Article
Chemistry, Analytical
Aman K. K. Bhasin, Pooja Chauhan, Savita Chaudhary
Summary: In the recent decade, coumarin and its congeners have been extensively evaluated for their biological potency in drug-like molecules. However, there are relatively fewer reports on their utility as a pincer-type ligand against biochemical analytes. This study reports the synthesis and characterization of a potentially novel coumarin-derived schiff base (M) as a sensor of Zn2+ in semi-aqueous medium, showing significant fluorescence enhancement in the presence of Zn2+ compared to other competitive cations like Cd2+. The coordination stoichiometry of M: Zn2+ was found to be 1:1 with a low detection limit, indicating effective sensing capabilities towards Zn2+ in environmental water samples.
SENSORS AND ACTUATORS B-CHEMICAL
(2021)
Article
Biochemistry & Molecular Biology
Nika Zurga, Thomas Moragues, Andrew J. Demello
Summary: This article re-evaluates the ability of C460 to detect Pd2+ concentration and finds that it is actually a pH sensor rather than a fluorescence sensor. Furthermore, the article points out inaccuracies or incompleteness in the description of the experimental procedures, particularly in sample preparation.
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY B-BIOLOGY
(2023)
Review
Chemistry, Applied
Farid Ahmed, Hai Xiong
Summary: This review summarizes the latest developments in chemosensors based on click generated triazoles for a range of metal cations, anions, and neutral analytes, highlighting the need for continuous research accumulation in this rapidly growing field to meet demand.
Article
Chemistry, Multidisciplinary
Wei Tuo, Jean-Philippe Renault, Aashini Rajpal, Serge Pin, Thierry Le Gall, Frederic Taran
Summary: This study presents the use of benzothiazolines as radiosensitive compounds that can produce gamma-irradiation and fluorescent benzothiazoles, as well as release amines or carboxylic acids upon treatment with Cs-137 in water. The proof of concept study demonstrated that benzothiazolines can be utilized as cleavable linkers that are triggered by irradiation.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Applied
Wei Yang, Chenyuan Weng, Xiaoyun Li, Wei Xu, Jianwen Fei, Junli Hong, Jun Zhang, Wanying Zhu, Xuemin Zhou
Summary: Fe3O4 nanoparticles were used as a magnetic artificial peroxidase to create a high-sensitivity and high-selectivity ratiometric photoluminescence sensor for coumarin based on photoinduced electron transfer. This method showed excellent selectivity and had a detection limit of 0.016 mg/L for coumarin, making it suitable for quantitative analysis in complex matrix samples.
Article
Biochemistry & Molecular Biology
Sumit Kumar, Aditi Arora, Rajesh Kumar, Nihar Nalini Senapati, Brajendra K. Singh
Summary: Naturally occurring coumarin and sugar molecules have versatile applications and superior biocompatibility. Coumarin, a member of the benzopyrone family, exhibits a wide spectrum of medicinal properties, while the sugar moiety functions as a central scaffold for the synthesis of complex molecules and contributes to their excellent biocompatibility. Conjugates of coumarin with sugar or nucleoside molecules have significant biological properties. Therefore, an update on the synthesis, characterization, and therapeutic applications of coumarin conjugates, including sugar and nucleoside coumarin conjugates, is necessary.
CARBOHYDRATE RESEARCH
(2023)
Article
Multidisciplinary Sciences
Tiberiu S. Mihaila, Carina Bate, Lynn M. Ostersehlt, Jasmin K. Pape, Jan Keller-Findeisen, Steffen J. Sahl, Stefan W. Hell
Summary: With the recent advancements in fluorescence nanoscopes, the ability to dissect nanoscopic biological structures is limited by the size of protein labels. Bioorthogonal chemical groups provide a powerful tool for specific detection of biomolecules. In this study, we introduced an engineered aminoacyl-tRNA synthetase/tRNA pair to allow for the site-specific introduction of amino acids with clickable side chains into proteins. This enhanced genetic code expansion machinery was then used to label beta-actin in cells for high-resolution imaging. Our findings highlight the need for further improvements in labeling methods to fully exploit the potential of molecular-scale optical three-dimensional resolution.
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
(2022)
Article
Multidisciplinary Sciences
Qiaoqiao Ruan, Cheng Zhao
Summary: A protocol is provided for better control of protein labeling using Copper-free Click Chemistry reagents. This approach offers a simpler and more economical way to perform microscale labeling and has been shown to provide more stable conjugation than standard NHS-fluorophore labeling.
SCIENTIFIC REPORTS
(2023)
Article
Chemistry, Multidisciplinary
Leona L. Rodrigues, Aaron S. Micallef, Michael C. Pfrunder, Vinh X. Truong, John C. McMurtrie, Tim R. Dargaville, Anja S. Goldmann, Florian Feist, Christopher Barner-Kowollik
Summary: A highly efficient ligation system based on visible light-induced rearrangement was introduced, generating a thiophenol for rapid thiol-Michael additions without the need for additives. The self-catalyzed ligation through pyridine mediated deprotonation of the photochemically generated thiophenol was described, leading to additive-free thiol-Michael reactions. The study explored various reaction conditions, solvents, and substrates, showcasing excellent end group fidelity in polymer modification.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Biochemistry & Molecular Biology
Naying Chu, Yitong Wang, Hao Jia, Jie Han, Xiaoyi Wang, Zhuang Hou
Summary: In this study, a series of new carbohydrate-based coumarin carbonic anhydrase IX inhibitors were designed and synthesized. These compounds showed better CA IX inhibitory activity than initial coumarin fragments. Compound 10a possessed the most potent CA IX inhibitory activity with high selectivity for CA I and CA II. These compounds also demonstrated anti-cancer effects and good stability. Furthermore, docking studies provided insights into the interactions between these compounds and the protein target CA IX.
Article
Polymer Science
Hong Xue, De-Shan Li, Hua-Wen Cai, Xiao-Li Sun, Wen-Ming Wan
Summary: Nontraditional intrinsic luminescent (NTIL) polymers are a new class of luminescent polymer materials. In this study, a series of aggregation-induced emission (AIE) type NTIL polymers were successfully synthesized through reversible addition-fragmentation chain transfer (RAFT) polymerization-induced emission (PIE). The triphenylmethyl azide moiety was found to be a novel PIE luminogen for the molecular design of NTIL polymers. These NTIL polymers showed potential applications in explosive detection and luminescence energy transfer.
Article
Nanoscience & Nanotechnology
Hua-Yun Lee, Po-Yu Chiang, Hsi-Ju Wu, Ting-Yi Wang, Tzu-Ching Yang, Wei-Chieh Cheng, Lee-Chiang Lo, Wei-Ssu Liao
Summary: A bottom-up approach was adopted to synthesize azido-functionalized carbon dots (CDs) and functionalize them with other molecules using click chemistry. Folate-decorated CDs showed fluorescence in tumor cells with elevated folate receptors. This method has great potential for future applications.
ACS APPLIED NANO MATERIALS
(2022)
Article
Chemistry, Multidisciplinary
Philipp Geng, Eileen List, Franziska Ronicke, Hans-Achim Wagenknecht
Summary: Two green fluorescent tetrazine-modified cyanine-styryl dyes were synthesized for bioorthogonal labelling of DNA. The fluorescence of these dyes can be released by their interaction with DNA and through the conjugated tetrazine as quencher moiety. The dyes can penetrate cells at low concentrations and undergo fluorogenic reactions with BCN-modified DNA in living cells. The two-factor fluorescence release significantly improves the signal-to-noise ratio, eliminating the need for washing procedures prior to cell imaging.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Christelle F. F. Ancajas, Adam J. J. Carr, Jinchao Lou, Ruhani Sagar, Yue Zhou, Todd B. B. Reynolds, Michael D. D. Best
Summary: This study reports the use of clickable monoacylglycerol (MAG) analogs as probe for labeling glycerolipids in lipid metabolism. Azide tags were incorporated into the glycerol region to design probes that can label glycerolipids without being removed. Different acyl chain lengths in clickable MAG probes resulted in varying cell imaging and cytotoxicity profiles. A probe with short acyl chain (C-4-MAG-N-3) was found to infiltrate natural lipid biosynthetic pathways and label neutral and phospholipid products. This work demonstrates the tunability of lipid metabolic labeling profiles and provides valuable tools for studying alterations in lipid metabolism.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Nanoscience & Nanotechnology
Brandaise Martinez, Yann R. Leroux, Philippe Hapiot, Charles S. Henry
Summary: Cu(I)-catalyzed 1,3-dipolar cycloaddition (CuAAC), also known as click chemistry, is a highly robust and versatile surface chemistry. In this study, we demonstrate the feasibility of using CuAAC and TPEs electrodes to develop a customizable and versatile biosensing platform.
ACS APPLIED MATERIALS & INTERFACES
(2023)
Article
Chemistry, Multidisciplinary
Hidetomo Yokoo, Hiroyuki Kagechika, Ayumi Ohsaki, Tomoya Hirano
Article
Chemistry, Organic
Ko Urushibara, Tatsunori Yamada, Akihiro Yokoyama, Hirotoshi Mori, Hyuma Masu, Isao Azumaya, Hiroyuki Kagechika, Tsutomu Yokozawa, Aya Tanatani
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Biochemistry & Molecular Biology
Hitomi Koga, Mai Negishi, Marie Kinoshita, Shinya Fujii, Shuichi Mori, Mari Ishigami-Yuasa, Emiko Kawachi, Hiroyuki Kagechika, Aya Tanatani
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2020)
Article
Chemistry, Medicinal
Shinya Fujii, Eriko Kikuchi, Yuko Watanabe, Honoka Suzuyama, Mari Ishigami-Yuasa, Takayasu Mori, Kiyoshi Isobe, Shinichi Uchida, Hiroyuki Kagechika
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2020)
Article
Chemistry, Organic
Daiki Kato, Takuya Shiraishi, Hiroyuki Kagechika, Tomoya Hirano
Summary: Coumarin serves as a core structure for photofunctional molecules, offering regulatory functionality for fluorescent sensors and photoremovable protecting groups. The study demonstrates that the 6-arylcoumarin moiety can provide a multi-functional regulatory property, showing OFF-ON-OFF change in response to different pH values.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Maiko Arimura, Kimiko Tanaka, Midori Kanda, Ko Urushibara, Shinya Fujii, Kosuke Katagiri, Isao Azumaya, Hiroyuki Kagechika, Aya Tanatani
Summary: The study synthesized N,N'-dimethylated oligosquaramides, which exhibit folded structures in the crystalline state and retain well-ordered folded structures in solution. These compounds have unique steric and electronic properties that can provide access to novel functional aromatic multilayered and helical foldamers.
Article
Chemistry, Medicinal
Shinya Fujii, Takahiro Miura, Tsuyoshi Oikawa, Xian-Yang Qin, Soichi Kojima, Hiroyuki Kagechika
Summary: In this study, a series of phthalazine-1,4-dione-based menaquinone analogs were designed and synthesized, with compounds bearing intact isoprene chain showing selective antiproliferative activity towards HCC cell line JHH7. The geranyl derivative 10 exhibited submicromolar potency, indicating its potential as a promising lead compound for anticancer agents.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2021)
Article
Chemistry, Medicinal
Shinya Fujii, Eriko Kikuchi, Honoka Suzuyama, Yuko Watanabe, Mari Ishigami-Yuasa, Hiroyuki Masuno, Takayasu Mori, Kiyoshi Isobe, Shinichi Uchida, Hiroyuki Kagechika
Summary: Hypertension is a crucial target for drug discovery, with a focus on the WNK-OSR1/SPAK-NCC signaling cascade. Through a screening system, the study investigated the structure-activity relationship of salicylanilide derivatives as SPAK kinase inhibitors. Compound 10 a was identified as a potent SPAK inhibitor with reduced toxicity, showing promising potential for a new class of antihypertensive drugs.
Article
Biochemistry & Molecular Biology
Ayana Yoshihara, Haru Kawasaki, Hiroyuki Masuno, Koki Takada, Nobutaka Numoto, Nobutoshi Ito, Naoya Hirata, Yasunari Kanda, Michiyasu Ishizawa, Makoto Makishima, Hiroyuki Kagechika, Aya Tanatani
Summary: This study synthesized amide derivatives of lithocholic acid derivative 3 and found that N-cyanoamide 6 is more active than 1 and 3.
Article
Chemistry, Medicinal
Tsuyoshi Oikawa, Shinya Fujii, Shuichi Mori, Hiroyuki Masuno, Emiko Kawachi, Hiroyuki Kagechika
Summary: A series of retinobenzoic acids were synthesized to investigate the structure-activity relationship of retinoids at the hydrophobic moiety. Compound 24c with a t-butyldimethylsilyl group showed potent retinoid activity, especially towards RARγ. This study provides insights for the development of new RARγ ligands.
Article
Chemistry, Organic
Shuichi Mori, Nozomi Tsuemoto, Emiko Kawachi, Chiharu Takubo, Aya Tanatani, Hiroyuki Kagechika
Summary: In this study, novel retinoids containing a trans-SF4-alkynyl group as a structural element were designed and synthesized. The compounds showed antagonistic activity towards retinoid acid receptors (RARs) and altered the binding mode of RARα ligand-binding domain.
Article
Biochemistry & Molecular Biology
Jennifer Nhieu, Liming Milbauer, Thomas Lerdall, Fatimah Najjar, Chin-Wen Wei, Ryosuke Ishida, Yue Ma, Hiroyuki Kagechika, Li-Na Wei
Summary: All-trans-retinoic Acid (atRA), derived from Vitamin A, plays crucial roles in various biological processes. It can modulate gene expression through nuclear RA receptors (RARs) or regulate cytoplasmic kinase signaling via cellular retinoic acid binding protein 1 (CRABP1). This study focuses on identifying CRABP1-binding ligands without RAR activity for potential therapeutic applications. The researchers developed a P19-MN differentiation system to investigate the effects of CRABP1 ligands in motor neuron (MN) differentiation and discovered C32 and C4 as CRABP1 ligands that can modulate CaMKII activation and protect against excitotoxicity-triggered MN death. These findings suggest the potential of selective and CRABP1-binding ligands in mitigating MN degenerative diseases.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Organic
Kimiko Tanaka, Fumi Takeda, Midori Kanda, Masatoshi Kawahata, Shinya Fujii, Kosuke Katagiri, Hyuma Masu, Hiroyuki Kagechika, Aya Tanatani
Summary: This study found that the crystal structure of aromatic N-monomethylsquaramide is in the (trans, cis) form, but in solution, it exhibits a solvent-dependent conformational equilibrium. Therefore, aromatic N-monomethylsquaramides could be used as components of environmentally responsive molecular switches.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Jason P. Mansell, Aya Tanatani, Hiroyuki Kagechika
Summary: The combination of the new VDR agonist LCA-150 with LPA has synergistic effects on promoting osteoblast maturation, surpassing the efficacy of vitamin D.
Article
Biochemistry & Molecular Biology
Erika Cione, Maria Cristina Caroleo, Hiroyuki Kagechika, Fabrizio Manetti
Summary: A classical drug repurposing approach was used to identify potential allosteric binders for GPR40, with three prioritised compounds showing significant effects on insulin secretion and breast cancer growth activities. These new GPR40 modulators could be promising tools for therapeutic intervention in type 2 diabetes.
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
