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Enantioselective reductive conjugate alkenylation of α,β-enones with keto alkenyl acetates by nickel catalysis

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Science China Chemistry 2025年第1期68卷 157-162页

作者： Rong-de He Yun-Lei Luo Qiu-Quan Pan Qi-wei Yao Xing-zhong Shu State Key Laboratory of Applied Organic Chemistry College of Chemistry and Chemical Engineering Lanzhou University

Reactions involving alkenyl acetates offer cost-effective and environmentally friendly routes for alkene synthesis, yet their asymmetric variant remains elusive. Concurrently, asymmetric conjugate alkenylation predominantly centered on nucleophilic addition using alkenyl–M. This manuscript presents an asymmetric reductive conjugate alkenylation reaction involving alkenyl acetates. The method facilitates the enantioselective addition of keto alkenyl groups to α,β-enones, resulting in the formation of unsaturated diketones—a class of useful structural motifs that are challenging to access otherwise. The use of electron-rich Pyroxy ligand is essential for achieving both high reaction efficiency and enantioselectivity.

关键词： nickel alkenylation asymmetric cross-coupling alkenes

Mannose inhibits the growth of prostate cancer through a mitochondrial mechanism

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Asian Journal of Andrology 2022年第5期24卷 540-548页

作者： Yu-Lin deng Ren Liu Zhou-Da Cai Zhao-Dong Han Yuan-Fa Feng Shang-Hua Cai Qing-Biao Chen Jian-Guo Zhu wei-de zhong Guangdong Provincial Institute of Nephrology Nanfang HospitalSouthern Medical UniversityGuangzhou 510515China department of Andrology Guangzhou First People’s HospitalSchool of MedicineSouth China University of TechnologyGuangzhou 510180China department of Urology Guangdong Key Laboratory of Clinical Molecular Medicine and DiagnosticsGuangzhou First People’s HospitalSchool of MedicineSouth China University of TechnologyGuangzhou 510180China Urology Key Laboratory of Guangdong Province The First Affiliated Hospital of Guangzhou Medical UniversityGuangzhou Medical UniversityGuangzhou 510230China department of Urology Guizhou Provincial People’s HospitalThe Affiliated Hospital of Guizhou Medical UniversityGuiyang 550002China department of Urology Surgery Affiliated Foshan Hospital of Southern Medical UniversityFoshan 528000China

The limited treatment options for advanced prostate cancer(PCa)lead to the urgent need to discover new anticancer ***,an isomer of glucose,has been reported to have an anticancer effect on various ***,the anticancer effect of mannose in PCa remains *** this study,we demonstrated that mannose inhibits the proliferation and promotes the apoptosis of PCa cells in vitro,and mannose was observed to have an anticancer effect in mice without harming their *** of intracellular mannose simultaneously decreased the mitochondrial membrane potential,increased mitochondrial and cellular reactive oxygen species(ROS)levels,and reduced adenosine triphosphate(ATP)production in PCa *** treatment of PCa cells induced changes in mitochondrial morphology,caused dysregulated expression of the fission protein,such as fission,mitochondrial 1(FIS1),and enhanced the expression of proapoptotic factors,such as BCL2-associated X(Bax)and BCL2-antagonist/killer 1(Bak).Furthermore,lower expression of mannose phosphate isomerase(MPI),the key enzyme in mannose metabolism,indicated poorer prognosis in PCa patients,and downregulation of MPI expression in PCa cells enhanced the anticancer effect of *** study reveals the anticancer effect of mannose in PCa and its clinical significance in PCa patients.

关键词： mannose mannose phosphate isomerase metabolism mitochondria prostate cancer

Synergistic anticancer effect of exogenous wild-type p53 gene combined with 5-FU in human colon cancer resistant to 5-FU in vivo

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World Journal of Gastroenterology 2016年第32期22卷 7342-7352页

作者： Qi Xie Min-Yi Wu Ding-Xuan Zhang Yi-Ming Yang Bao-Shuai Wang Jing Zhang Jin Xu wei-de zhong Jia-ni Hu Medical Imaging department Nansha Central Hospital Guangzhou First People's Hospital Guangzhou Medical University Guangzhou 511457 Guangdong Province China department of Pathology Cancer Center SunYat-sen University Guangzhou 510080 Guangdong Province China department of Pathology Guangzhou First People's Hospital Guangzhou Medical University Guangzhou 510180 Guangdong Province China Clinical Molecular Medicine and Molecular Diagnostics Laboratory Guangzhou First People's Hospital Guangzhou Medical University Guangzhou 510180 Guangdong Province China Karmanos Cancer Institute Wayne State University Detroit MI 48201 United States

AIM To investigate the anticancer effect of a recombinant adenovirus-mediated p53(r Ad-p53) combined with 5-fluorouracil(5-FU) in human colon cancer resistant to 5-FU in vivo and the mechanism of r Ad-p53 in reversal of 5-FU *** nude mice bearing human colon cancer SW480/5-FU(5-FU resistant) were randomly assigned to four groups(n = 25 each): control group, 5-FU group, r Ad-p53 group, and r Ad-p53 + 5-FU group. At 24 h, 48 h, 72 h, 120 h and 168 h after treatment, 5 mice were randomly selected from each group and sacrificed using an overdose of anesthetics. The tumors were removed and the protein expressions of p53, protein kinase C(PKC), permeability-glycoprotein(P-gp) and multidrug resistance-associated protein 1(MRP1)(Western blot) and apoptosis(TUNEL) were *** The area ratios of tumor cell apoptosis were larger in the r Ad/p53 + 5-FU group than that in the control, 5-FU and r Ad/p53 groups(P < 0.05), and were larger in the r Ad/p53 group than that of the control group(P < 0.05) and the 5-FU group at more than 48 h(P < 0.05). The p53 expression was higher in the r Ad/p53 and the r Ad/p53 + 5-FU groups than that of the control and 5-FU groups(P < 0.05), and were higher in the r Ad/p53 + 5-FU group than that of the r Ad/p53 group(P < 0.05). Overexpression of PKC, P-gp and MRP1 was observed in the 5-FU and control groups. In the r Ad/p53 + 5-FU group, the expression of P-gp and MRP1 was lower that of the control and 5-FU groups(P < 0.05), and the expression of PKC was lower than that of the control, 5-FU and r Ad/p53 groups at more than 48 h(P < 0.05). In the r Ad/p53 group, the expression of P-gp and MRP1 was lower that of the control and 5-FU groups at more than 48 h(P < 0.05), and the expression of PKC was lower than that of the control and 5-FU groups at more than 120 h(P < 0.05).CONCLUSION5-FU combined with r Ad-p53 has a synergistic anticancer effect in SW480/5-FU(5-FU resistance), which contributes to reversal of 5-FU resistance.

关键词： Human colon cancer Multidrug resistance 5-Fluorouracil Recombinant adenovirus-mediated p53 Xenografts in nude mice

Evaluation of dot immunogold filtration assay for anti-HAV IgM antibody

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World Journal of Gastroenterology 1999年第2期5卷 44-46页

作者： WU wei, XU de zhong, YAN Yong Ping, ZHANG Jing Xia, LIU Ying and LI Ru Lin

AIM To detect hepatitis A virus-specific immunoglobulin M (IgM) antibody *** Colloidal gold with an average dia-meter of 15 nm was prepared by controlled reduction of a boiling solution of 0.2 g/ L chloroauric acid with 10 g/ L sodium citrate and labeled with anti-HAVIgG as gold probe. Dot immunogold filtration assay (DIGFA) has been developed by coating anti-human μ chain on nitrocellulose membrane (NCM) for capturing the anti-HAV IgM in serum, then using cultured hepatitis A antigen as a 'bridge', connecting anti-HAV IgM in sample and anti-HAV IgG labeled colloidal gold. If there was anti-HAV IgM in sample, gold probes would concentrate on NCM, which will appear a pink *** A total of 264 serum samples were comparatively detected with both DIGFA and ELISA by 'blind' method. Among them, 88 were positive and 146 were negative with the two methods. The sensitivity and the specificity of DIGFA were 86.27% and 90.12%, respectively. Fifteen negative serum samples and 15 positive serum samples were detected 3 times repeatedly, the results were the *** DIGFA is a simple, rapid, sensitive, specific and reliable method without expensive equipment and is not interfered with rheumatoid factor (RF) in serum. It is suitable for basic medical laboratories. The test could be applied for diagnosis and epidemiological survey of hepatitis A. It has a broad prospect in *** A virus-specific immunoglobulin M antibody (anti-HAV IgM) is the specific serological marker for the early diagnosis of acute hepatitis A. It can be detected by radioimmunoassay (RIA), enzyme-linked immunosorbent assay (ELISA), solid phase hemagglutination inhibition test (SPHIA) and other methods. At present, double sandwich ELISA is in widespread use[1]. However, it takes more time to finish the test and the procedure is complicated. The need of a simple, rapid, and noninstrumented test is evident in many basic units, where laboratory facilities and tra

关键词： hepatitis A virus immunoglobulin/analysis immunogold filtration assay

Real-time quantitative RT-PCR assessment of PIM-1 and hK2 mRNA expression in benign prostate hyperplasia and prostate cancer

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Real-time quantitative RT-PCR assessment of PIM-1 and hK2 mR...

第十五届全国泌尿外科学术会议

作者： Hui-chan He, Xue-cheng Bi, Qi-shan Dai, Hong-ai wei, wei-de zhong 广州医学院附属广州市第一人民医院

Aim: To investigate the expression of PIM-1 and hK2 mRNA in normal prostate, benign prostatic glandular hyperplasia (BPH), and prostate cancer (PCa), and to explore the association of PIM-1 and hK2 expression with PCa progression. Methods: The samples were harvested from 37 patients with BPH, 23 patients with PCa and 3 normal prostate tissues. Total RNA was extracted from their prostate

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Expression of SOCSs in human prostate cancer and their association in prognosis

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Expression of SOCSs in human prostate cancer and their assoc...

2013年贵州省泌尿外科学术会议

作者： Jian-guo Zhu Fu-neng Jiang wei-hong Chen Zhao-lin Sun wei-de zhong department of Urology Guizhou Provincial People's Hospital Guangdong Provincial Institute of Nephrology Southern Medical University department of Urology Guangdong Key Laboratory of Clinical Molecular Medicine and DiagnosticsGuangzhou First People's HospitalGuangzhou Medical University Urology Key Laboratory of Guangdong Province Guangzhou Medical College

Background:Suppressors of cytokine signaling(SOCS)proteins have been identified as negative feedback regulators of cytokine-mediated signaling in various tissues,and demonstrated to play critical roles in tumorigenesis and tumor development of different *** involvement of SOCSs in human prostate cancer(PCa)has not been fully ***,the aim of this study was to investigate the expression patterns and the clinical significance of SOCSs in ***:The expression changes of SOCSs at mRNA and protein levels in human PCa tissues compared with non-cancerous prostate tissues were respectively detected using real-timequantitative reverse transcriptase-polymerase chain reaction(QRT-PCR)and immunohositochemistry *** associations of SOCSs expression with clinicopathological features and clinical outcome of PCa patients were further statistically ***:Among SOCSs,both QRT-PCR and immunohistochemistry analyses found that S0CS2 expression was upregulated(at mRNA level:Change ratio=1.98,P=0.031;at protein level:5.12±0.60 vs.2.68±0.37,P=0.016)and SOCS6 expression was downregulated(at mRNA level:Change ratio=-1.65,P=0.008;at protein level:3.03±0.32 vs.4.72±0.39,P=0.004)in PCa tissues compared with those in non-cancerous prostate *** addition,the upregulation of SOCS2 in PCa tissues was correlated with the lower Gleason score(Pdependent predictor of shorter biochemical recurrence ***:Our data offer the convinced evidence for the first time that the dysregulation of SOCS2 and SOCS6may be associated with the aggressive progression o

关键词： prostate cancer suppressor of cytokine signaling proteins clinicopathological feature biochemical recurrence free-survival

CD147/EMMPRIN over-expression associated with clinicopathologic parameters and poor outcome of carcinomas in urinary system

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CD147/EMMPRIN over-expression associated with clinicopatholo...

第十五届全国泌尿外科学术会议

作者： Zhao-dong Han, Xue-cheng Bi, wei-jun Qin, Hui-chan He, wei-de zhong 广州医学院附属广州市第一人民医院

Aim: CD147/EMMPRIN expressed by tumor cells stimulates peri-tumorous fibroblasts to produce MMPs, thus contributing to tumor invasion and metastasis. To assess its suitability as potential therapeutic target, the expression of CD147/EMMPRIN in neoplastic tissues of urinary system was analyzed, as well as its association with the clinicopathologic features and the prognosis of patients.

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MicroRNA—23b downregulates peroxiredoxinⅢ in human prostate cancer

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MicroRNA—23b downregulates peroxiredoxinⅢ in human prostat...

2013年贵州省泌尿外科学术会议

作者： Jiang-guo Zhu Xi-bin Chen Hui-chan He wei-de zhong department of Urology Guangdong Key Laboratory of Clinical Molecular Medicine and DiagnosticsGuangzhou First Municipal People's HospitalAffiliated Guangzhou Medical College Guangdong Provincial Institute of Nephrology Southern Medical University department of Urology Guizhou Provincial People's Hospital Urology Key Laboratory of Guangdong Province Guangzhou Medical College

Background:Although the overexpression of peroxiredoxin III(PRDX3)in human prostate cancer(PCa)has been reported by several research groups and also validated by our previous study,the mechanism by which PRDX3 is altered in PCa has not been extensively ***:To address this problem,we used microRNA(miRNA)target prediction program

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Protective Effect of Glycyrrhizin on Nephrotic Syndrome Induced by Adriamycin in rats

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Protective Effect of Glycyrrhizin on Nephrotic Syndrome Indu...

第十五届全国泌尿外科学术会议

作者： wei-de zhong, Hui-Chan HE, Xue-Cheng BI,Jun Zhou,Zhao-Dong Han 广州医学院附属广州市第一人民医院

Objective: To explore the protective effects of glycyrrhizin on nephrotic syndrome (NS) induced by adriamycin (ADR) in rats. Methods: 30 SD male rats were divided into three groups: control group, untreated model

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