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  • Shuheng Zhang, Yuanyuan Zhang, Wanyu Wang, Yuzhu Hu, Xinchuan Chen, Bilan Wang, Xiang Gao
    Chinese Chemical Letters. 2024, 35(12): 109658-.

    Lymphoma is a hematological malignancy with an increasing mortality rate. Nevertheless, the treatment strategy against lymphoma remains limited. Doxorubicin (DOX) is a broad-spectrum anti-tumor chemotherapeutic drug, the clinical application of which is limited by serious adverse effects and drug resistance. In this work, biodegradable methoxy poly(ethylene glycol)-block-poly(lactic acid) (mPEG-PLA) nanomicelles co-delivering of DOX and apatinib (AP) (DOX-AP/m) was developed for lymphoma therapy. The average particle size of the self-assembled drug-loaded nano-micelle was 31.94 nm. It is revealed that AP can enhance the uptake of DOX by tumor cells. The in vivo and in vitro experimental results revealed that DOX-AP/m combination therapy could inhibit proliferation and promote apoptosis of lymphoma cells, and greatly suppress tumor growth. Our study indicated that DOX-AP/m might provide new insight and hold great potential in the treatment of lymphoma.

  • Yunjie Dang, Yanru Feng, Xiao Chen, Chaoxing He, Shujie Wei, Dingyang Liu, Jinlong Qi, Huaxing Zhang, Shaokun Yang, Zhiyun Niu, Bai Xiang
    Chinese Chemical Letters. 2024, 35(12): 109660-.

    The combination of nucleic acid and small-molecule drugs in tumor treatment holds significant promise; however, the precise delivery and controlled release of drugs within the cytoplasm encounter substantial obstacles, impeding the advancement of formulations. To surmount the challenges associated with precise drug delivery and controlled release, we have developed a multi-level pH-responsive co-loaded drug lipid nanoplatform. This platform first employs cyclic cell-penetrating peptides to exert a multi-level pH response, thereby enhancing the uptake efficiency of tumor cells and endow the nanosystem with effective endosomal/lysosomal escape. Subsequently, small interferring RNA (siRNA) complexes are formed by compacting siRNA with stearic acid octahistidine, which is capable of responding to the lysosome-to-cytoplasm pH gradient and facilitate siRNA release. The siRNA complexes and docetaxel are simultaneously encapsulated into liposomes, thereby creating a lipid nanoplatform capable of co-delivering nucleic acid and small-molecule drugs. The efficacy of this platform has been validated through both in vitro and in vivo experiments, affirming its significant potential for practical applications in the co-delivery of nucleic acids and small-molecule drugs.

  • Yunkang Tong, Haiqiao Huang, Haolan Li, Mingle Li, Wen Sun, Jianjun Du, Jiangli Fan, Lei Wang, Bin Liu, Xiaoqiang Chen, Xiaojun Peng
    Chinese Chemical Letters. 2024, 35(12): 109663-.

    The prodrug strategy provides an opportunity for improving the therapeutic index of drugs and avoiding their side effects. The main challenge lies in the fast and effective release of the parent drugs at the desired site under specific stimuli. Herein, a cooperative prodrug activation approach with exogenous native enzyme and endogenous tumor small molecule biomarkers was developed. Chemically, precursors of methylene blue (MB) and resorufin (RSF) react with horseradish peroxidase (HRP)/hydrogen peroxide (H2O2) to quickly and quantitatively release parent dyes and drugs containing amines or carboxylic acids. The application of this approach in mammalian cells was demonstrated with cooperative-activated photodynamic therapy based on a precursor of MB. Compared with free MB, much higher selectivity toward cancer cells was achieved with this approach as evaluated by the selectivity index (SI). This study provides a new method for fast and effective targeted prodrug activation with no need for antibody modification compared with traditional enzyme/prodrug therapy.

  • Xiang Huang, Dongzhen Xu, Yang Liu, Xia Huang, Yangfan Wu, Dongmei Fang, Bing Xia, Wei Jiao, Jian Liao, Min Wang
    Chinese Chemical Letters. 2024, 35(12): 109665-.

    Increasing interests of difluorinated amino acids (DFAAs) have been raised in recent years due to their widespread bio-organic and medical applications. However, to date, only few investigations focused on their asymmetric synthesis. Exploring difluoromethyl reagent to tailor a novel pathway and developing efficient catalytic system are highly desirable for constructing structurally diverse chiral DFAAs. Herein, a copper-catalyzed asymmetric difluorobenzylation of aldimine esters is described. By using α,α-difluorinated benzyltriflones as difluoromethyl reagents, this protocol allows the asymmetric synthesis of α-quaternary DFAAs with wide scope, good yields and excellent enantioselectivities (90%-98% ee). Control experiments and DESI-MS analysis demonstrate the reaction probably proceeds via a key difluorocarbocation intermediate. Moreover, polyfluoroarenes are found efficient candidates to polyfluoroaryl amino acids via C-F activation. Gram-scale experiment, late-stage functionalization, synthesis of difluorinated dipeptides and bioactive molecular analogues revealed the utility of the protocol, thereby largely enriching the structural diversity of FAAs and providing more potential opportunities in drug discovery.

  • Xueyan Zhang, Jicong Chen, Songren Han, Shiyan Dong, Huan Zhang, Yuhong Man, Jie Yang, Ye Bi, Lesheng Teng
    Chinese Chemical Letters. 2024, 35(12): 109668-.

    Osteoporosis is a disease of bone metabolism homeostasis imbalance with obvious bone loss, damage to bone microstructure, and increased risk of fracture. The occurrence and development of osteoporosis is related to the augmentation of active osteoclasts. Receptor activator of nuclear factor kappa B (RANK) small interfering RNA (siRNA) knockdowns the expression of RANK mRNA to inhibit the osteoclast precursors differentiate into osteoclasts as a treatment in osteoporosis. Salmon calcitonin (sCT) is a commonly used anti-osteoporotic agent that inhibits osteoclast activity and induces osteoclast apoptosis, and it also could promote the osteogenesis by osteoblasts. A cocktail therapy improves the therapeutic effect of osteoporosis between RANK siRNA and sCT. A size-switchable microsphere from micro to nano scale was developed to address the delivery barriers of biomacromolecules with poor stability and frequent administration. RANK siRNA and sCT were incorporated into the microspheres with a nanoparticle/micelle-microsphere double-layer structure to achieve sustained release when the particle size shrunk and dual protection of RANK siRNA and sCT. The size-switchable microspheres MS@(AL-NPs/ARM) had an optimal therapeutic effect and reduced the frequency of administration in glucocorticoid induced osteoporosis (GIOP) mouse model. RANK siRNA and sCT co-delivery system based on size-switchable microsphere is a promising strategy to treat osteoporosis through the controlled release of biomacromolecules.

  • Yinglan Yu, Sajid Hussain, Jianping Qi, Lei Luo, Xuemei Zhang
    Chinese Chemical Letters. 2024, 35(12): 109673-.

    In polarized cells, the differential distribution of proteins results in the formation of apical and basolateral membranes. The basolateral membrane contacts basal lamina and mediates cell-to-cell communication, which is crucial for maintaining homeostasis and enabling drug absorption. To establish and maintain the basolateral domain, intricate mechanisms are necessary to ensure the proper sorting and transportation of molecules. Sorting signals play a crucial role in regulating the distributions of basolateral proteins, determining their trafficking route and final residence. Newly synthesized proteins can be segregated into different carrier vesicles at either trans-Golgi network (TGN) or endosomes. Additionally, understanding basolateral transport in polarized epithelial cells is important for predicting diseases and delivering drugs. This review provides a summary of recent advancements in the mechanisms and applications of basolateral sorting and trafficking.

  • Hongjin Shi, Guoyin Yin, Xi Lu, Yangyang Li
    Chinese Chemical Letters. 2024, 35(12): 109674-.

    2-Deoxy-α-C-Glycosides are a significant class of carbohydrates found in numerous bioactive molecules and medicines. Developing a concise strategy for the assembly of these α-configured C-glycosides is crucial in the field of carbohydrate chemistry. However, current methods are restricted to the utilization of glycosyl radical precursors, which are required for pre-syntheses. Herein, we present a novel approach for the synthesis of 2-deoxy-α-C-glycosides using a nickel-catalyzed stereoselective coupling reaction with commercially available glycals. Notably, this method circumvents the preparation for diverse glycosyl radical precursors. The developed protocol exhibits a broad substrate scope and remarkable stereoselectivity under mild reaction conditions. Furthermore, the raw materials required for this process are readily accessible, eliminating the necessity for pre-functionalization modifications of the glycosyl substrates and ensuring high atomic economy.

  • Zhuwen Wei, Jiayan Chen, Congzhen Xie, Yang Chen, Shifa Zhu
    Chinese Chemical Letters. 2024, 35(12): 109677-.

    Pyrroles are important structural units of natural products, drug molecules, biomolecules and functional material molecules. Efficient synthesis of α-functionalized pyrroles with different substituents from easily accessible starting materials is still challenging. Herein, a facile and regioselective coarctate reaction of enynals involving a free carbene intermediate has been developed, which allows the divergent and practical de novo synthesis of various α-furanyl pyrroles and α-cyclopropenyl pyrroles derivatives with good to excellent yields and high efficiency under mild conditions. This approach features readily accessible starting materials, high functional group compatibility, step economy and scalability, which would complement previous methods and support expansion of the toolbox for the synthesis of valuable, but previously inaccessible, highly substituted and electron-rich α-functionalized pyrroles.

  • Xu Qu, Pengzhao Wu, Kaixuan Duan, Guangwei Wang, Liang-Liang Gao, Yuan Guo, Jianjian Zhang, Donglei Shi
    Chinese Chemical Letters. 2024, 35(12): 109681-.

    Human β-galactosidase (β-gal) is recognized as a crucial biomarker for evaluating senescence at the cellular and tissue levels in humans. However, tools to precisely track the endogenous β-gal are still limited. Herein, we present two novel self-calibrating β-gal probes 7a and 7b which were constructed on a unique green/red dual-emissive fluorescence platform. The two probes inherently exhibited a stable green fluorescence signal impervious to β-gal activity, serving as a reliable internal reference. They also displayed a progressively diminishing red fluorescence signal with the increasing of β-gal expression levels. The dual behavior endows them with self-calibration capacity and then renders excellently selective and sensitive for precisely monitoring β-gal activity. Notably, compared with E. coli β-gal, the two probes are more effectively response to A. oryzae β-gal homologous to human β-gal, indicating their unique species-selectivity. Furthermore, 7a was validated for its effectiveness in determining senescence-associated β-galactosidase (SA-β-gal) expression in senescent NRK-52E and HepG2 cells, underscoring its practical applicability in senescence research.

  • Xue-Jiao Wang, Jun-Li Xin, Hong Xiang, Ze-Yu Zhao, Yu-Hang He, Haibo Wang, Guangyao Mei, Yi-Cheng Mao, Juan Xiong, Jin-Feng Hu
    Chinese Chemical Letters. 2024, 35(12): 109682-.

    Two lindenane-type sesquiterpene (LDS) trimers with unprecedented carbon skeletons, holotrichones A (1) and B (2), were obtained from the whole plant of Chloranthus holostegius var. trichoneurus by a ultra performance liquid chromatography-photodiode array detector-mass spectrometry (UPLC-PDA-MS)-guided isolation strategy. Compound 1 represents the first LDS trimer incorporating a unique 3/5/6/6-fused framework, in which a lindenane-type monomer and the 2-methylbutyryl substituent of an LDS dimer is bridged by a six-membered ring system. Compound 2 is the first hetero-trimer fused by an LDS dimer with a p-benzoquinone-meroterpenoid, featuring an unusual 3/5/6/6/3/5/6/6/6 nonacyclic system fused by the sesquiterpenoid unit and a 2-geranyl-6-methyl-2,5-cyclohexadien-1,4-dione moiety. In compound 2, the dimeric LDS moiety is equipped with a rare oxaspiro[4.5]decane system. Their structures, including absolute configurations, were established by spectroscopic methods, GIAO NMR calculations and DP4+ probability analyses, electronic circular dichroism (ECD) calculations, and single-crystal X-ray diffraction analysis. The plausible biogenetic pathway speculation indicated that hetero- and homo-Diels-Alder additions may dominate the formation of these highly fused polycyclic frameworks. Both compounds 1 and 2 induced the human acute myeloid leukemia MV-4–11 cell death via apoptosis induction, which deserves further investigation on this new chemical class of LDS oligomers for their anti-leukemic potential.

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