scholarly journals Asymmetric and Reduced Xanthene Fluorophores: Synthesis, Photochemical Properties, and Application to Activatable Fluorescent Probes for Detection of Nitroreductase

Molecules ◽  
2019 ◽  
Vol 24 (17) ◽  
pp. 3206 ◽  
Author(s):  
More ◽  
Lim ◽  
Kang ◽  
Yun ◽  
Yee ◽  
...  

Xanthene fluorophores, including fluorescein, rhodol, and rhodamines, are representative classes of fluorescent probes that have been applied in the detection and visualization of biomolecules. “Turn on” activatable fluorescent probes, that can be turned on in response to enzymatic reactions, have been developed and prepared to reduce the high background signal of “always-on” fluorescent probes. However, the development of activity-based fluorescent probes for biological applications, using simple xanthene dyes, is hampered by their inefficient synthetic methods and the difficulty of chemical modifications. We have, thus, developed a highly efficient, versatile synthetic route to developing chemically more stable reduced xanthene fluorophores, based on fluorescein, rhodol, and rhodamine via continuous Pd-catalyzed cross-coupling. Their fluorescent nature was evaluated by monitoring fluorescence with variation in the concentration, pH, and solvent. As an application to activatable fluorescent probe, nitroreductase (NTR)-responsive fluorescent probes were also developed using the reduced xanthene fluorophores, and their fluorogenic properties were evaluated.

2021 ◽  
Author(s):  
Yongkang Yao ◽  
Yutao Zhang ◽  
Chenxu Yan ◽  
Wei-Hong Zhu ◽  
Zhiqian Guo

This review highlights the molecular design strategy of β-galactosidase-activatable probes from turn-on mode to ratiometric mode, from ACQ to AIE-active probes, from NIR-I to NIR-II imaging and dual-mode of chemo-fluoro-luminescence imaging.


2020 ◽  
Vol 07 ◽  
Author(s):  
Tanmay Chatterjee ◽  
Nilanjana Mukherjee

Abstract: A natural driving force is always working behind the synthetic organic chemists towards the development of ‘green’ synthetic methodologies for the synthesis of useful classes of organic molecules having potential applications. The majority of the essential classes of organic transformations, including C-C and C-X (X = heteroatom) bond-forming crosscoupling reactions, cross dehydrogenative-coupling (CDC) mostly rely on the requirement of transition-metal catalysts and hazardous organic solvents. Hence, the scope in developing green synthetic strategies by avoiding the use of transitionmetal catalysts and hazardous organic solvents for those important and useful classes of organic transformations is very high. Hence, several attempts are made so far. Water being the most abundant, cheap, and green solvent in the world; numerous synthetic methods have been developed in an aqueous medium. In this review, the development of transitionmetal- free green synthetic strategies for various important classes of organic transformations such as C-C and C-X bondforming cross-coupling, cross dehydrogenative-coupling, and oxidative-coupling in an aqueous media is discussed.


Chemosensors ◽  
2021 ◽  
Vol 9 (3) ◽  
pp. 44
Author(s):  
Muhammad Aminu Auwalu ◽  
Shanshan Cheng

Biological applications of fluorescent probes are rapidly increasing in the supramolecular chemistry research field. Several organic dyes are being utilized currently in developing and advancing this attractive research area, of which diketopyrrolopyrrole (DPP) organic dyes show an exceptional photophysical features (high-fluorescence quantum yield (FQY), good photochemical and thermal stability) that are essential properties for biological applications. Great efforts have been made in recent years towards developing novel fluorescent DPPs by different chemists for such applications, and some positive results have been reported. As a result, this review article gives an account of the progress that has so far been made very recently, mainly within the last decade, in that we selectively focus on and discuss more from 2015 to present on some recent scholarly achievements of fluorescent DPPs: quantum yield, aggregation-induced emission (AIE), solid-state emission, bio-imaging, cancer/tumor therapy, mitochondria staining and some polymeric fluorescent DPPs. Finally, this review article highlights researchers working on luminescent DPPs and the future prospects in some key areas towards designing DPP-based fluorescent probes in order to boost their photophysical and biological applications more effectively.


2021 ◽  
Vol 22 (12) ◽  
pp. 6645
Author(s):  
Doina Sirbu ◽  
Nicolas Chopin ◽  
Ivana Martinić ◽  
Moussa Ndiaye ◽  
Svetlana Eliseeva ◽  
...  

Pyridazino-1,3a,6a-triazapentalenes (PyTAP) are compact fused 6/5/5 tricyclic scaffolds which exhibit promising fluorescent properties. Chemically stable, they can be post-functionalized using standard Pd-catalyzed cross-coupling chemistry. Several original PyTAP bearing additional unsaturated substituents in positions 2 and 8 were synthetized and their spectroscopic properties analyzed. They have been successfully tested as fluorescent probes for cellular imaging.


Viruses ◽  
2021 ◽  
Vol 13 (5) ◽  
pp. 932
Author(s):  
Annekathrin Haberland ◽  
Oxana Krylova ◽  
Heike Nikolenko ◽  
Peter Göttel ◽  
Andre Dallmann ◽  
...  

COVID-19 is a pandemic respiratory disease that is caused by the highly infectious severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2). Anti-SARS-CoV-2 antibodies are essential weapons that a patient with COVID-19 has to combat the disease. When now repurposing a drug, namely an aptamer that interacts with SARS-CoV-2 proteins for COVID-19 treatment (BC 007), which is, however, a neutralizer of pathogenic autoantibodies in its original indication, the possibility of also binding and neutralizing anti-SARS-CoV-2 antibodies must be considered. Here, the highly specific virus-neutralizing antibodies have to be distinguished from the ones that also show cross-reactivity to tissues. The last-mentioned could be the origin of the widely reported SARS-CoV-2-induced autoimmunity, which should also become a target of therapy. We, therefore, used enzyme-linked immunosorbent assay (ELISA) technology to assess the binding of well-characterized publicly accessible anti-SARS-CoV-2 antibodies (CV07-209 and CV07-270) with BC 007. Nuclear magnetic resonance spectroscopy, isothermal calorimetric titration, and circular dichroism spectroscopy were additionally used to test the binding of BC 007 to DNA-binding sequence segments of these antibodies. BC 007 did not bind to the highly specific neutralizing anti-SARS-CoV-2 antibody but did bind to the less specific one. This, however, was a lot less compared to an autoantibody of its original indication (14.2%, range 11.0–21.5%). It was also interesting to see that the less-specific anti-SARS-CoV-2 antibody also showed a high background signal in the ELISA (binding on NeutrAvidin-coated or activated but noncoated plastic plate). These initial experiments suggest that the risk of binding and neutralizing highly specific anti-SARS CoV-2 antibodies by BC 007 should be low.


2015 ◽  
Vol 137 (2) ◽  
pp. 757-769 ◽  
Author(s):  
Baoxin Zhang ◽  
Chunpo Ge ◽  
Juan Yao ◽  
Yaping Liu ◽  
Huichen Xie ◽  
...  

2019 ◽  
Vol 91 (5) ◽  
pp. 865-874 ◽  
Author(s):  
Armando Córdova ◽  
Samson Afewerki ◽  
Rana Alimohammadzadeh ◽  
Italo Sanhueza ◽  
Cheuk-Wai Tai ◽  
...  

Abstract A sustainable strategy for the neat production and surface functionalization of nanocellulose from wood pulp is disclosed. It is based on the combination of organocatalysis and click chemistry (“organoclick” chemistry) and starts with nanocellulose production by organic acid catalyzed hydrolysis and esterification of the pulp under neat conditions followed by homogenization. This nanocellulose fabrication route is scalable, reduces energy consumption and the organic acid can be efficiently recycled. Next, the surface is catalytically engineered by “organoclick” chemistry, which allows for selective and versatile attachment of different organic molecules (e.g. fluorescent probes, catalyst and pharmaceuticals). It also enables binding of metal ions and nanoparticles. This was exemplified by the fabrication of a heterogeneous nanocellulose-palladium nanoparticle catalyst, which is used for Suzuki cross-coupling transformations in water. The disclosed surface functionalization methodology is broad in scope and applicable to different nanocelluloses and cellulose based materials as well.


2020 ◽  
Vol 306 ◽  
pp. 127567 ◽  
Author(s):  
Jiemin Wang ◽  
Zhidong Teng ◽  
Ting Cao ◽  
Jing Qian ◽  
Lei Zheng ◽  
...  

2019 ◽  
Vol 18 (6) ◽  
pp. 1342-1349 ◽  
Author(s):  
Sumit Roy ◽  
Ashim Maity ◽  
Naren Mudi ◽  
Milan Shyamal ◽  
Ajay Misra

Rhodamine and its derivatives have been widely used in designing fluorescent ‘turn on’ cation sensors, while very few rhodamine based fluorescent probes have been reported to date for the detection of anions in water.


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