Cytarabine 5’-monophosphate

Cytarabine 5′-monophosphate is a metabolite of the nucleoside analog Cytarabine (HY-13605), catalyzed by deoxycytidine kinase. Cytarabine 5′-monophosphate is incorporated into DNA by DNA polymerase α, which reduces the rate of DNA synthesis. At a concentration of 15 mM, Cytarabine 5′-monophosphate inhibits nuclear and mitochondrial DNA replication in Saccharomyces cerevisiae (S. cerevisiae) . Additionally, Cytarabine 5′-monophosphate (3.5-75.1 mg/kg) improves survival in leukemia mice (L1210 mice) . Cytarabine 5′-monophosphate can be used in cancer research[1].

Product Specifications

CAS Number

[7075-11-8]

UNSPSC

12352005

Hazard Statement

H302-H315-H319-H335

Target

DNA/RNA Synthesis; Drug Metabolite

Related Pathways

Cell Cycle/DNA Damage; Metabolic Enzyme/Protease

Field of Research

Cancer

Purity

98.04

Solubility

H2O : 4.17 mg/mL (ultrasonic)

Smiles

O[C@H]1[C@H](O)[C@@H](COP(O)(O)=O)O[C@H]1N2C(N=C(N)C=C2)=O

Molecular Formula

C9H14N3O8P

Molecular Weight

323.20

Precautions

P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

References & Citations

[1]Momparler RL, et al. Mammalian deoxynucleoside kinase. I. Deoxycytidine kinase: purification, properties, and kinetic studies with cytosine arabinoside. J Biol Chem. 1968 Aug 25;243 (16) :4298-304.|[2]Huang S, et al. Development and application of a rapid and sensitive liquid chromatography-mass spectrometry method for simultaneous analysis of cytarabine, cytarabine monophosphate, cytarabine diphosphate and cytarabine triphosphate in the cytosol and nucleus. J Pharm Biomed Anal. 2022 Mar 20;211:114582.|[3]Perrino FW, et al. Incorporation of cytosine arabinoside monophosphate into DNA at internucleotide linkages by human DNA polymerase alpha. J Biol Chem. 1992 Nov 15;267 (32) :23043-51.|[4]McIntosh EM, et al. Inhibition of DNA replication in Saccharomyces cerevisiae by araCMP. Curr Genet. 1986;10 (8) :579-85. |[5]Schrecker AW, et al. Antitumor effect and mode of action of 1-beta-D-arabinofuranosylcytosine 5'-phosphate in leukemia L1210. Cancer Res. 1968 Apr;28 (4) :802-3.