2-Chloro-2prime-deoxyadenosineAn apoptosis inducer

2-Chloro-2′-deoxyadenosine (CAS 4291-63-8)

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Synonym: Cladribine; 2CdA
Application: An apoptosis inducer
CAS Number: 4291-63-8
Purity: ≥99%
Molecular Weight: 285.7
Molecular Formula: C10H12ClN5O3
* Refer to Certificate of Analysis for lot specific data (including water content).
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2-Chloro-2'-deoxyadenosine is a deoxyadenosine analog that induces apoptosis in chronic lymphocytic leukemia (CLL) cells. Studies show that 2-chloro-2′-deoxyadenosine can be produced from intact cells of Escherichia coli that produce B-2194 thermostable purine-nucleoside phosphorylase II. In addition, in vitro studies show that 2-Chloro-2′-deoxyadenosine can inhibit human T and B cell lymphoproliferative responses possibly by inhibiting DNA repair. Furthermore, Staphylococcus aureus Cowan-induced expression of CD25 on B-cells is suppressed by 2-Chloro-2′-deoxyadenosine. 2-Chloro-2′-deoxyadenosine is an inhibitor of Adenosine deaminase.


References

1. Baltz, J.K. and Montello, M.J. 1993. Clin Pharm. 12: 805-813. PMID: 7903917
2. Górski, A., et al. 1993. Immunopharmacology. 26: 197-202. PMID: 7904595
3. Taran, S.A., et al. 2008. Prikl. Biokhim. Mikrobiol. 44: 181-186. PMID: 18669260

Physical State :
Solid
Solubility :
Soluble in DMSO ( ≥57 mg/ml), water (<1 mg/ml), ethanol (<1 mg/ml), and methanol.
Storage :
Store at 4° C
Melting Point :
181-185° C (lit.)
Boiling Point :
597.58° C at 760 mmHg (Predicted)
Density :
2.04 g/cm3 (Predicted)
Refractive Index :
n20D 1.87 (Predicted)
Optical Activity :
α20/D -23.5°, c = 1.15 in DMSO
IC50 :
adenosine deaminase: IC50 = 0.2 µM; CT26: IC50 = 131 nM (Mus musculus); Raji: IC50 = 9 nM (human); CCRF-CEM : IC50 = 0.5 nM (human)
pK Values :
pKa: 13.75, pKb: 1.25
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
AU7357560
PubChem CID :
20279
Merck Index :
14: 2337
MDL Number :
MFCD00153939
Beilstein Registry :
624220
SMILES :
C1[C@@H]([C@H](O[C@H]1N2C=NC3=C2N=C(N=C3N)Cl)CO)O

Download SDS (MSDS)

Certificate of Analysis

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