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Phenylhydrazone anions excitation for the photochemical carbonylation of aryl iodides with aldehydes

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Chinese Chemical Letters 2024年第4期35卷 346-351页

作者： Lei Shen Yang Zhang Linlin Zhang Chuanwang Liu Zhixian Ma Kangjiang Liang Chengfeng Xia Key laboratory of medicinal chemistry for Natural Resource Ministry of EducationYunnan Provincial Center for Research&Development of Natural ProductsSchool of PharmacyYunnan UniversityKunming 650500China

Spectroscopic investigations discovered that the in-situ generated phenylhydrazone anion was significantly bathochromically shifted to visible light region for photoactivation under irradiation. The photoexcited phenylhydrazone anion was potential to reduce aryl iodides via single electron transfer process for the subsequent radical chain reaction. A redox-neutral photochemical carbonylation of aryl iodides was developed on basis of the special spectroscopic features of phenylhydrazone anion. This protocol provided a convenient and efficient synthetic tool for accessing carbonylation products under redox neutral conditions without the need of transition-metals.

关键词： Organic anion Hydrazone Carbonylation Visible light Single electron transfer

In-situ synthesis of quantum dots in the nucleus of live cells

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National Science Review 2024年第3期11卷 172-182页

作者： Yusi Hu Zhi-Gang Wang Haohao Fu Chuanzheng Zhou Wensheng Cai Xueguang Shao Shu-Lin Liu Dai-Wen Pang State Key laboratory of medicinal Chemical Biology Frontiers Science Centre for New Organic MatterTianjin Key Laboratory of Biosensing and Molecular Recognition Research Centre for Analytical Sciences College of Chemistry School of Medicine and Frontiers Science Centre for Cell Responses Nankai University Haihe laboratory of Sustainable Chemical Transformations

The cell nucleus is the main site for the storage and replication of genetic material, and the synthesis of substances in the nucleus is rhythmic, regular and strictly regulated by physiological processes. However,whether exogenous substances, such as nanoparticles, can be synthesized in situ in the nucleus of live cells has not been reported. Here, we have achieved in-situ synthesis of CdSxSe1-xquantum dots（QDs） in the nucleus by regulation of the glutathione（GSH） metabolic pathway. High enrichment of GSH in the nucleus can be accomplished by the addition of GSH with the help of the Bcl-2 protein. Then, high-valence Se is reduced to low-valence Se by glutathione-reductase-catalyzed GSH, and interacts with the Cd precursor formed through Cd and thiol-rich proteins, eventually generating QDs in the nucleus. Our work contributes to a new understanding of the syntheses of substances in the cell nucleus and will pave the way for the development of advanced ‘supercells’.

关键词： glutathione live cell nucleus quantum dot intracellular synthesis

Syntheses of new di-nuclear and tetra-nuclear lanthanide 9-anthracenecarboxylates:Magnetocaloric effect,slow magnetic relaxation and luminescent properties

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Journal of Rare Earths 2024年第6期42卷 1101-1109,I0004页

作者： Xing Liu Ruonan Yang Lu Zhang Jian Zhou Chunmei Huang Huahong Zou Zunhong Xiao Chongqing Key laboratory of Inorganic Functional Materials College of ChemistryChongqing Normal UniversityChongqing401331China Key laboratory for the chemistry and Molecular Engineering of medicinal Resources(Ministry of Education of China) School of Chemistry and Chemical Engineering of Guangxi Normal UniversityGuilin541004China School of chemistry and Materials Guizhou Normal UniversityGuiyang550025China

Lanthanide complex-based materials with magnetic and luminescent properties have received a great deal of attention,owing to their importantly potential applications in diverse *** this work,the 9-anthracenecarboxylic acid(9-Haca)as bridging ligand was applied in combination with optically activeπ-conjugated 2,4,6-tri(2-pyridyl)-1,3,5-triazine(tptz)to construct a series of new di-nuclear and tetranuclear lanthanide 9-anthracenecarboxylates[La_(2)(9-aca)_(6)(tptz)_(2)(μ-H_(2)O)]·0.25H_(2)O(1),[Ln_(2)(9-aca)_(6)(tptz)_(2)(H_(2)O)_(2)]·0.5AQ·CH_(3)COOH_(2)H_(2)O[Ln=Sm(2a),Eu(2b),Gd(2c),Tb(2d),Dy(2e),Tm(2f);AQ=9,10-anthracenedione]and[Ln_(4)(9-aca)_(10)(tptz)_(2)(CH3COO)2]·H_(2)O[Ln=Eu(3a),Gd(3b),Dy(3c)].1 displays a di-nuclear centrosymmetric moiety[La_(2)(9-aca)_(6)(tptz)_(2)(μ-H_(2)O)]built up from two complex[La(9-aca)_(2)(tptz)]groups bridged by one H_(2)O molecule and two syn-syn-μ2-η1:η1-9-aca-bridging ligands,while 2a-2f are isostructural and co mprise another di-nuclear centrosymmetric moieties[Ln_(2)(9-aca)_(6)(tptz)_(2)(H_(2)O)_(2)]based on two complex[Ln(9-aca)_(2)(tptz)(H_(2)O)]groups connected by two syn-syn-μ2-η1:η1-9-aca-bridging ligands,3a-3c are isostructural and show tetra-nuclear centro symmetric moieties[Ln4(9-aca)10(tptz)2(CH3COO)2]containing three types of coordination modes of *** present compounds offer the only examples of lanthanide 9-anthracenecarboxylates decorated by optically active *** investigations of 2a,2c-2f,and 3b-3c indicate that 3c is typical of slow relaxation of the magnetization,while 2c and 3b show significant magnetocaloric effect(MCE)with the value of-ΔSm of 5.26 J/(kg·K)at 4 K and 15.65 J/(kg·K)at 2 K(ΔH=7 T),*** luminescent properties were also studied and reveal that the characteristic luminescent properties of the 7r-conjugated aromatic ligands are introduced into magnetic lanthanide 9-anthracenecarboxylates,simultaneously exhibiting slow magnetic relaxation(or MCE)and luminescen

关键词： Lanthanide complexes Luminescence Magnetic properties Magnetocaloric effect Slow magnetic relaxation Rare earths

The p38/MAPK pathway as a therapeutic target to prevent therapeutic escape of breast cancer stem cells

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Science China Life Sciences 2024年第9期67卷 1867-1880页

作者： Weixiao Yan Xiaotong Wang Wenjing Wang Qi Guo Na Huang Hao Chen Xing-Jie Liang Yu Han Dandan Liu Jinchao Zhang State Key laboratory of New Pharmaceutical Preparations and Excipients Key laboratory of medicinal chemistry and Molecular Diagnosis of the Ministry of Education College of chemistry and Materials Science Chemical Biology Key Laboratory of Hebei Province Hebei University CAS Key laboratory for Biological Effects of Nanomaterials and Nanosafety National Center for Nanoscience and Technology

Cancer stem cells(CSCs) play an important role in metastasis development, tumor recurrence, and treatment resistance, and are essential for the eradication of cancer. Currently, therapies fail to eradicate CSCs due to their therapeutic stress-induced cellular escape, which leads to enhanced aggressive behaviors compared with CSCs that have never been treated. However, the underlying mechanisms regulating the therapeutic escape remain unknown. To this end, we established a model to isolate the therapeutic escaped CSCs(TSCSCs) from breast CSCs and performed the transcription profile to reveal the mechanism. Mechanistically, we demonstrated that the behavior of therapeutic escape was regulated through the p38/MAPK signaling pathway, resulting in TSCSCs exhibiting enhanced motility and metastasis. Notably,blocking the p38/MAPK signaling pathway effectively reduced motility and metastasis ability both in vitro and in vivo, which were further supported by downregulated motility-related genes and epithelial-mesenchymal transition(EMT)-related proteins vimentin and *** obtained findings reveal the p38/MAPK pathway as a potential therapeutic target for TSCSCs and would provide profound implications for cancer therapy.

关键词： therapeutic escape breast cancer stem cells motility p38/MAPK signaling pathway molecular mechanism

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Uncovering the dominant contribution of intermediate volatility compounds in secondary organic aerosol formation from biomass-burning emissions

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National Science Review 2024年第3期11卷 150-158页

作者： Kun Li Jun Zhang David M.Bell Tiantian Wang Houssni Lamkaddam Tianqu Cui Lu Qi Mihnea Surdu Dongyu Wang Lin Du Imad El Haddad Jay G.Slowik Andre S.H.Prevot Environment research Institute Shandong University laboratory of Atmospheric chemistry Paul Scherrer Institute

Organic vapors from biomass burning are a major source of secondary organic aerosols(SOAs). Previous smog chamber studies found that the SOA contributors in biomass-burning emissions are mainly volatile organic compounds(VOCs). While intermediate volatility organic compounds(IVOCs) are efficient SOA precursors and contribute a considerable fraction of biomass-burning emissions, their contribution to SOA formation has not been directly observed. Here, by deploying a newly-developed oxidation flow reactor to study SOA formation from wood burning, we find that IVOCs can contribute ～70% of the formed SOA, i.e.>2 times more than VOCs. This previously missing SOA fraction is interpreted to be due to the high wall losses of semi-volatile oxidation products of IVOCs in smog chambers. The finding in this study reveals that SOA production from biomass burning is much higher than previously thought, and highlights the urgent need for more research on the IVOCs from biomass burning and potentially other emission sources.

关键词： atmospheric chemistry biomass burning secondary organic aerosol intermediate volatility organic compounds

Synthesis of Anti-Pancreatic Cancer Natural Product Majusculamide D and Analogues Reveals a Preliminary Structure-Activity Relationships

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Chinese Journal of chemistry 2024年第6期42卷 605-610页

作者： Xiuhe Zhao Mengxue Lv Xiaonan Xi Yaxin Lu Liang Wang Yue Chen The State Key laboratory of medicinal Chemical Biology College of PharmacyNankai UniversityTianjin300350 China College of chemistry Nankai UniversityTianjin300071 China

The total synthesis of majusculamide D(1)was achieved from commercially available *** addition,we synthesized eight analogues including three stereoisomers of majusculamide D that differ in the fatty acid *** analogues including a simplified analogue 29 exhibited significant nanomolar-level IC50 values against Panc-1 cells in MTT assays.A preliminary SAR analysis indicated that the hydroxyl group at C10 and C2−C3 unsaturated double bond of majusculamide D were essential in maintaining the high activity against Panc-1 cells and the orientation of C40-Me and C42-Me groups was tolerable.

关键词： Majusculamide D Natural products SAR Anti-pancreatic cancer Lipopentapeptide

Intracellular redox potential-driven live-cell synthesis of CdSe quantum dots in Staphylococcus aureus

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Science China chemistry 2024年第3期67卷 990-999页

作者： Cai-Qin Wu An-An Liu Xu Li Jia-Wei Tu Juan Kong Ling-Ling Yang Jian-Hong Jia Chuan Wang Bin Hu Zhi-Xiong Xie Dai-Wen Pang The Institute for Advanced Studies College of Chemistry and Molecular SciencesCollege of Life SciencesHubei Key Laboratory of Cell HomeostasisWuhan UniversityWuhan 430072China research Center for Analytical Sciences College of ChemistryState Key Laboratory of Medicinal Chemical BiologyTianjin Key Laboratory of Biosensing and Molecular RecognitionFrontiers Science Center for New Organic MatterFrontiers Science Center for Cell Responsesand Haihe Laboratory of Sustainable Chemical TransformationsNankai UniversityTianjin 300071China

Biosynthesized semiconductor quantum dots(QDs) have bright fluorescence,adjustable particle sizes,and environmental friendliness,endowing them with convenience and potential for biological *** to the unclear mechanism of the cellular environment on the live-cell synthesis of QDs,it is still difficult to regulate their optical ***,the critical role of the intracellular redox environment in regulating the fluorescence properties of biosynthesized CdSe QDs in Staphylococcus aureus(***) has been *** glutathione peroxidase(GPx) activity directly affects the intracellular H_(2)O_(2) produced in the SeO_(3)^(2-) reduction,which further manipulates the glutathione redox cycle to determine the content of low-valence *** a result,the fluorescence intensity of the synthesized CdSe QDs increases by 60% in the GPx overexpressed *** cellular redox potential that is controlled by the GSH redox cycle provides the driving force for the reduction of SeO_(3)^(2-),facilitating the synthesis of CdSe QDs in *** *** proposed mechanism of the cellular redox state provides a new perspective for regulating the synthesis of semiconductor nanomaterials in live cells.

关键词： redox H_(2)O_(2) peroxidase quantum dot Staphylococcus aureus

Rhodium-catalyzed Doyle-Kirmse rearrangement reactions of sulfoxoniun ylides

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Chinese Chemical Letters 2024年第4期35卷 363-366页

作者： Ying-Di Hao Zhi-Qian Lin Xiao-Yu Guo Jiao Liang Can-Kun Luo Qian-Tao Wang Li Guo Yong Wu Key laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Department of medicinal chemistry Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial TechnologyWest China School of PharmacySichuan UniversityChengdu 610041China

Doyle-Kirmse rearrangement reactions have received continuous attention as an important method for constructing complex chemical structures. Herein, we disclosed an efficient rhodium-catalyzed DoyleKirmse rearrangement reaction, which can simultaneously construct C–C bonds and C–X(X = S/Se) bonds using sulfoxonium ylides as starting materials to obtain sulfur-or selenium-containing compounds. This strategy is characterized by the safer and greener carbene precursor, high yields and broad substrate scope, possessing a wide range of application.

关键词： Sulfoxonium ylides Rhodium(Ⅱ)-catalyzed Carbene Rearrangement reactions One-pot process

Design and optimization of piperidinesubstituted thiophene[3,2-d]pyrimidine-based HIV-1 NNRTIs with improved drug resistance and pharmacokinetic profiles

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Acta Pharmaceutica Sinica B 2024年第7期14卷 3110-3124页

作者： Yanying Sun Zhenzhen Zhou Zhongling Shi Fabao Zhao Minghui Xie Zongji Zhuo Erik De Clercq Christophe Pannecouqueb Dongwei Kang Peng Zhan Xinyong Liu Department of medicinal chemistry Key Laboratory of Chemical Biology(Ministry of Education)School of Pharmaceutical SciencesShandong UniversityJinan 250012China Rega Institute for Medical research Laboratory of Virology and ChemotherapyK.U.LeuvenLeuven B-3000Belgium China-Belgium Collaborative research Center for Innovative Antiviral Drugs of Shandong Province Jinan 250012China

HIV-1 reverse transcriptase(RT)has received great attention as an attractive therapeutic target for acquired immune deficiency syndrome(AIDS),but the inevitable drug resistance and side effects have always been major challenges faced by non-nucleoside reverse transcriptase inhibitors(NNRTIs).This work aimed to identify novel chemotypes of anti-HIV-1 agents with improved drugresistance profiles,reduced toxicity,and excellent druggability.A series of diarylpyrimidine(DAPY)derivatives were prepared via structural modifications of the leads K-5a2 and *** them,15a with dimethylphosphine oxide moiety showed the most prominent antiviral potency against all of the tested viral panel,being 1.6-fold(WT,EC_(50) Z 1.75 nmol/L),3.0-fold(L100I,EC_(50) Z 2.84 nmol/L),2.4-fold(K103N,EC_(50) Z 1.27 nmol/L),3.3-fold(Y181C,EC50 Z 5.38 nmol/L),2.9-fold(Y188L,EC_(50) Z 7.96 nmol/L),2.5-fold(E138K,EC_(50) Z 4.28 nmol/L),4.8-fold(F227L/V106A,EC_(50) Z 3.76 nmol/L)and 5.3-fold(RES056,EC_(50) Z 15.8 nmol/L)more effective than that of the marketed drug *** docking results illustrated the detailed interactions formed by compound 15a and WT,F227L/V106A,and RES056 ***,15a-HCl carried outstanding pharmacokinetic(t1/2 Z 1.32 h,F Z 40.8%)and safety profiles(LD_(50)>2000 mg/kg),which demonstrated that 15a HCl is a potential anti-HIV-1 drug candidate.

关键词： HIV-1 NNRTIs NNIBP Structural alert Anti-HIV-1 drug candidate