Stable cyclopropene-containing analogs of the amino acid neurotransmitter glutamate

Kumar, Pratik; Huang, Wei; Shukhman, David; Camarda, Frank M.; Laughlin, Scott T.

doi:10.1016/j.tetlet.2019.04.046

Cited by 7 publications

(4 citation statements)

References 42 publications

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“…StA 24 was much slower to react ( k 2 = 52±3 M −1 s −1 ) than the TCO‐modified nutrients, and CpQ showed no measurable reaction with 17 . This is in agreement with reference [41] in which the synthesis of CpQ was first reported [41] . In this paper, the reactivity was tested with dipyridinyl tetrazine, giving a rate constant of 2*10 −3 M −1 s −1 for this fastest of tetrazines.…”

Section: Resultssupporting

confidence: 90%

“…This is in agreement with reference [41] in which the synthesis of CpQ was first reported. [41] In this paper, the reactivity was tested with dipyridinyl tetrazine, giving a rate constant of 2*10 À 3 M À 1 s À 1 for this fastest of tetrazines. Our hypothesis is therefore that the rate of 17 reacting with CpQ is too slow to be detected in our system.…”

Section: Forschungsartikelsupporting

confidence: 93%

“…[39,40] Axial-TCO was used to make all TCOmodified nutrients. The previously reported cyclopropenecontaining free fatty acid (FFA), sterculic acid (24), [20] and finally the previously reported cyclopropene-modified glutamate analogue (CpQ, 27), [41] were also included in the nutrient library.…”

Section: Resultsmentioning

confidence: 99%

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A Bioorthogonal Dual Fluorogenic Probe for the Live‐Cell Monitoring of Nutrient Uptake by Mammalian Cells

Wang,

Torres‐García,

Mostert

et al. 2024

Angewandte Chemie

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Cells rely heavily on the uptake of exogenous nutrients for survival, growth, and differentiation. Yet quantifying the uptake of small molecule nutrients at the single cell level is difficult. Here we present a new approach to studying the nutrient uptake in live single cells using Inverse Electron‐Demand Diels Alder (IEDDA) chemistry. We have modified carboxyfluorescein‐diacetate‐succinimidyl esters (CFSE) – a quenched fluorophore that can covalently react with proteins and is only turned on in the cytosol of a cell following esterase activity – with a tetrazine. This tetrazine serves as a second quencher for the pendant fluorophore. Upon reaction with nutrients modified with an electron‐rich or strained dienophile in an IEDDA reaction, this quenching group is destroyed, thereby enabling the probe to fluoresce. This has allowed us to monitor the uptake of a variety of dienophile‐containing nutrients in live primary immune cell populations using flow cytometry and live‐cell microscopy.

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Section: Resultssupporting

confidence: 90%

Section: Forschungsartikelsupporting

confidence: 93%

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A Bioorthogonal Dual Fluorogenic Probe for the Live‐Cell Monitoring of Nutrient Uptake by Mammalian Cells

Wang,

Torres‐García,

Mostert

et al. 2024

Angewandte Chemie

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“…Bioorthogonal modification schemes allow for the modification of virtually any biomolecules. Indeed, there are examples of the selective labeling of various biopolymers (e.g., carbohydrates [ 9 , 10 ], nucleic acids [ 11 , 12 ], lipids [ 13 , 14 ], and proteins [ 15 , 16 ]) or small-molecular ligands [ 17 , 18 ]. Yet, protein-related bioorthogonal labeling schemes are, by far, the most popular, possibly owing to the advanced technology for the incorporation of bioorthogonal handles into proteins [ 8 ].…”

Section: Introductionmentioning

confidence: 99%

Bioorthogonal Reactions in Bioimaging

Kozma,

Kele

2024

Top Curr Chem (Z)

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Visualization of biomolecules in their native environment or imaging-aided understanding of more complex biomolecular processes are one of the focus areas of chemical biology research, which requires selective, often site-specific labeling of targets. This challenging task is effectively addressed by bioorthogonal chemistry tools in combination with advanced synthetic biology methods. Today, the smart combination of the elements of the bioorthogonal toolbox allows selective installation of multiple markers to selected targets, enabling multicolor or multimodal imaging of biomolecules. Furthermore, recent developments in bioorthogonally applicable probe design that meet the growing demands of superresolution microscopy enable more complex questions to be addressed. These novel, advanced probes enable highly sensitive, low-background, single- or multiphoton imaging of biological species and events in live organisms at resolutions comparable to the size of the biomolecule of interest. Herein, the latest developments in bioorthogonal fluorescent probe design and labeling schemes will be discussed in the context of in cellulo/in vivo (multicolor and/or superresolved) imaging schemes. The second part focuses on the importance of genetically engineered minimal bioorthogonal tags, with a particular interest in site-specific protein tagging applications to answer biological questions.

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Synthetic Applications of Cyclopropene and Cyclopropenone: Recent Progress and Developments

et al. 2020

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Stable cyclopropene-containing analogs of the amino acid neurotransmitter glutamate

Cited by 7 publications

References 42 publications

A Bioorthogonal Dual Fluorogenic Probe for the Live‐Cell Monitoring of Nutrient Uptake by Mammalian Cells

A Bioorthogonal Dual Fluorogenic Probe for the Live‐Cell Monitoring of Nutrient Uptake by Mammalian Cells

Bioorthogonal Reactions in Bioimaging

Synthetic Applications of Cyclopropene and Cyclopropenone: Recent Progress and Developments

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