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AZT triphosphate

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Category Human immunodeficiency Virus (HIV)
CAS 92586-35-1
Description AZT triphosphate, an active triphosphate metabolite of Zidovudine (AZT), shows anti-retroviral activity, inhibits HIV replication, and also inhibits HBV DNA polymerase. It activates mitochondrial mediated apoptosis pathway.
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Product Information

Synonyms 3'-Azido-3'-deoxythymidine 5'-triphosphate; Zidovudine triphosphate; Combivir; AZTTP; Azt-TP; Azidothymidine triphosphate; Zidovudine 5'-triphosphate; 3'-Deoxy-3'-azidothymidine triphosphate; 3'-azido-3'-deoxythymidine 5'-(tetrahydrogen triphosphate); 1-(3'-Azido-2',3'-dideoxy-beta-D-xylofuranosyl)thymine 5'-triphosphate
IUPAC Name [[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
Molecular Weight 507.18
Molecular Formula C10H16N5O13P3
Canonical SMILES CC1=CN(C(=O)NC1=O)C2CC(C(O2)COP(=O)(O)OP(=O)(O)OP(=O)(O)O)N=[N+]=[N-]
InChI InChI=1S/C10H16N5O13P3/c1-5-3-15(10(17)12-9(5)16)8-2-6(13-14-11)7(26-8)4-25-30(21,22)28-31(23,24)27-29(18,19)20/h3,6-8H,2,4H2,1H3,(H,21,22)(H,23,24)(H,12,16,17)(H2,18,19,20)/t6-,7+,8+/m0/s1
InChIKey GLWHPRRGGYLLRV-XLPZGREQSA-N
Purity ≥95%
Solubility Soluble in DMSO
Appearance Solid
Storage Store at -20°C
Exact Mass 506.99600
In Vitro After 48 h of action by 100 μM zidovudine (AZT), the accumulation of AZT triphosphate (AZT-TP) in H9c2 cells disrupts the mitochondrial tubule network. AZT triphosphate accumulation leads to downregulation of Opa1 and upregulation of Drp1. AZT-triphosphate can cause mitochondrial dysfunction, increase the production of cytotoxic reactive oxygen species (ROS), and impair the balance of mitochondrial quality control systems in H9c2 cell models established from rat embryonic myoblasts.
PSA 303.09000
Target HIV; DNA/RNA Synthesis; HBV; Reactive Oxygen Species; Apoptosis

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