5-Aza-dCTP
5-Aza-dCTP (5-Aza-2'-deoxycytidine-5′-triphosphate) is a nucleotide analog that acts as a substrate for mammalian DNA polymerase α (Km = 3.0 μM) and a weak competitive inhibitor of this enzyme (Ki = 4.3 μM). 5-Aza-dCTP inhibits DNA polymerase α via incorporation into DNA through Watson-Crick base pairing, inhibits DNA methyltransferases via incorporation into hemimethylated DNA, and induces mutations in HIV-1 via incorporation into viral DNA during synthesis. 5-Aza-dCTP reverses the inhibitory effect of dTTP on dCMP deaminase, and allosterically activates dCMP deamination to the same extent as dCTP. 5-Aza-dCTP is applicable to research related to leukemia and type 1 human immunodeficiency virus infection.
For research use only. We do not sell to patients.
- CAS No.: 72052-96-1
- Formula: C8H15N4O13P3
- Molecular Weight:468.14
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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
- Protocols
- Purity & Documentation
- References
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Help & FAQs
Biological Activity
Description
IC50 & Target
[1]|
DNA Polymerase 4.3 μM (Ki) |
In Vitro
5-Aza-2'-deoxycytidine-5′-triphosphate is a good substrate for purified mammalian DNA polymerase α (Km = 3.0 μM), acts as a weak competitive inhibitor of the enzyme (Ki = 4.3 μM), incorporates selectively into poly(dIC) but not poly(dAT) templates, and inhibits purified mammalian DNA methylase activity when incorporated into hemimethylated DNA[1].
5-Aza-dCTP reverses dTTP-mediated inhibition of 5-AZA-dCMP deamination and exhibits equivalent allosteric activation of purified spleen dCMP deaminase-mediated dCMP deamination as dCTP[3].
5-Aza-dCTP (5 nM-500 μM; 5 min) is incorporated by purified HIV-1 NL4-3 RT at least 10,000-fold more efficiently than 5-Aza-CTP in an in vitro single nucleotide extension assay, with detectable incorporation at concentrations as low as 50 nM[2].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only. Further protocols information, click here.
Chemical Information
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CAS No. 72052-96-1
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Molecular Weight 468.14
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Formula C8H15N4O13P3
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SMILES
NC(N=CN1[C@H]2C[C@H](O)[C@@H](COP(OP(OP(O)(O)=O)(O)=O)(O)=O)O2)=NC1=O
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Synonyms
5-Aza-2'-deoxycytidine-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.
Protocols
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Research Protocol for Infectious Diseases
Infectious-disease experiments test how pathogens interact with host barriers, innate immune receptors, inflammatory signaling, pathogen replication, and tissue injury; pattern-recognition receptors such as TLRs, RIG-I-like receptors, NOD-like receptors, and inflammasomes detect microbial molecules and activate NF-κB, interferon, and cytokine responses. The central hypothesis is that infection severity reflects the balance between pathogen burden and host response: protective inflammation restricts pathogen growth, whereas excessive or mislocalized inflammation contributes to tissue damage and disease phenotype. Unresolved questions include which host pathways are protective versus pathogenic, why some infection models fail to translate to human disease, and which combined readouts best predict clinically relevant infection outcomes.
Purity & Documentation
References
[1]. Bouchard J, et al. Incorporation of 5-Aza-2'-deoxycytidine-5'-triphosphate into DNA. Interactions with mammalian DNA polymerase alpha and DNA methylase. Molecular pharmacology. 1983 Jul;24(1):109-14. [Content Brief]
[2]. Rawson JM, et al. 5-Azacytidine Enhances the Mutagenesis of HIV-1 by Reduction to 5-Aza-2'-Deoxycytidine. Antimicrobial agents and chemotherapy. 2016 Apr;60(4):2318-25. [Content Brief]
[3]. Momparler RL, et al. Kinetic interaction of 5-AZA-2'-deoxycytidine-5'-monophosphate and its 5'-triphosphate with deoxycytidylate deaminase. Molecular pharmacology. 1984 May;25(3):436-40. [Content Brief]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
5-Aza-dCTP Related Classifications
HY-185899 Related Classifications
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Keywords
- 5-Aza-dCTP
- 72052-96-1
- 5-Aza-2'-deoxycytidine-5′-triphosphate
- DNA/RNA Synthesis
- DNA Methyltransferase
- HIV
- HIV-1 NL4-3 RT
- ribonucleotide reductase
- human immunodeficiency virus type 1 infection
- DNA methylase
- leukemia
- U373-MAGI cells
- mammalian DNA polymerase alpha
- HIV-1 reverse transcriptase
- dCMP deaminase
- HIV-1 proviral DNA
- Inhibitor
- inhibitor
- inhibit