4-Deoxy-4-fluoro-xyloside derivatives as inhibitors of glycosaminoglycan biosynthesis

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 24, 2010, Pages 7269-7273

  Tsuzuki, Yasuhiro ^a   Nguyen, Thao Kim Nu ^b   Garud, Dinesh R ^c   Kuberan, Balagurunathan ^b,d,e   Koketsu, Mamoru ^a  

^a GIFU UNIVERSITY   (Japan)

^b Department of Electrical and Computer Engineering   (United States)

^c Sir Parashurambhau College   (India)

^d UNIVERSITY OF UTAH   (United States)

^e UNIVERSITY OF UTAH SCHOOL OF MEDICINE   (United States)

Author keywords

Click chemistry; Glycosaminoglycan; Inhibitor; Proteoglycan; Xyloside

Indexed keywords

1 (4 DEOXY 4 FLUORO BETA DEXTRO XYLOPYRANOSYL) 1,2,3 TRIAZOLE DERIVATIVE; ASCORBIC ACID; CHONDROITIN SULFATE; COPPER; GLYCOSAMINOGLYCAN; HEPARAN SULFATE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BIOSYNTHESIS; CELL VIABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMERISM; NONHUMAN;

ANIMALS; AZIDES; CATALYSIS; CATTLE; CHONDROITIN SULFATES; CLICK CHEMISTRY; COPPER; ENDOTHELIAL CELLS; GLYCOSAMINOGLYCANS; GLYCOSIDES; HEPARITIN SULFATE; ISOMERISM;

EID: 78449293027     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.10.085     Document Type: Article

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21. 2 as a negative control. CellTiter-Blue reagent (25 μl) was added to each well and incubated for 2 h. The reaction was then stopped by the addition of 50 μl of 3% SDS solution. The fluorescence was measured using a Spectra-Max M5 microplate reader (Molecular Devices, Sunnyvale, CA) at an excitation wavelength of 560 nm and an emission wavelength of 590 nm.
22. 3H-glucosamine (Perkin-Elmer, 100 μCi in deionized water) was added to each well to radiolabel the GAG chains. After 24 h, pronase solution was added to each well and incubated at 37 °C overnight to harvest the GAG chains. The treated samples were centrifuged at 16,000g for 5 min and the supernatant was diluted with half-a-volume of 0.016% Triton X-100 and loaded on a 0.2 ml DEAE-sepharose column (Amersham Biosciences). The column was first pre-equilibrated with 2 ml of wash buffer (20 mM NaOAc, 0.1 M NaCl and 0.01% Triton X-100, pH 6.0) and then washed with 6 ml of wash buffer. The bound GAGs were eluted with 1.2 ml of elution buffer (20 mM NaOAc, 1 M NaCl, pH 6.0). Fifty microliter of eluate from each well were analyzed for radioactivity using a liquid scintillation counter.
23. Anion exchange chromatography: The extent of inhibition of GAG biosynthesis was determined by analyzing the elution profile of the GAG chains on an anion exchange column coupled with an in-line radiometric detector. Radiolabeled GAGs were loaded onto a DEAE-HPLC column and then eluted for 80 min with a linear gradient of 0.2-1 M NaCl.