Article
Chemistry, Organic
Kasper M. Beck, Linette Ruder, Tine S. Nicolai, Robert L. Pham, Nikolaj A. Risgaard, Mick Hornum, Poul Nielsen
Summary: Double-headed nucleotides theoretically store twice as much information as native nucleotides, but the two newly developed analogs still need improvement in enhancing base-pairing specificity. Additionally, an improved synthetic strategy is proposed to avoid using doubly protected diaminopurines and complicated deprotections.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Kaivin Hadidi, Yitzhak Tor
Summary: Analogues of N,N-dimethyladenine with thieno- and isothiazolo-pyrimidine cores were modified using 3-substituted azetidines to produce fluorescent fluorophores with high emission quantum yields. The substituents on the azetidine ring correlated with the emission quantum yields. Ribosylation of the modified nucleobase resulted in a lower emission quantum yield in water compared to the precursor nucleobase, but the high emission quantum yield was restored in deuterium oxide, indicating the potential impact of the sugar moiety on the photophysical features of fluorescent nucleosides.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Review
Chemistry, Multidisciplinary
Shantanu Pal, Girish Chandra, Samridhi Patel, Sakshi Singh
Summary: Fluorination on nucleoside has become a promising tool in the past twenty years, as it enables the production of biologically active compounds that can impact pharmacodynamics and pharmacokinetics to support clinical trials. The unique properties of fluorine and its careful introduction into the molecule make the corresponding nucleoside metabolically stable and lipophilic, while also creating a new site for intermolecular binding.
Article
Chemistry, Multidisciplinary
Artis Klapars, John Y. L. Chung, John Limanto, Ralph Calabria, Louis-Charles Campeau, Kevin R. Campos, Wenyong Chen, Stephen M. Dalby, Tyler A. Davis, Daniel A. DiRocco, Alan M. Hyde, Amude M. Kassim, Mona Utne Larsen, Guiquan Liu, Peter E. Maligres, Aaron Moment, Feng Peng, Rebecca T. Ruck, Michael Shevlin, Bryon L. Simmons, Zhiguo Jake Song, Lushi Tan, Timothy J. Wright, Susan L. Zultanski
Summary: A highly efficient route to the HCV antiviral agent uprifosbuvir was developed in 5 steps from readily available uridine, achieving a 50% overall yield. This new synthesis method significantly improves the yield of uprifosbuvir and expands the tool set available for the synthesis of antiviral nucleotides.
Article
Chemistry, Organic
Matthieu Roignant, Jun Zhang, Julien Brioche, Serge R. Piettre
Summary: This study describes a new approach to protected modified dinucleotides using a difluorophosphinothioyl unit to replace the phosphoryl diester. The authors report a simple and high-yielding method for the preparation of 6'-iodonucleosides and successfully synthesize bisfuranosyl derivatives featuring both a difluorophosphinothioyl unit and a nucleobase. However, the introduction of the second nucleobase resulted in low yields and the formation of mixtures of homo- and heterodinucleotides due to the trans-N-glycosylation process.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Sergii Afonin, Serhii Koniev, Laetitia Preau, Masanari Takamiya, Alexander Strizhak, Oleg Babii, Andrii Hrebonkin, Vasyl G. Pivovarenko, Margitta Dathe, Ferdinand le Noble, Sepand Rastegar, Uwe Straehle, Anne S. Ulrich, Igor Komarov
Summary: This study successfully utilized fluorescent labeling of peptides with an amino acid bearing a fluorophore, demonstrating the importance of fluorescent labeling in studying peptide activity. The behavior of labeled peptides was observed in human cells and zebrafish embryos using various techniques.
FRONTIERS IN CHEMISTRY
(2021)
Article
Engineering, Environmental
Guangrong Sun, Pei Guo, Han Yeong Kaw, Meijiao Zhou, Wei Wang
Summary: This study reports the identification of five halogenated nucleobases as emerging disinfection byproducts (DBPs) in drinking water, with 2-chloroadenine exhibiting significant toxicological risk. A solid phase extraction-ultraperformance liquid chromatography-tandem mass spectrometry method was developed to detect these DBPs, with detection frequencies ranging from 73 to 100% and maximum concentrations of up to 65.3 ng/L in representative drinking water samples. The cytotoxicity of 2-chloroadenine was found to be three times higher than that of the commonly found DBP 2,6-dichloro-1,4-benzoquinone. These findings provide important insights for further research on the mutagenicity and human health risk of halogenated nucleobase-DBPs.
ENVIRONMENTAL SCIENCE & TECHNOLOGY
(2023)
Article
Polymer Science
Yeoju Yoon, Seonyoung Jo, Dong Hoon Lee, Taek Seung Lee
Summary: A conjugated polymer containing the o-AN group was synthesized and showed distinct color and fluorescence in solution. The polymer demonstrated excellent F-ion detection ability and ratiometric color change properties.
Article
Chemistry, Analytical
Yuanqiang Hao, Yintang Zhang, Qiuling Sun, Shu Chen, Zilong Tang, Rongjin Zeng, Maotian Xu
Summary: Hypochlorous acid (HOCl) is a potent reactive oxygen species essential in biological processes. A new ratiometric fluorescent probe has been designed and synthesized for sensitive and selective detection of HOCl, with advantages including rapid response, high signal to noise ratio, and utility for visualizing HOCl in cells and organisms.
MICROCHEMICAL JOURNAL
(2021)
Article
Chemistry, Medicinal
Isaac L. Downs, David Ordonez Luna, Krishna P. Kota, Sarah K. Rubin, Serena S. Shirsekar, Michael D. Ward, Rekha G. Panchal, Vladislav A. Litosh
Summary: Nucleoside and nucleobase analogs have been essential in fighting infectious diseases, but they often have off-target intracellular effects. Modifying the N4-hydroxycytidine molecule may provide novel antiviral compounds with reduced side effects.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2023)
Article
Chemistry, Applied
Yongming Guo, Junyan Shi, Chengwei Wei, Tiancheng Fang, Tao Tao
Summary: A facile one-pot solvothermal strategy was used to fabricate fluorescent aminoclay (F-AC) using MgCl2, 3-aminopropyltrimethoxysilane, and m-phenylenediamine. The synthesized F-AC showed blue-green fluorescence and good photostability, with the strongest fluorescence observed at pH = 4.0. The F-AC was successfully employed for ratiometric fluorescence determination of sunset yellow, showing good sensitivity with a linear range of 0-30 mu M and a LOD of 0.195 mu M. The F-AC was also utilized for anti-counterfeiting and fabricated as fluorescent gel and membrane, demonstrating its potential optical applications.
Article
Chemistry, Applied
Zhentao Li, Xinyue Cui, Zhuang Hu, Changjun Hu, Zilin Chen
Summary: The sensitive detection of trace water in solid food products is crucial for maintaining their stability and quality. A novel crystalline COF TAPT-BPTA with fluorescence was developed for this purpose, which can be quenched by trace water due to disruption of the intermolecular charge transfer process. The COF TAPT-BPTA demonstrated rapid response and wide sensing ranges in various organic solvents. It was also successfully used in a ratiometric fluorescent sensor for detecting trace water in milk powder samples.
MICROPOROUS AND MESOPOROUS MATERIALS
(2023)
Article
Chemistry, Multidisciplinary
Manisha B. Walunj, Seergazhi G. Srivatsan
Summary: Nucleoside-lipid conjugates are useful building blocks for constructing self-assembled architectures in biomedical and material applications. By synthetically manipulating these nucleoside derivatives, additional functionalities can be added to enhance the assembling process and impart interesting properties.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Article
Chemistry, Analytical
Ya-Nan Wei, Bo Lin, Yang Shu, Jian-Hua Wang
Summary: A novel fluorescent probe ANET was designed to target mitochondria for detecting Cys, showing advantages of ratiometric fluorescence, high selectivity, and a large Stokes shift. Imaging of Cys was confirmed in HepG2 cells using this probe.
Article
Materials Science, Multidisciplinary
Xue-Chun Sun, Zhen-Zhong Cong, Shuang-Yan Wu, Ying Zhang, Ming-Chang Zhu, Xiao-Jue Bai
Summary: The rational design and synthesis of isostructural Ln-MOFs as fluorescent probes for the detection of riboflavin (RF) is investigated in this study. Among the prepared Ln-BPTA systems, Eu-BPTA exhibits the best response performance with rapid response, ultralow limit of detection, excellent durability, and high selectivity. The fluorescence detection process is attributed to the Forster resonance energy transfer (FRET) mechanism between Ln-BPTA and RF.
JOURNAL OF MATERIALS CHEMISTRY C
(2022)
Article
Chemistry, Physical
Giacomo Fanciullo, Irene Conti, Pascal Didier, Andrey Klymchenko, Jeremie Leonard, Marco Garavelli, Ivan Rivalta
Summary: A new macroscopic model incorporating contributions from molecular aggregate quenchers was introduced to analyze the decay process of exciton density. The study demonstrated that the model is applicable to molecular systems with ultrafast decays, and the presence of molecular aggregate quenchers can be monitored by evaluating the long time decay of exciton density. This model could potentially be used in future studies for global fitting of experimental data with support from first-principles simulations.
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2022)
Article
Chemistry, Multidisciplinary
Fei Liu, Dmytro Danylchuk, Bohdan Andreiuk, Andrey S. Klymchenko
Summary: Organelle-specific targeting is crucial for enhancing the effectiveness of drugs and visualizing cellular processes. In this study, a novel concept of dynamic covalent targeting of organelles was proposed, where the molecule is conjugated with its ligand directly inside live cells through a dynamic covalent bond. Experimental results showed that this targeting method enabled fluorescence imaging in live cells and achieved preferential localization of drugs and dyes in specific organelles.
Article
Chemistry, Multidisciplinary
Anna Poryvai, Maksym Galkin, Volodymyr Shvadchak, Tomas Slanina
Summary: In this work, a water-soluble caging group based on a pi-extended BODIPY scaffold was developed to release carboxylate-containing cargo upon red light illumination. Mechanistic studies showed new insights into the photoreactivity of these cages, and the structure of the carboxylate cargo was found to significantly influence the rate and efficiency of the uncaging process. The method was successfully used for selective delivery, visualization, and photorelease of a signaling lipid in cell plasma and internal membranes, inducing Ca2+ release in cells expressing the GPR40 receptor.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Multidisciplinary
Andrey S. Klymchenko
Summary: Biomembranes, as lipid structures, play a crucial role in cellular processes. The development of chemical tools, such as fluorescent probes, for sensing and imaging biomembranes is a rapidly growing field. This Account focuses on advances in smart molecules for membrane targeting and sensing, with a particular emphasis on plasma membranes and organelles.
ACCOUNTS OF CHEMICAL RESEARCH
(2023)
Article
Chemistry, Multidisciplinary
Lazare Saladin, Ophelie Dal Pra, Andrey S. S. Klymchenko, Pascal Didier, Mayeul Collot
Summary: Dual-emissive photoconvertible fluorophores (DPCFs) are useful for tracking labeled cells in bioimaging. The directed photooxidation-induced conversion (DPIC) mechanism allows efficient DPCFs to be obtained by conjugating a coumarin to aromatic singlet-oxygen reactive moieties (ASORMs). Pyrrole is a suitable ASORM that provides a high hypsochromic shift and fast conversion. By modifying pyrrole, we can tune the photoconversion properties of the DPCFs, leading to an improved dual emissive converter, SCP-Boc, with high brightness and a 63% enhanced photoconversion yield. SCP-Boc was successfully used for sequential cell photoconversion using laser scanning confocal microscopy.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Physical
Germain A. Brou, Gildas K. Gbassi, Ievgen Shulov, Aidar Seralin, Andrey S. Klymchenko, Thierry F. Vandamme, Nicolas Anton
Summary: In this study, we investigated the characterization and tracking of chemical reactions of amphiphile compounds on model interfaces. By using a custom-made surfactant and interfacial crosslinking through click chemistry, we observed changes in monolayer properties and dilatational elasticity. Through bulk phase exchange and washing, we specifically measured the interfacial effects of the entities adsorbed and trapped at the interface.
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2023)
Article
Nanoscience & Nanotechnology
Fei Liu, Nicolas Anton, Yosuke Niko, Andrey S. Klymchenko
Summary: Current biomedical applications of nanocarriers focus on controlled drug delivery, but this study proposes a different approach where toxic molecules are extracted from biological tissues using lipid nanoemulsion (NE) droplets. By designing a highly lipophilic amine (LipoAmine), cargo-aldehydes can be reacted and encapsulated inside lipid NEs through dynamic covalent chemistry. The formation of imine conjugates was validated and the NEs successfully extracted fluorescent dye and toxic aldehydes from cells, demonstrating the potential for developing detoxification platforms.
ACS APPLIED BIO MATERIALS
(2023)
Article
Biochemistry & Molecular Biology
Maksym Galkin, Oleksandra Topcheva, Anastasiia Priss, Tatiana Borisova, Volodymyr V. Shvadchak
Summary: Parkinson's disease is characterized by the death of certain neurons in the midbrain and the accumulation of alpha-synuclein fibrils. Current treatment involves increasing dopamine levels, but this can produce toxic oligomers. In our study, we found that these oligomers can inhibit alpha-synuclein fibrillization, providing insights into the effects of dopamine-enhancing therapy on Parkinson's disease.
ACS CHEMICAL NEUROSCIENCE
(2023)
Article
Chemistry, Multidisciplinary
Deep Sekhar Biswas, Paraskevi Gaki, Elisabete Cruz Da Silva, Antoine Combes, Andreas Reisch, Pascal Didier, Andrey S. Klymchenko
Summary: By studying the FRET phenomenon between fluorescent organic nanoparticles, it is found that the efficiency does not follow the Forster law and can achieve high efficiency at long distances. This opens up the possibility of using advanced optical nanomaterials for amplified FRET-based biosensing.
ADVANCED MATERIALS
(2023)
Article
Chemistry, Analytical
Reimi Pelletier, Dmytro I. Danylchuk, Hela Benaissa, Fanny Broch, Romain Vauchelles, Arnaud Gautier, Andrey S. Klymchenko
Summary: Genetically encoded protein labels combined with polarity-sensitive fluorescent probes provide information about the nanoscale environments of proteins within subcellular compartments. A solvatochromic HaloTag probe, NR12-Halo, specifically labels a variety of proteins localized in different cell compartments and distinguishes proteins within lipid membranes. This probe also reveals changes in protein environments during their life cycle, heterogeneity in membrane protein polarity, and the effects of mechanical stress and fatty acid diet on protein nanoenvironments. The solvatochromic HaloTag probe is a promising tool for studying protein interactions and nanoscale environments within subcellular structures.
ANALYTICAL CHEMISTRY
(2023)
Editorial Material
Chemistry, Multidisciplinary
L. Saladin, O. Dal Pra, A. S. S. Klymchenko, P. Didier, M. Collot
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Physical
Tesla Yudhistira, Elisabete Cruz Da Silva, Antoine Combes, Maxime Lehmann, Andreas Reisch, Andrey S. S. Klymchenko
Summary: This study reports a method of antibody labeling using biotinylated zwitterionic dye-loaded polymeric nanoparticles. The prepared biotinylated nanoparticles are small (14 nm) and bright, capable of carrying a large amount of cationic rhodamine dye. The method significantly improves fluorescence imaging of target epidermal growth factor receptors and becomes a useful tool in the high-sensitivity detection of disease biomarkers.
Article
Materials Science, Multidisciplinary
Deep Sekhar Biswas, Nina Melnychuk, Caterina Severi, Pascal Didier, Andrey S. Klymchenko
Summary: Light-harvesting is a fundamental process in nature that drives the development of artificial systems for various applications. Researchers have discovered that using blank hydrophobic salts can suppress dye aggregation within nanoparticles, improving their fluorescence properties and enabling efficient energy transfer and antenna effects.
ADVANCED OPTICAL MATERIALS
(2023)
Article
Materials Science, Multidisciplinary
Lucie Haye, Nour Fayad, Richard C. Knighton, Antoine Combes, Olivier Jeannin, Andrey Klymchenko, Thibault Gallavardin, Niko Hildebrandt, Loic J. Charbonniere, Andreas Reisch
Summary: This study investigates the physicochemical and photophysical properties of Re diimine complexes and Cy5 dyes coencapsulated in polymer nanoparticles (NPs), and their compatibility for bioimaging. The results show that encapsulation significantly enhances the photoluminescence brightness and lifetimes of Re complexes, while coencapsulation of Cy5 leads to bright near-infrared emission upon Re complex excitation. Furthermore, the Re-Cy5 NPs exhibit high-contrast photoluminescence imaging in mammalian cells.
ADVANCED MATERIALS TECHNOLOGIES
(2023)
Review
Chemistry, Multidisciplinary
Anila Hoskere Ashoka, Ilya O. Aparin, Andreas Reisch, Andrey S. Klymchenko
Summary: Brightness is crucial for (bio)molecular detection and optical bioimaging. This tutorial review provides definitions of brightness and describes the major approaches to its analysis. It also discusses the current chemical methods to combat Aggregation-Caused Quenching and compares the brightness and other properties of different fluorescent organic nanoparticles. The importance of brightness in biological applications is also analyzed.
CHEMICAL SOCIETY REVIEWS
(2023)
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.
