Harnessing Intramolecular Rotation To Enhance Two‐photon Imaging of Aβ Plaques through Minimizing Background Fluorescence

Shin, Jin Woo; Verwilst, Peter; Choi, Hyungkil; Kang, Sangrim; Han, Jiyou; Kim, Na Hee; Choi, Jin Gyu; Oh, Myung Sook; Hwang, Ji Sun; Kim, Dokyoung; Mook‐Jung, Inhee; Kim, Jong Seung

doi:10.1002/anie.201900549

Cited by 79 publications

(51 citation statements)

References 28 publications

(19 reference statements)

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“…For most hydrophobic fluorescence probes (for nonactivatable probes), the restricted conformation of a probe and the hydrophobicity of the residing environment of the probe have strong influence on the turn-on effect of fluorescence 31 , 43 , 65 – 67 . Similarly, this principle can be applied to chemiluminescence probes.…”

Section: Discussionmentioning

confidence: 99%

Turn-on chemiluminescence probes and dual-amplification of signal for detection of amyloid beta species in vivo

et al. 2020

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Turn-on fluorescence imaging is routinely studied; however, turn-on chemiluminescence has been rarely explored for in vivo imaging. Herein, we report the design and validation of chemiluminescence probe ADLumin-1 as a turn-on probe for amyloid beta (Aβ) species. Two-photon imaging indicates that ADLumin-1 can efficiently cross the blood–brain barrier and provides excellent contrast for Aβ plaques and cerebral amyloid angiopathy. In vivo brain imaging shows that the chemiluminescence signal of ADLumin-1 from 5-month-old transgenic 5xFAD mice is 1.80-fold higher than that from the age-matched wild-type mice. Moreover, we demonstrate that it is feasible to further d ually- a mplify s ignal via c hemiluminescence r esonance e nergy t ransfer (DAS-CRET) using two non-conjugated smart probes (ADLumin-1 and CRANAD-3) in solutions, brain homogenates, and in vivo whole brain imaging. Our results show that DAS-CRET can provide a 2.25-fold margin between 5-month-old 5xFAD mice and wild type mice. We believe that our strategy could be extended to other aggregating-prone proteins.

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Section: Discussionmentioning

confidence: 99%

Turn-on chemiluminescence probes and dual-amplification of signal for detection of amyloid beta species in vivo

et al. 2020

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“…Recently, our research team has focused on the development of a naphthalene-based donor (D)-acceptor (A) type of dipolar fluorescent dyes and its applications for the detection of metal ions, enzyme activity, amino acid, cell sub-organelles, disease biomarkers, and carcinogens [20,21,22,23,24,25]. During the research process, we found a fast hydrazone-formation between D-A type naphthaldehyde and hydrazine by o -MOM assistant, and we utilized this property in developing a fluorescent probe, HyP-1 [18] .…”

Section: Resultsmentioning

confidence: 99%

Hydrazine-Selective Fluorescent Turn-On Probe Based on Ortho-Methoxy-Methyl-Ether (o-MOM) Assisted Retro-aza-Henry Type Reaction

Jung

Park

Kang

et al. 2019

Sensors

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Hydrazine (N2H4) is one of the most widely used industrial chemicals that can be utilized as a precursor of pesticides, pharmaceutics, and rocket propellant. Due to its biological and environmental toxicity with potential health risks, various sensing tools have been developed. Among them, fluorescence-based molecular sensing systems have been highlighted due to its simple-operation, high selectivity and sensitivity, and biocompatibility. In our recent report, we disclosed a ratiometric type fluorescent probe, called HyP-1, for the detection of hydrazine, which is based on ortho-methoxy-methyl-ether (o-MOM) moiety assisted hydrazone-formation of the donor (D)-acceptor (A) type naphthaldehyde backbone. As our follow-up research, we disclose a turn-on type fluorescent probe, named HyP-2, as the next-generation hydrazine probe. The sensing rational of HyP-2 is based on the o-MOM assisted retro-aza-Henry type reaction. The dicyanovinyl moiety, commonly known as a molecular rotor, causes significant emission quenching of a fluorescent platform in aqueous media, and its cleavage with hydrazone-formation, which induces a significant fluorescence enhancement. The high selectivity and sensitivity of HyP-2 shows practical explicabilities, including real-time paper strip assay, vapor test, soil analysis, and real water assay. We believe its successful demonstrations suggest further applications into a wide variety of fields.

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“…Probe 61 could label Aβ plaques in the frontal cortex of 5xFAD‐Tg mice with good BBB penetration and excellent two‐photon cross‐sections. [ 50 ]…”

Section: Alzheimer's Diseasementioning

confidence: 99%

Fluorescent Diagnostic Probes in Neurodegenerative Diseases

et al. 2020

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Both chronic and acute neurodegenerative diseases have been associated with high morbidity and mortality, along with the death of neurons in different areas of the brain, and there are few or no effective curative therapy options for treatment of patients. [3,4] These disorders are a major cause of concern for the health and quality of life in the aging society, since age is the greatest risk factor for neurodegenerative disease. [5] The World Health Organization has predicted that in next 20 years neurodegenerative disease will become the second most common cause of mortality after cardiovascular disease. [6] Neurodegenerative processes begin long before their clinical symptoms are evident, and evolve for years slowly and irreversibly. Hence, there is an urgent need to diagnose neurodegenerative disease as early as possible and to distinguish between different neurodegenerative disorders with shared and unique symptoms to facilitate decision making regarding choice of treatment. Timely diagnosis is important for the adoption of therapeutic modalities in clinical trials prior to moderate dementia exhibition, to appraise and apply antidotes to maximally preserve the cognitive functions or to slow down the course of these disorders. The ability to analyze and identify risk factors for cognitive deficit would represent an extraordinary advancement in the field of dementia. [5] The main modern diagnostic technologies for the early examination of neurodegenerative disease pathology, neuroimaging techniques, include radioligandsbased positron emission tomography (PET), 3D single-photon emission-computed tomography (SPECT), and structural magnetic resonance imaging (MRI). Although PET and SPECT are the most used imaging techniques for neurodegenerative diseases, their application is limited by high cost, involvement of hazardous radiolabeled compounds, need for sophisticated instruments, and application of complex data acquisition and analysis protocols. The MRI technique has relatively low spatial resolution as well as intrinsically poor sensitivity to distinguish morphological differences between disease biomarkers and the surrounding tissue. Recently, fluorescence diagnosis technology has become an attractive and potential alternative to diagnose and probe the progression of neurodegenerative diseases, because of being rapid, noninvasive, sensitive, simple, real-time, low-cost, and high-resolution in nature. [7] There are several uses for Neurodegenerative diseases are debilitating disorders that feature progressive and selective loss of function or structure of anatomically or physiologically associated neuronal systems. Both chronic and acute neurodegenerative diseases are associated with high morbidity and mortality along with the death of neurons in different areas of the brain; moreover, there are few or no effective curative therapy options for treating these disorders. There is an urgent need to diagnose neurodegenerative disease as early as possible, and to distinguish between different disorders with overlap...

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Harnessing Intramolecular Rotation To Enhance Two‐photon Imaging of Aβ Plaques through Minimizing Background Fluorescence

Cited by 79 publications

References 28 publications

Turn-on chemiluminescence probes and dual-amplification of signal for detection of amyloid beta species in vivo

Turn-on chemiluminescence probes and dual-amplification of signal for detection of amyloid beta species in vivo

Hydrazine-Selective Fluorescent Turn-On Probe Based on Ortho-Methoxy-Methyl-Ether (o-MOM) Assisted Retro-aza-Henry Type Reaction

Fluorescent Diagnostic Probes in Neurodegenerative Diseases

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