Aracytidine, Ara-C Oligonucleotide Modification

Aracytidine, Ara-C modified base can be incorporated at any position within an oligonucleotide at Bio-Synthesis, Inc. This antimetabolite drug aracytidine, also known as cytarabine or cytosine arabinoside (Ara-C), has been used extensively for the chemotherapy of several forms of blood cancers including acute lymphocytic leukemia (ALL) chronic myelogenous leukemia (CML) and non-Hodgkin’s lymphoma. It is also effective against acute myeloid leukemia (AML) and used to prevent its relapse (Wu et al., 2017). Ara-C’s uniqueness lies in that the modification affects the sugar rather than the base moiety of the nucleoside. Its anti-cancer property is primarily associated with the ability to interfere with DNA synthesis. After the administration, the prodrug Ara-C translocates through the cell membrane through facilitated diffusion by human equilibrative nucleoside transporter (hENT-1) (Sundaram et al, 2001). It is then converted to cytarabine triphosphate by deoxycytidine kinase, which competes with deoxycytidine triphosphate to inhibit DNA polymerase (Graham et al., 1970). An alternate anti-cancer activity of Ara-C results from its incorporation into DNA, causing chain-termination. The cessation of DNA synthesis blocks cell cycle progression in S phase, which eventually leads to cell death. Consistently, a significant relationship was observed between the incorporation of Ara-C into cellular DNA and the loss of clonogenic survival (Kufe et al., 1980). Side effects of Ara-C include anemia, thrombocytopenia and leukopenia.

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Product Information

 

Product Name:

Aracytidine, Ara-C Oligonucleotide Modification

Category:

Sugar Modified Bases

Modification Code:

[Ara-C]

Structure:

Purification:

HPLC or PAGE

Delivery Format:

Lyophilized

Shipping Conditions:

Room Temperature

Storage Conditions:

-20°C To -70°C
Oligonucleotides are stable in solution at 4°C for up to 2 weeks. Properly reconstituted material stored at -20°C should be stable for at least 6 months. Dried DNA (when kept at -20°C) in a nuclease-free environment should be stable for years.

References/Citations:

1.  Graham FL, Whitmore GF. Studies in mouse L-cells on the incorporation of 1-beta-D-arabinofuranosylcytosine into DNA and on inhibition of DNA polymerase by 1-beta-D-arabinofuranosylcytosine 5'-triphosphate. (1970). Cancer Res. 30:2636-44. PMID: 5530558
2. Kufe DW, Major PP, Egan EM, Beardsley GP. Correlation of cytotoxicity with incorporation of ara-C into DNA. (1980) J Biol Chem 255:8997-900. PMID: 7410404
3. Sundaram M, Yao SY, Ingram JC, Berry ZA, Abidi F, Cass CE, Baldwin SA, Young JD. Topology of a human equilibrative, nitrobenzylthioinosine (NBMPR)-sensitive nucleoside transporter (hENT1) implicated in the cellular uptake of adenosine and anti-cancer drugs. (2001) J Biol Chem 276:45270–45275. PMID: 11584005 DOI: 10.1074/jbc.M107169200
4. Wu D, Duan C, Chen L. Efficacy and safety of different doses of cytarabine in consolidation therapy for adult acute myeloid leukemia patients: a network meta-analysis. (2017) Sci Rep. 7: 9509. PMCID: PMC5572788 PMID: 28842676 doi: 10.1038/s41598-017-10368-0

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