171032-74-9Relevant articles and documents
The Small Molecule 2-Azido-2-deoxy-glucose Is a Metabolic Chemical Reporter of O-GlcNAc Modifications in Mammalian Cells, Revealing an Unexpected Promiscuity of O-GlcNAc Transferase
Zaro, Balyn W.,Batt, Anna R.,Chuh, Kelly N.,Navarro, Marisol X.,Pratt, Matthew R.
, p. 787 - 794 (2017)
Glycans can be directly labeled using unnatural monosaccharide analogs, termed metabolic chemical reporters (MCRs). These compounds enable the secondary visualization and identification of glycoproteins by taking advantage of bioorthogonal reactions. Most widely used MCRs have azides or alkynes at the 2-N-acetyl position but are not selective for one class of glycoprotein over others. To address this limitation, we are exploring additional MCRs that have bioorthogonal functionality at other positions. Here, we report the characterization of 2-azido-2-deoxy-glucose (2AzGlc). We find that 2AzGlc selectively labels intracellular O-GlcNAc modifications, which further supports a somewhat unexpected, structural flexibility in this pathway. In contrast to the endogenous modification N-acetyl-glucosamine (GlcNAc), we find that 2AzGlc is not dynamically removed from protein substrates and that treatment with higher concentrations of per-acetylated 2AzGlc is toxic to cells. Finally, we demonstrate that this toxicity is an inherent property of the small-molecule, as removal of the 6-acetyl-group renders the corresponding reporter nontoxic but still results in protein labeling.
An efficient, inexpensive, and shelf-stable diazotransfer reagent: Imidazole-1-sulfonyl azide hydrochloride
Goddard-Borger, Ethan D.,Stick, Robert V.
, p. 3797 - 3800 (2007)
The design and synthesis of a new diazotransfer reagent, imidazole-1-sulfonyl azide hydrochloride, are reported. This reagent has proven to equal triflyl azide in its ability to act as a "diazo donor" in the conversion of both primary amines into azides and activated methylene substrates into diazo compounds. Crucially, this reagent can be prepared in a one-pot reaction on a large scale from inexpensive materials, is shelf-stable, and is conveniently crystalline.
A glucose-responsive controlled release system using glucose oxidase-gated mesoporous silica nanocontainers
Chen, Mengjie,Huang, Chusen,He, Chunsheng,Zhu, Weiping,Xu, Yufang,Lu, Yunfeng
, p. 9522 - 9524 (2012)
A glucose-responsive controlled-release system based on the competitive combination between glucose oxidase, glucosamine and glucose has been described, which exhibits perfect controlled release properties and high selectivity for glucose over other monosaccharides. This paved the way for a new generation of stimuli-responsive delivery systems.
Synthesis of a hyaluronan neoglycopolymer by ring-opening metathesis polymerization.
Iyer, Suri,Rele, Shyam,Grasa, Gabriela,Nolan, Steven,Chaikof, Elliot L
, p. 1518 - 1519 (2003)
A hyaluronan (HA)-derived disaccharide was synthesized bearing an n-pentenyl spacer arm, which facilitated disaccharide derivatization with a norbornene template. Subsequent ring opening metathesis polymerization of the monomer produced an HA-mimetic neog
Synthesis of 7-O-(2-deoxy-2-sulfamido-α-D-glucopyranosyl)-4-methylcoumarin sodium salt: A fluorogenic substrate for sulfamidase
Dasgupta, Falguni,Masada, R.Irene
, p. 1055 - 1058 (2002)
The title compound, useful for testing the efficacy of heparin sulfamidase, was synthesized in good yield starting from 2-azido-2-deoxy-3,4,6-tri-O-acetyl-D-glucopyranosyl fluoride, reducing the azido group efficiently with SnCl2-PhSH-Et3N reagent and finally crystallizing the N-sulfated product from methanol after deacetylation.
Discovery of 4,6- O-Thenylidene-β- d -glucopyranoside-(2″-acetamido, 3″-acetyl-di- S-5-fluorobenzothizole/5-fluorobenzoxazole)-4′-demethylepipodophyllotoxin as Potential Less Toxic Antitumor Candidate Drugs by Reducing DNA Damage and Less Inhibition of PI3K
Cheng, Jie,Zhao, Wei,Yao, Hui,Shen, Yuemao,Zhang, Youming,Li, Yue-Zhong,Qi, Qingsheng,Wongprasert, Kanokpan,Tang, Ya-Jie
, p. 2877 - 2893 (2020)
As an FDA-approved drug, teniposide, was utilized in cancer treatment but was accompanied by a strong side effect in long-term clinical trials. This work discovered potential candidate drugs with low toxicity by modifying the molecule structure of teniposide through a structure-guided drug design approach. The IC50 value of novel 4,6-O-thenylidene-β-d-glucopyranoside-(2″-acetamido, 3″-acetyl-di-S-5-fluorobenzothizole/5-fluorobenzoxazole)-4′-demethylepipodophyllotoxin (compounds 15 and 16) was 120.4-125.1 μM, which was significantly improved by around 10 times more than teniposide (11.5-22.3 μM) against healthy human cells (i.e., HL-7702, H8, MRC-5, and HMEC). In vivo studies demonstrated compounds 15 and 16 significantly suppressed the tumor growth in the HepG2 cell xenograft model without exhibiting obvious toxicity (LD50 values of 208.45 and 167.52 mg/kg), which was lower than that of teniposide (LD50 = 46.12 mg/kg). Compounds 15 and 16 caused mild γH2AX phosphorylation for low DNA toxicity and less inhibition of PI3K/Akt. Compounds 15 and 16 might be potential antitumor drugs with low toxicity.
Improvement of the stereoselectivity of the glycosylation reaction with 2-azido-2-deoxy-1-thioglucoside donors
Louren?o,Ventura
, p. 33 - 39 (2016)
2-Azido-2-deoxy-1-thioglucoside donors with an electron withdrawing group at position 6 were employed to study the stereoselectivity of the glycosylation reaction with several acceptors, ranging from unhindered small primary alcohols to other sugars and s
A Direct Fluorescent Activity Assay for Glycosyltransferases Enables Convenient High-Throughput Screening: Application to O-GlcNAc Transferase
Alteen, Matthew G.,Busmann, Jil A.,Cardoso, David A.,Davies, Gideon J.,Deen, Matthew C.,Gros, Christina,McCluskey, Adam,Meek, Richard W.,Robinson, Phillip J.,Russell, Cecilia C.,Sangouard, Gontran,Shen, David L.,Tan, Hong-Yee,Vocadlo, David J.
supporting information, p. 9601 - 9609 (2020/04/09)
Glycosyltransferases carry out important cellular functions in species ranging from bacteria to humans. Despite their essential roles in biology, simple and robust activity assays that can be easily applied to high-throughput screening for inhibitors of t
Teniposide derivative, preparation method therefor and application of teniposide derivative
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Paragraph 0085; 0090-0091, (2020/08/07)
The invention discloses a teniposide derivative, a synthesis method therefor and application of the teniposide derivative. The teniposide derivative represented by a formula (V) shown in the description. The anti-tumor activity of the teniposide derivative is improved remarkably and the toxic or side effects are lowered, is obtained through introducing a heteroaromatic compound with low toxicity such as 5-fluoro-benzothiazol-2-thiol or 5-fluoro-benzoxazol-2-thiol into 2' and 3' positions of a saccharide ring of teniposide by means of an ester bond or amide bond. Shown by in-vitro tumor cell activity inhibiting experiments, the toxic or side effects of the compound represented by the formula (V) disclosed by the invention are remarkably lowered compared with those of the teniposide on the basis that the anti-tumor activity of the compound is equivalent to that of the teniposide.
2 - (1 ', 2', 3 '- Triazole - 4' - methyl pyridine oxyalkylene) - 1, 3, 4, 6 - O - acetyl - D - glucose and its preparation method and application
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Paragraph 0024; 0026-0028, (2018/04/01)
The invention discloses 2-(1',2',3'-triazolyl-4'-oxymethylenepyridyl)-1,3,4,6-O-acetyl-D-glucose with anti-rectal cancer activity. The 2-(1',2',3'-triazolyl-4'-oxymethylenepyridyl)-1,3,4,6-O-acetyl-D-glucose has a core structure of 1,3,4,6-O-acetyl-D-glucose subjected to 1,2,4-triazole derivative 2-site substitution. The above compound has good rectal cancer cell inhibition activity and can be used as a drug for resisting rectal cancer. A compound synthesis method comprises that 2-amino-D-glucose hydrochloride and an azidation reagent as raw materials undergo a reaction under alkaline conditions to produce a 2-azido-1,3,4,6-O-acetyl-D-glucose intermediate, 3-propargyl bromide and aromatic methanol undergo a reaction under the action of sodium hydride to produce aromatic propargyl ether, and the 2-azido-1,3,4,6-O-acetyl-D-glucose intermediate and the aromatic propargyl ether undergo a click reaction in a solvent in the presence of monovalent copper as a catalyst to produce 2-(1', 2', 3'-triazolyl-4'-oxymethylenepyridyl)-1,3,4,6-O-acetyl-D-glucose.
