72052-96-1
Chemical Structure
5-Aza-dCTP
Synonym(s): 5-Aza-2'-deoxycytidine-5′-triphosphate
- CAS No.: 72052-96-1
- Formula:C8H15N4O13P3
- Molecular Weight:468.14
InChIKey: GCYYBBDIYHRTCW-KVQBGUIXSA-N
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
Biological Activity: 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[1][2][3].
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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. | |||||||||||||||||||||
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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]
