5-azidomethyl-2'-deoxyuridine

Description

Azidomethyl-dU (AmdU) is a nucleoside that contains an azide group. The structure of the nucleoside is similar to thymidine, and it is incorporated into nascent DNA by cellular polymerases, similar to EdU.

In contrast to EdU which needs to be further modified with azides in the presence of the copper catalyst, AmdU can also react in the absence of copper catalyst using SPAAC click chemistry with strained cycloalkynes, such as cyclooctynes. This enables the detection of nascent DNA in benign, copper-free conditions.

Uses

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.

References

[1] 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. DOI:10.1021/acs.orglett.8b03035
[2] 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. DOI:10.1021/acs.jpcb.2c08257