Article
Chemistry, Multidisciplinary
Muhammad Siddique Ahmad, Ruqiya Qasim, Qing Zhang, Bing Zeng, Jiamin Chen, Qifeng Wang, Kamel Meguellati
Summary: In this study, we report a Cu(ii)-mediated reaction that couples a-haloacetonitrile derivatives and aryl tetrahydroisoquinolines via C(sp(3))-Br and C(sp(3))-H bond activation, resulting in the formation of cyanomethylated tetrahydroisoquinolines. This methodology provides a diverse range of tetrahydroisoquinoline products, including those substituted with electron donating and electron withdrawing groups, as well as heterocyclic ring substituents. The high yields (47%-89%) and valuable insights obtained from this reaction offer significant potential for the design of versatile biologically active products.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Sumit Garai, Devarajulu Sureshkumar
Summary: In this study, a palladium-catalyzed efficient and versatile method for C(sp(2))-H ortho-cyanomethylation of arylamides with a broad substrate scope and moderate to excellent yields was developed. An inexpensive and commercially available chloroacetonitrile was used as the cyanomethylating source. The synthetic feasibility of this technique was also demonstrated by gram-scale synthesis and functional group transformation of the products.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Muhammad Siddique Ahmad, Ruqiya Qasim, Qing Zhang, Bing Zeng, Jiamin Chen, Qifeng Wang, Kamel Meguellati
Summary: In this study, a Cu(ii)-mediated C-C reaction was developed for the synthesis of cyanomethylated tetrahydroisoquinolines via the coupling of C(sp(3))-Br and C(sp(3))-H bonds. This method offers a versatile approach for the synthesis of various tetrahydroisoquinolines and provides valuable insights for the design of biologically active compounds.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Weiyou Zhou, Anwei Wang, Zhenji Kong, Xiaoting Tian, Zhenzhen Xia, Zhihui Zhang, Mingyang He, Qun Chen, Shixin Sun
Summary: A convenient catalytic protocol using CuCoFe layered double hydroxide (LDH) for efficiently constructing indoline-fused tetrahydroisoquinolines has been described. The research offers a unique opportunity to develop a synthetic methodology for N-containing polycyclic compounds.
Article
Chemistry, Applied
Changzhen Yin, Wei Liu, Qiang Wu, Miao Wang, Peng Hu
Summary: A new iron-catalyzed deconstructive cyanomethylation reaction has been developed for the selective functionalization of cyclic and linear alcohols. This reaction involves the cleavage of C-C single bonds and C(sp3)-H bonds, leading to the formation of C(sp3)-C(sp3) bonds.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Bin Sun, Yu Jiang, Pan-Yi Huang, Pei-Xuan Li, Chun Lv, Yan Xu, Jia-Yang Wang, Can Jin
Summary: In this study, a photoinduced desaturative β-C(sp(3))-H bond amidation of N-phenylpiperidine using phthalimide as an aminating source enabled by an electron donor-acceptor (EDA) complex was explored. This protocol offers an environmentally friendly, simple, and efficient method for accessing β-C(sp(2))-H amidation piperidine derivatives without the need for high temperatures, transition metals, and photosensitizers required for traditional C(sp(3))-H functionalization. Moreover, the obtained products can be further modified and transformed into enamines by treatment with hydrazine.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Dianpeng Chen, Jianming Li, Xiuhua Zhang, Gongle Liu, Xin Wang, Yongwei Liu, Xuan Liu, Yingying Shan
Summary: A novel method for the synthesis of fused tetracyclic N-heterocycles is described using palladium-catalyzed cyclization of isocyanides with alkyne-tethered aryl iodides. The reaction involves a unique amino-to-alkyl 1,5-palladium migration/intramolecular C(sp(3))-C(sp(2)) coupling sequence. Isocyanide plays multiple roles in this transformation, serving as a C1 synthon, a C1N1 synthon, and the donor of C(sp(3)) for C(sp(3))-C(sp(2)) coupling, and it represents the only successful example of C(sp(3))-H activation of isocyanide.
Article
Chemistry, Organic
Xiu Juan Xu, Adila Amuti, Wen Jing Hu, Qiaerbati Adelibieke, Abudureheman Wusiman
Summary: A TEMPO-promoted method for the synthesis of symmetric bis-N-Mannich bases via sequential activation of two alpha,alpha'-amino C(sp3)-H bonds of N,N-dimethylanilines under mild conditions is developed. This methodology is further extended for monoimidation of alpha-amino-functionalized methylanilines to give unsymmetric N-Mannich bases in good to high yields. Control experiments indicate the involvement of oxoammonium (TEMPO+) species in the coupling reaction outcomes.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Ming-Yu Qi, Yi-Jun Xu
Summary: Solar-driven CO2 reduction integrated with C-C/C-X bond-forming organic synthesis offers a promising opportunity to achieve carbon neutrality and create an atom-/redox-economical chemical synthesis simultaneously.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Qinhua Zhang, Bo An, Yu Lei, Zhixiao Gao, Haonan Zhang, Sheng Xue, Xin Jin, Wengang Xu, Zihan Wu, Mingbo Wu, Xin Yang, Wenting Wu
Summary: Developing new reactive pathway to activate inert C(sp3) H bonds for valuable oxygenated products remains a challenge. We prepared a series of triazine conjugated organic polymers to photoactivate C H into aldehyde/ketone via O2!H2O2!*OH!Cl *!Cl2 *. Experiment results showed Cl2 * could successively activate C(sp3) H more effectively than Cl * to generate unstable dichlorinated intermediates, increasing the kinetic rate ratio of dichlorination to monochlorination by a factor of 2,000 and thus breaking traditional dichlorination kinetic constraints. These active intermediates were hydrolyzed into aldehydes or ketones easily, when compared with typical stable dichlorinated complexes, avoiding chlorinated by-product generation. Moreover, an integrated two-phase system in an acid solution strengthened the Cl2 * mediated process and inhibited product overoxidation, where the conversion rate of toluene reached 16.94 mmol/g/h and the selectivity of benzaldehyde was 99.5%. This work presents a facile and efficient approach for selective conversion of inert C(sp3) H bonds using Cl2 *.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Andrea Geraci, Uros Stojiljkovic, Kevin Antien, Nihad Salameh, Olivier Baudoin
Summary: Chiral 1,2-diamines are important structures in bioactive natural products, active pharmaceutical ingredients, ligands for asymmetric catalysis, and organocatalysts. However, constructing chiral 1,2-diamine motifs is still challenging. To address this, researchers developed an iridium(III)-catalyzed intermolecular C(sp3)-H amidation reaction using a new and cleavable exo-protecting/directing group. This method allows for the synthesis of scalemic free 1,2-diamines from easily accessible precursors.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Multidisciplinary Sciences
Daniel A. Strassfeld, Chia-Yu Chen, Han Seul Park, D. Quang Phan, Jin-Quan Yu
Summary: The functionalization of C-H bonds in organic molecules is a direct approach for chemical synthesis. Recent advances in catalysis have allowed various chemical groups to control and direct C(sp(3))-H activation, but alcohols, a common functionality, have remained difficult to react due to their low affinity for catalysts. This study describes ligands that enable alcohol-directed arylation of C(sp(3))-H bonds through charge balance and hydrogen-bonding interactions, thus enhancing substrate-catalyst affinity and enabling previously unknown reactivity.
Article
Chemistry, Multidisciplinary
Pengfei Han, Xin Mao, Yichao Jin, Sarina Sarina, Jianfeng Jia, Eric R. Waclawik, Aijun Du, Steven E. Bottle, Jin-Cai Zhao, Huai-Yong Zhu
Summary: Selective activation of specific C(sp(3))-H bond and cleavage of unreactive ether C-beta-O bond can be achieved by illuminated plasmonic silver metal nanoparticles. This plasmon-driven process enables hydrogen abstraction and precise scission of targeted C-O bond, resulting in the formation of aromatic compounds with unsaturated, substituted groups in excellent yields.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Liang Hu, Guangrong Meng, Xiangyang Chen, Joseph S. S. Yoon, Jing-Ran Shan, Nikita Chekshin, Daniel A. A. Strassfeld, Tao Sheng, Zhe Zhuang, Rodolphe Jazzar, Guy Bertrand, K. N. Houk, Jin-Quan Yu
Summary: The discovery of a ligand scaffold containing a remote amide motif that can form a favorable hydrogen bonding interaction with the aliphatic acid substrate is reported. This ligand scaffold is used in the development of an unprecedented C(sp(3))-H bromination of α-tertiary and α-quaternary free carboxylic acids, which exhibits high mono-selectivity. The geometric relationship between the NHAc hydrogen bond donor and the coordinating quinoline ligand is crucial for the formation of the macrocyclic-like hydrogen bonding interaction, providing a guideline for future catalyst design using secondary interactions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Han Gao, Lingfei Hu, Yanlei Hu, Xiangying Lv, Yan-Bo Wu, Gang Lu
Summary: The origins of regioselectivity in Ni-catalyzed alkene hydrofunctionalizations were computationally investigated using energy decomposition analysis. The results indicate that the Markovnikov selectivity with aryl-substituted alkenes is favored due to the stabilizing charge transfer effect, while the anti-Markovnikov selectivity with alkyl-substituted alkenes is favored because of the destabilizing Pauli repulsion effect.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Lu An, Chengbin Wang, Qiwei Tian, Cheng Tao, Fengfeng Xue, Shiping Yang, Xuesu Zhou, Xiaoyuan Chen, Gang Huang
Summary: Chemodynamic therapy (CDT) is a method used to modulate the tumor microenvironment and extend the benefits of immune checkpoint therapy. A Near-Infrared (NIR)-II laser-mediated photoFenton-like reaction was proposed as an enhancement strategy to enhance the immune response. The experimental results show that this strategy effectively induces immunogenic cell death and dendritic cell maturation.
Review
Biochemistry & Molecular Biology
Shangjun Chen, Lu An, Shiping Yang
Summary: This mini-review summarizes the recent progress on low-molecular-weight Fe(III) complexes, which are considered as promising alternatives to clinically used Gd(III)-based contrast agents in MRI. The relationships between the structure of the complexes and their relaxivity and thermodynamic stability are highlighted. Future perspectives for the design of low-molecular-weight Fe(III) complexes for MRI contrast agents are also suggested.
Article
Chemistry, Analytical
Zhiguang Wang, Ruipeng Chen, Yue Hou, Yingkai Qin, Shuang Li, Shiping Yang, Zhixian Gao
Summary: In this study, a portable and sensitive method for detecting melamine using stimuli-responsive DNA hydrogels and microfluidic chips was developed. The method utilized melamine aptamer and DNA hydrogel-coated AuNPs for colorimetric detection and quantitative analysis. The combination of microfluidic chips and DNA hydrogels enabled quantitative detection of melamine by taking photos and analyzing the gray value.
ANALYTICA CHIMICA ACTA
(2022)
Article
Chemistry, Multidisciplinary
Chao Li, Yucong Gao, Yuanyue Wang, Jie Wang, Jiaomin Lin, Jing Du, Zhiguo Zhou, Xiaoming Liu, Shiping Yang, Hong Yang
Summary: The synthesized IrPc-NPs nano-assembly exhibits bifunctionality, alleviating the hypoxia of tumor cells and improving the efficacy of sonodynamic therapy (SDT). It also shows excellent biocompatibility, benignancy towards overall tumor growth in vivo, and the controllability of timely applying ultrasound (US) irradiation during treatment.
ADVANCED FUNCTIONAL MATERIALS
(2023)
Article
Engineering, Environmental
Ying Wan, Lu An, Zixuan Zhu, Qiwei Tian, Jiaomin Lin, Shiping Yang
Summary: Based on dendrimers, a series of polyphenol compounds (P1, P2, and P3) were coordinated with iron (III) (Fe3+) to investigate the effect of polyphenol structures on their T1 contrast performance. These new Fe3+-based complexes, featuring regular amplification of their phenolic hydroxyl groups, exhibit enhanced longitudinal relaxivity (r1) due to proton exchange facilitated by a hydrogen-bonding network. Furthermore, these designed Fe3+-based complexes demonstrate good T1 contrast effect in vitro and in vivo. Modifying the coordination structure of Fe3+-based contrast agents can potentially improve their relaxivity properties and facilitate the development of excellent magnetic resonance imaging agents for disease diagnosis.
CHEMICAL ENGINEERING JOURNAL
(2023)
Article
Chemistry, Physical
Fengfeng Xue, Shuntao Zhu, Qiwei Tian, Ruomeng Qin, Zerong Wang, Gang Huang, Shiping Yang
Summary: Magnetothermal therapy (MHT) is a promising non-/minimal invasive and efficient approach for tumor treatment. However, the development of small MHT agents (< 50 nm) with excellent magnetothermal conversion performance and high tumor enrichment remains challenging. In this study, a macrophage-mediated delivery system was designed for enhanced magnetic resonance imaging (MRI) and MHT of solid tumors using small Fe@Fe3O4-DHCA nanoparticles. The aggregation of Fe@Fe3O4-DHCA nanoparticles in macrophages resulted in enhanced MRI and magnetothermal performance in vitro. Moreover, the in vivo MHT effect of macrophages loaded with Fe@Fe3O4-DHCA was superior to that of Fe@Fe3O4-DHCA alone, attributed to the tumor-targeting capability of macrophages. This macrophage-mediated delivery system presents a new strategy for enhanced MHT based on Fe@Fe3O4-DHCA nanoparticles, with great potential for clinical tumor therapy.
JOURNAL OF COLLOID AND INTERFACE SCIENCE
(2023)
Article
Computer Science, Artificial Intelligence
Patrick Bilic, Patrick Christ, Hongwei Bran Li, Eugene Vorontsov, Avi Ben-Cohen, Georgios Kaissis, Adi Szeskin, Colin Jacobs, Gabriel Efrain Humpire Mamani, Gabriel Chartrand, Fabian Lohoefer, Julian Walter Holch, Wieland Sommer, Felix Hofmann, Alexandre Hostettler, Naama Lev-Cohain, Michal Drozdzal, Michal Marianne Amitai, Refael Vivanti, Jacob Sosna, Ivan Ezhov, Anjany Sekuboyina, Fernando Navarro, Florian Kofler, Johannes C. Paetzold, Suprosanna Shit, Xiaobin Hu, Jana Lipkova, Markus Rempfler, Marie Piraud, Jan Kirschke, Benedikt Wiestler, Zhiheng Zhang, Christian Huelsemeyer, Marcel Beetz, Florian Ettlinger, Michela Antonelli, Woong Bae, Miriam Bellver, Lei Bi, Hao Chen, Grzegorz Chlebus, Erik B. Dam, Qi Dou, Chi-Wing Fu, Bogdan Georgescu, Xavier Giro-I-Nieto, Felix Gruen, Xu Han, Pheng-Ann Heng, Jurgen Hesser, Jan Hendrik Moltz, Christian Igel, Fabian Isensee, Paul Jaeger, Fucang Jia, Krishna Chaitanya Kaluva, Mahendra Khened, Ildoo Kim, Jae-Hun Kim, Sungwoong Kim, Simon Kohl, Tomasz Konopczynski, Avinash Kori, Ganapathy Krishnamurthi, Fan Li, Hongchao Li, Junbo Li, Xiaomeng Li, John Lowengrub, Jun Ma, Klaus Maier-Hein, Kevis-Kokitsi Maninis, Hans Meine, Dorit Merhof, Akshay Pai, Mathias Perslev, Jens Petersen, Jordi Pont-Tuset, Jin Qi, Xiaojuan Qi, Oliver Rippel, Karsten Roth, Ignacio Sarasua, Andrea Schenk, Zengming Shen, Jordi Torres, Christian Wachinger, Chunliang Wang, Leon Weninger, Jianrong Wu, Daguang Xu, Xiaoping Yang, Simon Chun-Ho Yu, Yading Yuan, Miao Yue, Liping Zhang, Jorge Cardoso, Spyridon Bakas, Rickmer Braren, Volker Heinemann, Christopher Pal, An Tang, Samuel Kadoury, Luc Soler, Bram van Ginneken, Hayit Greenspan, Leo Joskowicz, Bjoern Menze
Summary: This study reports the setup and results of the Liver Tumor Segmentation Benchmark (LiTS), which involved diverse image datasets and evaluated multiple segmentation algorithms. The best algorithms achieved high scores for liver segmentation, but varied performance for tumor segmentation. Further research is needed for tumor detection. LiTS remains an active benchmark and resource for liver-related segmentation tasks.
MEDICAL IMAGE ANALYSIS
(2023)
Article
Materials Science, Biomaterials
Yeping Liu, Likai Wang, Fengyuan Wei, Ya Tian, Juan Mou, Shiping Yang, Huixia Wu
Summary: In this study, a smart Mn3O4/OCN-PpIX@BSA nanoplatform was developed to enhance the combinational therapeutic efficacy of CDT and SDT through TME modulation. The nanoplatform effectively catalyzed endogenous H2O2 to produce O-2, relieved hypoxia, and generated oxidative stress by releasing Mn2+ ions. The results provide a new strategy for the construction of TME-regulating smart theranostic nanoagents.
BIOMATERIALS SCIENCE
(2023)
Article
Materials Science, Biomaterials
Qi Yang, Yajun Yu, Chaojie Tang, Yucong Gao, Wu Wang, Zhiguo Zhou, Shiping Yang, Hong Yang
Summary: We developed iridium(iii)-cyanine complex/bovine serum albumin-based nanoparticles conjugated with folic acid, which can serve as a photoacoustic imaging probe for lymph node imaging. These nanoparticles exhibit good biocompatibility, strong near-infrared absorption, and impressive lymph node accumulation. Our study demonstrates the potential of this new photoacoustic imaging technique for real-time imaging and quantitative analysis of lymph nodes, providing a more efficient and reliable evaluation method for lymphadenectomy.
BIOMATERIALS SCIENCE
(2023)
Article
Materials Science, Biomaterials
Likai Wang, Ya Tian, Kexin Lai, Yeping Liu, Juan Mou, Shiping Yang, Huixia Wu
Summary: Ultrasound-triggered sonodynamic therapy (SDT) has gained significant attention as a non-invasive and deep tissue penetration alternative for cancer treatment. However, the efficacy of SDT alone is limited by the hypoxic nature of solid tumors. Therefore, this study develops an intelligent theranostic nanoplatform that combines SDT and nitric oxide (NO) therapy to enhance cancer treatment.
ACS BIOMATERIALS SCIENCE & ENGINEERING
(2023)
Article
Biochemistry & Molecular Biology
Hai -Lin Zhang, Yi Wang, Qi Tang, Bing Ren, Shi-Ping Yang, Jin -Gang Liu
Summary: A hollow mesoporous manganese dioxide-based multifunctional nanoplatform was developed for synergistic cancer treatment, which loaded a histone deacetylase inhibitor AFIPB in its hollow cavity and covalently decorated a ruthenium nitrosyl donor and a folic acid targeting group on its covered polydopamine layer. The nanoplatform exhibited tumor microenvironment-responsive properties and could deplete glutathione to disrupt the antioxidant defense system and deliver drugs on demand. Furthermore, it could generate highly toxic hydroxyl radicals through the catalysis of released Mn2+ and produce controlled nitric oxide delivery and significant photothermal effect under 808 nm light irradiation, resulting in high mortality of cancer cells.
JOURNAL OF INORGANIC BIOCHEMISTRY
(2023)
Article
Materials Science, Multidisciplinary
Jing He, Wei He, Run Wang, Jingjing Jiao, Shiping Yang
Summary: We developed a nanoplatform for combined chemotherapy and enhanced chemodynamic therapy by self-assembling a water-soluble and amphipathic ferrous metallacage (FM), hydrophilic copolymer (PEG2000-COOH), and oxaliplatin (OXA). The FM acted as a catalyst for the Fenton reaction and potential agent for chemodynamic therapy. OXA not only served as an anti-tumor drug but also activated intracellular enzymes to enhance the chemodynamic therapy effect. In vitro and in vivo experiments demonstrated that FM@OXA-PEG showed minimal toxicity to normal cells, while effectively killing tumor cells and inhibiting tumor growth.
MATERIALS ADVANCES
(2023)
Article
Chemistry, Multidisciplinary
Kaiwen Chen, Xiangwei Wang, Xiaoping Xu, Xiao Wang, Simin He, Jianping Zhang, Yuyun Sun, Shiping Yang, Shaoli Song
Summary: A novel HER2-targeted PET imaging probe was successfully developed, showing significant potential for the detection of HER2 expression in tumors.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Shasha Zhao, Kexin Lai, Zhen Gao, Xueli Ye, Juan Mou, Shiping Yang, Huixia Wu
Summary: This article introduces a clever combination of nano-enzymes and therapeutic drugs that can promote the production of reactive oxygen species (ROS) in cancer cells, enhancing the therapeutic efficacy of nanomedicines on malignant tumors. By loading the specific drug onto PEGylated Ce-doped hollow mesoporous silica nanoparticles, a smart nanoplatform is constructed to improve tumor therapy efficiency. The carrier showed multi-enzyme activities, with Ce3+ ions converting endogenous H2O2 into highly toxic OH for chemodynamic therapy and Ce4+ ions exhibiting catalase-like activity to reduce tumor hypoxia and glutathione (GSH) peroxidase-mimicking properties to effectively deplete GSH in tumor cells. Moreover, the loaded drug disrupts mitochondrial functions, causing the accumulation of superoxide anions (O-2(-)) and H2O2 within tumor cells. By combining the advantages of the carrier and the drug, the prepared nanoplatform can efficiently induce cancer cell death and inhibit tumor growth through significantly enhanced ROS production. Therefore, this positive combination therapy strategy has a promising application prospect for enhancing antitumor efficacy.
Article
Materials Science, Biomaterials
Minmin Liang, Weixiu Zhou, Haifeng Zhang, Jutian Zheng, Jiaomin Lin, Lu An, Shiping Yang
Summary: In this study, a pH- and glutathione (GSH)-responsive T-1-T-2 dual-mode contrast agent, Fe3O4@ZIF-8-Zn-Mn nanoparticles (NPs), was constructed to improve the sensitivity and accuracy of magnetic resonance imaging (MRI). The NPs showed good stability and weak T-1-T-2 dual-mode MRI contrast effect under neutral conditions, but could be disassembled and release Fe3O4 NPs and paramagnetic Mn2+ ions under acidic environment (pH = 6.5-5.5) and in the presence of GSH (0-4 mM), resulting in enhanced T-1 and T-2 imaging performances. In vivo MRI experiments demonstrated the potential of Fe3O4@ZIF-8-Zn-Mn NPs as a tumor microenvironment-responsive T-1-T-2 dual-mode contrast agent for sensitive tumor imaging.
JOURNAL OF MATERIALS CHEMISTRY B
(2023)
