Ultrasensitive chemiluminescent neuraminidase probe for rapid screening and identification of small-molecules with antiviral activity against influenza A virus in mammalian cells

Shelef, Omri; Gutkin, Sara; Feder, Daniel; Ben-Bassat, Ariel; Mandelboim, Michal; Haitin, Yoni; Ben‐Tal, Nir; Bacharach, Eran; Shabat, Doron

doi:10.1039/d2sc03460c

Cited by 19 publications

(14 citation statements)

References 57 publications

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“… [6] Importantly, this groundbreaking development enabled the use of chemiluminescent probes as a sole component with no required additives. Numerous research groups worldwide, including ours, took advantage of the ortho ‐substituted phenoxy‐adamantyl‐1,2‐dioxetane luminophore to develop new useful chemiluminescent probes for detection and imaging of a variety of enzymes and analytes in living systems [7–21] …”

Section: Figurementioning

confidence: 99%

“…Numerous research groups worldwide, including ours, took advantage of the ortho-substituted phenoxy-adamantyl-1,2-dioxetane luminophore to develop new useful chemiluminescent probes for detection and imaging of a variety of enzymes and analytes in living systems. [7][8][9][10][11][12][13][14][15][16][17][18][19][20][21] Despite the encouraging progress in the field, further advancement has been limited by the synthetic inaccessibility of new dioxetane compounds. Typical synthetic methods for the preparation of phenoxy-dioxetane compounds are laborious and cannot be performed on substrates with unprotected functional groups.…”

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confidence: 99%

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Synthesis and Chemiexcitation of a Distinct Chemiluminescent Luminophore based on a Curcumin Scaffold

Tannous,

Gutkin,

Baran

et al. 2023

Israel Journal of Chemistry

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Natural fluorogenic dyes are composed of unique molecular structures that could be harnessed for the design of new chemiluminescent luminophores. Here we demonstrated how to simply transform an emissive curcumin scaffold into a novel chemiluminescent luminophore. An appropriate bromo‐curcumin intermediate was synthesized as a substrate for a Stille cross‐coupling reaction with an adamantyl‐stannane reagent. This late‐stage functionalization afforded in one step a curcumin enolether precursor that can then be oxidized with singlet oxygen to produce a curcumin chemiluminescent luminophore. This curcumin dioxetane luminophore produced an intense light signal with an emission spectrum that correlates with its curcumin scaffold. This is the first example of a chemiluminescent luminophore that is based on the emissive nature of the curcumin molecular structure. We expect that the method described herein would be useful for the synthesis of new chemiluminescent luminophores by transforming other known emissive dyes into dioxetane precursors via the Stille cross‐coupling approach.

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Section: Figurementioning

confidence: 99%

mentioning

confidence: 99%

Synthesis and Chemiexcitation of a Distinct Chemiluminescent Luminophore based on a Curcumin Scaffold

Tannous,

Gutkin,

Baran

et al. 2023

Israel Journal of Chemistry

Self Cite

View full text Add to dashboard Cite

show abstract

“… [6] Importantly, this game‐changer development enabled the use of chemiluminescent probes as a sole component with no required additives. Numerous research groups worldwide, including ours, took advantage of the ortho ‐substituted phenoxy‐adamantyl‐1,2‐dioxetane luminophore to develop useful chemiluminescent probes for detection and imaging of a variety of enzymes and analytes in living systems [7–27] …”

Section: Introductionmentioning

confidence: 99%

Dual Chemiexcitation by a Unique Dioxetane Scaffold Gated by an OR Logic Set of Triggers

David

Jaber

Fridman

et al. 2023

Chemistry A European J

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Chemiexcitation of phenoxy-1,2-dioxetane chemiluminescent luminophores is initiated by electron transfer from a meta-positioned phenolate ion to the peroxide-dioxetane bond. Here we report the development of a unique 1,2dioxetane chemiluminescent scaffold with chemiexcitation gated by an OR logic dual-set of triggering events. This scaffold is composed of meta-dihydroxyphenyl-1,2-dioxetaneadamantyl molecules, equipped with acrylic acid and chlorine substituents, that chemiexcitation under physiological conditions. A dual-mode chemiluminescent probe, armed with two different triggering substrates designed for activation by the enzymes β-galactosidase and alkaline phosphatase, was synthesized. The probe emitted intense light signals in the response to each enzyme, demonstrating its ability to serve as a single-component chemiluminescent sensor for dualanalyte detection. We also demonstrated the ability of the probe to detect β-galactosidase and phosphatase activities in bacteria. This is the first 1,2-dioxetane scaffold capable of responding to two different chemiexcitation events from two different positions on the same dioxetane molecule. We anticipate that the OR-gated mode of chemiexcitation, described herein, will find utility in the preparation of chemiluminescent probes with a dual-analyte detection/ imaging mode.

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“…Numerous research groups worldwide, including ours, took advantage of an ortho -substituted phenoxy-adamantyl-1,2-dioxetane luminophore to develop useful chemiluminescent probes for use in cells and in vivo assays. 25–48…”

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confidence: 99%

Chemiluminescent duplex analysis using phenoxy-1,2-dioxetane luminophores with color modulation

et al. 2023

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Ultrasensitive chemiluminescent neuraminidase probe for rapid screening and identification of small-molecules with antiviral activity against influenza A virus in mammalian cells

Abstract: Influenza A virus is the most virulent influenza subtype and is associated with large-scale global pandemics characterized by high levels of morbidity and mortality. Developing simple and sensitive molecular methods...

Cited by 19 publications

References 57 publications

Synthesis and Chemiexcitation of a Distinct Chemiluminescent Luminophore based on a Curcumin Scaffold

Synthesis and Chemiexcitation of a Distinct Chemiluminescent Luminophore based on a Curcumin Scaffold

Dual Chemiexcitation by a Unique Dioxetane Scaffold Gated by an OR Logic Set of Triggers

Chemiluminescent duplex analysis using phenoxy-1,2-dioxetane luminophores with color modulation

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