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C5134

Sigma-Aldrich

2-Chloroadenosine

Synonym(s):

2-CADO, 6-Amino-2-chloropurine riboside

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About This Item

Empirical Formula (Hill Notation):
C10H12ClN5O4
CAS Number:
146-77-0
Molecular Weight:
301.69
Beilstein:
43957
EC Number:
205-678-3
MDL number:
MFCD00005734
UNSPSC Code:
12352200
PubChem Substance ID:
24277688
NACRES:
NA.77

form

powder

SMILES string

Nc1nc(Cl)nc2n(cnc12)[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O

InChI

1S/C10H12ClN5O4/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

BIXYYZIIJIXVFW-UUOKFMHZSA-N

Gene Information

human ... ADORA1(134) , ADORA3(140)
rat ... Adora1(29290) , Adora2a(25369) , Adora3(25370)

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Application

2-Chloroadenosine has been used:
  • as an agonist of adenosine receptors (A1R) in dorsal hippocampus (DH) and ventral hippocampus (VH) of mice
  • as a component of artificial cerebrospinal fluid (aCSF) for electrophysiological experiments using hippocampal slices
  • as an internal standard in solid phase extraction coupled with liquid chromatography-tandem mass spectrometry (XLC-MS/MS) for the quantification of certain metabolites from axonal lysates and dorsal root ganglia (DRG) neurons

Biochem/physiol Actions

2-Chloroadenosine is an analog of adenosine. It is an adenosine A1 receptor agonist. It might possess anti-oxidant property.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sheila Weitzman et al.
Pediatric blood & cancer, 53(7), 1271-1276 (2009-09-05)
A prospective phase II Histiocyte Society study, LCH-S-98, evaluated the efficacy of 2-chlorodeoxyadenosine (2-CdA) monotherapy as salvage therapy in Langerhans cell histiocytosis (LCH). Patients with poor and intermediate risk LCH not responsive to initial therapy and patients with low-risk chronic
Effect of locally infused 2-chloroadenosine, an A1 receptor agonist, on spontaneous and evoked dopamine release in rat neostriatum
Ballarin M, et al.
Neuroscience Letters, 185(1), 29-32 (1995)
2-Chloroadenosine decreases long-term potentiation in the hippocampal CA1 area of the rat
de Mendoncca A and Ribeiro J A
Neuroscience Letters, 118(1), 107-111 (1990)
Wen-Li Gao et al.
Bioresource technology, 118, 82-88 (2012-06-19)
2-Methyltetrahydrofuran (MeTHF), a biomass-derived compound, is a promising medium for biocatalysis and organometallic reactions. The regioselective acylation of 8-chloroadenosine (8-Cl-Ado) and its analogs was carried out in MeTHF with immobilized Penicillium expansum lipase. The lipase displayed more than twofold higher
David Tandio et al.
Scientific reports, 9(1), 13555-13555 (2019-09-21)
Adenosine has been reported to be transported by equilibrative nucleoside transporter 4 (ENT4), encoded by the SLC29A4 gene, in an acidic pH-dependent manner. This makes hENT4 of interest as a therapeutic target in acidic pathologies where adenosine is protective (e.g.
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