26993-16-8Relevant academic research and scientific papers
What Is Hidden behind Schiff Base Hydrolysis? Dynamic Covalent Chemistry for the Precise Capture of Sialylated Glycans
Xiong, Yuting,Li, Xiuling,Li, Minmin,Qin, Haijuan,Chen, Cheng,Wang, Dongdong,Wang, Xue,Zheng, Xintong,Liu, Yunhai,Liang, Xinmiao,Qing, Guangyan
, p. 7627 - 7637 (2020)
The aberrant expression of sialylated glycans (SGs) is closely associated with the occurrence, progression, and metastasis of various cancers, and sialylated glycoproteins have been widely used as clinical biomarkers for cancers. However, the identification and comprehensive analysis of SGs are exceptionally complex, which urgently need an innovative and effective method of capturing SGs from biosamples prior to MS analysis. Here, we report that a novel dynamic covalent chemistry strategy based on Schiff base hydrolysis can be applied to the precise capture of SGs. The prepared glucopyranoside-Schiff base-modified silica gel displays extraordinary enrichment selectivity (even at a ratio of 1:5000 with interference), high adsorption capacity (120 mg·g-1), and satisfying enrichment recovery (95.5%) toward sialylated glycopeptides, contributing to a highly specific, efficient, mild, and reversible SG capturing approach that can remarkably promote the development of glycoproteomics and sialic acid sensing devices and can be considerably promising in cancer biomarker discovery. Meanwhile, the facile hydrolysis characteristic of our Schiff base material completely subverts conventional knowledge of enrichment materials, the chemical stability of which is usually regarded as a prerequisite. Importantly, we find an exciting story hidden behind the Schiff base hydrolysis reaction, which demonstrates the unique advantage of dynamic covalent chemistry in glycoproteomics and biomolecule sensing.
Potential Dental Biofilm Inhibitors: Dynamic Combinatorial Chemistry Affords Sugar-Based Molecules that Target Bacterial Glucosyltransferase
Hartman, Alwin M.,Jumde, Varsha R.,Elgaher, Walid A. M.,Te Poele, Evelien M.,Dijkhuizen, Lubbert,Hirsch, Anna K. H.
, p. 113 - 123 (2020/07/13)
We applied dynamic combinatorial chemistry (DCC) to find novel ligands of the bacterial virulence factor glucosyltransferase (GTF) 180. GTFs are the major producers of extracellular polysaccharides, which are important factors in the initiation and development of cariogenic dental biofilms. Following a structure-based strategy, we designed a series of 36 glucose- and maltose-based acylhydrazones as substrate mimics. Synthesis of the required mono- and disaccharide-based aldehydes set the stage for DCC experiments. Analysis of the dynamic combinatorial libraries (DCLs) by UPLC-MS revealed major amplification of four compounds in the presence of GTF180. Moreover, we found that derivatives of the glucose-acceptor maltose at the C1-hydroxy group act as glucose-donors and are cleaved by GTF180. The synthesized hits display medium to low binding affinity (KD values of 0.4–10.0 mm) according to surface plasmon resonance. In addition, they were investigated for inhibitory activity in GTF-activity assays. The early-stage DCC study reveals that careful design of DCLs opens up easy access to a broad class of novel compounds that can be developed further as potential inhibitors.
Two-Dimensional Design Strategy to Construct Smart Fluorescent Probes for the Precise Tracking of Senescence
Gao, Ying,Hu, Yulu,Liu, Qimeng,Li, Xiaokang,Li, Xinming,Kim, Chu-Young,James, Tony D.,Li, Jian,Chen, Xi,Guo, Yuan
, p. 10756 - 10765 (2021/03/31)
The tracking of cellular senescence usually depends on the detection of senescence-associated β-galactosidase (SA-β-gal). Previous probes for SA-β-gal with this purpose only cover a single dimension: the accumulation of this enzyme in lysosomes. However, this is insufficient to determine the destiny of senescence because endogenous β-gal enriched in lysosomes is not only related to senescence, but also to some other physiological processes. To address this issue, we introduce our fluorescent probes including a second dimension: lysosomal pH, since de-acidification is a unique feature of the lysosomes in senescent cells. With this novel design, our probes achieved excellent discrimination of SA-β-gal from cancer-associated β-gal, which enables them to track cellular senescence as well as tissue aging more precisely. Our crystal structures of a model enzyme E. coli β-gal mutant (E537Q) complexed with each probe further revealed the structural basis for probe recognition.
Gastrodin derivatives and preparation method, preparation and application thereof
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Paragraph 0022, (2018/03/13)
The invention discloses gastrodin derivatives and a preparation method, a preparation and an application thereof. The X-ray powder diffraction spectrum of the gastrodin derivative radiated by a Cu-Kalpha ray: lamda=1.5405A, represented by 2theta+/-0.2 degrees is characterized in that characteristic diffraction peaks occur at reflex angles of 9.1+/-0.2 degrees, 14.1+/-0.2 degrees, 29.1+/-0.2 degrees, 29.9+/-0.2 degrees, 30.6+/-0.2 degrees, 33.3+/-0.2 degrees. X-ray diffraction powder diffraction analysis, DSC and TG-DTA analysis, IR and HPLC analysis show that the gastrodin derivative is a novel crystal form. The gastrodin derivative crystal II is high in purity and stable to light, wet and heat. The invention also provides a preparation method of the gastrodin derivatives. The gastrodin derivative crystal II is applied to preparing drugs for treating central nervous system diseases. The preparation method is simple to operate, low in production cost, easy for industrialized production and high in product purity which reaches 99% or above.
COMPOSITIONS AND METHODS FOR IMMUNOTHERAPY
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Paragraph 0090, (2016/02/26)
The present invention provides novel immunotherapeutic compositions and methods useful for treating or preventing microbial infections, weakened immune systems, diseases in which cells have become obligately anerobic and cellular proliferative disorders including cancer. The immunotherapeutics herein use benzaldehyde derivatives, precursors and intermediaries alone or in combination with additional therapeutic agents to stimulate the immune system and inhibit cellular proliferation. The immunotherapeutics of the present invention are particularly useful in the treatment of microbial infections and cellular proliferative disorders which are resistant to traditional methods of treatment such as antibiotics and chemotherapy
Discovery of 4-functionalized phenyl-O-β-d-glycosides as a new class of mushroom tyrosinase inhibitors
Yi, Wei,Cao, Rihui,Wen, Huan,Yan, Qin,Zhou, Binhua,Ma, Lin,Song, Huacan
body text, p. 6157 - 6160 (2010/06/16)
A series of 4-functionalized phenyl-O-β-d-glycosides were designed, synthesized and evaluated as a new class of mushroom tyrosinase inhibitors. The results demonstrated that compounds 6a-13a bearing a thiosemicarbazide moiety exhibited potent activities with IC50 values range from 0.31 to 52.8 μM. Particularly, compound 9a containing acetylated glucose moiety was found to be the most active molecule with an IC50 value of 0.31 μM. SARs analysis suggested that (1) the thiosemicarbazide moiety remarkably contributed to the increase of inhibitory effects on tyrosinase; (2) the configuration and bond type of sugar moiety also played a very important role in determining their inhibitory activities. The inhibition kinetics and inhibition mechanism study revealed that compound 9a was reversible and competitive type inhibitor, whereas compound 13a was reversible and competitive-uncompetitive mixed-II type inhibitor.
Synthesis and biological evaluation of helicid analogues as novel acetylcholinesterase inhibitors
Wen, Huan,Lin, Chonglan,Que, Ling,Ge, Hui,Ma, Lin,Cao, Rihui,Wan, Yiqian,Peng, Wenlie,Wang, Zihou,Song, Huacan
, p. 166 - 173 (2008/09/17)
A series of helicid analogues were prepared and evaluated in vitro for the cholinesterase (AChE and BuChE) inhibitory activities via UV spectroscopy. The results indicated that compounds 5, 6d and 8 exhibited potent AChE inhibitory activities with IC50 values of 0.45 ± 0.02 μM, 0.49 ± 0.02 μM, and 0.20 ± 0.01 μM, respectively. High selectivity for AChE over BuChE was also observed. Kinetic study showed that the mechanism of AChE inhibition of compounds 5, 6d and 8 was all mixed-type.
A mild and selective method for cleavage of O-acetyl groups with dibutyltin oxide
Liu, Hong-Min,Yan, Xuebin,Li, Wen,Huang, Conghai
, p. 1763 - 1767 (2007/10/03)
A mild and efficient neutral method for the cleavage of O-acetyl groups with dibutyltin oxide has been developed. This method is especially useful in the synthesis of glycosides containing base- or acid-sensitive multifunctional groups.
