AZT triphosphate
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.
The free form of the compound is prone to instability, it is advisable to consider the stable salt form (AZT triphosphate tetraammonium) that retains the same biological activity.
For research use only. We do not sell to patients.
- CAS No.: 92586-35-1
- Formula: C10H16N5O13P3
- Molecular Weight:507.18
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Storage:
Please store the product under the recommended conditions in the Certificate of Analysis.
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Biological Activity
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Chemical Information
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- References
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Biological Activity
Description
IC50 & Target
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DNA Polymerase |
Cellular Effect
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Cell Line
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Type | Value | Description | References |
|---|---|---|---|---|
| H9 | IC50 |
0.022 μM
Compound: 2
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Compound concentration that causes 50 % inhibition of HIV-1 peptide-derived reverse transcriptase (RT) obtained from HIV-1-infected H9 cell cultures
Compound concentration that causes 50 % inhibition of HIV-1 peptide-derived reverse transcriptase (RT) obtained from HIV-1-infected H9 cell cultures
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10.1016/S0960-894X(01)80472-8 |
| HFF | IC50 |
22.1 μM
Compound: AZT-TP
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Inhibition of HCMV DNA polymerase infected in HFF cells
Inhibition of HCMV DNA polymerase infected in HFF cells
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[PMID: 20403696] |
| HFF | IC50 |
5.8 μM
Compound: AZT-TP
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Inhibition of VZV KOS DNA polymerase infected in HFF cells
Inhibition of VZV KOS DNA polymerase infected in HFF cells
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[PMID: 20403696] |
| Sf9 | IC50 |
22100 nM
Compound: AZT-TP
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Inhibition of HCMV recombinant DNA polymerase expressed in baculovirus infected SF9 cells after 12 mins by scintillation proximity assay
Inhibition of HCMV recombinant DNA polymerase expressed in baculovirus infected SF9 cells after 12 mins by scintillation proximity assay
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[PMID: 20167488] |
| Sf9 | IC50 |
5800 nM
Compound: AZT-TP
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Inhibition of Varicella zoster virus recombinant DNA polymerase expressed in baculovirus infected SF9 cells after 12 mins by scintillation proximity assay
Inhibition of Varicella zoster virus recombinant DNA polymerase expressed in baculovirus infected SF9 cells after 12 mins by scintillation proximity assay
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[PMID: 20167488] |
| Vero | IC50 |
3.3 μM
Compound: AZT-TP
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Inhibition of HSV1 KOS DNA polymerase infected in african green monkey Vero cells
Inhibition of HSV1 KOS DNA polymerase infected in african green monkey Vero cells
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[PMID: 20403696] |
In Vitro
AZT triphosphate (3'-Azido-3'-deoxythymidine-5'-triphosphate) accumulation disrupts the mitochondrial tubular network in H9c2 cells through Treatment with 100 μM Zidovudine (AZT) for 48h. 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].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Chemical Information
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CAS No. 92586-35-1
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Molecular Weight 507.18
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Formula C10H16N5O13P3
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SMILES
O=C1NC(N([C@@H](C[C@@H]2N=[N+]=[N-])O[C@@H]2COP(OP(O)(OP(O)(O)=O)=O)(O)=O)C=C1C)=O
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Synonyms
3'-Azido-3'-deoxythymidine-5'-triphosphate
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Purity & Documentation
References
[1]. Ryosuke Nomura, et al. Azidothymidine-triphosphate Impairs Mitochondrial Dynamics by Disrupting the Quality Control System. Redox Biol. 2017 Oct;13:407-417. [Content Brief]
[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. [Content Brief]
[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. [Content Brief]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
AZT triphosphate Related Classifications
HY-116364 Related Classifications
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