5-Azidomethyl-2'-deoxyuridine

5-Azidomethyl-2'-deoxyuridine (5-AmdU) is a purine nucleoside analog. 5-Azidomethyl-2'-deoxyuridine demonstrates effective radiosensitization in EMT6 tumor cells.[1]. 5-Azidomethyl-2'-deoxyuridine is a click chemistry reagent, it contains an Azide group and can undergo copper-catalyzed azide-alkyne cycloaddition reaction (CuAAc) with molecules containing Alkyne groups. It can also undergo strain-promoted alkyne-azide cycloaddition (SPAAC) reactions with molecules containing DBCO or BCN groups.

Product Specifications

CAS Number

[59090-48-1]

Product Name Alternative

5-AmdU; α-Azidothymidine

UNSPSC

12352005

Target

Nucleoside Antimetabolite/Analog

Type

Oligonucleotides

Related Pathways

Cell Cycle/DNA Damage

Applications

Cancer-programmed cell death

Field of Research

Cancer

Assay Protocol

https://www.medchemexpress.com/α-azidothymidine.html

Purity

99.67

Solubility

DMSO : 125 mg/mL (ultrasonic)

Smiles

O=C(C(CN=[N+]=[N-])=CN1[C@H]2C[C@H](O)[C@@H](CO)O2)NC1=O

Molecular Formula

C10H13N5O5

Molecular Weight

283.24

References & Citations

[1]Adjei D, Reyes Y, Kumar A, et al. Pathways of the Dissociative Electron Attachment Observed in 5- and 6-Azidomethyluracil Nucleosides: Nitrogen (N2) Elimination vs Azide Anion (N3-) Elimination. J Phys Chem B. 2023;127 (7) :1563-1571. |[2]Wen Z, Peng J, Tuttle PR, et al. Electron-Mediated Aminyl and Iminyl Radicals from C5 Azido-Modified Pyrimidine Nucleosides Augment Radiation Damage to Cancer Cells. Org Lett. 2018;20 (23) :7400-7404.