F2773

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
• 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

Properties

• 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)

Description

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.

Safety Information

• Pictograms: GHS08
• Signal Word: Warning
• Hazard Statements: H341,H361d
• Precautionary Statements: P201 - P202 - P280 - P308 + P313 - P405 - P501
• 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