A fluorogenic probe for detecting CO with the potential integration of diagnosis and therapy (IDT) for cancer

Yue, Lizhou; Tang, Yonghe; Huang, Huawei; Song, Wenhui; Lin, Weiying

doi:10.1016/j.snb.2021.130245

Cited by 16 publications

(11 citation statements)

References 52 publications

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“…Another probe NAP−CO was also developed by the same group to detect the CO. It showed a great potential for integrating diagnosis and therapeutics [111] . This probe could detect CO and showed therapeutic effects on cancer, successfully proved in cells, tissues, and mice models.…”

Section: Activity‐based Fluorescent Probe For Reactive Mono Carbonylsmentioning

confidence: 99%

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Activity‐Based Fluorescent Probes for Sensing and Imaging of Reactive Carbonyl Species (RCSs)

Jana

Baruah

Samanta

2022

Chemistry An Asian Journal

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This review explains various strategies for developing fluorescent probes to detect reactive carbonyl species (RCS). There are several mono and diacarbonyls among 30 varieties of reactive carbonyl species (RCSs) so far discovered, which play pivotal roles in pathological processes such as cancer, neurodegenerative diseases, cardiovascular disease, renal failure, and diabetes mellitus. These RCSs play essential roles in maintaining ion channel regulation, cellular signaling pathways, and metabolisms. Among RCSs, carbon monoxide (CO) is also utilized for its cardioprotective, anti-inflammatory, and anti-apoptotic effects. Fluorescence-based non-invasive optical tools have come out as one of the promising methods for analyzing the concentrations and co-localizations of these small metabolites. There has been a tremendous eruption in developing fluorescent probes for selective detection of specific RCSs within cellular and aqueous environments due to their high sensitivity, high spatial and temporal resolution of fluorescence imaging. Fluorescence-based sensing mechanisms such as intramolecular charge transfer (ICT), photoinduced electron transfer (PeT), excited-state intramolecular proton transfer (ESIPT), and fluorescence resonance energy transfer (FRET) are described. In particular, probes for dicarbonyls such as methylglyoxal (MGO), malondialdehyde (MDA), along with monocarbonyls that include formaldehyde (FA), carbon monoxide (CO) and phosgene are discussed. One of the most exciting advances in this review is the summary of fluorescent probes of dicarbonyl compounds.

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Section: Activity‐based Fluorescent Probe For Reactive Mono Carbonylsmentioning

confidence: 99%

“…It showed a great potential for integrating diagnosis and therapeutics. [111] This probe could detect CO and showed therapeutic effects on cancer, successfully proved in cells, tissues, and mice models. Recently Zhang et al also developed a coumarin-based NCCA probe for detecting CO (Figure 9G).…”

Section: Carbon Monoxide (Co)mentioning

confidence: 99%

Activity‐Based Fluorescent Probes for Sensing and Imaging of Reactive Carbonyl Species (RCSs)

Jana

Baruah

Samanta

2022

Chemistry An Asian Journal

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“…The 1, 8-naphthalimides have a very wide range of applications [1][2] and are often reported extensively as fluorescent dyes, probes and antitumour agents [3][4][5][6][7][8][9][10]. Both the imide site and the naphthalene ring of this class of compounds can be structurally modified and derivatised to obtain new derivatives, showing structural diversity.…”

Section: Introductionmentioning

confidence: 99%

Improvement of Synthesis Process of 4-Amino-1, 8 Naphthalene Anhydride

2023

analc

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Objective: By optimizing the reaction conditions for synthesizing 4-amino-1, 8 naphthalene anhydride compound through three steps of nitration, oxidation and reduction based on the raw material acenaphthene, the yield is improved and the synthesis cost is reduced, so that it can be used for large-scale preparation in the laboratory. Methods: The single variable method was used to explore the effect of temperature conditions on the yield of nitration reaction; to explore the effect of the amount of oxidant, heating and refluxing time, and product post-treatment on the yield of the oxidation reaction; to explore the effect of the amount of absolute ethanol and concentrated hydrochloric acid on the yield of the reduction reaction influences. After the reduction reaction, the gradient elution method of dichloromethane:methanol = 120:1~50:1 was adopted to separate and obtain pure 4-amino-1,8 naphthalene anhydride. Results: The yield of nitration reaction is up to 92.16%, the yield of oxidation reaction is up to 59.49%, and the yield of reduction reaction is up to 77.47%. The purified reduction products are analyzed by 1H-NMR, 13C-NMR and MS (ESI) and the structure was confirmed. Conclusion: The synthesis reaction conditions of 4-amino-1, 8 naphthalene anhydride were optimized, which was helpful for its large-scale preparation in the laboratory, and accumulated important basic experimental data for the industrial production of this compound.

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“…It also needs to be noted that there are several nitro-reduction-based probes that initially were reported to detect CO. ,, However, the detection mechanism was later found to be dependent on the reactivity of the ruthenium–CO complex, not on CO per se . Thus, they ,, should be regarded not as general CO probes but as probes for ruthenium-based CORMs. ,,,− Such results underscore the necessity of using CO gas to authenticate CO sensing and detection.…”

Section: Introductionmentioning

confidence: 99%

De Novo Construction of Fluorophores via CO Insertion-Initiated Lactamization: A Chemical Strategy toward Highly Sensitive and Highly Selective Turn-On Fluorescent Probes for Carbon Monoxide

et al. 2022

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Extensive studies in the last few decades have led to the establishment of CO as an endogenous signaling molecule and subsequently to the exploration of CO’s therapeutic roles. In the current state, there is a critical conundrum in CO-related research: the extensive knowledge of CO’s biological effects and yet an insufficient understanding of the quantitative correlations between the CO concentration and biological responses of various natures. This conundrum is partially due to the difficulty in examining precise concentration–response relationships of a gaseous molecule. Another reason is the need for appropriate tools for the sensitive detection and concentration determination of CO in the biological system. We herein report a new chemical approach to the design of fluorescent CO probes through de novo construction of fluorophores by a CO insertion-initiated lactamization reaction, which allows for ultra-low background and exclusivity in CO detection. Two series of CO detection probes have been designed and synthesized using this strategy. Using these probes, we have extensively demonstrated their utility in quantifying CO in blood, tissue, and cell culture and in cellular imaging of CO from exogenous and endogenous sources. The probes described will enable many biology and chemistry labs to study CO’s functions in a concentration-dependent fashion with very high sensitivity and selectivity. The chemical and design principles described will also be applicable in designing fluorescent probes for other small molecules.

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A fluorogenic probe for detecting CO with the potential integration of diagnosis and therapy (IDT) for cancer

Cited by 16 publications

References 52 publications

Activity‐Based Fluorescent Probes for Sensing and Imaging of Reactive Carbonyl Species (RCSs)

Activity‐Based Fluorescent Probes for Sensing and Imaging of Reactive Carbonyl Species (RCSs)

Improvement of Synthesis Process of 4-Amino-1, 8 Naphthalene Anhydride

De Novo Construction of Fluorophores via CO Insertion-Initiated Lactamization: A Chemical Strategy toward Highly Sensitive and Highly Selective Turn-On Fluorescent Probes for Carbon Monoxide

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