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  • Dan Yuan, Huihong Yan, Jiahui Liu, Jiajun Liu, Chunmei Li, Jian Wang
    Chinese Chemical Letters. 2020, 31(2): 455-458.

    Ribonucleotides are usually functioned as biomarkers to diagnose diseases and monitor the life activities in living organisms, and their discrimination is of great significance but challenging. Taking advantage of the unique characteristics of gold nanorods (AuNRs), herein, a colorimetric sensor array for discrimination of twelve ribonucleotides was developed based on the chemical etching of AuNRs with controllable aspect ratios. During the etching process, AuNRs were preferentially shortened and eventually turned into Au(Ⅲ) state by Fenton's reaction. The morphological change of AuNRs led to the significant color change and blue shift in the corresponding extinction spectrum. However, when Fe2+ bound with ribonucleotides, the Fenton's reaction was prevented and the ability to etch AuNRs was weakened or disappeared. Due to the different structures of nucleotides, the binding ability of them with Fe2+ was distinct, resulting in the discrepancy in the chemical etching of AuNRs, which could be developed for distinguishing ribonucleotides. Moreover, the proposed sensor array was successfully explored to distinguish ribonucleotides in complex human urine samples.

  • Huan Xu, Chaoyu Zhou, Chuanjiang Jian, Sunhai Yang, Miaochang Liu, Xiaobo Huang, Wenxia Gao, Huayue Wu
    Chinese Chemical Letters. 2020, 31(2): 369-372.

    Host-guest supramolecular gels were developed via the self-assembly of inclusion complexes (ICs) of β-cyclodextrins/phenylboronic acid gelator (PBA). Salts and current were involved in the self-assembly to stabilize the host-guest gels. The stability of the gels was greatly improved after salts were added. The stable time of gels was extended from 2.5 h to 120 h with the addition of NH4NO3 at the concentration of 2.5×10-2 g/mL. The morphology of the gel was affected by the concentrations of NH4NO3. SEM images revealed that the gels were three-dimensional nanofibrous networks, the sizes of fibers decreased with decreasing NH4NO3 concentrations, which affected the stability of gels, further proved by the rheological properties of gels. More stable gels were obtained with current stimulation, the stable time of the gel was increased from 2.5 h to 55 h with current by adding NaBF4. The current also exhibited significant influence on the aggregation as the voltage varied (0-500 mV) with a constant concentration of salts. The result showed the self-assembly process of host-guest gel could be well controlled via the addition of salts and current to desired morphology and stability.

  • Yongjin Cao, Min Zheng, Weihua Cai, Zongcai Wang
    Chinese Chemical Letters. 2020, 31(2): 463-467.

    A simple and feasible potentiometric immunosensing platform based on enzymatic biocatalytic precipitation technique was designed for the sensitive detection of thyroid-stimulating hormone (TSH; a typical kind of biomarkers for thyroid carcinoma), using horseradish peroxidase (HRP)-loaded liposome for the signal amplification. To construct such an assay system, a sandwich-type immunoreaction was readily carried out on monoclonal anti-TSH capture antibody-coated electrode by using polyclonal antiTSH secondary antibody-conjugated HRP-loaded liposome. Accompanying the formation of sandwichtype immunocomplex, the carried liposome was lysed through the added Triton X-100 to release the entrapped HRP molecules, which catalyzed the oxidation of 4-chloro-1-naphthol to produce an insoluble and uncharged organic precipitation on the electrode surface, thereby causing the change of the local electrical potential. Two labeling protocols with and without the liposome were investigated for detection of target TSH, improved analytical features were achieved with HRP-entrapped liposome. Under optimal conditions, the potentiometric immunosensor had good responses for TSH detection within the linear range of 0.01-30 μIU/mL at a detection limit of 0.0067 μIU/mL. Good reproducibility, high specificity and long-time stability were acquired during the assay procedure. Importantly, a wellmatched accuracy between the potentiometric immunosensor and commercial human TSH ELISA kit was gave for the analysis of human serum samples.

  • Hongyan Pei, Yanyan Bai, Jianman Guo, Zhiliang Gao, Qiong Dai, Qun Yu, Jiwei Cui
    Chinese Chemical Letters. 2020, 31(2): 505-508.

    Over the past two decades, layer-by-layer (LbL) assembly of micro/nanocapsules has been of interest for the investigation of bio-nano interactions to explore bio-applications, such as drug delivery. The choice of an appropriate template that can be easily dissolved under mild conditions is one of the challenges for the assembly of LbL capsules. Herein, we report the engineering of LbL capsules with tunable morphologies using cuprous oxide (Cu2O) particles as templates. Cu2O particles with cubic, tetradecahedral or spherical morphologies were synthesized via hydrothermal processes, which can be dissolved under mild condition (e.g., sodium thiosulfate solution). The influence of capsule morphologies on cell association was investigated, which indicates that LbL capsules with cubic geometry promoted cell association up to 4 and 9-fold than tetradecahedral and spherical capsules, respectively. The reported method provides a new avenue for the assembly of LbL capsules with different morphologies, which has the potential for better understanding of biological interactions of LbL capsules.

  • Xiaolong Wang, Yamin Pan, Huan Yuan, Meng Su, Chunguang Shao, Chuntai Liu, Zhanhu Guo, Changyu Shen, Xianhu Liu
    Chinese Chemical Letters. 2020, 31(2): 365-368.

    Polylactic acid (PLA) is one of the most suitable candidates for environmental pollution treatment because of its biodegradability which will not cause secondary pollution to the environment after application. However, there is still a lack of a green and facile way to prepare PLA oil-water separation materials. In this work, a water-assisted thermally induced phase separation method for the preparation of superhydrophobic PLA oil-water separation material with honeycomb-like structures is reported. The PLA material shows great ability in application and could adsorb 27.3 times oil to its own weight. In addition, it could also be applicated as a filter with excellent efficiency (50.9 m3 m-2 h-1).

  • Shuo Yuan, Sixi Wang, Min Zhao, Danqing Zhang, Jinjie Chen, Jian-Xin Li, Jingya Zhang, Yihui Song, Jinyi Wang, Bin Yu, Hongmin Liu
    Chinese Chemical Letters. 2020, 31(2): 349-352.

    The isoindolinone and biaryl scaffolds are prevalent in natural products and drug molecules, which have showed broad and interesting biological activities. The efficient construction of such hybridized molecules and biological evaluation are of great interest to medicinal chemistry community. In this communication, we report an efficient Brønsted acid-promoted C(sp3)-H functionalization approach that enables the rapid construction of biologically important isoindolinone/[1,2,4]triazolo[1, 5-a]pyrimidine hybrids from 5-methyl-7-(2, 4, 6-trimethoxyphenyl)-[1,2,4]triazolo[1, 5-a]pyrimidine, 2-formylbenzoic acid and various anilines. The title compounds were generated in high to excellent yields (up to 96%) regardless of the electronic nature and steric effects of the substituents. In this reaction, an isoindolinone scaffold, one C-C single bond, and two C-N bonds were formed simultaneously with high atom economy. In this work, we have envisioned that the methyl group linked to the electron-deficient Nheterocycles could be used as a new synthetic handle for late-state diversification and may have broad applications in the field of organic and medicinal chemistry. Besides, the title compounds have exhibited promising activity against the SKP2-CKS1 interaction.

  • Jun Liu, Cancan Zhang, Shaoxuan Zhang, Huajiang Yu, Wei Xie
    Chinese Chemical Letters. 2020, 31(2): 539-542.

    The toxic organic dye contaminants in wastewater are extremely harmful to the ecosystem. Surface enhanced Raman scattering (SERS) is a technique with high sensitivity and chemical specificity which fulfills the requirements for monitoring dye contaminants in wastewater. However, as one of the common dye contaminants, methyl orange (MO) has very weak affinity to metallic surfaces and is difficult to be detected by SERS at low concentrations. Therefore, a new type of SERS substrate with Ag nanoparticle monolayer functionalized by mono-6-deoxy-6-thio-β-cyclodextrin (β-CD-SH) was prepared to efficiently capture and detect MO in wastewater with a limit of detection of 5×10-7 mol/L. The hydrophobic cavity of β-CD is responsible for the efficient trap and enrichment of MO on the Ag NPs surface, achieving a strong SERS signal of MO at low concentrations and at different pH values. This study provides new insight into designing a well-performed adsorbent for the capture and detection of organic contaminants.

  • Zhen Wu, Xue-Xin Feng, Qing-Dong Wang, Xuan-Yu Liu, Weidong Rao, Jin-Ming Yang, Zhi-Liang Shen
    Chinese Chemical Letters. 2020, 31(2): 391-395.

    An efficient water-based bismuth-mediated addition reaction of carbonyl compound with cyclic allylic halide was developed. The reactions proceeded smoothly in aqueous DMF in the presence of ammonium iodide to afford the corresponding syn-homoallylic alcohols in moderate to good yields with excellent diastereoselectivities (>99:1 syn:anti). Reversal of product diastereoselectivity was observed when heteroaryl aldehyde possessing an adjacent chelating nitrogen atom was employed as substrate.

  • Min Zhang, Jun-Xin Wang, Shun-Qin Chang, Xiong-Li Liu, Xiong Zuo, Ying Zhou
    Chinese Chemical Letters. 2020, 31(2): 381-385.

    A quinine-derived thiourea-catalyzed inter-/intramolecular Michael cycloaddition of chromoneoxindole/benzofuranone synthons with 3-substituted methylenebenzofuranones has been established, which constructed enantiomerically pure bispiro[benzofuran-oxindole/benzofuran-chromanone]s bearing five consecutive stereocenters including two spiro quaternary carton centers in good yields (up to 93%) with high diastereoselectivities (up to >20:1 dr) and good enantioselectivities (up to >99% ee). Moreover, this is the first example of bifunctional chromone-benzofuranone synthon directed organocatalytic tandem reaction, and also the first example of the bispiro[benzofuran-oxindole] and bispirobenzofuranone, potentially useful in medicinal chemistry.

  • Qiang Huang, Lei Zhu, Dong Yi, Xiaohui Zhao, Wei Wei
    Chinese Chemical Letters. 2020, 31(2): 373-376.

    A new silver mediated aminophosphinoylation of propargyl alcohols with aromatic amines and Hphosphine oxides for the construction of α-aminophosphine oxides has been developed. The C-N and C-P bond could be efficiently formed in one pot operation via sequential C-C and C-O bond cleavage of propargylic alcohols. This present methodology, which not only provides a simple and alternative strategy for the synthesis of α-aminophosphine oxides, but also opens a new window for the cleavage reactions of propargyl alcohols via dealkynalation coupling.

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