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F2773

Sigma-Aldrich

2-Fluoroadenine-9-β-D-arabinofuranoside

DNA synthesis and methylation inhibitor

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C10H12FN5O4
Numero CAS:
21679-14-1
Peso molecolare:
285.23
Beilstein:
1225932
Numero CE:
244-525-5
Numero MDL:
MFCD00132942
Codice UNSPSC:
12352202
ID PubChem:
24894830
NACRES:
NA.77

Livello qualitativo

200

Temperatura di conservazione

2-8°C

Stringa SMILE

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
HBUBKKRHXORPQB-FJFJXFQQSA-N

Informazioni sul gene

human ... ADORA3(140)
rat ... Adora1(29290) , Adora2a(25369) , Adora3(25370)

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Applicazioni

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

Azioni biochim/fisiol

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.

Attenzione

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.

Pittogrammi

Health hazard
GHS08

Avvertenze

Warning

Indicazioni di pericolo

H341,H361d

Classi di pericolo

Muta. 2 - Repr. 2

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

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

Certificati d'analisi (COA)

Cerca il Certificati d'analisi (COA) digitando il numero di lotto/batch corrispondente. I numeri di lotto o di batch sono stampati sull'etichetta dei prodotti dopo la parola ‘Lotto’ o ‘Batch’.

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Lenalidomide ≥95%

Sigma-Aldrich

901558

Lenalidomide

Cytosine β-D-arabinofuranoside crystalline, ≥90% (HPLC)

Sigma-Aldrich

C1768

Cytosine β-D-arabinofuranoside

5-Fluorouracil ≥99% (HPLC), powder

Sigma-Aldrich

F6627

5-Fluorouracil

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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