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Merck
CN

F2773

Sigma-Aldrich

2-氟肾上腺素-9-β-D-阿拉伯呋喃糖苷

DNA synthesis and methylation inhibitor

别名:

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

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About This Item

经验公式(希尔记法):
C10H12FN5O4
CAS号:
分子量:
285.23
Beilstein:
1225932
EC 号:
MDL编号:
UNSPSC代码:
12352202
PubChem化学物质编号:
NACRES:
NA.77

质量水平

储存温度

2-8°C

SMILES字符串

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

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应用

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

生化/生理作用

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.

警告

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.

象形图

Health hazard

警示用语:

Warning

危险声明

危险分类

Muta. 2 - Repr. 2

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

dust mask type N95 (US), Eyeshields, Faceshields, Gloves


历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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访问文档库

Direct and complement dependent cytotoxicity in CLL cells from patients with high-risk early-intermediate stage chronic lymphocytic leukemia (CLL) treated with alemtuzumab and rituximab
Zent CS, et al.
Leukemia Research, 32(12), 1849-1856 (2008)
Qin Yang et al.
FEBS open bio, 11(3), 880-889 (2021-01-16)
Periodontitis is an autoimmune disease of periodontal tissues initiated by plaque. It is known that there is a close connection between periodontitis and CKD with hypertension, but the underlying mechanisms are unknown. STAT1 has been reported to play a regulatory
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
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)

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