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Merck

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號碼:
MDL號碼:
分類程式碼代碼:
12352202
PubChem物質ID:
NACRES:
NA.77

品質等級

儲存溫度

2-8°C

SMILES 字串

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 密鑰

HBUBKKRHXORPQB-FJFJXFQQSA-N

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應用

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. 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.

象形圖

Health hazard

訊號詞

Warning

危險聲明

危險分類

Muta. 2 - Repr. 2

儲存類別代碼

11 - Combustible Solids

水污染物質分類(WGK)

WGK 3

閃點(°F)

Not applicable

閃點(°C)

Not applicable

個人防護裝備

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


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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)
Alessandro Natoni et al.
Methods in molecular biology (Clifton, N.J.), 986, 217-226 (2013-02-26)
Chronic Lymphocytic Leukaemia (CLL) is an incurable disease that warrants new therapeutic treatments. CLL cells accumulate in the peripheral blood, in the bone marrow and in secondary lymphoid organs. Unlike circulating CLL cells, CLL cells resident in these last two
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
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)
M J Keating et al.
Blood, 74(1), 19-25 (1989-07-01)
Fludarabine was used to treat 68 patients with previously treated chronic lymphocytic leukemia (CLL). Nine (13%) patients achieved a complete remission and 30 (44%) a partial remission. The response rates for Rai stages 0 to 2, 3, and 4 were

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