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miR-126-5p affects the chemosensitivity of colorectal cancer cells by regulating SPRED1, ERK1/2 pathway and apoptosis

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Genes & Diseases 2023年第3期10卷 675-678页

作者： Mingshi Xu Gang Zhang Xiaofan Gu Fangqin Zhao Zhongmin Yang Xiongwen Zhang Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development School of Chemistry and Molecular EngineeringEast China Normal UniversityShanghai 200241China

Chemoresistance is still one of the main obstacles to treat colorectal cancer(CRC).Substantial studies on biomarkers related to chemoresistance have emerged in recent years.Many microRNAs(miRNA)have been reported to involved in drug resistance and CRC.1 MiR-126-5p participates in malignant behaviors of numerous cancers.2,3 However,it is not known if miR-126-5p participates in multidrug resistance in CRC.Especially,the impact of miR-126-5p on drug resistance of CRC and its drug resistance mechanism have not been reported.

关键词： colorectal miR cancer

Monitoring the in vivo siRNA release from lipid nanoparticles based on the fluorescence resonance energy transfer principle

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Asian Journal of Pharmaceutical Sciences 2023年第1期18卷 72-85页

作者： Lei Sun Jinfang Zhang Jing-e Zhou JingWang Zhehao Wang Shenggen Luo Yeying Wang Shulei Zhu Fan Yang Jie Tang Wei Lu Yiting Wang Lei Yu Zhiqiang Yan Institute of Biomedical engineering and Technology Shanghai Engineering Research Center of Molecular Therapeutics and New Drug DevelopmentSchool of Chemistry and Molecular EngineeringEast China Normal UniversityShanghai 200062China Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development School of Chemistry and Molecular EngineeringEast China Normal UniversityShanghai 200062China

The siRNA-loaded lipid nanoparticles have attracted much attention due to its significant gene silencing effect and successful marketization.However,the in vivo distribution and release of siRNA still cannot be effectively monitored.In this study,based on the fluorescence resonance energy transfer(FRET)principle,a fluorescence dye Cy5-modified survivin siRNA was conjugated to nanogolds(Au-DR-siRNA),which were then wrapped with lipid nanoparticles(LNPs)for monitoring the release behaviour of siRNA in vivo.The results showed that once Au-DR-siRNA was released from the LNPs and cleaved by the Dicer enzyme to produce free siRNA in cells,the fluorescence of Cy5 would change from quenched state to activated state,showing the location and time of siRNA release.Besides,the LNPs showed a significant antitumor effect by silencing the survivin gene and a CT imaging function superior to iohexol by nanogolds.Therefore,this work provided not only an effective method for monitoring the pharmacokinetic behaviour of LNP-based siRNA,but also a siRNA delivery system for treating and diagnosing tumors.

关键词： Survivin siRNA Lipid nanoparticles In vivo release Nanogolds Fluorescence resonance energy transfer

Enantioselective trapping of oxonium ylide intermediates by N-benzhydryl-α-imino ester：Synthesis of β-tetrasubstituted α-amino acids

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Chinese Chemical Letters 2017年第2期28卷 213-217页

作者： Shi-Kun Jia Yu-Bing Lei Long-Long Song Shun-Ying Liu Wen-Hao Hu Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development School of Chemistry and Chemical Engineering East China Normal University Shanghai 200062 China

A synergistic rhodium（Ⅱ）/phosphoric acid catalyzed three component reaction of 3-diazooxindoles,alcohols and N-benzhydryl-α-imino ester is developed for the efficient construction of chiral β-alkoxy C-β-tetrasubstituted α-amino acid derivatives in good yields and with excellent diastereoselectivities and high enantioselectivities.The synthetic application of the resulting products was illustrated by reducing with Pd/C under H_2 atmosphere followed reacting with CSCl_2 at room temperature to rapid afford 3-spirocyclic oxindole in a good yield with a chirality retainment.The three-component reaction is proposed to proceed through an electrophilic trapping of the oxonium ylides by N-benzhydryl-α-imino ester.

关键词： Three-component reaction Oxonium ylide N-Benzhydryl-α-imino ester β-Tetrasubstituted α-amino acids Chiral phosphoric acid

Role of miR-124 in the regulation of retinoic acid-induced Neuro-2A cell differentiation

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Neural Regeneration research 2020年第6期15卷 1133-1139页

作者： Qun You Qiang Gong Yu-Qiao Han Rou Pi Yi-Jie Du Su-Zhen Dong Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development School of Chemistry and Molecular EngineeringEast China Normal UniversityShanghaiChina Department of Integrative Medicine Huashan HospitalFudan UniversityShanghaiChina Institutes of Integrative Medicine Fudan UniversityShanghaiChina

Retinoic acid can cause many types of cells,including mouse neuroblastoma Neuro-2 A cells,to differentiate into neurons.However,it is still unknown whether microRNAs(miRNAs)play a role in this neuronal differentiation.To address this issue,real-time polymerase chain reaction assays were used to detect the expression of several differentiation-related miRNAs during the differentiation of retinoic acid-treated Neuro-2 A cells.The results revealed that miR-124 and miR-9 were upregulated,while miR-125 b was downregulated in retinoic acid-treated Neuro-2 A cells.To identify the miRNA that may play a key role,miR-124 expression was regulated by transfection of miRNA mimics or inhibitors.Morphological analysis results showed that inhibition of miR-124 expression reversed the effects of retinoic acid on neurite outgrowth.Moreover,miR-124 overexpression alone caused Neuro-2 A cells to differentiate into neurons,and its inhibitor could block this effect.These results suggest that miR-124 plays an important role in retinoic acid-induced differentiation of Neuro-2 A cells.

关键词： immunofluorescence MAP2 micro RNA mi R-124 Neuro-2A cells neurite outgrowth neuronal differentiation overexpression real-time PCR retinoic acid

Spectral and biodistributional engineering of deep near-infrared chromophore

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中国化学快报:英文版 2023年第9期34卷 176-182页

作者： Yan Dong Xicun Lu Yi Li Weichao Chen Lei Yin Jie Zhao Xinru Hu Xinran Li Zuhai Lei Yuyang Wu Hao Chen Xiao Luo Xuhong Qian Youjun Yang State Key Laboratory of Bioreactor engineering Shanghai Key Laboratory of Chemical BiologySchool of PharmacyEast China University of Science and TechnologyShanghai 200237China Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development School of Chemistry and Molecular EngineeringEast China Normal UniversityShanghai 200241China molecular Imaging center Shanghai Institute of Materia MedicaChinese Academy of SciencesShanghai 201203China

Fluorescence-guided surgery calls for development of near-infrared fluorophores.Despite the wide-spread application and a safe clinical record of Indocyanine Green(ICG),its maximal absorption wavelength at780 nm is rather short and longer-wavelength dyes are desired to exploit such benefits as low phototoxicity and deep penetration depth.Here,we report ECY,a stable deep near-infrared(NIR)fluorochromic scaffold absorbing/emitting at 836/871 nm with a fluorescence quantum yield of 16%in CH_(2)Cl_(2).ECY was further rationally engineered for biological distribution specificity.Analogous bearing different numbers of sulfonate group or a polyethylene glycol chain were synthesized.By screening this focused library upon intravenous injection to BALB/c mice,ECYS2 was identified to be a suitable candidate for bioimaging of organs involved in hepatobiliary excretion,and ECYPEG was found to be a superior candidate for vasculature imaging.They have potentials in intraoperative imaging.

关键词： Near infrared fluorophore In vivo imaging molecular engineering Biological distribution Angiography

Biomimetic nanoparticles for inflammation targeting

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Acta Pharmaceutica Sinica B 2018年第1期8卷 23-33页

作者： Kai Jin Zimiao Luo Bo Zhang Zhiqing Pang School of Pharmacy Fudan University Key Laboratory of Smart Drug Delivery Ministry of Education Biomedical engineering and Technology Institute Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development School of Chemistry and Molecular Engineering East China Normal University

There have been many recent exciting developments in biomimetic nanoparticles for biomedical applications. Inflammation, a protective response involving immune cells, blood vessels,and molecular mediators directed against harmful stimuli, is closely associated with many human diseases.As a result, biomimetic nanoparticles mimicking immune cells can help achieve molecular imaging and precise drug delivery to these inflammatory sites. This review is focused on inflammation-targeting biomimetic nanoparticles and will provide an in-depth look at the design of these nanoparticles to maximize their benefits for disease diagnosis and treatment.

关键词： Biomimetic nanoparticles Inflammation targeting Immune cells Targeting ligands Cell membrane Cell membrane proteins molecular imaging

Catalytic[2+2+2]Tandem Cyclization with Alkyl Substituted Methylene Malonate Enabling Concise Total Synthesis of Four Malagasy Alkaloids

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CCS Chemistry 2023年第1期5卷 124-132页

作者： Yu-Jing Cheng Liu-Peng Zhao Lijia Wang Yong Tang State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic ChemistryChinese Academy of SciencesUniversity of Chinese Academy of SciencesShanghai 200032 Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development Shanghai Frontiers Science Center of Molecule Intelligent SynthesesSchool of Chemistry and Molecular EngineeringEast China Normal UniversityShanghai 200062

Myrtoidine and malagashanine,highly complex indole alkaloids,are effective adjuvants in developing cures for plasmodium malaria and potent multi-drug resistant agents.Despite nearly 30 years of progress,myrtoidine and the related family of Malagasy alkaloids still present formidable challenges for synthetic chemists.Here,we developed a diastereoselective[2+2+2]tandem cyclization reaction with alkyl-substituted methylene malonate,enabling highly efficient collective total synthesis of four Malagasy alkaloids from commercially available tryptamines within 10-13 steps.The synthetic strategy included rapid and highly stereoselective assembly of the tetracyclic indoline core containing 5-7 contiguous stereogenic carbon centers,rarely seen in indole alkaloids.Among the four natural products,(±)-myrtoidine,(±)-11-demethoxymyrtoidine,and(±)-12-hydroxymalagashanine were synthesized for the first time,and the work on(±)-malagashanine represented the shortest synthetic route so far.Our current study should enable further explorations of chemical and biological spaces based on myrtoidine,malagashanine,and related natural products.

关键词： tandem cyclization [2+2+2] methylene malonate indole alkaloids myrtoidine malagashanine

A highly efficient In(OTf)3-catalyzed[3+3]annulation of spirocyclopropyl oxindoles with 1,4-di-thiane-2,5-diol

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Chinese Chemical Letters 2020年第3期31卷 681-684页

作者： Yongjia Hao Yi Gong Zhongyan Cao Ying Zhou Jian Zhou School of Pharmacy Guizhou University of Traditional Chinese MedicineGuiyang 550025China Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development East China Normal UniversityShanghai 200062China

Spirooxindoles play an important role in drug discove ry and development.The development of efficient methods for the synthesis of spirooxindoles from easily available sta rting materials is of curre nt interest Herein,we report in detail the In(OTf)3-catalyzed[3+3]annulation of spirocyclopropyl oxindoles and 1,4-di-thiane-2,5-diol,which allows the facile preparation of spiro[indoline-3,4'-thiopyran]-2-ones bearing(tetrahydro)thiopyran skeleton.

关键词： Spirooxindoles Lewis acid catalysis [3+3]cycloaddition Sulfur heterocycles Cyclopropane

Design,synthesis and biological evaluation of LpxC inhibitors with novel hydrophilic terminus

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Chinese Chemical Letters 2015年第6期26卷 763-767页

作者： Shi Ding Wen-Ke Wang Qiao Cao Wen-Jing Chu Le-Fu Lan Wen-Hao Hu Yu-She Yang State Key Laboratory of drug research Shanghai Institute of Materia MedicaChinese Academy of Sciences Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development East China Normal University

In order to develop novel LpxC inhibitors with good activities and metabolic stability, two series of compounds with hydrophilic terminus have been synthesized and their in vitro antibacterial activities against Escherichial coil and Pseudomonas aemginosa were evaluated. Especially, compounds 22b and c exhibited comparable antibacterial activities to CHIR-090 and better metabolic stability than CHIR-090 and LPC-011 in liver microsomes （rat and mouse）, which indicated the terminal methylsulfone may be a preferred structure in the design of LpxC inhibitors and worthy of further investigations.

关键词： LpxC CHIR-090 Kojic acid derivatives Methylsulfone derivatives Metabolic stability