162239-35-2

Basic information

• Product Name: idoxuridine
• Synonyms: 2,4(1H,3H)-Pyrimidinedione, 1-(2-deoxy-β-L-erythro-pentofuranosyl)-5-iodo-;ent-Idoxuridine;1-(2-Deoxy-β-L-erythro-pentofuranosyl)-5-iodo-2,4(1H,3H)-pyriMidinedione;2'-Deoxy-L-5-iodouridine;5-Iodo-2'-deoxy-L-uridine
• CAS NO: 162239-35-2
• Molecular Formula: C9H11IN2O5
• Molecular Weight: 354.09851
• Product Categories: Bases & Related Reagents;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals;Nucleotides, Bases & Related Reagents, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 162239-35-2.mol
• Article Data: 34

Chemical Properties

• Appearance: /
• CAS DataBase Reference: idoxuridine(CAS DataBase Reference)
• NIST Chemistry Reference: idoxuridine(162239-35-2)
• EPA Substance Registry System: idoxuridine(162239-35-2)

Safety Data

• Hazardous Substances Data: 162239-35-2(Hazardous Substances Data)

Usage

Uses

The enantiomer of Idoxuridine (I205750). Antitumor nucleoside enantiomer thymidine kinase used as potential antiviral agents.

Upstream product

• 65505-76-2 C⁵-chloromercuri-2'-deoxyuridine 
• 51592-06-4 1,3,4,6-tetrachloro-3α,6α-diphenyl glycoluril 
• 951-78-0 2'-deoxyuridine 
• 699002-91-0 1-(5-O-trityl-2-deoxy-β-D-lyxofuranosyl)-5-iodoracil 
• 951-78-0 L-Deoxyuridine 
• 4330-21-6 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride 
• 452-51-7 D-2-deoxyribose 
• 78185-64-5 1-O-methyl-2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranose 
• 871664-01-6 5-iodo-2'-deoxy-3',5'-di-O-p-toluoyl-uridine 
• 31356-86-2 1-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-5-iodouracil 
• 54-42-2 5-Iodo-2'-deoxyuridine 
• 104267-95-0 3',5'-di-O-(p-toluoyl)-5-iodo-α-2'-desoxyuridine 
• 696-07-1 5-iodouracil 
• 50-89-5 thymidine 

Downstream Products

• 60110-67-0 5-iodo-α-2'-desoxyuridine 
• 1449768-54-0 C₄₇H₅₁N₄O₉P 
• 1449768-53-9 C₃₈H₃₄N₂O₈ 
• 1627941-97-2 3-O-{2-cyanoethyl(diisopropylamino)phosphino}-5'-O-(4,4'-dimethoxytrityl)-5-(4-phenyldiazenylphenyl)ethynyl-2'-deoxyuridine 
• 1627941-87-0 5-(4-phenyldiazenylphenyl)ethynyl-2'-deoxyuridine 
• 56045-73-9 AIdUrd 
• 666847-54-7 5’-O-(tert-butyldimethylsilyl)-2’-deoxy-5-(N-trifluoroacetyl-3-aminopropynyl)uridine 
• 179101-49-6 5-(3-amino-1-propynyl)-2'-deoxyuridine 5'-triphosphate 
• 24514-32-7 3-Methyl-2'-desoxy-uridin 
• 382137-74-8 3-(β-D-2-deoxyribofuranosyl)-3,7-dihydro-6-methyl-2H-pyrrolo[2,3-d]pyrimidin-2-one 
• 383897-60-7 3-(β-D-2-deoxyribofuranosyl)-6-methylfuro[2,3-d]pyrimidin-2-one 
• 119644-23-4 5-iodo-2',3'-dideoxy-3'-fluorouridine 
• 144989-72-0 1-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-5-iodo-uracil 
• 101039-82-1 5-iodo-3'-O-mesyl-5'-O-trityl-2'-deoxyuridine 

Relevant articles and documents

Site-specific incorporation of multiple units of functional nucleotides into DNA using a step-wise approach with polymerase and its application to monitoring DNA structural changes

We have developed a new method, a step-wise approach with polymerase, for site-specific incorporation of multiple units of functional nucleotides into DNA to form hairpin secondary structures. The fluorescence of the resulting DNA incorporating the functional nucleotides varied upon transitioning from single-strand to hairpin and duplex structures.

Radiolabeling kit/generator for 5-radiohalogenated uridines

A rapid, simple and inexpensive synthesis of 5-radiohalogenated-2'- deoxyuridine from 5-trimethylstannyl-2'-deoxyuridine is described. The total reaction and purification time including thin layer chromatography (tlc) for quality control is less than 30 min. This method produces excellent yields (>95%) of 123I-, 125I-, 131I-UdR. The radiochemical purity of all tested preparations (>20) was determined to be greater than 99%. This new method is the basis of a radiolabeling kit/generator for preparation of radiohalogenated nucleosides. 2'-Deoxyuridine (UdR) halogenated with a stable isotope of bromine was also synthesized indicating that the method can be applied to the preparation of 5-radiobromo-2'-deoxyuridine (BUdR).

Bio-catalytic synthesis of unnatural nucleosides possessing a large functional group such as a fluorescent molecule by purine nucleoside phosphorylase

Unnatural nucleosides are attracting interest as potential diagnostic tools, medicines, and functional molecules. However, it is difficult to couple unnatural nucleobases to the 1′-position of ribose in high yield and with β-regioselectivity. Purine nucleoside phosphorylase (PNP, EC2.4.2.1) is a metabolic enzyme that catalyses the conversion of inosine to ribose-1α-phosphate and free hypoxanthine in phosphate buffer with 100% α-selectivity. We explored whether PNP can be used to synthesize unnatural nucleosides. PNP catalysed the reaction of thymidine as a ribose donor with purine to produce 2′-deoxynebularine (3, β form) in high conversion (80%). It also catalysed the phosphorolysis of thymidine and introduced a pyrimidine base with a halogen atom substituted at the 5-position into the 1′-position of ribose in moderate yield (52-73%), suggesting that it exhibits loose selectivity. For a bulky purine substrate [e.g., 6-(N,N-di-propylamino)], the yield was lower, but addition of a polar solvent such as dimethyl sulfoxide (DMSO) increased the yield to 74%. PNP also catalysed the reaction between thymidine and uracil possessing a large functional fluorescent group, 5-(coumarin-7-oxyhex-5-yn) uracil (C4U). Conversion to 2′-deoxy-[5-(coumarin-7-oxyhex-5-yn)] uridine (dRC4U) was drastically enhanced by DMSO addition. Docking simulations between dRC4U and E. coli PNP (PDB 3UT6) showed the uracil moiety in the active-site pocket of PNP with the fluorescent moiety at the entrance of the pocket. Thus, the bulky fluorescent moiety has little influence on the coupling reaction. In summary, we have developed an efficient method for producing unnatural nucleosides, including purine derivatives and modified uracil, using PNP.

Synthesis of Phosphoramidite Monomers Equipped with Complementary Bases for Solid-Phase DNA Oligomerization

We describe the preparation of two monomers that bear complementary nucleobases at the edges (guanine-2′-deoxycytidine and 2-aminoadenine-2′-deoxyuridine) and that are conveniently protected and activated for solid-phase automated DNA synthesis. We report the optimized synthetic routes leading to the four nucleobase derivatives involved, their cross-coupling reactions into dinucleobase-containing monomers, and their oligomerization in the DNA synthesizer.