74131-06-9

Basic information

• Product Name: (E)-5-(2-CARBOXYVINYL)-2'-DEOXYURIDINE
• Synonyms: (E)-5-(2-CARBOXYVINYL)-2'-DEOXYURIDINE;(2E)-3-[1-(2-Deoxy-beta-D-erythro-pentofuranosyl)-1,2,3,4-tetrahydro-2,4-dioxo-5-pyrimidinyl]-2-propenoic acid
• CAS NO: 74131-06-9
• Molecular Formula: C₁₂H₁₄N₂O₇
• Molecular Weight: 298.25
• Mol File: 74131-06-9.mol

Chemical Properties

• Boiling Point: (deg C): 627.63 (Adapted Stein & Brown method)
• Appearance: /
• Density: 1.682
• Solubility: DMSO; Pyridine
• PKA: 4.20±0.10(Predicted)
• CAS DataBase Reference: (E)-5-(2-CARBOXYVINYL)-2'-DEOXYURIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-5-(2-CARBOXYVINYL)-2'-DEOXYURIDINE(74131-06-9)
• EPA Substance Registry System: (E)-5-(2-CARBOXYVINYL)-2'-DEOXYURIDINE(74131-06-9)

Safety Data

• Hazardous Substances Data: 74131-06-9(Hazardous Substances Data)

Usage

Uses

Used in Reversible Photoligation:
(E)-5-(2-CARBOXYVINYL)-2'-DEOXYURIDINE is used as a building block for reversible photoligation, a technique that allows the controlled formation and cleavage of covalent bonds in biomolecules using light. This application is particularly useful in the development of novel materials and devices for biotechnology and biomedical research.
Used in Genomic Research:
In genomic research, (E)-5-(2-CARBOXYVINYL)-2'-DEOXYURIDINE serves as a valuable tool for studying the structure, function, and interactions of nucleic acids. Its unique chemical properties enable the design of new strategies for DNA and RNA manipulation, which can lead to advancements in gene editing, gene regulation, and the understanding of genetic diseases.
Used in Biotechnology:
(E)-5-(2-CARBOXYVINYL)-2'-DEOXYURIDINE is used as a key component in the development of new biotechnological applications. Its incorporation into synthetic genetic systems can enhance the capabilities of existing technologies and facilitate the creation of novel biosensors, biocatalysts, and other bioactive molecules.
Used in Biomedical Agents:
In the biomedical field, (E)-5-(2-CARBOXYVINYL)-2'-DEOXYURIDINE has potential applications as a therapeutic agent or a component of drug delivery systems. Its unique structure and properties may contribute to the development of new drugs for the treatment of various diseases, including cancer, viral infections, and genetic disorders.
Overall, (E)-5-(2-CARBOXYVINYL)-2'-DEOXYURIDINE is a versatile molecule with a wide range of potential applications in science and medicine. Its unique properties and reactivity make it an attractive candidate for further research and development in various industries.

Upstream product

• 54-42-2 5-Iodo-2'-deoxyuridine 
• 292638-85-8 acrylic acid methyl ester 
• 140-88-5 ethyl acrylate 
• 86163-17-9 methyl (E)-3-(1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)acrylate 

Downstream Products

• 1056651-22-9 5'-O-(4,4'-dimethoxytrityl)-5-(2-[2-[N,N-bis(2-trifluoroacetamidoethyl)]aminoethyl]carbamoyl-(E)-vinyl)-2'-deoxyuridine 3'-[(2-cyanoethyl)(N,N-diisopropyl)]phosphoramidite 
• 1056651-21-8 5'-O-(4,4'-dimethoxytrityl)-5-(2-[2-[N,N-bis(2-trifluoroacetamidoethyl)]aminoethyl]carbamoyl-(E)-vinyl)-2'-deoxyuridine 
• 840506-24-3 (E)-5-(2-bromovinyl)-2’-deoxyuridine-5’-(1-phenylmethoxy-L-phenylalanyl)phosphate 
• 1253522-51-8 (2E)-N-(2-(bis((pyridin-2-yl)methyl)amino)ethyl)-3-(1,2,3,4-tetrahydro-1-((2R,4S,5R)-tetrahydro-4-hydroxy-5-(hydroxymethyl)furan-2-yl)-2,4-dioxopyrimidin-5-yl)acrylamide 
• 923023-62-5 5'-O-(4,4'-dimethoxytrityl)-5-(E)-(2-carboxyvinyl)-2'-deoxyuridine 
• 114494-95-0 (E)-5-(2-bromovinyl)-2'-deoxy-3'-O-methyl-5'-O-t-butyldiphenylsilyluridine 
• 114494-94-9 (E)-5-(2-bromovinyl)-2'-deoxy-5'-O-t-butyldiphenylsilyluridine 
• 84218-85-9 (E)-5-(2-bromovinyl)-2'-deoxy-5'-O-p-toluenesulphonyluridine 
• 86214-06-4 (E)-5-(2-bromovinyl)-2'-deoxy-3-methyluridine 
• 111375-56-5 2'-deoxy-5-<1-(2,4,5-trichlorophenylthio)ethyl>uridine 
• 111375-59-8 2'-deoxy-5-(2-phenylsulphonylethyl)uridine 
• 111375-60-1 2'-deoxy-5-(1-phenylsulphonylethyl)uridine 

Relevant articles and documents

Nucleic acid probe, method for designing nucleic acid probe, and method for detecting target sequence

The present invention provides a nucleic acid probe that can achieve high detection sensitivity and high specificity in mutation detection, mismatch detection, etc. by the PCR method, a method for designing such a nucleic acid probe, and a method for detecting a target sequence. The nucleic acid probe includes a nucleic acid molecule, and the nucleic acid molecule includes a plurality of fluorescent dye moieties that exhibit an excitonic effect. At least two of the fluorescent dye moieties that exhibit an excitonic effect are bound to the same base or two adjacent bases in the nucleic acid molecule with each fluorescent dye moiety being bound via a linker (a linking atom or a linking atomic group). The extension-side end of the nucleic acid molecule is chemically modified, thereby preventing an extension reaction of the nucleic acid molecule.

ProTides of BVdU as potential anticancer agents upon efficient intracellular delivery of their activated metabolites

Nucleosides represent a major chemotherapeutic class for treating cancer, however their limitations in terms of cellular uptake, nucleoside kinase-mediated activation and catabolism are well-documented. The monophosphate pro-nucleotides known as ProTides represents a powerful strategy for bypassing the dependence on active transport and nucleoside kinase-mediated activation. Herein, we report the structural tuning of BVdU ProTides. Forty six phosphoramidates were prepared and biologically evaluated against three different cancer cell lines; murine leukemia (L1210), human CD4+T-lymphocyte (CEM) and human cervical carcinoma (HeLa). Twenty-fold potency enhancement compared to BVdU was achieved against L1210 cells. Interestingly, a number of ProTides showed low micromolar activity against CEM and HeLa cells compared to the inactive parent BVdU. The ProTides showed poor, if any measurable toxicity to non-tumourigenic human lung fibroblast cell cultures. Separation of four pairs of the diastereoisomeric mixtures and comparison of their spectral properties, biological activities and enzymatic activation rate is reported.

Pd-imidate complexes as recyclable catalysts for the synthesis of C5-alkenylated pyrimidine nucleosides via Heck cross-coupling reaction

Pd-imidate complexes have been employed as efficient catalysts for the Heck alkenylation of unprotected 5-iodo-2′-deoxyuridine in acetonitrile. The protocol was also shown to work well for the unprotected 5-iodo-2′-deoxycytidine. A highly efficient scale-up synthesis of the HSV-1 inhibitor Brivudine (BVDU) is also accomplished in an overall yield of 72% over 3-steps. The catalyst also showed recyclability for 3 consecutive runs.

COMPOUND, NUCLEIC ACID, METHOD FOR PRODUCING NUCLEIC ACID, AND KIT FOR PRODUCING NUCLEIC ACID

A compound is represented by the following formula (1), (2), or (3) (where, in the above formulae (1), (2), and (3), Z11 and Z12 independently have a fluorescent property and are an uncharged atomic group exhibiting an exciton effect).

Synthesis, cytotoxicity, and insight into the mode of action of Re(CO) 3 thymidine complexes

Nucleoside analogues are extensively used in the treatment of cancer and viral diseases. The antiproliferative properties of organorhenium(I) complexes, however, have been scarcely explored to date. Herein we present the syntheses, characterization, and in vitro evaluation of ReI(CO)3 core complexes of thymidine and uridine. For the binding of the Re I(CO)3 core, a tridentate dipicolylamine metal chelate was introduced at positions C5′, C2′, N3, and C5 with spacers of various lengths. The corresponding organometallic thymidine complexes were fully characterized by IR and NMR spectroscopy and mass spectrometry. Their cytotoxicity was assessed against the A549 lung carcinoma cell line. Toxicity is dependent on the site and mode of conjugation as well as on the nature and the length of the tether. Moderate toxicity was observed for conjugates carrying the rhenium moiety at position C5′ or N3 (IC50=124-160 μm). No toxicity was observed for complexes modified at C2′ or C5. Complex 53, with a dodecylene spacer at C5′, exhibits remarkable toxicity and is more potent than cisplatin, with an IC50 value of 6.0 μm. To the best of our knowledge, this is the first report of the antiproliferative properties of [M(CO)3]+1-nucleoside conjugates. In competitive inhibition experiments with A549 cell lysates and purified recombinant human thymidine kinase 1 (hTK-1), enzyme inhibition was observed for complexes modified at either N3 or C5′, but our results suggest that the toxicity cannot be attributed solely to interaction with hTK-1.

COMPOUND HAVING STRUCTURE DERIVED FROM MONONUCLEOSIDE OR MONONUCLEOTIDE, NUCLEIC ACID, LABELING SUBSTANCE, AND METHOD AND KIT FOR DETECTION OF NUCLEIC ACID

Disclosed is a labeling substance which enables to detect a double-stranded structure in a nucleic acid effectively. Specifically disclosed is: a compound having a structure derived from a mononucleoside or mononucleotide, wherein the structure is represe

Primer, primer set, and nucleic acid amplification method and mutation detection method using the same

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A light-controlled reversible DNA photoligation via carbazole-tethered 5-carboxyvinyluracil

We describe a light-controlled template-directed reversible DNA photoligation via carbazole-tethered 5-carboxyvinyluracil. Carbazole-tethered 5-carboxyvinyl-2'-deoxyuridine-containing oligodeoxynucleotide (ODN) can be ligated by irradiation at 366 nm in the presence of template ODN, and the ligated ODN can be split by irradiation at 366 nm in the absence of template ODN.

A ligand-free solid-supported system for Sonogashira couplings: Applications in nucleoside chemistry

A mild heterogeneous, ligand-free protocol for Sonogashira and Heck couplings has been developed and used to access several biologically important deoxynucleoside derivatives in a facile manner. The Royal Society of Chemistry 2005.

CHEMICAL COMPOUNDS

Phosphoramidate derivatives of nucleotides and their use in the treatment of cancer are described. The base moieties of, for example, each of deoxyuridine, cytarabine, gemcitabine and citidine may be substituted at the 5-position. The phosphoramidate moiety has attached to the P atom an aryl-O moiety and an α-amino acid moiety. The α-amino acid moiety may correspond to or be derived from either a naturally occurring or a non-naturally occurring amino acid.