Development of surface immobilized 3-azidocoumarin-based fluorogenic probe via strain promoted click chemistry

Bharathi, M. Vijaya; Chhabra, Mohit; Paira, Priyankar

doi:10.1016/j.bmcl.2015.10.078

Cited by 13 publications

(13 citation statements)

References 40 publications

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“…Most commonly, fluorescent tags installed on a biomolecule permit visualization inside a cell and/or quantitation using techniques such as flow cytometry. Sivakumar et al developed a pro-fluorescent coumarin molecule (coumarin-N 3 , Figure H), having negligible fluorescence in the unconjugated form, and becoming fluorescent after the click reaction extends the conjugated system . This molecule has been useful in optimizing reaction conditions and for studying kinetics of the click reaction. , A number of radiolabels (Figure I) have also been described in the literature, enabling access to both targeted radiotherapy and in vivo visualization and quantitation techniques not possible with fluorescent labels, such as positron emission tomography (PET) and single photon emission computed tomography (SPECT) .…”

Section: Payload Molecules For Detecting or Modulating Biomolecule Fu...mentioning

confidence: 99%

Practical Considerations, Challenges, and Limitations of Bioconjugation via Azide–Alkyne Cycloaddition

et al. 2017

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Interrogating biological systems is often limited by access to biological probes. The emergence of "click chemistry" has revolutionized bioconjugate chemistry by providing facile reaction conditions amenable to both biologic molecules and small molecule probes such as fluorophores, toxins, or therapeutics. One particularly popular version is the copper-catalyzed azide-alkyne cycloaddition (AAC) reaction, which has spawned new alternatives such as the strain-promoted azide-alkyne cycloaddition reaction, among others. This focused review highlights practical approaches to AAC reactions for the synthesis of peptide or protein bioconjugates and contrasts current challenges and limitations in light of recent advances in the field. The conical success of antibody drug conjugates has expanded the toolbox of linkers and payloads to facilitate practical applications of bioconjugation to create novel therapeutics and biologic probes. The AAC reaction in particular is poised to enable a large set of functionalized molecules as a combinatorial approach to high-throughput bioconjugate generation, screening, and honing of lead compounds.

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Section: Payload Molecules For Detecting or Modulating Biomolecule Fu...mentioning

confidence: 99%

Practical Considerations, Challenges, and Limitations of Bioconjugation via Azide–Alkyne Cycloaddition

et al. 2017

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“…Depending on the chemical structure of cyclooctyne, reaction rates of SPAAC are different. Reaction rates of these reactants in SPAAC click reaction are in the order: MOFO < DIBO < DIFO < DBCO < BARAC …”

Section: Introductionmentioning

confidence: 99%

Site‐Specific Surface Functionalization via Microchannel Cantilever Spotting (µCS): Comparison between Azide–Alkyne and Thiol–Alkyne Click Chemistry Reactions

Dadfar

Sekula-Neuner

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et al. 2018

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Different types of click chemistry reactions are proposed and used for the functionalization of surfaces and materials, and covalent attachment of organic molecules. In the present work, two different catalyst-free click approaches, namely azide-alkyne and thiol-alkyne click chemistry are studied and compared for the immobilization of microarrays of azide or thiol inks on functionalized glass surfaces. For this purpose, the surface of glass is first functionalized with dibenzocyclooctyne-acid (DBCO-acid), a cyclooctyne with a carboxyl group. Then, the DBCO-terminated surfaces are functionalized via microchannel cantilever spotting with different fluorescent and nonfluorescent azide and thiol inks. Although both routes work reliably for surface functionalization, the protein binding experiments reveal that using a thiol-alkyne route will obtain the highest surface density of molecular immobilization in such spotting approaches. The obtained achievements and results from this work can be used for design and manufacturing of microscale patterns suitable for biomedical and biological applications.

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“… 15 Azide chemistry has also been employed for therapeutic advantage in the development of self-assembling drugs, unnatural DNA sequences, and delivery of therapeutic nanoparticles to tumors. 16 − 23 In a different mode of reactivity, azide-containing dyes have been used to detect hydrogen sulfide. In particular Chang 24 − 26 and Wang 27 have published pioneering work in this area.…”

Section: Introductionmentioning

confidence: 99%

CYP450 Enzymes Effect Oxygen-Dependent Reduction of Azide-Based Fluorogenic Dyes

et al. 2016

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Azide-containing compounds have broad utility in organic synthesis and chemical biology. Their use as powerful tools for the labeling of biological systems in vitro has enabled insights into complex cellular functions. To date, fluorogenic azide-containing compounds have primarily been employed in the context of click chemistry and as sensitive functionalities for hydrogen sulfide detection. Here, we report an alternative use of this functionality: as fluorogenic probes for the detection of depleted oxygen levels (hypoxia). Oxygen is imperative to all life forms, and probes that enable quantification of oxygen tension are of high utility in many areas of biology. Here we demonstrate the ability of an azide-based dye to image hypoxia in a range of human cancer cell lines. We have found that cytochrome P450 enzymes are able to reduce these probes in an oxygen-dependent manner, while hydrogen sulfide does not play an important role in their reduction. These data indicate that the azide group is a new bioreductive functionality that can be employed in prodrugs and dyes. We have uncovered a novel mechanism for the cellular reduction of azides, which has implications for the use of click chemistry in hypoxia.

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Development of surface immobilized 3-azidocoumarin-based fluorogenic probe via strain promoted click chemistry

Cited by 13 publications

References 40 publications

Practical Considerations, Challenges, and Limitations of Bioconjugation via Azide–Alkyne Cycloaddition

Practical Considerations, Challenges, and Limitations of Bioconjugation via Azide–Alkyne Cycloaddition

Site‐Specific Surface Functionalization via Microchannel Cantilever Spotting (µCS): Comparison between Azide–Alkyne and Thiol–Alkyne Click Chemistry Reactions

CYP450 Enzymes Effect Oxygen-Dependent Reduction of Azide-Based Fluorogenic Dyes

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