F2773
2-Fluoroadenine-9-β-D-arabinofuranoside
DNA synthesis 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:
Molecular Weight:
285.23
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352202
EC Number:
244-525-5
MDL number:
Beilstein/REAXYS Number:
1225932
Product Name
2-Fluoroadenine-9-β-D-arabinofuranoside, DNA synthesis and methylation inhibitor
Quality Level
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)
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.
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.
Disclaimer
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.
signalword
Warning
hcodes
Hazard Classifications
Muta. 2 - Repr. 2
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
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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)
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
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
Global Trade Item Number
| SKU | GTIN |
|---|---|
| F2773-10MG | 04061832947532 |
| F2773-5MG | 04061832947549 |