(2′S)-2′-Deoxy-2′-fluoro-5-ethynyluridine (F-ara-EdU) - ≥95% , CAS No.95740-26-4

CAS: 95740-26-4 Cat. No.: S479901 Peso molecular: 270.21 PubChem CID: 514810

GRADE & PURITY ≥95%

Synonyms

5-ethynyl-1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione | Q27460255 | 1-(2-Deoxy-2-Fluoro-Beta-D-Arabinofuranosyl)-5-Ethynylpyrimidine-2,4(1h,3h)-Dione | 1-(2-Deoxy-2-fluoropentofuranosyl)-5-ethynyl-4-hydroxypyrimid

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Descripción general

A probe for DNA synthesis in vivo that is less toxic than both EdU and BrdU. Ideally suited for metabolic DNA labeling when prolonged cell survival and undisturbed cell cycle progression are required.

Application：

F-ara-EdU (2’-deoxy-2’-fluoro-5-ethynyluridine) is a synthetic analog of thymidine used to study de novo DNA synthesis and cell proliferation. It is a less cytotoxic alternative for BrdU (5-Bromo-2’-deoxyuridine) and EdU (5-Ethynyl-2’-deoxyuridine).
F-ara-EdU incorporates into replicating DNA during the S-phase of the cell cycle instead of natural thymidine. Metabolic incorporation of F-ara-EdU into DNA can be detected by copper-catalyzed click reaction with fluorescent or biotin-labeled azides.
In contrast to EdU, F-ara-EdU causes little or no cellular arrest or DNA synthesis inhibition. Therefore, F-ara-EdU is ideally suited for pulse-chase experiments aimed at birth-dating DNA in vivo and long-term cell survival estimation.

Specifications

Sinónimos

5-ethynyl-1-[(2R, 3S, 4R, 5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2, 4-dione | Q27460255 | 1-(2-Deoxy-2-Fluoro-Beta-D-Arabinofuranosyl)-5-Ethynylpyrimidine-2, 4(1h, 3h)-Dione | 1-(2-Deoxy-2-fluoropentofuranosyl)-5-ethynyl-4-hydroxypyrimid

Especificaciones y pureza

≥95%

Condiciones de almacenamiento de almacenamiento

Store at -20°C

Enviado en

Ice chest + Ice pads

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Tipo de acción

SUBSTRATE

Pureza

≥95%

Nombres e identificadores

• Sonrisas canónicas: C#CC1=CN(C(=O)NC1=O)C2C(C(C(O2)CO)O)F
• IUPAC Name: 5-ethynyl-1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• InChIKey: YEEGMPUOCRQFRV-IBCQBUCCSA-N
• INCHI: 1S/C11H11FN2O5/c1-2-5-3-14(11(18)13-9(5)17)10-7(12)8(16)6(4-15)19-10/h1,3,6-8,10,15-16H,4H2,(H,13,17,18)/t6-,7+,8-,10-/m1/s1
• Isómeros SMILES: C#CC1=CN(C(=O)NC1=O)[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)F
• PubChem CID: 514810
• Peso molecular: 270.21

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Nucleosides, nucleotides, and analogues
    • Clase Pyrimidine nucleosides
      • Subclass Pyrimidine 2'-deoxyribonucleosides

• Kingdom: Organic compounds
• Superclass: Nucleosides, nucleotides, and analogues
• Clase: Pyrimidine nucleosides
• Subclass: Pyrimidine 2'-deoxyribonucleosides
• Intermediate Tree Nodes: Not available
• Direct Parent: Pyrimidine 2'-deoxyribonucleosides
• Alternative Parents: Pyrimidones Hydropyrimidines Vinylogous amides Tetrahydrofurans Heteroaromatic compounds Ureas Secondary alcohols Fluorohydrins Lactams Acetylides Oxacyclic compounds Azacyclic compounds Organic oxides Hydrocarbon derivatives Organofluorides Organonitrogen compounds Organopnictogen compounds Alkyl fluorides Primary alcohols
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Pyrimidine 2'-deoxyribonucleoside - Pyrimidone - Hydropyrimidine - Pyrimidine - Tetrahydrofuran - Vinylogous amide - Heteroaromatic compound - Fluorohydrin - Halohydrin - Lactam - Secondary alcohol - Urea - Oxacycle - Azacycle - Acetylide - Organoheterocyclic compound - Organic oxide - Organic oxygen compound - Primary alcohol - Organooxygen compound - Organonitrogen compound - Organofluoride - Organohalogen compound - Alkyl halide - Organic nitrogen compound - Alkyl fluoride - Alcohol - Hydrocarbon derivative - Organopnictogen compound - Aromatic heteromonocyclic compound
• Descripción: This compound belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. These are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Objetivos asociados (no humanos)

TK Thymidine kinase (276 Activities)

Discover Target: TK

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Human alphaherpesvirus 2 (4932 Activities)

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Human alphaherpesvirus 1 (11089 Activities)

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L1210 (27553 Activities)

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P815 (244 Activities)

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Mecanismos de acción

Propiedades químicas y físicas

• Peso molecular: 270.210 g/mol
• XLogP3: -1.000
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 270.065 Da
• Monoisotopic Mass: 270.065 Da
• Topological Polar Surface Area: 99.100 Ų
• Heavy Atom Count: 19
• Formal Charge: 0
• Complexity: 497.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1