27][28][29][30][31][32][33][34] Ar emarkable enhancement of light emission was obtained by simply improving the emissive nature of the excited species,f ormed during the chemiexcitation of Schaapsdioxetanes. Positive results are available after 96-144 h(4-6 days), depending on the growth of the bacteria.…”

mentioning

confidence: 99%

Ultrasensitive Detection of Salmonella and Listeria monocytogenes by Small‐Molecule Chemiluminescence Probes

et al. 2019

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Detection of Salmonella and L. monocytogenes in food samples by current diagnostic methods requires relatively long time to results (2-6 days). Furthermore,t he ability to perform environmental monitoring at the factory site for these pathogens is limited due to the need for laboratory facilities. Herein, we report new chemiluminescence probes for the ultrasensitive direct detection of viable pathogenic bacteria. The probes are composed of ab right phenoxy-dioxetane luminophore masked by triggering group,whichisactivated by aspecific bacterial enzyme,and could detect their corresponding bacteria with an LOD value of about 600-fold lower than that of fluorescent probes.M oreover,w ew ere able to detect am inimum of 10 Salmonella cells within 6hincubation. The assayallows for bacterial enrichment and detection in one test tube without further sample preparation. We anticipate that this design strategy will be used to prepare analogous chemiluminescence probes for other enzymes relevant to specific bacteria detection and point-of-care diagnostics.

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“…Additionally,m ice were used to monitor and trace the NTR catalytic kinetics with Zn-MPB'L-NO 2 .M ice fluorescent imaging [39,40] tests were performed at an excitation wavelength of 470 nm and emission was collected at 530 nm by using Bruker In Vivo FPro system. MCF-7 and MDA-MB-231 tumor-bearing mice were used to conduct the smallanimal fluorescence imaging experiments of Zn-MPB'L-NO 2 in vivo and explore the fluorescence signal changes over time ( Figure 4A-F).…”

Section: Angewandte Chemiementioning

confidence: 99%

A Cofactor‐Substrate‐Based Supramolecular Fluorescent Probe for the Ultrafast Detection of Nitroreductase under Hypoxic Conditions

Jiao

Zhang²,

Gao

et al. 2020

Angewandte Chemie

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Identifying the location and expression levels of enzymes under hypoxic conditions in cancer cells is vital in early‐stage cancer diagnosis and monitoring. By encapsulating a fluorescent substrate, L‐NO2, within the NADH mimic‐containing metal–organic capsule Zn‐MPB, we developed a cofactor‐substrate‐based supramolecular luminescent probe for ultrafast detection of hypoxia‐related enzymes in solution in vitro and in vivo. The host–guest structure fuses the coenzyme and substrate into one supramolecular probe to avoid control by NADH, switching the catalytic process of nitroreductase from a double‐substrate mechanism to a single‐substrate one. This probe promotes enzyme efficiency by altering the substrate catalytic process and enhances the electron transfer efficiency through an intra‐molecular pathway with increased activity. The enzyme content and fluorescence intensity showed a linear relationship and equilibrium was obtained in seconds, showing potential for early tumor diagnosis, biomimetic catalysis, and prodrug activation.

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Chemiluminescent Probes for Activity‐Based Sensing of Formaldehyde Released from Folate Degradation in Living Mice

Cited by 171 publications

References 52 publications

Chemiluminescent Carbapenem‐Based Molecular Probe for Detection of Carbapenemase Activity in Live Bacteria

Chemiluminescent Carbapenem‐Based Molecular Probe for Detection of Carbapenemase Activity in Live Bacteria

Ultrasensitive Detection of Salmonella and Listeria monocytogenes by Small‐Molecule Chemiluminescence Probes

A Cofactor‐Substrate‐Based Supramolecular Fluorescent Probe for the Ultrafast Detection of Nitroreductase under Hypoxic Conditions

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