96206-45-0Relevant academic research and scientific papers
Novel design and synthesis of a radioiodinated glycolipid analog as an acceptor substrate for N-acetylglucosaminyltransferase v
Arimitsu, Kenji,Kimura, Hiroyuki,Kajimoto, Tetsuya,Ono, Masahiro,Ohmomo, Yoshiro,Yamashita, Masayuki,Node, Manabu,Saji, Hideo
, p. 562 - 572 (2013)
Guided by the known molecular recognition interactions between N-acetylglucosaminyltransferase V (GnT-V) and certain synthetic substrates, we synthesized a radiolabeled double-stranded glycolipid composed of a long-chain alkyl unit and a radioiodinated phenylalkyl unit, [125I]-2-[N-(2- hydroxy-3-hexadecyloxy)propyl-15-(4-iodophenyl)pentadecanecarboxamido]ethyl 2-acetamido-2-deoxy-β-d-glucopyranosyl-(1→2)-α-d-mannopyranosyl- (1→6)-β-d-glucopyranoside ([125I]2), as a novel intravital glycolipid mimic substrate of GnT-V. The radioactive iodine (125I) was incorporated via iododestannylation of the phenyltributyltin derivative, 2-[N-(2-acetoxy-3-hexadecyloxy)propyl-15-(4-tributylstannylphenyl) pentadecanecarboxamido]ethyl 3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-d- glucopyranosyl-(1→2)-3,4,6-O-acetyl-α-d-mannopyranosyl-(1→6)-2, 3,4-tri-O-acetyl-β-d-glucopyranoside (26). Subsequent deacetylation at the final step afforded [125I]2. Copyright
The 2′-caged-tethered-siRNA shows light-dependent temporal controlled RNAi activity for GFP gene into HEK293T cells
Bollu, Amarnath,Hassan, Md. Khurshidul,Dixit, Manjusha,Sharma, Nagendra K.
, (2020/12/17)
Small interfering RNA (siRNA) exhibits gene-specific RNAi activity by the formation of RISC complex with mRNA of gene. The structural modification of siRNA at appropriate positions affects the structure of RISC complex and then RNAi activity. The modified siRNA are mostly prepared from the incorporation of sugar ring modified, and nucleobase modified RNA nucleotides. It is learned that the introduction of the sterically hindered nucleoside at the specific position of siRNA, severely affects siRNA-RISC complex formation. This report describes the syntheses of bulkier siRNA from 2′-caged-tethered-siRNAs, containing bulkier photolabile protecting group (o-nitrobenzyl) at 2′-position of ribose nucleoside. Importantly, these 2′-caged-siRNAs exhibit the light-dependent RNA interference (RNAi) activity into HEK293T cells for the GFP gene expression. The 2′-caged-siRNAs are synthesized by caging the sense and antisense strand of siRNA. The biochemical evaluations of these caged-siRNAs show that antisense-strand caged-siRNAs decrease RNAi activity temporarily in dark while enhancing RNAi activity, almost like control, after exposure withUV- light. However, 2′-caged sense strand siRNA increase RNAi activity temporarily while decreasing RNAi activity after exposure with light. These caged-siRNAs are also stable in the serum (fetal bovine serum) as like native siRNA. Hence these results strongly support that 2′-caged-tethered-siRNAs are promising analogues to control RNAi activity by UV-light.
Synthesis and properties of photolabile (Caged) phosphotriester derivatives of dinucleoside phosphates
Abramova,Leonetti,Vlassov,Lebleu
, p. 174 - 182 (2007/10/03)
Dinucleoside phosphates that harbor phosphate groups transiently blocked (caged) by o-nitrobenzyl or o-nitroveratryl residues were synthesized. It was shown that the conditions of the UV-induced deprotection largely depend on the nature of the protective
Synthesis and characterization of photolabile choline precursors as reversible inhibitors of cholinesterase: Release of choline in the microsecond time range
Peng,Goeldner
, p. 185 - 191 (2007/10/03)
Three o-nitrobenzyl ether derivatives of choline (compounds A-C) were synthesized as photolabile cholinesterase inhibitors in order to study the mechanism of choline release from the enzyme active site. The key step of the synthesis was a simple and efficient Lewis acid-catalyzed opening of dioxolane rings derived from o-nitrobenzaldehyde and o-nitroacetophenone. Laser flash photolyses of compounds A-C were analyzed by UV spectroscopy, HPLC, and an enzymatic assay for choline. The quantum yields of photoconversion were determined, and the kinetics of choline release were analyzed by studying the decay of the transient aci-nitro intermediate at 405 nm.The observed rates varied considerably in function of both pH and the substituent at the α-benzylic position. Furthermore, we demonstrated that all three compounds possessed reversible inhibitory properties on both purified Torpedo acetylcholinesterase and purified human plasma butyrylcholinesterase. Compound A, O-[1-(2-nitrophenyl)ethyl]choline iodide, which displayed the highest quantum yield (0.27) and the most rapid photolysis rate (6.8 x 104 s-1 at pH 6.5), represents therefore an interesting tool for the study of the fast process of choline release from cholinesterases by time-resolved Laue crystallography.
