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2-Fluoroadenine-9-β-D-arabinofuranoside

SIGMA/F2773 - DNA synthesis and methylation inhibitor

Synonym: 9-β-D-Arabinofuranosyl-2-fluoroadenine; F-ara-A; Fludarabine des-phosphate

CAS Number: 21679-14-1
Empirical Formula (Hill Notation): C10H12FN5O4
Molecular Weight: 285.23
EC Number: 244-525-5
MDL Number: MFCD00132942
Linear Formula: C10H12FN5O4
Product Type: Chemical
Catalog Number PKG Qty. Price Quantity
45-F2773-5MG 5 mg
 $195.00
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45-F2773-10MG 10 mg
 $350.00
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This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: F2773-10MG

 

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
Quality Level 200 
SMILES string Nc1nc(F)nc2n(cnc12)[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3O
storage temp. 2-8°C
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.
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.
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.
Packaging: 5, 10 mg in glass bottle
Storage Temp. 2-8°C
UNSPSC 12352202

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