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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Tel: 609-228-6898 E-mail: [email protected] [email protected]
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Biological Activity
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Chemical Information
- Purity & Documentation
- References
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Help & FAQs
Biological Activity
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DNA Polymerase 4.3 μM (Ki) |
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.
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.
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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- 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