104495-48-9

Basic information

• Product Name: 1-((2R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-fluoropyrimidine-2,4(1H,3H)-dione
• Synonyms: 1-((2R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-fluoropyrimidine-2,4(1H,3H)-dione
• CAS NO: 104495-48-9
• Molecular Weight: 548.568
• Mol File: 104495-48-9.mol

Chemical Properties

• CAS DataBase Reference: 1-((2R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-fluoropyrimidine-2,4(1H,3H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-((2R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-fluoropyrimidine-2,4(1H,3H)-dione(104495-48-9)
• EPA Substance Registry System: 1-((2R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-fluoropyrimidine-2,4(1H,3H)-dione(104495-48-9)

Safety Data

• Hazardous Substances Data: 104495-48-9(Hazardous Substances Data)

Upstream product

• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 50-91-9 5-Fluoro-2'-deoxyuridine 

Downstream Products

• 142246-63-7 (2R,3S,5R)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-5-(5-fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl (2-cyanoethyl) diisopropylphosphoramidite 
• 879895-44-0 3′-O-(tert-butyldimethylsilyl)-5′-O-(4,4′-dimethoxytrityl)-5-fluoro-2′-deoxyuridine 
• 443751-31-3 thymidylyl(3'->5')P₁-thio-2'-deoxyadenylyl(3'->5')5-fluoro-2'-deoxyuridine 

Relevant articles and documents

DNA Trojan Horses: Self-Assembled Floxuridine-Containing DNA Polyhedra for Cancer Therapy

Based on their structural similarity to natural nucleobases, nucleoside analogue therapeutics were integrated into DNA strands through conventional solid-phase synthesis. By elaborately designing their sequences, floxuridine-integrated DNA strands were sy

Preparation of oligomeric 2'-deoxy-5-fluorouridylate of defined length and backbone composition: A novel pro-drug form of the potent anti-cancer drug 2'-deoxy-5-fluorouridylate

A recursive protection scheme for FdUMP is employed by synthesizing oligonucleotides consisting of only FdU. 3'-O-exonuclease action releases FdUMP and a shortened oligonucleotide from which further exonuclease action releases more FdUMP. Such oligonucleo

Discovery of an Orally Active and Liver-Targeted Prodrug of 5-Fluoro-2′-Deoxyuridine for the Treatment of Hepatocellular Carcinoma

We report a series of novel O-(substituted benzyl) phosphoramidate prodrugs of 5-fluoro-2′-deoxyuridine for the treatment of hepatocellular carcinoma. Through structure optimization, the o-methylbenzyl analog (1t) was identified as an orally bioavailable and liver-targeted lead compound. This lead prodrug is well-tolerated at a dose up to 3 g/kg in Kuming mice via oral administration. An efficacy study demonstrated that it possesses good inhibitory effect (61.67% and 72.50%, respectively) on tumor growth in a mouse xenograft model. A metabolism study in Sprague-Dawley rats suggested that 1t can release the desired 5′-monophosphate in the liver with high liver-targeting index.

Fluorine at the C5 Position of 2′-Deoxyuridine Enhances Repair of a O4-Methyl Adduct by O6-Alkylguanine DNA Alkyltransferases

Alkylation damage at the O6- and O4-atoms of 2′-deoxyguanosine (dG) and thymidine (T), respectively, can be removed by O6-alkylguanine-DNA alkyltransferases (AGTs). Previous studies have shown that human AGT (hAGT) repairs

Selective targeting of 2′-deoxy-5-fluorouridine to urokinase positive malignant cells in vitro

A urokinase targeting conjugate of 2′-deoxy-5-fluorouridine (5-FUdr) was synthesized and tested for tumor-cell selective cytotoxicity in vitro. The 5-FUdr prodrug 2′-deoxy-5-fluoro-3′-O-(3-carboxypropanoyl)uridine (5-FUdrsuccOH) containing an ester-labile

γ-Radiolysis of 2'-deoxy-5-fluorouridine derivatives with sulfur-containing substituents

2'-Deoxy-5-fluorouridine (5-FUdR) derivatives having various types of sulfur-containing substituents at the 5'-O-position were synthesized and their γ-radiolyses were studied in aqueous solutions. The γ-radiolysis of compounds having 1,3-dithiol-2-yl and 1,3-dithian-2-yl substituents at the 5'-O-position efficiently gave 5-FUdR, specifically via the attack of hydroxyl radical. On the other hand, the γ-radiolysis of a compound having a sulfonylmethyl substituent at the 5'-O-position gave less efficiently 5-FUdR, specifically via the attack of the hydrated electron. The mechanistic features of these reactions are discussed.

Floxuridine Homomeric Oligonucleotides “Hitchhike” with Albumin In Situ for Cancer Chemotherapy

Automated attachment of chemotherapeutic drugs to oligonucleotides through phosphoramidite chemistry and DNA synthesis has emerged as a powerful technology in constructing structure-defined and payload-tunable oligonucleotide–drug conjugates. In practice,

Enhancing antitumor efficacy of nucleoside analog 5-fluorodeoxyuridine on her2-overexpressing breast cancer by affibody-engineered DNA nanoparticle

Background: Chemotherapy, as an adjuvant treatment strategy for HER2-positive breast cancer, can effectively improve clinical symptoms and overcome the drug resistance of therapeutic monoclonal antibodies. Nucleoside analogues are a class of traditional c

Targeting nano carrier bearing nucleoside anti-tumor drugs and preparation method and application thereof

The invention provides a targeting nano carrier bearing nucleoside anti-tumor drugs and preparation method and application thereof. The targeting nano carrier comprises DNA tetrahedron, Affibody molecule and nucleoside anti-tumor drugs. The preparation me

THERAPEUTIC NANOCONJUGATES AND USES THEREOF

The present invention relates to nanostructured conjugates, more specifically to nanostructured fusion proteins suitable for the selective delivery of their conjugated therapeutic agents to specific cell and tissue types. It also relates to nanoparticles comprising such nanostructured proteins and the therapeutic uses thereof.