F2773
2-氟肾上腺素-9-β-D-阿拉伯呋喃糖苷
DNA synthesis inhibitor
别名:
9-β-D-Arabinofuranosyl-2-fluoroadenine, F-ara-A, Fludarabine des-phosphate
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关于此项目
经验公式（希尔记法）:
C10H12FN5O4
化学文摘社编号:
分子量:
285.23
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352202
EC Number:
244-525-5
MDL number:
Beilstein/REAXYS Number:
1225932
产品名称
2-氟肾上腺素-9-β-D-阿拉伯呋喃糖苷, DNA synthesis and methylation inhibitor
Quality Segment
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
存储类别
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