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  • Ying He, Mengjia Liu, Shun Teng, Lukasz Wojtas, Guangxin Gu, Xiaodong Shi
    Chinese Chemical Letters. 2022, 33(9): 4203-4207.

    Fluorescence (FL) active 8-aryl guanosine derivatives were prepared and applied for cation mediated self-assembly to form the H-bonded G8-quadruplexes. The p-cyano (p-CN) and 8-anthracene (8-An) substituted guanosines were identified to give the strongest fluorescence with the formation of G8-octamers (G8) both in solution (NMR) and solid state (X-ray). This well-defined G8-octamer system has provided the first direct evidence on the self-assembled G-quadruplex fluorescence emission with aggregation-induced emission (AIE), which could be applied as the foundation for FL molecular probe design toward G-quadruplex recognition.

  • Longlong Xi, Liting Du, Zhuangzhi Shi
    Chinese Chemical Letters. 2022, 33(9): 4287-4292.

    A nickel-catalyzed reductive cross-coupling reactions between polyfluoroarenes and alkyl electrophiles is reported to access substituted fluoroarenes through chelation-assisted C–F activation. Diverse primary and secondary alkyl (pseudo)halides can be employed to couple with polyfluoroarenes, showing excellent regioselectivity. Furthermore, the nickel-catalyzed asymmetric cross-coupling of polyfluoroarenes with racemic alkyl halides is preliminarily explored. In addition, the practicability of the title transformation is also demonstrated by total synthesis of losmapimod and an analog as key steps. The developed method exhibits many advantages, including economic catalytic systems, commercially available alkyl electrophiles, and lack of sensitive organometallic reagents.

  • Junping Bai, Junliang Zhou, Xin Ji, Nannan Wang, Xiaochun Dong, Wei Wu, Weili Zhao
    Chinese Chemical Letters. 2022, 33(9): 4175-4178.

    Fluorescent dyes play a crucial role in fluorescence imaging and sensing technology. However, there is a dilemma that they are usually intrinsically hydrophobic which lacks of emission in water and modification with ionic groups to access water solubility may result in poor membrane permeability. Fluorescent dyes with strong fluorescence emission in both nonpolar and polar solvents are highly desirable. In this manuscript, we reported a strategy to develop fluorescent BODIPY dyes via installation of amide moiety at meso position of 1, 3, 5, 7-tetramethyl-BODIPY and discovered that N, N'-dialkylsubstituted BODIPY amides possessed highly fluorescent emission with favorable environment-insensitive properties.

  • Yanyan Sun, Xiaonan Zhou, Liyuan Sun, Xiuxiu Zhao, Yongrui He, Ge Gao, Weina Han, Jin Zhou
    Chinese Chemical Letters. 2022, 33(9): 4229-4232.

    Available online The abnormal carboxylesterase (CES) expression is closely related to many diseases such as hyperlipidemia, atherosclerosis, obesity, liver cancer, type 2 diabetes mellitus and gastrointestinal stromal tumors. The detection of a single enzyme in practical samples is often constrained by the structural diversity of CESs. Thus, the development of broad-carboxylesterase responsive fluorescent probe, which can detect the presence of wide variety of CESs, may provide overall or category information from another point of view, supplementing the deficiency of single detection for CES subspecies. Organelle lysosome is involved in various cell processes, such as cell signaling, apoptosis, secretion, and energy metabolism. Up to date, lysosome-targeted fluorescent probes, especially those with red emission (over 550 nm, with relatively low biological harmfulness), for CES detection are still rare. A lysosomes-targeted red fluorescent probe CES-Lyso was designed to monitor intracellular a variety of carboxylesterases alteration with wonderful selectivity and sensitivity, which was further applied to distinguish different derived breast cancer cells and monitor carboxylesterase activity in the anticancer drug treatment.

  • Shuanggang Ma, Rubing Wang, Rongmei Gao, Xiaojing Wang, Yunbao Liu, Yong Li, Li Li, Yuhuan Li, Jing Qu, Shishan Yu
    Chinese Chemical Letters. 2022, 33(9): 4248-4252.

    Two unprecedented polycyclic spirooliganones C and D (1 and 2) with a novel spiro[bicyclo[2.2.2]octane-2, 2′-bicyclo[3.1.0]hexane] carbon skeleton, one known dimeric prenylated C6C3 compound (3), and a pair of new enantiomeric prenylated C6C3 compounds (+)-5 and (−)-5 together with their direct precursors (+)-4 and (−)-4 were isolated from the roots of Illicium oligandrum. Their structures and absolute configurations were elucidated by spectroscopic analysis, single crystal X-ray diffraction data, and electronic circular dichroism calculations. A possible biosynthetic pathway for compounds 1 and 2 involving the Diels-Alder reaction between (−)-sabinene and cyclic prenylated tetrahydropyrano-type C6C3 compounds was proposed. The characteristic prenylated C6C3 compounds (+)-4 and (−)-4 were separated on a chiral stationary phase and their absolute configurations were determined by calculated ECD for the first time. In the antiviral bioassays, compounds 1 and (+)-5 exhibited significant inhibitory activity against CVB3 with IC50 values of 11.11 µmol/L and 1.11 µmol/L, respectively. Compounds 1 and 2 also showed moderate inhibition against influenza A (H1N1) virus.

  • Peng-Jun Zhou, Yi Zang, Cong Li, Lin Yuan, Huaqiang Zeng, Jia Li, Jin-Feng Hu, Juan Xiong
    Chinese Chemical Letters. 2022, 33(9): 4264-4268.

    Forrestiacids C (1) and D (2), a pair of C-25 epimeric triterpene–diterpene adducts were isolated from the needles and twigs of the vulnerable conifer Pseudotsuga forrestii. This unprecedented class of compounds might be generated via an intermolecular Michael addition reaction of a rearranged 6/6/5/5-fused spiro-lanostene with an abietene. Their structures were established by spectroscopic data and X-ray crystallography. The adducts showed inhibitory activities against the ATP-citrate lyase (ACL) and acetyl-CoA carboxylase 1 (ACC1), two rate-limiting enzymes in the de novo lipogenesis pathway.

  • Taotao Li, Yu Zheng, Chenqin Wu, Chengyu Yan, Cheng Zhang, Hong Gao, Qian Chen, Kui Zhang
    Chinese Chemical Letters. 2022, 33(9): 4238-4242.

    Room temperature phosphorescence (RTP) films have recently attracted increasing attention due to their excellent luminescent properties for information encryption, optoelectronic devices, and sensors. However, polyvinyl alcohol (PVA) films with abundant hydrogen bonds to suppress triplet energy dissipation suffered from the humidity induced phosphorescence quenching under storage in the air for a long time. In this work, poly(acrylic acid) (PAA) was selected to crosslink PVA matrix through esterification reactions for preparing water resistant RTP films. The blue, cyan, and orange emissive RTP films were successfully obtained by incorporating three different organic compounds into PVA-PAA crosslinking films. Crosslinking strategy significantly improved the phosphorescence emissions of the doped films, and effectively blocked the absorption of water molecular, leading to the excellent photostability of the developed films. As a proof of concept, the white light phosphorescence film and anti-counterfeiting applications were successfully demonstrated.

  • Yan Yu, Meng Pan, Jinrong Peng, Danrong Hu, Ying Hao, Zhiyong Qian
    Chinese Chemical Letters. 2022, 33(9): 4133-4145.

    Hydrogen peroxide (H2O2) is a very simple bioactive small molecule. In living organisms, H2O2 plays an important role in intracellular signaling. It is involved in many physiological processes including cellular physiology, intracellular signaling, oxidative damage and disease progression. The tumor microenvironment enriched with H2O2. Several electrochemical sensors have been developed and some have been put on the market. Such electrochemical sensors provide efficient, cost-effective, rapid and highly selective method of H2O2 detection. So far, much progress has been made in the designing of materials and construction of H2O2 sensors. This review describes the advances in the application of H2O2 electrochemical sensors in cell detection. Enzyme-based sensors have been applied in diverse applications. In addition, recent advancements in nanotechnology have improved the development of nanozymes-based sensors. The application of noble metals, metal oxides, polymers, carbon materials and other two-dimensional materials in the design of H2O2 sensors are discussed in detail. Moreover, the bio-stimulant types of H2O2 sensor are summarized. Finally, the challenges and future perspectives in the application of H2O2 electrochemical sensors in biological detection are discussed.

  • Lihua Huang, Zonghao Sun, Qian Shen, Zhongxi Huang, Shuangxi Wang, Naidi Yang, Gongqiang Li, Qiong Wu, Wei Wang, Lin Li, Changmin Yu
    Chinese Chemical Letters. 2022, 33(9): 4146-4156.

    Well-developed mitochondria-targeted nanocarriers for function regulation are highly desirable. Numerous studies have been conducted on the treatment of mitochondria-related diseases; however, further improvements are required to develop more effective drug delivery methods. Herein, we comprehensively introduce recent developments progress in rational design of mitochondria-targeted nanocarriers, and discuss the different strategies of available nanocarriers for targeting mitochondria. We also highlight the advantages and disadvantages of various carrier systems that are currently in use. Finally, perspective on new generation for mitochondria-targeted delivery systems in the emerging area of drug-based therapeutics is also discussed.

  • Quan Wang, Zhao Zhang, Chen Zou, Changle Chen
    Chinese Chemical Letters. 2022, 33(9): 4363-4366.

    The tuning of olefin-polymerization catalyst properties through ligand modifications is efficient but requires complicated and costly syntheses. In this contribution, a simple Bu2Mg-based cocatalyst strategy is designed that can simultaneously enhance the catalytic properties (activity, thermal stability, polymer molecular weight, branching density, melting point, etc.) of various nickel catalysts (α-diimine nickel, pyridine imine nickel and iminopyridine-N-oxide nickel) in ethylene polymerization, and enable great product morphology control. For example, a simple α-diimine nickel catalyst can demonstrate polymerization activity of up to 1.29 × 107 g mol−1 h−1 and molecular weight of up to 1.90 × 106 g/mol in the presence of Bu2Mg cocatalyst. The resulting polyethylenes exhibit excellent mechanical properties, with tensile stress of up to 47.4 MPa and strain of up to 1020%. This cocatalyst strategy is generally applicable to different nickel catalysts, and can lead to property enhancement in ethylene copolymerization with a series of polar comonomers such as methyl 10-undecylenate, 10-undecylenic acid and 10-undecenol.

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