Cytarabine, 98%

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Cytarabine, 98%

Name: Cytarabine, 98%
SKU: 449560010

Cytarabine, CAS # 147-94-4, is an inhibitor of DNA synthesis that is used as an anticancer and antiviral agent. | CAS: 147-94-4 | C₉H₁₃N₃O₅ | 243.22 g/mol

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1 g

5 g

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Glass bottle

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Catalog number 449560010

Price (EUR)

Quantity:

1 g

Packaging:

Glass bottle

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Chemical Identifiers

CAS147-94-4

IUPAC Name4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one

Molecular FormulaC9H13N3O5

InChI KeyUHDGCWIWMRVCDJ-CCXZUQQUSA-N

SMILESNC1=NC(=O)N(C=C1)[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O

Specifications

Specification Sheet

Appearance (Color)White to Beige

Infrared spectrumConforms

Appearance (Form)Crystalline powder

HPLC>=97.5 %

Specific optical rotation+155° to +162° (20°C, 589 nm) (c=1, water)

This Thermo Scientific Chemicals brand product was originally part of the Acros Organics product portfolio. Some documentation and label information may refer to the legacy brand. The original Acros Organics product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

General Description

Cytarabine is a nucleoside analog that acts as an antileukemic agent
Cytarabine becomes cytotoxic following conversion to its triphosphorylated form, which can be incorporated into DNA primers by DNA polymerase alpha
Can induce S phase cell cycle arrest and apoptosis in leukemic and neuronal cells

Applications

Has been used to study chemotherapeutic regimens in laboratory studies of leukemia
Useful for laboratory studies of cytarabine resistance mechanisms
At nanomolar concentrations, cytarabine has been seen to induce mitochondrial apoptosis in leukemic cells through upregulation of multiple Bcl-2 family members
It can induce neuronal cell death via inducing γ-H2AX phosphorylation in histones, in the absence of double-stranded DNA breaks

RUO – Research Use Only

General References:

Song, J.; Du, L.; Liu, P.; Wang, F.; Zhang, B.; Xie, Y.; Lu, J.; Jin, Y.; Zhou, Y.; Lv, G.; Zhang, J.; Chen, S.; Chen, Z.; Sun, X.; Zhang, Y.; Huang, Q. Intra-heterogeneity in transcription and chemoresistant property of leukemia-initiating cells in murine Setd2-/- acute myeloid leukemia. Cancer Commun (Lond). 2021, 41(9), 867-888.
Galmarini, C.M.; Thomas, X.; Calvo, F.; Rousselot, P.; Rabilloud, M.; El Jaffari, A.; Cros, E.; Dumontet, C. In vivo mechanisms of resistance to cytarabine in acute myeloid leukaemia. Br J Haematol. 2002 Jun;117(4):860-8.
Nakayama, S.; Adachi, M.; Hatano, M.; Inahata, N.; Nagao ,T.; Fukushima, N. Cytosine arabinoside induces phosphorylation of histone H2AX in hippocampal neurons via a noncanonical pathway. Neurochem Int. 2021, 142, 104933.