3006-60-8Relevant articles and documents
Glycodendrimers and modified ELISAs: Tools to elucidate multivalent interactions of galectins 1 and 3
Wolfenden, Mark,Cousin, Jonathan,Nangia-Makker, Pratima,Raz, Avraham,Cloninger, Mary
, p. 7059 - 7096 (2015)
Multivalent protein-carbohydrate interactions that are mediated by sugar-binding proteins, i.e., lectins, have been implicated in a myriad of intercellular recognition processes associated with tumor progression such as galectin-mediated cancer cellular migration/metastatic processes. Here, using a modified ELISA, we show that glycodendrimers bearing mixtures of galactosides, lactosides, and N-acetylgalactosaminosides, galectin-3 ligands, multivalently affect galectin-3 functions. We further demonstrate that lactose functionalized glycodendrimers multivalently bind a different member of the galectin family, i.e., galectin-1. In a modified ELISA, galectin-3 recruitment by glycodendrimers was shown to directly depend on the ratio of low to high affinity ligands on the dendrimers, with lactose-functionalized dendrimers having the highest activity and also binding well to galectin-1. The results depicted here indicate that synthetic multivalent systems and upfront assay formats will improve the understanding of the multivalent function of galectins during multivalent protein carbohydrate recognition/interaction.
Synthesis and biological evaluation of 3β-O-neoglycosides of caudatin and its analogues as potential anticancer agents
Li, Xiao-San,Chen, Tang-Ji,Xu, Zhi-Peng,Long, Juan,He, Miao-Ying,Zhan, He-Hui,Zhuang, Hai-Cai,Wang, Qi-Lin,Liu, Li,Yang, Xue-Mei,Tang, Jin-Shan
, (2021/12/30)
In order to study the structure–activity relationship (SAR) of C21-steroidal glycosides toward human cancer cell lines and explore more potential anticancer agents, a series of 3β-O-neoglycosides of caudatin and its analogues were synthesized. The results revealed that most of peracetylated 3β-O-monoglycosides demonstrated moderate to significant antiproliferative activities against four human cancer cell lines (MCF-7, HCT-116, HeLa, and HepG2). Among them, 3β-O-(2,3,4-tri-O-acetyl-β-L-glucopyranosyl)-caudatin (2k) exhibited the highest antiproliferative activity aganist HepG2 cells with an IC50 value of 3.11 μM. Mechanical studies showed that compound 2k induced both apoptosis and cell cycle arrest at S phase in a dose dependent manner. Overall, these present findings suggested that glycosylation is a promising scaffold to improve anticancer activity for naturally occurring C21-steroidal aglycones, and compound 2k represents a potential anticancer agent deserved further investigation.
2,3-Carbamate mannosamine glycosyl donors in glycosylation reactions of diacetone-D-glucose. An experimental and theoretical study
Morelli, Laura,Legnani, Laura,Ronchi, Silvia,Confalonieri, Laura,Imperio, Daniela,Toma, Lucio,Compostella, Federica
, (2021/08/26)
The role of the cyclic 2,3-N,O-carbamate protecting group in directing the selectivity of mannosylation reactions of diacetone-D-glucose, promoted by BSP/Tf2O via α-triflate intermediates, has been investigated through a combined computational
A silyl ether-protected building block forO-GlcNAcylated peptide synthesis to enable one-pot acidic deprotection
Yan, Bingjia,Li, Wenyi,Hackenberger, Christian P. R.
supporting information, p. 8014 - 8017 (2021/10/04)
In this report, we introduce a novel building block for Fmoc/tBu solid phase peptide synthesis (SPPS) of β-linkedO-GlcNAcylated peptides. This building block carries acid labile silyl ether protecting groups, which are fully removed under TFA-mediated peptide cleavage conditions from the resin, thus requiring fewer synthetic steps and no intermediate purification as compared to other acid or base labile protecting group strategies.
S-ANTIGEN TRANSPORT INHIBITING OLIGONUCLEOTIDE POLYMERS AND METHODS
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Paragraph 0068; 0467, (2021/06/22)
Various embodiments provide STOPS? polymers that are S-antigen transport inhibiting oligonucleotide polymers, processes for making them and methods of using them to treat diseases and conditions. In some embodiments the STOPS? modified oligonucleotides include an at least partially phosphorothioated sequence of alternating A and C units having modifications as described herein. The sequence independent antiviral activity against hepatitis B of embodiments of STOPS? modified oligonucleotides, as determined by HBsAg Secretion Assay, is an EC50 that is less than 100 nM.
Synthesis of Asparagine Derivatives Harboring a Lewis X Type DC-SIGN Ligand and Evaluation of their Impact on Immunomodulation in Multiple Sclerosis
Doelman, Ward,Marqvorsen, Mikkel H. S.,Chiodo, Fabrizio,Bruijns, Sven C. M.,van der Marel, Gijsbert A.,van Kooyk, Yvette,van Kasteren, Sander I.,Araman, Can
supporting information, p. 2742 - 2752 (2020/12/29)
The protein myelin oligodendrocyte glycoprotein (MOG) is a key component of myelin and an autoantigen in the disease multiple sclerosis (MS). Post-translational N-glycosylation of Asn31 of MOG seems to play a key role in modulating the immune response towards myelin. This is mediated by the interaction of Lewis-type glycan structures in the N-glycan of MOG with the DC-SIGN receptor on dendritic cells (DCs). Here, we report the synthesis of an unnatural Lewis X (LeX)-containing Fmoc-SPPS-compatible asparagine building block (SPPS=solid-phase peptide synthesis), as well as asparagine building blocks containing two LeX-derived oligosaccharides: LacNAc and Fucα1-3GlcNAc. These building blocks were used for the glycosylation of the immunodominant portion of MOG (MOG31-55) and analyzed with respect to their ability to bind to DC-SIGN in different biological setups, as well as their ability to inhibit the citrullination-induced aggregation of MOG31-55. Finally, a cytokine secretion assay was carried out on human monocyte-derived DCs, which showed the ability of the neoglycopeptide decorated with a single LeX to alter the balance of pro- and anti-inflammatory cytokines, inducing a tolerogenic response.
Protein S-Glyco-Modification through an Elimination-Addition Mechanism
Qin, Ke,Zhang, Hao,Zhao, Zhenqi,Chen, Xing
supporting information, p. 9382 - 9388 (2020/06/04)
Per-O-acetylated unnatural monosaccharides containing a bioorthogonal group have been widely used for metabolic glycan labeling (MGL) in live cells for two decades, but it is only recently that we discovered the existence of an artificial "S-glycosylation" between protein cysteines and per-O-acetylated sugars. While efforts are being made to avoid this nonspecific reaction in MGL, the reaction mechanism remains unknown. Here, we present a detailed mechanistic investigation, which unveils the "S-glycosylation" being an atypical glycosylation termed S-glyco-modification. In alkaline protein microenvironments, per-O-acetylated monosaccharides undergo base-promoted β-elimination to form thiol-reactive α,β-unsaturated aldehydes, which then react with cysteine residues via Michael addition. This S-glyco-modification produces 3-thiolated sugars in hemiacetal form, rather than typical glycosides. The elimination-addition mechanism guides us to develop 1,6-di-O-propionyl-N-azidoacetylgalactosamine (1,6-Pr2GalNAz) as an improved unnatural monosaccharide for MGL.
GalNAc-modified methylene blue derivative, preparation method and application thereof, liver-targeted fluorescent probe and HClO detection method
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Paragraph 0050-0051, (2020/10/20)
The invention provides a GalNAc-modified methylene blue derivative, a preparation method and an application thereof, a liver-targeted fluorescent probe and an HClO detection method. The fluorescent probe takes N-acetyl-D-galactosamine as a liver targeting group, can be used as an HClO detection reagent, and shows extremely high response speed, extremely high selectivity and extremely low detectionlimit on HClO. The preparation method of the fluorescent probe is simple, the fluorescent probe is targeted to hepatocytes and liver tissues, and the HClO level can be monitored in real time.
N-acetamido galactose modified 3-nitrophthalimide derivative, preparation method, application and liver targeting probe
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Paragraph 0041-0042, (2020/10/20)
The invention provides an N-acetamido galactose modified 3-nitrophthalimide derivative, a preparation method and an application of the N-acetamido galactose modified 3-nitrophthalimide derivative, anda liver targeting probe. The preparation method of the fluorescent probe is simple, and the obtained fluorescent probe takes N-acetamido galactose as a liver targeting group and 3-nitrophthalimide asa CO response group, can be used as a CO detection reagent, is good in selectivity and high in sensitivity, can target liver cells and liver tissues, and can be used for dynamically monitoring the COlevel.
A terpyridine zinc complex for selective detection of lipid pyrophosphates: A model system for monitoring bacterial O- And N-transglycosylations
Fang, Jim-Min,Hsu, Tse-Wei,Hsu, Hsin-Chuan,Chan, Hsin-Yu
, p. 12747 - 12753 (2020/11/10)
To develop an effective method for probing O- and Nglycosyltransfer reactions that are accompanied by the release of undecaprenyl pyrophosphate, solanesyl pyrophosphate (SPP) is used as a surrogate to bind a terpyridine zinc complex (Tpy-Zn), forming a fluorescent [Tpy-Zn]-SPP complex (Kass 106,000 M-1 in EtOH-CHCl3) with 5.8 μM LOD in HEPES buffer (10 mM, pH 7.4) containing 10 mM CaCl2 and 0.08% decyl PEG, which is similar to the bioassay conditions for lipid II polymerization.
