AZT triphosphate

Names

[ Name ]:
AZT triphosphate

[Synonym ]:
3'-Azidothymidine triphosphate
3'-AZIDO-3'-DEOXYTHYMIDINE 5'-TRIPHOSPHATE
AZTTP
3'-Azido-3'-deoxythymidine 5'-triphosphate
3'-Azido-3'-deoxythymidine triphosphate
AZT triphosphate

Biological Activity

[Description]:

AZT triphosphate (3'-Azido-3'-deoxythymidine-5'-triphosphate) is a active triphosphate metabolite of Zidovudine (AZT). AZT triphosphate exhibits antiretroviral activity and inhibits replication of HIV. AZT triphosphate also inhibits the DNA polymerase of HBV. AZT triphosphate activates the mitochondria-mediated apoptosis pathway[1][2][3].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Signaling Pathways >> Anti-infection >> HIV

Research Areas >> Infection

Signaling Pathways >> Cell Cycle/DNA Damage >> DNA/RNA Synthesis

Signaling Pathways >> Anti-infection >> HBV

[Target]

HIV[2] HBV[3] DNA polymerase[3] Reactive oxygen species (ROS)[1]

[In Vitro]

Treatment with 100 µM Zidovudine (AZT) for 48h disrupts the mitochondrial tubular network via accumulation of AZT triphosphate (AZT-TP) in H9c2 cells. AZT triphosphate accumulation causes downregulation of Opa1 and upregulation of Drp1. AZT triphosphate causes mitochondrial dysfunction, increases the production of cytotoxic reactive oxygen species (ROS), and impairs the balance of the mitochondrial quality control system in H9c2 cell model established from rat embryonic myoblasts[1].

[References]

[1]. Ryosuke Nomura, et al. Azidothymidine-triphosphate Impairs Mitochondrial Dynamics by Disrupting the Quality Control System. Redox Biol. 2017 Oct;13:407-417.

[2]. Takeya Sato, et al. Engineered Human tmpk/AZT as a Novel Enzyme/Prodrug Axis for Suicide Gene Therapy. Mol Ther. 2007 May;15(5):962-70.

[3]. K Y Hostetler, et al. Enhanced Oral Absorption and Antiviral Activity of 1-O-octadecyl-sn-glycero-3-phospho-acyclovir and Related Compounds in Hepatitis B Virus Infection, in Vitro. Biochem Pharmacol. 1997 Jun 15;53(12):1815-22.

Chemical & Physical Properties

[ Molecular Formula ]:
C₁₀H₁₆N₅O₁₃P₃

[ Molecular Weight ]:
507.18100

[ Exact Mass ]:
506.99600

[ PSA ]:
303.09000