Article
Chemistry, Physical
Yuping Wang, Jinsong Han, Yu Liu, Panpan Zhang, Wanyao Wei, Yajun Jian
Summary: A novel systematic on water Michael addition reaction using alpha,beta-unsaturated ketone and nitromethane was developed by introducing an N-methyl imidazole group to enhance electrophilic activity, leading to a higher reaction rate in water. The results suggest that N-methyl imidazole bearing substrates are prone to form hydrogen bonds with water, providing insights for selecting suitable substrates for on water reactions.
Article
Multidisciplinary Sciences
Amberley D. Stephens, Muhammad Nawaz Qaisrani, Michael T. Ruggiero, Gonzalo Diaz Miron, Uriel N. Morzan, Mariano C. Gonzalez Lebrero, Saul T. E. Jones, Emiliano Poli, Andrew D. Bond, Philippa J. Woodhams, Elyse M. Kleist, Luca Grisanti, Ralph Gebauer, J. Axel Zeitler, Dan Credgington, Ali Hassanali, Gabriele S. Kaminski Schierle
Summary: Fluorescence in biological systems is often influenced by aromatic groups. In this study, it was found that specific hydrogen bond networks can greatly impact fluorescence, with short hydrogen bonds enhancing optical properties. This research has implications for the design of new photoactive materials with biophotonic applications.
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
(2021)
Article
Chemistry, Organic
Xin Huang, Tatiana Besset, Philippe Jubault, Samuel Couve-Bonnaire
Summary: In this study, the phosphorus-Michael addition (PMA) was reported for the first time on alpha-trifluoromethylacrylates and alpha-fluoromethylacrylates. The reaction showed high tolerance towards the substrates and yielded original products with good to excellent yields and diastereoselectivities.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Jiawei You, Shuai Zhang, Qiuying Li, Weijie Zhang, Huili Ma, Jianquan Hou, Engui Zhao, Zikai He
Summary: This article presents two new azobenzene derivatives with photoisomerization properties and solid-state fluorescence. The study reveals that these derivatives exhibit unusual fluorescence in the solid state, with TPE-Azo-2OH showing even stronger fluorescence due to the suppression of photoisomerization by intramolecular hydrogen bonds. Additionally, these azobenzene derivatives undergo fluorescence transformation from red to green upon reduction. These new derivatives with AIE attributes and stimuli-responsiveness are expected to provide a new platform for developing photo-responsive luminescent materials.
Article
Chemistry, Multidisciplinary
Connor Q. Kabes, Bailey L. Jameson, John A. Gladysz
Summary: Enantioselective additions of malonate esters to nitroalkenes have been catalyzed by chiral cobalt(iii) trications, achieving a new green synthetic method. By probing various reaction variables, optimized conditions were found, leading to shorter reaction times and solvent-free reactions using ball milling.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Physical
Turkan Gencoglu, Tugce Nur Eren, Jacques Lalevee, Duygu Avci
Summary: Multifunctional polymeric photoinitiators were successfully synthesized in this study, showing excellent polymerization initiating performances under different light conditions due to their unique chemical properties. Experimental validation demonstrated the good polymerization efficiency and high conversion rates of these photoinitiators under specific conditions.
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
(2021)
Article
Chemistry, Analytical
Na Zhou, Caixia Yin, Yongkang Yue, Fangjun Huo
Summary: In this study, a rapid specific addition reaction between norepinephrine and pyranium salt was discovered, and a ratiometric fluorescence response was generated using coumarin conjugation. The selectivity and reaction rate of the probe were improved, providing a new idea for the design of norepinephrine fluorescent probe and enhancing the understanding of its physiological and pathological mechanisms.
SENSORS AND ACTUATORS B-CHEMICAL
(2022)
Article
Chemistry, Organic
Bin Mao, Zhi-Wei Chen, Jian-Fei Wang, Chao-Huan Zhang, Zhi-Qian Du, Chuan-Ming Yu
Summary: In this study, the enantioselective organocatalytic conjugate alkenylation of fi-substituted alkenyl benzimidazoles was achieved, leading to the formation of beta-stereogenic 2-alkyl benzimidazole derivatives with excellent enantio-selectivities. Chiral binaphthols were found to be effective catalysts for promoting the nucleophilic addition of bench-stable alkenyl trifluoroborate salts under mild conditions. By utilizing C=N-containing azaarenes as activating groups, the applications of these catalysts were expanded. The synthetic utility of this strategy was demonstrated by converting the products into several useful enantiomerically enriched benzimidazole building blocks.
Article
Chemistry, Analytical
Livia Oliveira Alves Ferreira, Szilard Molnar, Felipe Terra Martins, Pal Perjesi, Luiz Henrique Keng Queiroz, Caridad Noda-Perez
Summary: The study on symmetrical halogenated bischalcones (SHBCs) and their Michael addition reaction with reduced glutathione (GSH) revealed that the formation of adducts did not directly correlate with their cytotoxic effects on cancer cells.
MICROCHEMICAL JOURNAL
(2021)
Article
Materials Science, Multidisciplinary
Sara Azmi, Amelia Klimek, Elzbieta Frackowiak
Summary: Urea can improve the corrosion resistance and electrochemical performance of carbon electrode-based capacitors in aqueous electrolytes without affecting the electrolyte conductivity.
Article
Chemistry, Organic
Alison P. Hart, Caroline J. Degraw, Gavin J. Rustin, Matthew G. Donahue, Julie A. Pigza
Summary: A method for the enantioselective addition of a silyl-protected masked acyl cyanide (MAC) reagent to various beta-nitrostyrenes using squaramide-organocatalysis is described. The reactions are carried out at low catalyst loadings in a freezer, yielding clean products with high enantioselectivities. The unmasking of the adducts provides functional groups in different oxidation states, highlighting the utility of MAC reagents in the preparation of beta-amino acids.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Chen Li, Ting Wang, Mengting Fan, Ning Wang, Xiaofeng Lin, Yan Sun, Xiaoyan Cui
Summary: Silicon-substituted coumarin (SiC) is an important family of fluorescent probes, both intramolecularly and intermolecularly enhanced by hydrogen bonds (H-bond), for sensitively tracking proteins in vivo through the assembly and disassembly of nanoaggregates. SiC with intramolecular H-bond exhibits significant aggregation, solvatochromism, and strong fluorescence with a red-shifted spectra in polar, protic environments. Without additional organic linkers, the compact skeleton of SiC with H-bond ensures sensitive and selective sensing of targeted proteins through efficient disassembly of the aggregates. In the presence of strong intermolecular H-bonds with the target protein pocket, SiC shows fluorescence enhancement as high as >250-fold. Selectively tracking proteins in complex biological systems has confirmed SiC as a versatile skeleton for sensitive monitoring of proteins.
Article
Spectroscopy
Songsong Liu, Ming Qin, Qi Lu, Lili Lin, Chuan-Kui Wang, Jianzhong Fan, Yuzhi Song
Summary: The study investigates the excited state behavior of chemosensor 1 and reveals its sensing mechanism for Cu2+ using density functional theory. It is found that the hydrogen bond strength is enhanced in the first singlet excited state, enabling an ultra-fast excited state intramolecular proton transfer process. The theoretical analysis confirms the inhibition of the ESIPT behavior, leading to fluorescence quenching and demonstrating the high selectivity of chemosensor 1 to Cu2+.
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
(2021)
Article
Chemistry, Organic
Sadhanendu Samanta, Jin Cui, Hidetoshi Noda, Takumi Watanabe, Masakatsu Shibasaki
Summary: In this study, a gram-scale syn-selective asymmetric vinylogous addition of butenolides to chromones was developed using an Al-Li-BINOL (ALB) complex catalyst. The reaction showed high diastereoselectivity with ratios up to 20:1 and enantioselectivity of 84-98% for various substrate combinations. This method is complementary to previous reports and improves selectivity for several chromones. Computational studies support the role of ALB as a bifunctional catalyst in this reaction and provide insights into the origin of the observed stereoselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Sadhanendu Samanta, Jin Cui, Hidetoshi Noda, Takumi Watanabe, Masakatsu Shibasaki
Summary: A gram-scale syn-selective asymmetric vinylogous addition of butenolides to chromones, catalyzed by an Al-Li-BINOL (ALB) complex, was developed in this study. The diastereoselectivity reached 20:1 with 84-98% ee for various combinations of substrates. This protocol complements previous methods and improves selectivity for multiple chromones.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Young-Hee Shin, Hana Cho, Bo Young Choi, Jonghoon Kim, Jaeyoung Ha, Sang Won Suh, Seung Bum Park
Summary: The study revealed that the small molecule SB1617 could suppress abnormal tau protein aggregation and regulate proteostasis in tauopathies by transiently enhancing the PERK signaling pathway. The promising efficacy of SB1617 was demonstrated in neuronal cells and a mouse model with traumatic brain injury, known to involve ER stress.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Medicinal
Ala Jo, Mingi Kim, Jong-In Kim, Jaeyoung Ha, Yoon Soo Hwang, Hyunsung Nam, Injae Hwang, Jae Bum Kim, Seung Bum Park
Summary: The study identified a potential anti-obesity compound SB1501 through high-content screening, which reduces lipid droplets in adipocytes and improves metabolic state by modulating mitochondrial activities. This compound shows promise as a therapeutic agent for obesity treatment.
Article
Chemistry, Multidisciplinary
Young-Hee Shin, Kiyoung Jeong, Jihye Lee, Hyo Jung Lee, Junhyeong Yim, Jonghoon Kim, Seungtaek Kim, Seung Bum Park
Summary: A novel small molecule has been discovered that can inhibit SARS-CoV-2 infection by modulating ACE2 without impairing its normal function. This finding may provide a new therapeutic strategy to block viral entry.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Youngjun Lee, Dahham Kim, Seung Bum Park
Summary: The photophysical behaviors of fluorescent molecules largely determine their utility in biological studies. This study proposes a novel heterocyclic core fluorescent platform that allows flexible control of its photophysical properties through synergistic interaction between functional groups. The platform enables broad tunability of emission wavelength, Stokes shift, fluorescent brightness, and charge transfer characteristics. Furthermore, by reorganizing functional groups, the platform can be used to develop live-cell imaging probes with distinct optical features.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Review
Biochemistry & Molecular Biology
Wan Gi Byun, Donghyun Lim, Seung Bum Park
Summary: This review discusses the potential of targeting PRIs using small molecules, the tools for observing PRIs in biochemical and cell-based experiments, and various PRI modulators. Emerging technologies and challenges in the development of PRI modulators are also highlighted.
CURRENT OPINION IN CHEMICAL BIOLOGY
(2022)
Article
Biochemical Research Methods
Yun Lim Jung, Sourav Sarkar, Jaeyoung Ha, Seung Bum Park, Kyo Han Ahn
Summary: In this study, a new TRC platform was developed for fluorescent molecule labeling on biomolecules under spatiotemporal control. The o-quinone methide chemistry was utilized to achieve efficient labeling of proteins using different aryl alcohol fluorophores. The versatility and uniqueness of this TRC system were demonstrated in both cellular and tissue bioconjugation, showing potential for in situ fluorophore labeling of proteins in biological systems.
BIOCONJUGATE CHEMISTRY
(2022)
Review
Chemistry, Medicinal
Jesang Lee, Seung Bum Park
Summary: Covalent inhibitors have been accepted as a practical tool for targeting previously undruggable proteins. Despite the clinical success, there are still unmet medical needs. Categorizing and reviewing covalent inhibitors provide insights into the future development of this field.
Article
Chemistry, Medicinal
Hyun-Jin Jang, Yae Jin Yoon, Jiyeon Choi, Yu-Jin Lee, Sangku Lee, Wansang Cho, Wan Gi Byun, Seung Bum Park, Dong Cho Han, Byoung-Mog Kwon
Summary: Metastasis is a major cause of cancer death and treatment failure. Previous research identified benproperine (Benp) as a potential inhibitor of cancer cell migration. However, the active stereoisomer of Benp was unclear. This study found that S-Benp is the active stereoisomer, which effectively inhibits cancer cell migration and invasion without affecting normal cells. The study also validated the binding of S-Benp to ARPC2, suggesting its potential as a metastasis inhibitor.
Article
Chemistry, Multidisciplinary
Wansang Cho, Solchan Won, Yoona Choi, Sihyeong Yi, Jong Beom Park, Jun-Gyu Park, Caroline E. Kim, Chintam Narayana, Ju Hee Kim, Junhyeong Yim, Young Il Choi, Dong-Sup Lee, Seung Bum Park
Summary: Modulating target proteins via the ubiquitin-proteasome system has expanded the scope of pharmacological inventions. STING, an auspicious target for immunotherapy, has been found to have importance as well as utility in immunotherapy outcomes. The proposed UPPRIS strategy utilizing the small molecule SB24011 enhances STING immunity and potentiates the efficacy of immunotherapy, suggesting targeted protein upregulation as a promising approach for immuno-oncology.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Kannan Vaithegi, Sihyeong Yi, Ji Hyae Lee, Begur Vasanthkumar Varun, Seung Bum Park
Summary: Substituted pyridines with diverse functional groups are important in bioactive molecules. This study reports a method for introducing multiple functional groups to pyridine via ring cleavage reaction. The robustness of the methodology was demonstrated by synthesizing a variety of 5-aminoaryl and 5-phenol pyridines, and the application of the methodology provided a privileged pyridine scaffold for drug conjugation.
COMMUNICATIONS CHEMISTRY
(2023)
Article
Biology
Jinjoo Jung, Jongbeom Park, Mingi Kim, Jaeyoung Ha, Hana Cho, Seung Bum Park
Summary: The small molecule SB2301 activates lipophagy and alters lipid droplet membrane composition, with the ethanolamine-phosphate cytidylyltransferase 2 (PCYT2) being a potential target of the compound. The excessive accumulation of lipid droplets is associated with various diseases, and understanding the molecular mechanism of LD degradation is important for academic and industrial research. Lipophagy, a selective autophagy process, has gained attention in the research community. This study reveals a novel lipophagy mechanism through the use of SB2301, which activates ubiquitin-mediated lipophagy. The potential target protein PCYT2 is identified, and SB2301 induces PCYT2 translocation to the LD surface and alters the LD membrane composition, leading to the activation of the lipophagy process.
COMMUNICATIONS BIOLOGY
(2023)
Article
Chemistry, Multidisciplinary
Dahham Kim, Hayoung Son, Seung Bum Park
Summary: This study synthesized a series of BODIPY-Tz probes for bioorthogonal cellular imaging and discovered their unique fluorescence behavior on BCN and TCO. Additionally, dual-color bioorthogonal cellular imaging with a single probe was achieved for the first time.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Editorial Material
Chemistry, Medicinal
Wansang Cho, Jung Ho Lee, Seung Bum Park
FUTURE MEDICINAL CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Hana Cho, Bo Young Choi, Young-Hee Shin, Sang Won Suh, Seung Bum Park
Summary: In this study, we investigated the neuroprotective function of SB1617 against tau aggregation mediated by microglia. Our findings showed that SB1617 deactivated pathogenic M1-like microglia, reduced the secretion of pro-inflammatory cytokines, induced microglial polarization towards the M2 phenotype, and enhanced phagocytic function. In addition, we observed the clearance of extracellular pathogenic tau aggregates through LC3-associated phagocytosis. Furthermore, in vivo experiments confirmed the neuroprotective effects of SB1617 in a mouse model of traumatic brain injury by reducing pathogenic tau levels through microglia-mediated anti-inflammatory activity. Our results indicate that SB1617-mediated microglial surveillance with LC3-associated phagocytosis is a critical molecular mechanism in the regulation of tau proteostasis.
ACS CHEMICAL NEUROSCIENCE
(2023)
Article
Chemistry, Multidisciplinary
Wan Gi Byun, Jihye Lee, Seungtaek Kim, Seung Bum Park
Summary: By modulating multimolecular crowding, small-molecule enhancers were found to sensitize the IRF3-mediated antiviral mechanism and inhibit the replication of SARS-CoV-2. This suggests a promising strategy against the virus.
CHEMICAL COMMUNICATIONS
(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)
