Fluorogenic Reactions in Chemical Biology: Seeing Chemistry in Cells

Chen, Yanyan; Jiang, Hao; Hao, Tingting; Zhang, Nan; Li, Mingyu; Xingyun, Wang; Wang, Xiuxiu; Wei, Wei; Zhao, Jing

doi:10.1021/cbmi.3c00029

Cited by 19 publications

(10 citation statements)

References 166 publications

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“…Fluorescent probes, which can specifically recognize targets and emit fluorescent signals, combined with fluorescence imaging technology, have the characteristics of high sensitivity, high spatiotemporal resolution, and simplicity [1][2][3]. They have been extensively researched in fields such as biological imaging and analytical detection [4][5][6][7]. Among them, organic small molecule fluorescent probes with a wide variety of molecular structures have advantages such as structural diversity, easy chemical modification, and good biocompatibility [8][9][10], which are highly favored by researchers.…”

Section: Introductionmentioning

confidence: 99%

An activatable azophenyl fluorescent probe for hypoxic fluorescence imaging in living cells

Liu,

Zhang,

et al. 2024

Luminescence

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Cellular hypoxia is a common pathological process in various diseases. Detecting cellular hypoxia is of great scientific significance for early diagnosis of tumors. The hypoxia fluorescence probe analysis method can efficiently and conveniently evaluate the hypoxia status in tumor cells. These probes are covalently linked by hypoxic recognition groups and organic fluorescent molecules. Currently, the fluorescent molecules used in these probes often exhibit the aggregation‐caused quenching effect, which is not conducive to fluorescence imaging in water. Herein, an activatable hypoxia fluorescence probe was constructed by covalently linking aggregation‐induced emission luminogens to the hypoxic recognition group azobenzene. It does not emit fluorescence in solution and in solid state under light excitation due to the presence of photosensitive azo bonds. It can be cleaved by intracellular azoreductase into fluorescent amino derivatives with aggregation‐induced emission characteristic. As the concentration of oxygen in cells decreases, its fluorescence intensity increases, making it suitable for fluorescence imaging to detect hypoxic environment in live cancer cells. This work broadens the molecular design approach for activatable hypoxia fluorescent probes.

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Section: Introductionmentioning

confidence: 99%

An activatable azophenyl fluorescent probe for hypoxic fluorescence imaging in living cells

Liu,

Zhang,

et al. 2024

Luminescence

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“…Additionally, the flexibility in peptide design (sequence, charge, structure, and length) allows for tailored physiochemical requirements in prodrug design. Peptides can be designed to self‐assemble into diverse nanostructures, [4] offering versatile applications in tissue engineering, [5] cancer therapy, [6] molecular imaging, [7] and drug delivery [8] . The short length of the peptides also minimize the immunogenicity of prodrugs, thereby improving safety.…”

Section: Introductionmentioning

confidence: 99%

Autocleaving Bonds for Better Drugs

Guo,

Chang,

2024

ChemMedChem

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While bond formation has historically been the mainstay of medicinal chemistry, the phenomenon of bond cleavage has received less focus. However, the success of numerous oral medications demonstrates the importance of controlled cleavage in prodrugs to achieve desired therapeutic outcomes. Nevertheless, effective strategies to control this cleavage remain limited. This concept article introduces a novel approach: employing peptides as conjugates to drugs to modulate the hydrolysis of these conjugates and enhance drug efficacy. The article begins by briefly outlining common prodrug strategies, followed by a few representative examples of how peptides can be leveraged to control the autohydrolysis of peptide‐conjugated prodrugs for bacterial and cancer cell inhibition. Finally, it provides a brief outlook on the future potential of this promising new research direction in molecular medicine.

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“…Bioorthogonal chemistry emerged as a powerful tool in luminescent bioimaging that relies of the use of luminescent click reagents. Some of these probes demonstrate 'switch-on' luminescence following a conjugation [1][2][3][4] Luminogenic probes are highly desirable, as the non-conjugated probe generates no luminescent background, ensuring high sensitivity of the probe without the need for laborious washing protocols. Phosphorescent cyclometallated iridium(III) complexes enrich the field of luminescent bioimaging by offering unique characteristics and several advantages over traditional organic probes.…”

Section: Introductionmentioning

confidence: 99%

Annealing 1,2,4-Triazine to Iridium(III) Complexes Induces Luminogenic Behaviour in Bioorthogonal Reactions with Stain Alkynes.

Cooke,

Gristwood,

Adamson

et al. 2024

Preprint

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Phenanthroline-type ligand containing annealed 1,2,4-triazine ring was used to prepare novel Ir(III) complexes 3 and 4. The complexes are non-luminescent but show luminogenic behaviour following inverse electron demand Diels-Alder (IEDDA) reaction with bicyclononyne (BCN) derivatives. It was observed that the complex 3 reacts with BCN-C10 three times faster than the corresponding free ligand 7. The magnitude of this accelerating metal-coordination effect, however, is less profound that in previously reported Ir(III) complexes of 1,2,4-triazines in which the triazine was directly coordinated to Ir(III) metal centre. Nevertheless, luminogenic behaviour opens prospects for the use of such complexes in bioimaging applications, which was demonstrated by developing a convenient methodology using “chemistry on the complex” concept for labelling antibodies with luminescent Ir(III) complexes. Bioorthogonal reactivity of the complex 4 was then evaluated by metabolically labelling live cells with BCN groups followed by luminogenic IEDDA reaction with the triazine iridium complex.

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Fluorogenic Reactions in Chemical Biology: Seeing Chemistry in Cells

Cited by 19 publications

References 166 publications

An activatable azophenyl fluorescent probe for hypoxic fluorescence imaging in living cells

An activatable azophenyl fluorescent probe for hypoxic fluorescence imaging in living cells

Autocleaving Bonds for Better Drugs

Annealing 1,2,4-Triazine to Iridium(III) Complexes Induces Luminogenic Behaviour in Bioorthogonal Reactions with Stain Alkynes.

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