69256-17-3Relevant academic research and scientific papers
S-ANTIGEN TRANSPORT INHIBITING OLIGONUCLEOTIDE POLYMERS AND METHODS
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, (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.
Analysis of Configuration and Conformation of Furanose Ring in Carbohydrate and Nucleoside by Vibrational Circular Dichroism
Taniguchi, Tohru,Nakano, Kie,Baba, Ryosuke,Monde, Kenji
supporting information, p. 404 - 407 (2017/04/21)
A reliable and convenient method for determining the configuration and conformation of the furanose ring in carbohydrates and nucleosides by vibrational circular dichroism (VCD) spectroscopy is described. Diastereomeric pairs of several furanose monosacch
NEIL1 Binding to DNA Containing 2'-Fluorothymidine Glycol Stereoisomers and the Effect of Editing
Onizuka, Kazumitsu,Yeo, Jongchan,David, Sheila S.,Beal, Peter A.
experimental part, p. 1338 - 1348 (2012/09/22)
Thymine glycol (Tg), one of the oxidized bases formed in DNA by reactive oxygen species, is repaired by the DNA glycosylases such as NEIL1, NTH1 and Endo III. In our recent studies, we showed that NEIL1's catalytic efficiency and lesion specificity are regulated by an RNA-editing adenosine deamination reaction. In this study, we synthesized oligodeoxynucleotides containing 2'-fluorothymidine glycol with either ribo or arabino configuration and investigated the binding of these modified DNAs with the unedited and edited forms of human NEIL1 along with E. coli Endo III. For the two forms of hNEIL1, binding affinities to FTg-containing DNA were similar indicating that the editing effect is more subtle than to simply alter substrate affinity. While the NEIL1-binding to FTg-containing DNAs was largely insensitive to C5 and 2' stereochemistry, a preference was observed for the FTg-G pair over the FTg-A pair. In addition, we found that optimal binding is observed with Endo III and duplex DNA with riboFTg(5S) paired with dG. The modified DNAs reported here will provide useful tools for further characterizing the interaction between DNA repair glycosylases and thymine glycol containing DNA.
Synthesis and anti-HIV activity of 2′-deoxy-2′-fluoro-4′-C-ethynyl nucleoside analogs
Wang, Qiang,Li, Yanfeng,Song, Chuanjun,Qian, Keduo,Chen, Chin-Ho,Lee, Kuo-Hsiung,Chang, Junbiao
supporting information; experimental part, p. 4053 - 4056 (2010/08/19)
Based on the favorable antiviral profiles of 4′-substituted nucleosides, novel 1-(2′-deoxy-2′-fluoro-4′-C-ethynyl-β-d-arabinofuranosyl)-uracil (1a), -thymine (1b), and -cytosine (2) analogs were synthesized. Compounds 1b and 2 exhibited potent anti-HIV-1 activity with IC50 values of 86 and 1.34 nM, respectively, without significant cytotoxicity. Compound 2 was 35-fold more potent than AZT against wild-type virus, and also retained nanomolar antiviral activity against resistant strains, NL4-3 (K101E) and RTMDR. Thus, 2 merits further development as a novel NRTI drug.
A general synthesis of 2′-deoxy-2′-[18F]fluoro-1-β-D- arabinofuranosyluracil and its 5-substituted nucleosides
Alauddin, Mian M.,Conti, Peter S.,Fissekis, John D.
, p. 285 - 289 (2007/10/03)
Several 2′-deoxy-2′-[18F]fluoro-1-β-D- arabinofuranosyluracil derivatives have been synthesized. Coupling of 1-bromo-2-deoxy-2-[18F]fluoro-3,5-di-O-benzoyl-α-D- arabinofuranose 2 with protected uracil derivatives 3a-e followed by hydrolysis and high-performance liquid chromatography purification produced the radiolabeled nucleosides 4a-e in 15-30% yield (d. c.), > 99% radiochemical purity and 55.5-103.6 GBq/μmol specific activities. Copyright
Synthesis of 2',3'-dideoxy-2'-fluoro-3'-thioarabinothymidine and its 3'-phosphoramidite derivative.
Elzagheid, Mohamed I,Tedeschi, Anna Lisa,Damha, Masad J
, p. 1343 - 1346 (2007/10/03)
An efficient method for the synthesis of 5'-O-monomethoxytrityl-2',3'-dideoxy-2'-fluoro-3'-thioarabinothymidine [(5'MMT)araF-T(3'SH), (5)] and its 3'-phosphoramidite derivative (6) suitable for automated incorporation into oligonucleotides, is demonstrated. A key step in the synthesis involves reaction of 5'-O-MMT-2,3'-O-anhydrothymidine (4) (Eleuteri, A.; Reese, C.B.; Song, Q. J. Chem. Soc. Perkin Trans. 1 1996, 2237 pp.) with sodium thioacetate to give (5'-MMT)araF-T(3'SAc) (5) (Elzagheid, M.I.; Mattila, K.; Oivanen, M.; Jones, B.C.N.M.; Cosstick, Loennberg, H. Eur. J. Org. Chem. 2000, 1987-1991). This nucleoside was then converted to its corresponding phosphoramidite derivative, 6, as described previously ((a) Sun, S.; Yoshida, A.; Piccirilli, J.A. RNA, 1997, 3, 1352-1363; (b) Matulic-Adamic, J.; Beigelman, L. Helvetica Chemica Acta 1999, 82, 2141-2150: (c) Fettes, K.J.; O'Neil, I.; Roberts, S.M.; Cosstick, R. Nucleosides, Nucleotides and Nucl. Acids 2001, 20, 1351-1354).
Antiviral Nucleosides. A Stereospecific, Total Synthesis of 2'-Fluoro-2'-deoxy-β-D-arabinofuranosyl Nucleosides
Howell, Henry G.,Brodfuehrer, Paul R.,Brundidge, Steven P.,Benigni, Daniel A.,Sapino, Chester
, p. 85 - 88 (2007/10/02)
A general, total synthesis of (2'-fluoro-2'-deoxy-β-D-arabinofuranosyl)uracils 1a-d is described.A study of the coupling reaction beetwen 3,5-di-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranosyl bromide (7) and silylated pyrimidines 11a-d has resulted in a high overall yield for the five-step stereospecific synthesis of β-nucleosides.
Anti-herpes virus compositions containing 5-substituted 1-2'(deoxy-2-'-substituted-β-d-arabinofuranosyl)pyrimedene nucleosides
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, (2008/06/13)
Veterinarian composition for the treatment of herpes virus in animals comprising a pyrimidine nucleoside, or veterinarianically acceptable acid addition salte thereof, of the formula STR1 wherein A is OR3, SR3, NR3 R4
Nucleosides. 123. Synthesis of Antiviral Nucleosides: 5-Substituted 1-(2-Deoxy-2-halogeno-β-D-arabinofuranosyl)cytosines and -uracils. Some Structure-Activity Relationships
Watanabe, Kyoichi A.,Su, Tsann-Long,Klein, Robert S.,Chu, Chung K.,Matsuda, Akira,et al.
, p. 152 - 156 (2007/10/02)
The syntheses of several 2'-halogeno-5-substituted-arabinofuranosylcytosines and -uracils are described, and relationships of structure to anti herpes virus activity in vitro were examined.Those arabinonucleosides containing the 2'-fluoro function exhibit
