Review
Chemistry, Physical
Ming Bao, Michael P. Doyle
Summary: The [3+n]-cycloaddition reactions using chiral catalysts and racemic cyclopropanes or achiral catalysts and chiral, non-racemic cyclopropanes have proven to be important transformations for the synthesis of carbocyclic and heterocyclic compounds, showing both mechanistic and structural advantages in ring formation.
Article
Chemistry, Multidisciplinary
Niklas Radhoff, Constantin G. G. Daniliuc, Armido Studer
Summary: The design, synthesis, and application of benzene bioisosteres have been a subject of great interest in the past two decades. Recently, bicyclo[2.1.1]hexanes have been established as highly attractive bioisosteres for ortho- and meta-substituted benzenes. In this study, we present a mild, scalable, and transition-metal-free method for constructing highly substituted bicyclo[2.1.1]hexan-2-ones through Lewis acid-catalyzed (3+2)-cycloaddition of bicyclo[1.1.0]-butane ketones with disubstituted ketenes. The reaction exhibits high functional group tolerance, as evidenced by the successful synthesis of various 3-alkyl-3-aryl and 3,3-bisalkyl bicyclo[2.1.1]hexan-2-ones (26 examples, up to 89% yield). Additionally, postfunctionalization of the exocyclic ketone moiety is demonstrated.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Organic
Michael P. Badart, Bill C. Hawkins
Summary: The spirocyclic motif is common in natural products, serving as an ideal three-dimensional template for interacting with biological targets. Different reaction strategies are used to construct these spirocyclic centers, creating a series of effective medicinal compounds.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Organic
Kai Matsui, Kohei Toh, Manabu Hatano, Kazuaki Ishihara
Summary: A multiselective Diels-Alder reaction involving alpha-arylacroleins and cyclopentadiene has been developed using BBr3-assisted chiral BINOL-derived phosphoric acid catalysts. The chiral cavity of the in situ-formed acid-base cooperative catalysts plays a key role in controlling the exo- and enantioselectivity, particularly by suppressing the competitive hetero Diels-Alder reaction effectively.
Article
Chemistry, Organic
Prasoon Raj Singh, Pratibha Kalaramna, Shamsad Ali, Avijit Goswami
Summary: A simple protocol has been developed to access thio-/selenopyrrolines through a (3+2)-cycloaddition reaction using SnCl4 as a Lewis acid catalyst. Good chemoselectivity was observed when DACs were treated, indicating that thiocyanate is more reactive than nitrile moiety in such reactions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Manjur O. Akram, John R. Tidwell, Jason L. Dutton, Caleb D. Martin
Summary: This passage describes a Lewis superacid called bis(1-methyl-ortho-carboranyl)borane, which can be rapidly synthesized in two steps. It is a highly effective hydroboration reagent capable of B-H addition to alkenes, alkynes, and cyclopropanes. To date, it is the first identified Lewis superacidic secondary borane and the most reactive neutral hydroboration reagent.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Jie Liu, Gregor S. Cremosnik, Felix Otte, Axel Pahl, Sonja Sievers, Carsten Strohmann, Herbert Waldmann
Summary: This study presents the design and synthesis of a collection of 155 pyrroquinoline pseudo-NPs, combining fragments characteristic of tetrahydroquinoline and pyrrolidine classes in novel arrangements. Cheminformatic analysis and biological evaluation revealed chemically diverse pseudo-NP classes with distinct bioactivity patterns, dependent on fragment connectivity and regioisomeric arrangement.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Tim Steinke, Patrick Wonner, Richard M. Gauld, Sascha Heinrich, Stefan M. Huber
Summary: This study investigates the activation of imines in a Povarov reaction using bidentate cationic chalcogen bond donors. Tellurium-based Lewis acids show superior catalytic properties compared to selenium-based catalysts. The activity of the chalcogen bonding donors is influenced by the strength of the binding anions, and the choice of solvent and catalyst affects the diastereomeric ratio of the product.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Eveline H. H. Tiekink, Pascal Vermeeren, Trevor A. A. Hamlin
Summary: We investigated the uncatalyzed and Lewis acid (LA)-catalyzed cycloaddition reaction between tropone and 1,1-dimethoxyethene using dispersion-corrected relativistic density functional theory (DFT). The LA catalysts BF3, B(C6H5)(3), and B(C6F5)(3) effectively accelerated both [4+2] and [8+2] cycloaddition reactions by lowering the activation barrier by up to 12 kcal mol(-1) compared to the uncatalyzed reaction. Our study revealed that the LA catalyst promoted the cycloaddition reaction pathways through LUMO-lowering catalysis and demonstrated that Pauli-lowering catalysis is not always the operative mechanism in cycloaddition reactions. Selecting the appropriate LA catalyst allowed for regiocontrol of the cycloaddition: B(C6H5)(3) yielded the [8+2] adduct while B(C6F5)(3) produced the [4+2] adduct. The regioselectivity shift was found to be due to the LA's ability to absorb distortion and adopt a trigonal pyramidal geometry around the boron atom.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Shuxuan Liu, Hui Qian, Tianyu Zhang, Hongling Xie, Zhengyu Han, Wengang Guo, Hai Huang, Jianwei Sun
Summary: This study presents a new method for accessing cyclopropanes embedded in a polycyclic bridged architecture through a mild intermolecular convergent process. Unlike conventional approaches, this protocol does not require highly active carbenoid intermediates or strong conditions. The key cyclopropane ring is formed between the well-positioned nucleophile and electrophile in the adduct, showing a new reactivity of the versatile isobenzopyryliums.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Grzegorz Mloston, Mateusz Kowalczyk, Andre U. Augustin, Peter G. Jones, Daniel B. Werz
Summary: The reactivity of donor-acceptor cyclopropanes towards thioketenes was investigated, leading to the formation of exocyclic thioenol ethers in moderate to good yields in a (3+2)-cycloaddition using Sc(OTf)(3) as a Lewis acidic catalyst. Unsymmetrical thioketenes provided E/Z mixtures at the double bond, with the Z isomer being preferred.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Pallavi Sarkar, Shubhajit Das, Swapan K. Pati
Summary: This article summarizes the progress in the study of non-boron Lewis acids since 2015, which are an important component of Frustrated Lewis pairs.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Review
Biochemistry & Molecular Biology
Raul R. Rodriguez-Berrios, Stephen R. Isbel, Alejandro Bugarin
Summary: Polypropionate units, found in many natural products, have antimicrobial and therapeutic potential. This review includes all epoxide-based methodologies developed by research groups such as Kishi, Katsuki, Marashall, Miyashita, Prieto, Sarabia, Jung, McDonald, etc. for the synthesis of polypropionates. The review also includes the isolation and biological activities of synthetized polypropionates and related natural products.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Multidisciplinary
Julian M. Feilner, Immanuel Plangger, Klaus Wurst, Thomas Magauer
Summary: This study utilized highly functionalized bifunctional alkenes to achieve a polyene tetracyclization, leading to the total synthesis of the tricyclic diterpenoid pimara-15-en-3 alpha-8 alpha-diol. The versatile route also allowed for the preparation of a diverse library of cyclization precursors for the total synthesis of the tetracyclic nor-diterpenoid norflickinflimiod C, providing insights into complex pentacyclic products.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
News Item
Chemistry, Multidisciplinary
Jun-Jie Chen, Huan-Ming Huang
Summary: In this study, a new strategy using N2O as the oxygen source under mild conditions was developed for the conversion of aryl halides to phenols.
Article
Microbiology
Yue Wang, Jingchun Kong, Xiaodong Zhang, Yan Liu, Zeyu Huang, Lu Yuan, Ying Zhang, Jianming Cao, Lijiang Chen, Yong Liu, Tieli Zhou
Summary: The emergence and spread of multi-drug resistant strains globally have raised concerns, especially with the re-emergence of colistin-resistant bacteria. A study has found that the combination of plumbagin and colistin effectively inhibits colistin-resistant P. aeruginosa, showing promising results in both in vitro and in vivo settings. This combination not only prevents biofilm formation but also eradicates mature biofilms, providing a potential treatment option for COL-R PA infections.
FRONTIERS IN MICROBIOLOGY
(2022)
Article
Chemistry, Multidisciplinary
Fan Wu, Jinghang Ma, Yang Wang, Lingping Xie, Xiaojian Yan, Linqi Shi, Yuanfeng Li, Yong Liu
Summary: To combat drug-resistant bacteria, researchers developed copper-doped guanine-derived nanosheets that have the catalytic properties of glucose oxidase and peroxidase. These nanosheets produce free radicals when exposed to light, effectively eliminating drug-resistant bacteria. The nanosheets also promote the activation of oxygen and the splitting of hydrogen peroxide, causing damage to the bacterial cell membrane and an increase in reactive oxygen inside the cells. This study showed that the nanosheets efficiently eliminated Staphylococci in infected wounds and accelerated wound closure in a mouse model, with minimal side effects on normal tissues. These nanosheets could serve as a non-antibiotic alternative for treating bacterial infections.
Article
Chemistry, Multidisciplinary
Yaran Wang, Jianan Zhou, Lu Yuan, Fan Wu, Lingping Xie, Xiaojian Yan, Huaping Li, Yuanfeng Li, Linqi Shi, Rongdang Hu, Yong Liu
Summary: This study reports the development of carboxylic acid-containing nano-networks with enzymatic activity for combating bacterial biofilms. The optimal nano-networks demonstrated high catalytic efficiency in damaging cell membranes and extracellular DNA of Streptococcus mutans biofilms. The neighboring carboxyl group aids the adsorption, free radical generation, and catalyst reactivation, resulting in superb catalytic efficiency. The nano-networks show great potential in inhibiting tooth decay and treating biofilm-associated diseases without affecting the commensal oral flora.
Article
Microbiology
Lingbo Wang, Ying Zhang, Yishuai Lin, Jianming Cao, Chunyan Xu, Liqiong Chen, Yaran Wang, Yao Sun, Xiangkuo Zheng, Yong Liu, Tieli Zhou
Summary: P. aeruginosa is a widespread bacterium associated with life-threatening infections. Improper use of antibiotics has led to the emergence of multidrug-resistant strains, including colistin-resistant strains. This study demonstrates that colistin/resveratrol combination therapy has a strong synergistic effect in eradicating colistin-resistant P. aeruginosa strains and their biofilms.
MICROBIOLOGY SPECTRUM
(2023)
Article
Chemistry, Multidisciplinary
Yuxun Ding, Xiaowen Hu, Yinzi Piao, Rong Huang, Lingping Xie, Xiaojian Yan, Hui Sun, Yuanfeng Li, Linqi Shi, Yong Liu
Summary: Prodrug nanoassemblies combining prodrug and nanomedicine advantages were developed via dynamic covalent boronate between catechol and boronic acid. The resulting LPNAs exhibited features such as dynamic covalent drug loading, charge reversal in acidic microenvironment, and specific drug release in acidic and/or oxidative microenvironment. LPNAs were more efficient in eradicating pathogens or cancer cells compared to free counterparts, both in vitro and in vivo. These LPNAs with intriguing properties may accelerate drug delivery development and facilitate clinical applications.
Article
Chemistry, Multidisciplinary
Yizhou Zhan, Xiaowen Hu, Yuanfeng Li, Yaran Wang, Hua Chen, Calvin Andeve Omolo, Thirumala Govender, Huaping Li, Fan Huang, Linqi Shi, Xiaoli Hu, Yong Liu
Summary: This study reports an antimicrobial hybrid amphiphile (aHA) that can eradicate staphylococcal biofilms. It is synthesized via dynamic covalent bonds and can self-assemble in aqueous solution. The aHA assemblies efficiently eradicate bacterial biofilms and show no notable side effects on normal tissues.
ADVANCED FUNCTIONAL MATERIALS
(2023)
Article
Chemistry, Multidisciplinary
Xiaowen Hu, Yuanfeng Li, Yinzi Piao, Mahdi Karimi, Yang Wang, Feng Wen, Huaqiong Li, Linqi Shi, Yong Liu
Summary: This research reports a novel class of antimicrobial molecules (T(2)A(2)) composed of nitric oxide (NO)-donor (DN) and various natural aldehydes, which self-assemble into nanoparticles and exhibit significant bactericidal efficacy. Cin-T(2)A(2) can kill multidrug-resistant staphylococci and eradicate their biofilms through multiple mechanisms. Furthermore, Cin-T(2)A(2) rapidly eradicates bacteria and alleviates inflammation in murine infection models.
ADVANCED MATERIALS
(2023)
Article
Chemistry, Multidisciplinary
Lei Chen, Mengna Peng, Jianan Zhou, Xiaowen Hu, Yinzi Piao, Huaping Li, Rongdang Hu, Yuanfeng Li, Linqi Shi, Yong Liu
Summary: A photothermal cascade nano-reactor (CPNC@GOx-Fe2+) is constructed through a supramolecular strategy, which exhibits excellent photothermal effects and generates hydroxyl radicals to achieve photothermal and chemodynamic combination therapy for bacteria-infected wounds. Proteomics, metabolomics, and all-atom simulation results indicate that the hydroxyl radical damages the cell membrane and enhances fluidity, resulting in synergistic antibacterial effects. In vivo experiments confirm that this nano-reactor accelerates the healing of infected wounds without affecting the commensal microbiota.
ADVANCED MATERIALS
(2023)
Article
Chemistry, Multidisciplinary
Jing Wu, Yong Liu, Lijun Peng, Qisijing Liu, Dawei Wang, Xu Jing, Yaozhong Hu, Jing Lin, Hanyue Fu, Xuemeng Ji, Jingmin Liu, Huan Lv, Bo Peng, Bowei Zhang, Liqiong Guo, Shuo Wang
Summary: This paper introduces a portable, origami-type paper device with a plasmonic fluor-labeled microneedle sensing module for the multiplexed quantification of anemia biomarkers in whole blood. The device can rapidly accomplish sequential steps, including serum separation, target enrichment, and multiplexed readout. It enables efficient sampling of trace targets and improves signal detection compared to traditional assays. The device has the potential for rapid and accurate diagnosis of anemia in real practice, with features such as small sample volume, short assay time, low cost, stability, and user-friendliness.
Review
Multidisciplinary Sciences
Yingying Pan, Dejun Yang, Min Zhou, Yong Liu, Jiandan Pan, Yunlong Wu, Lijiang Huang, Huaqiong Li
Summary: Pressure injuries (PIs) are localized tissue damage caused by prolonged compression or shear forces. Different stages of PIs exhibit similar characteristics, including oxidative stress, abnormal inflammatory response, cell death, and impaired tissue remodeling. Monitoring early-stage PIs is challenging, while healing late-stage PIs is difficult and has a negative impact on quality of life. This review discusses the underlying pathogenesis of PIs, key biochemical pathways leading to delayed wound healing, and recent advances in biomaterial-assisted prevention and healing.
Review
Nanoscience & Nanotechnology
Lingping Xie, Yuanfeng Li, Yong Liu, Zhihua Chai, Yuxun Ding, Linqi Shi, Jinhui Wang
Summary: The vagina has been recognized as a crucial route for drug delivery, but poor drug absorptivity remains a challenge due to various biological barriers. To overcome these barriers, different types of vaginal drug delivery systems (VDDSs) with excellent mucoadhesive and mucus-penetrating properties have been developed. This review provides an overview of vaginal administration, its biological barriers, commonly used VDDSs such as nanoparticles and hydrogels, and their applications in controlling microbe-associated vaginal infections. Challenges and concerns in VDDS design are also discussed.
ACS APPLIED BIO MATERIALS
(2023)
Review
Materials Science, Multidisciplinary
Yuanfeng Li, Junjie Chi, Xing Dong, Anh-Tuan Le, Keqing Shi, Yong Liu, Jian Xiao
Summary: G-quadruplex hydrogel is a self-assembled supramolecular hydrogel formed by guanine derivatives, which shows wide biomedical applications such as drug delivery, tissue engineering, and biosensing. Its advantages include biocompatibility, tunable multifunctionality, and cost-effective fabrication process. This review focuses on the fabrication and characterization of G-quadruplex hydrogels, as well as their applications in the biomedical area, aiming to promote the development of this field.
JOURNAL OF MATERIALS SCIENCE & TECHNOLOGY
(2023)
Article
Engineering, Biomedical
Yuanfeng Li, Yin-Zi Piao, Hua Chen, Keqing Shi, Juqin Dai, Siran Wang, Tieli Zhou, Anh-Tuan Le, Yaran Wang, Fan Wu, Rujiang Ma, Linqi Shi, Yong Liu
Summary: New antimicrobial dynamic covalent nano-networks (aDCNs) were synthesized, which are composed of antibiotics bearing multiple primary amines, polyphenols, and a cross-linker acylphenylboronic acid. These aDCNs are highly responsive to stimuli and have excellent antimicrobial performance, inhibiting biofilm formation and eliminating mature biofilms of drug-resistant bacteria. They also alleviate macrophage inflammation and minimize the side effects of free antibiotics.
BIOACTIVE MATERIALS
(2023)
Review
Polymer Science
Hua Chen, Li-yun Cui, Yuan-feng Li, Yong Liu, Ru-jiang Ma, Lin-qi Shi
Summary: Protein drugs have limited effectiveness due to poor cell membrane penetration, but phenylboronic acid-based nanocarriers show promise in improving intracellular delivery. This paper reviews the latest research on phenylboronic acid-functionalized polymer nanocarriers, including their chemical properties, binding modes with protein drugs, and responsive release mechanisms. It also discusses the potential of phenylboronic acid in enhancing cell uptake and permeation through the blood-brain barrier. Overall, this paper provides valuable insights for the design of novel intracellular delivery systems for protein drugs based on phenylboronic acid.
ACTA POLYMERICA SINICA
(2023)
Article
Chemistry, Multidisciplinary
Yuxun Ding, Xiaowen Hu, Yinzi Piao, Rong Huang, Lingping Xie, Xiaojian Yan, Hui Sun, Yuanfeng Li, Linqi Shi, Yong Liu
Summary: Prodrug nanoassemblies combine the advantages of prodrug and nanomedicines, offering targeted drug delivery and specific on-demand drug release. Lipid prodrug nanoassemblies prepared via dynamic covalent boronate reaction exhibit drug loading in a dynamic covalent manner, charge reversal in an acidic microenvironment, and specific drug release in an acidic and/or oxidative microenvironment. These LPNAs are more efficient in eradicating pathogens or cancer cells compared to their free counterparts, both in vitro and in vivo.
