Conversion of uridine into 2′-O-(2-methoxyethyl)uridine and 2′-O-(2-methoxyethyl)cytidine

Legorburu, Urtzi; Reese, Colin B.; Song, Quanlai

doi:10.1016/s0040-4020(99)00229-x

Cited by 41 publications

(24 citation statements)

References 15 publications

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“…This precursor sugar is easily accessible from commercially available material, and 2′-C-methyl-uridine (4) was prepared as described in the literature (Harry-O'kuru et al, 1997b;Tang et al, 1999), introducing only a slight modification that permitted easy isolation. For practical considerations, we prepared the cytosine derivative (5) converting the uracil nucleoside (Figure 1) via the transient generation of the 4-nitrophenoxy-derivative (Legorburu et al, 1999). Substitution with aqueous ammonia afforded the desired 2′-C-methyl-cytidine (5) as a crystalline solid with a 73% yield after chromatographic purification.…”

Section: Chemistrymentioning

confidence: 99%

2′-C-Methyl Branched Pyrimidine Ribonucleoside Analogues: Potent Inhibitors of RNA Virus Replication

Benzaria

Bardiot

Bouisset

et al. 2007

Antivir Chem Chemother

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Section: Chemistrymentioning

confidence: 99%

2′-C-Methyl Branched Pyrimidine Ribonucleoside Analogues: Potent Inhibitors of RNA Virus Replication

Benzaria

Bardiot

Bouisset

et al. 2007

Antivir Chem Chemother

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“…Support-bound chemically modified ONs were synthesized by using the corresponding phosphoramidite units [25][26][27] on a 0.2 mmol scale by following standard procedures for oligoribonucleotides. Each phosphoramidite unit was 0.1 m in dry acetonitrile, and the coupling time was 12 min for each step.…”

Section: Methodsmentioning

confidence: 99%

Chemistry, Properties, and in Vitro and in Vivo Applications of 2′‐O‐Methoxyethyl‐4′‐thioRNA, a Novel Hybrid Type of Chemically Modified RNA

et al. 2014

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We report the synthesis, properties, and in vitro and in vivo applications of 2'-O-methoxyethyl-4'-thioRNA (MOE-SRNA), a novel type of hybrid chemically modified RNA. In its hybridization with complementary RNA, MOE-SRNA showed a moderate improvement of Tm value (+3.4 °C relative to an RNA:RNA duplex). However, the results of a comprehensive comparison of the nuclease stability of MOE-SRNA relative to 2'-O-methoxyethylRNA (MOERNA), 2'-O-methyl-4'-thioRNA (Me-SRNA), 2'-O-methylRNA (MeRNA), 4'-thioRNA (SRNA), and natural RNA revealed that MOE-SRNA had the highest stability (t1/2 >48 h in human plasma). Because of the favorable properties of MOE-SRNA, we evaluated its in vitro and in vivo potencies as an anti-microRNA oligonucleotide against miR-21. Although the in vitro potency of MOE-SRNA was moderate, its in vivo potency was significant for the suppression of tumor growth (similar to that of MOERNA).

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“…Oligonucleotides andThermal Denaturation Measurements LNA oligonucleotides were synthesized according to methods described by Frieden et al (32) The 2 ¶-O-MOE amidites were prepared according to published procedures (33,34), except for the final phosphorylation step that was done according to Pedersen et al (35).…”

Section: Methodsmentioning

confidence: 99%

SPC3042: a proapoptotic survivin inhibitor

Hansen¹,

Fisker²,

Westergaard³

et al. 2008

Molecular Cancer Therapeutics

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The ability to regulate the cellular homeostasis of a higher organism through tight control of apoptosis and cell division is crucial for life. Dysregulation of these mechanisms is often associated with cancerous phenotypes in cells. Optimal cancer therapy is a fine balance between effective cancer cell killing and at the same time minimizing, or avoiding, damage to the surrounding healthy tissue. To obtain this, it is necessary to identify and inhibit molecular targets on which the cancer cells are strongly dependent. Survivin represents such a target, and it has been published previously that peptide vaccines, the small-molecule YM155, and the antisense molecule LY2181308/ISIS23722, via different mechanisms, have been used as survivin inhibitors. In this article, a new potent antisense inhibitor of survivin, SPC3042, is presented, and the properties of SPC3042 are compared with the previously published antisense drug, LY2181308/ ISIS23722. SPC3042 is a 16-mer locked nucleic acid (LNA) oligonucleotide and designed as a fully phosphorothiolated gapmer containing 7 LNA nucleotides in the flanks. The LNA nucleotides in SPC3042 provide nuclease stability and higher potency for survivin mRNA inhibition compared with earlier generations of antisense reagents. It is shown that the down-regulation of survivin with SPC3042 leads to cell cycle arrest, pronounced cellular apoptosis, and down-regulation of Bcl-2. It is also shown that SPC3042 is a sensitizer of prostate cancer cells to Taxol treatment in vitro and in vivo. [Mol Cancer Ther 2008;7(9):2736 -45]

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Conversion of uridine into 2′-O-(2-methoxyethyl)uridine and 2′-O-(2-methoxyethyl)cytidine

Cited by 41 publications

References 15 publications

2′-C-Methyl Branched Pyrimidine Ribonucleoside Analogues: Potent Inhibitors of RNA Virus Replication

2′-C-Methyl Branched Pyrimidine Ribonucleoside Analogues: Potent Inhibitors of RNA Virus Replication

Chemistry, Properties, and in Vitro and in Vivo Applications of 2′‐O‐Methoxyethyl‐4′‐thioRNA, a Novel Hybrid Type of Chemically Modified RNA

SPC3042: a proapoptotic survivin inhibitor

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