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  • Shujing Xu, Lin Sun, Waleed A. Zalloum, Xujie Zhang, Tianguang Huang, Dang Ding, Yucen Tao, Fabao Zhao, Shenghua Gao, Dongwei Kang, Erik De Clercq, Christophe Pannecouque, Alexej Dick, Simon Cocklin, Xinyong Liu, Peng Zhan
    Chinese Chemical Letters. 2023, 34(3): 107611-.

    HIV-1 capsid protein (CA) has emerged as a promising target for antiviral treatment considering its structural and regulatory roles in HIV-1 replication. Here, we disclose the design, synthesis, biological assessment, and mechanism investigation of a novel series of phenylalanine derivatives gained by further structural modification of PF74. The newly synthesized compounds demonstrated potent anti-HIV activity, represented by 7n displayed anti-HIV-1 activity 6.25-fold better than PF74, and 7h showed anti-HIV-2 activity with nearly 139 times improved efficacy over PF74. Surface plasmon resonance (SPR) studies of representative compounds proved that HIV-1 CA was the binding target. Competitive SPR studies using CPSF6 and NUP153 peptides identified that 7n binds to a vital CA assembly interface between the N-terminal and C-terminal domain (NTD-CTD interface). Action stage determination assay revealed that the newly synthesized compounds were antiviral with a dual-stage inhibitory profile. Molecular dynamics (MD) simulations offered the crucial foundation for the hopeful antiviral potency of 7n. Besides, 7m and 7n modestly increased metabolic stabilities in human liver microsome (HLM) and human plasma compared to PF74. Overall, these studies offer valuable insights and can regard as the beginning for succedent medicinal chemistry endeavors to discover promising HIV capsid inhibitors with improved efficacy and better drug-like characteristics.

  • Qingsong Liu, Man Zhang, Ye Fu, Shen Shen, Liangliang Zhu
    Chinese Chemical Letters. 2023, 34(3): 107612-.

    Developing efficient dual–phase emission emitters upon organoboron luminophores remains a formidable challenge due to the ubiquitous self–absorption and deleterious π-π interactions from aromatic structure. Here, a new family of benzothiazole–enolate–based organoboron luminophores (HN1–4) with effective dual–phase emission was constructed. HN4 showed almost the highest quantum yield (QY) among this type of compound so far. The three-ring–fused rigid skeleton and moderate intramolecular charge transfer (ICT) effect ensured that HN4 could give rise to extremely strong emission in any solution (QY up to 99%). X-ray crystallographic analysis showed that the twisted core structure constructed by the boronic coordination of two penta-fluorobenzene of HN4 was responsible for intense emission in the solid state (QY up to 68%). Besides, HN4 exhibited a unique response to mechanical force accompanied by a reversible change of the QY. We believe that this strategy provides beneficial inspiration and methodology to design materials with high emissive quantum yield that can be used in a variety of luminescent events.

  • Xiang Shi, Ge Gao, Xiaoyang Liu, Lingling Xu, Yu Deng, Rui Wang, Gaolin Liang
    Chinese Chemical Letters. 2023, 34(3): 107613-.

    Lipid droplet (LD) fluorescent imaging plays an important role in the detection of lipid-related diseases. Due to their poor photostability and low hydrophobicity of currently available LD imaging fluorophores, LD imaging is limited by its short imaging period and low imaging contrast. Herein, we reasonably designed a highly lipophilic compound Cou-Flu with excellent photostability and excimer-monomer transition property. It exhibited weak excimer emission in cytoplasm, but strong monomer emission in LDs, enabling high contrast LD imaging and LD movement tracing in cells. Zebrafish imaging study demonstrated that Cou-Flu was also suitable for in vivo LD detection with excellent sensitivity. We anticipate that Cou-Flu could be widely applied to understand LD-related intracellular activities and even LD-related diseases in the future.

  • Shan-Xiu Ni, Yan-Lin Li, Hui-Qi Ni, Yu-Xiang Bi, Jie Sheng, Xi-Sheng Wang
    Chinese Chemical Letters. 2023, 34(3): 107614-.

    A nickel-catalyzed direct hydromonofluoromethylation of unactivated olefins with industrial raw fluoroiodomethane is developed, furnishing various primary alkyl fluorides in a step-economic manner. The key factor to success is the use of pyridine-oxazoline as ligand and (MeO)2MeSiH as the hydrogen source. This transformation demonstrates high efficiency, mild conditions, good functional-group compatibility and great potential in the drug discovery.

  • Xiaolin Zhang, Xiuli Liu, Luhui Qin, Chao Tang, Yu Huo, Jinbin Wei, Ming Chen, Yutong Gao, Xiaoping Zhang, Yani Wu, Yongxiang Zhao, Renbin Huang, Liping Zhong, Bing Wang
    Chinese Chemical Letters. 2023, 34(3): 107618-.

    Liposomes have been widely exploited as a drug delivery system in treating tumors because of their advantage to enhance anti-tumor efficacy and reduce side effects. In this study, the tumor-targeted 2-dodecyl-6-methoxycyclohexa-2, 5-diene-1, 4-dione (DMDD, i.e., Averrhoa carambola extractive) liposomes (HA/TN-DLP) were conducted and assessed. HA/TN-DLP showed controllable drug loading (up to 83%) with high stability. In vitro and in vivo studies showed good cell uptake behavior and high inhibition rate of breast cancer compared to free DMDD. HA/TN-DLP might be the suitable for DMDD due to its better advantages in delivery, penetrability, and targeting-tumor capability. For in vivo mouse model tests, HA/TN-DLP effectively inhibited tumor growth compared to free DMDD. Further analyses indicated that HA/TN-DLP inhibited the glycerophospholipid metabolism pathway by reducing the biosynthesis of phosphatidylcholine and 1-acyl-sn-glycero-3-phosphocholine through regulating the expressions of CEPT1 and LYPLA1, and inhibited tumor cell growth by regulating the PI3K/Akt and NF-κB signaling pathways. In conclusion, the obviously enhanced antitumor effect further demonstrated that HA/TN-DLP may be a promising tumor-targeting agent.

  • Ping Li, Zheng Li, Dawei Zhang, Qiong Jia
    Chinese Chemical Letters. 2023, 34(3): 107619-.

    β-Cyclodextrin (β-CD) based materials have attracted great attention in the separation of hydrophilic glycopeptides due to the abundant hydroxyl groups in its exterior. However, the current materials based on β-CD generally has complex synthesis process and harsh experimental conditions, on the other hand, the interior cavity of β-CD is hydrophobic and is harmful to capture glycopeptides. Herein, a novel hydrophilic material based on β-CD was engineered via a self-assembly process utilizing l-cysteine (l-Cys) or glutathione (GSH) derived adamantane for highly efficient glycopeptide enrichment. It is the first attempt to make use of the hydrophobic interior cavity of β-CD for hydrophilic glycopeptide capture. Taking advantages of strong hydrophilicity and superparamagnetism, the as-prepared materials possess low detection limit, high selectively, and excellent reusability when employed to glycopeptide enrichment. In addition, the feasibility of the hydrophilic material based on β-CD was verified by enriching glycopeptides from human serum and saliva samples. This study provides a heuristic strategy for the application of β-CD-based self-assembly materials in the enrichment of glycopeptides. Importantly, this strategy certified a possible that the change of glycopeptide enrichment sites through host-guest interaction between β-CD and adamantane derivatives with different functional groups.

  • Xuechun Wang, Jiana Jing, Minghua Zhou, Raf Dewil
    Chinese Chemical Letters. 2023, 34(3): 107621-.

    As important emerging contaminants, antibiotics have caused potential hazards to the ecological environment and human health due to their extensive production and consumption. Among various techniques for removing antibiotics from wastewater, H2O2-based advanced oxidation processes (AOPs) have received increasing attention due to their fast reaction rate and strong oxidation capability. Hence this review critically discusses: (ⅰ) Recent research progress of AOPs with the addition of H2O2 for antibiotics removal through different methods of H2O2 activation; (ⅱ) recent advances in AOPs that can in-situ generate and activate H2O2 for antibiotics removal; (ⅲ) H2O2-based AOPs as a combination with other techniques for the degradation and mineralization of antibiotics in wastewater. Future perspectives about H2O2-based AOPs are also presented to grasp the future research trend in the area.

  • Xi Wang, Fujie Liu, Tao Xu
    Chinese Chemical Letters. 2023, 34(3): 107624-.

    Multiple contiguous quaternary carbon stereocenters (CQS) are highly challenging, yet important structural motifs in organic synthesis. Here, we describe a visible light induced catalytic [2 + 2] cycloaddition approach that constructed up to four CQS in a pentacyclic fused ring system diastereoselectively, from the readily accessible dienamides with pendent heteroaryls. Variously substituted dienamides have been cyclized with heteroaryls to provide a range of novel CQS-containing scaffolds (26 examples, up to 96% yield and > 20:1 dr ratio). Mechanistic studies revealed that it may proceed through an uncommon β-C radical initiated 7-endo cyclization from the biradical intermediate.

  • Yaohang Cheng, Xian Zhang, Guanghui An, Guangming Li, Zhenyu Yang
    Chinese Chemical Letters. 2023, 34(3): 107625-.

    Visible-light-mediated para-C–H difluoroalkylation of anilides via combination of steric effects and Lewis acid activation strategies has been developed. The addition of (C6H5O)2P(O)OH and Ag2CO3 properly tune the redox potential of ruthenium catalyst and leads to mild reaction conditions. The protocol exhibits broad functional group tolerance and allows the late-stage functionalization of complex bioactive molecules.

  • Huili Wang, Yishuo Sun, Xuemei Lin, Wei Feng, Zhanxian Li, Mingming Yu
    Chinese Chemical Letters. 2023, 34(3): 107626-.

    The normal operation of lysosome, mitochondria, Golgi apparatus and endoplasmic reticulum plays a significant role in maintaining cell homeostasis. Reflecting the state and function of lysosomes, viscosity is a pivotal parameter to assess the stability of microenvironment. Herein, based on TICT mechanism, a new NIR pH-dependent fluorescent probe DCIC with push-pull electronic moiety was synthesized to identify the lysosomes viscosity. In viscous media, DCIC was highly sensitive to viscosity, fluorescence intensity increased by 180 times as viscosity increased from 1.0 cp to 438.4 cp. In addition, DCIC have high localization ability for lysosome, mitochondria, Golgi apparatus, and endoplasmic reticulum and can monitor lysosomal viscosity fluctuations with laser confocal microscopy.

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