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F2773

Sigma-Aldrich

2-Fluoroadenine-9-β-D-arabinofuranoside

DNA synthesis and methylation inhibitor

Synonym(s):

9-β-D-Arabinofuranosyl-2-fluoroadenine, F-ara-A, Fludarabine des-phosphate

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About This Item

Empirical Formula (Hill Notation):
C10H12FN5O4
CAS Number:
21679-14-1
Molecular Weight:
285.23
Beilstein:
1225932
EC Number:
244-525-5
MDL number:
MFCD00132942
UNSPSC Code:
12352202
PubChem Substance ID:
24894830
NACRES:
NA.77

Quality Level

200

storage temp.

2-8°C

SMILES string

Nc1nc(F)nc2n(cnc12)[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3O

InChI

1S/C10H12FN5O4/c11-10-14-7(12)4-8(15-10)16(2-13-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,14,15)/t3-,5-,6+,9-/m1/s1

InChI key

HBUBKKRHXORPQB-FJFJXFQQSA-N

Gene Information

human ... ADORA3(140)
rat ... Adora1(29290) , Adora2a(25369) , Adora3(25370)

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Application

2-Fluoroadenine-9-β-D-arabinofuranoside (F-ara-A) has been used:
  • to assess its interaction with kinase inhibitor UCN-01 in human leukemia cells (U937 and HL-60) and primary patient samples
  • to assess its influence on endothelial cells by apoptosis assay and human microvascular endothelial cells (HMECs) by cytotoxicity assay
  • in comparative cytotoxicity studies with Alemtuzumab CDC in 17p13- chronic lymphocytic leukemia (CLL) patients

Biochem/physiol Actions

Fludarabine (the 5′-phosphate) is a prodrug that is converted to F-ara-A, which enters cells and accumulates primarily as the 5′-triphosphate. F-ara-A interferes with DNA synthesis and repair and induces apoptosis of cancer cells. F-ara-A also strongly inhibits DNA methylation, particularly methylation of cytosine in CpG dinucleotide sequences.

Warning

The name fludarabine refers to 9-β-D-arabinofuranosyl-2-fluoroadenine 5′-phosphate, but is sometimes erroneously used for this compound, which lacks the phosphate.

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H341,H361d

Hazard Classifications

Muta. 2 - Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Alessandro Natoni et al.
Methods in molecular biology (Clifton, N.J.), 986, 217-226 (2013-02-26)
Chronic Lymphocytic Leukaemia (CLL) is an incurable disease that warrants new therapeutic treatments. CLL cells accumulate in the peripheral blood, in the bone marrow and in secondary lymphoid organs. Unlike circulating CLL cells, CLL cells resident in these last two
Fludarabine induces apoptosis, activation, and allogenicity in human endothelial and epithelial cells: protective effect of defibrotide
Eissner G, et al.
Blood, 100(1), 334-340 (2002)
Valentina Griggio et al.
Haematologica, 105(4), 1042-1054 (2019-07-11)
In chronic lymphocytic leukemia (CLL), the hypoxia-inducible factor 1 (HIF-1) regulates the response of tumor cells to hypoxia and their protective interactions with the leukemic microenvironment. In this study, we demonstrate that CLL cells from TP53-disrupted (TP53dis) patients have constitutively
Candida Vitale et al.
Scientific reports, 13(1), 16950-16950 (2023-10-08)
Despite recent relevant therapeutic progresses, chronic lymphocytic leukemia (CLL) remains an incurable disease. Selinexor, an oral inhibitor of the nuclear export protein XPO1, is active as single agent in different hematologic malignancies, including CLL. The purpose of this study was
Interactions between 2-fluoroadenine 9-beta-d-arabinofuranoside and the kinase inhibitor UCN-01 in human leukemia and lymphoma cells
Harvey S, et al.
Clinical Cancer Research, 7(2), 320-330 (2001)
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