Uses
ChemicalBook > CAS DataBase List > 2-Chloroadenosine

2-Chloroadenosine

Uses
Product Name
2-Chloroadenosine
CAS No.
146-77-0
Chemical Name
2-Chloroadenosine
Synonyms
CHLOROADENOSINE;(2R,3R,4S,5R)-2-(6-aMino-2-chloro-9H-purin-9-yl)-5-(hydroxyMethyl)tetrahydrofuran-3,4-diol;CADO;Cl AS;Cl-Ado;2-CADO;CI-ADO;AT-265B;2-Cl-Ar;2-CL-ADO
CBNumber
CB5398979
Molecular Formula
C10H12ClN5O4
Formula Weight
301.69
MOL File
146-77-0.mol
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2-Chloroadenosine Property

Melting point:
162 °C
Boiling point:
591.8±60.0 °C(Predicted)
Density 
1.8359 (rough estimate)
refractive index 
-50 ° (C=0.1, H2O)
storage temp. 
Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
solubility 
H2O: 10 mg/mL, clear, colorless
pka
13.05±0.70(Predicted)
form 
Solid
color 
White to Off-White
Water Solubility 
Soluble in water.
BRN 
43957
InChIKey
BIXYYZIIJIXVFW-UUOKFMHZSA-N
CAS DataBase Reference
146-77-0(CAS DataBase Reference)
NIST Chemistry Reference
Adenosine, 2-chloro-(146-77-0)
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Safety

Safety Statements 
24/25
WGK Germany 
3
RTECS 
AU7357550
HS Code 
29349990
Toxicity
LD50 oral in mouse: > 100mg/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
C5134
Product name
2-Chloroadenosine
Packaging
10mg
Price
$106
Updated
2024/03/01
Sigma-Aldrich
Product number
C5134
Product name
2-Chloroadenosine
Packaging
1g
Price
$3110
Updated
2024/03/01
TCI Chemical
Product number
C2192
Product name
2-Chloroadenosine Hydrate
Purity
>98.0%(HPLC)(T)
Packaging
1g
Price
$151
Updated
2024/03/01
TCI Chemical
Product number
C2192
Product name
2-Chloroadenosine Hydrate
Purity
>98.0%(HPLC)(T)
Packaging
100mg
Price
$26
Updated
2024/03/01
Alfa Aesar
Product number
J63810
Product name
2-Chloroadenosine
Packaging
250mg
Price
$139.65
Updated
2024/03/01
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2-Chloroadenosine Chemical Properties,Usage,Production

Uses

2-Chloroadenosine is an adenosine analogue that is not hydrolyzed by adenosine deaminase. 2-Chloroadenosine increases the rate of dopa production in intact pheochromocytoma cells, it increases the content of cAMP in the cells, and it causes a stable activation of tyrosine hydroxylase, as measured in vitro. The action of 2-Chloroadenosine is not dependent upon extracellular Ca2+. In other experiments, we have found that 2-chloroadenosine increases the activity of adenylate cyclase in membrane fractions prepared from the pheochromocytoma. These data provide support for the hypothesis that 2-Chloroadenosine causes a cAMP-mediated phosphorylation of tyrosine hydroxylase in pheochromocytoma cells. Chromaffin cells and adrenergic neurons store and release adenine nuc1eotides together with catecho1amines. The adenosine formed by the hydrolysis of these nucleotides may be involved in the. physiological regulation of adenylate cyclase activity and of tyrosine hydroxylase activity. To date , however, we have no evidence for such a role of adenosine in normal chromaffin cells or in adrenergic neurons.

Chemical Properties

White to Off-White Crystalline Sold

Uses

A selective A1-adenosine receptor agonist. Induces apoptosis

Uses

Selective A1 adenosine receptor agonist. Since 2-chloroadenosine is not deaminated by adenosine deaminase and is less rapidly taken up by the brain than adenosine, 2-chloroadenosine led to more marked increase in CBF than adenosine.

Uses

2-Chloroadenosine is used as a selective A1-adenosine receptor agonist, and also Induces apoptosis.

Definition

A metabolically stable analog of adenosine which acts as an adenosine receptor agonist. The compound has a potent effect on the peripheral and central nervous system.

Biological Activity

Metabolically stable analog of adenosine that behaves as an adenosine receptor agonist (K i values are 300, 80 and 1900 nM for A 1 , A 2A and A 3 receptors respectively). Anticonvulsive in vivo .

Biochem/physiol Actions

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

Pharmacology

2-chloroadenosine (2-CAdo) is an adenosine deaminase-resistant analogue of adenosine, widely used as an adenosine receptor agonist. This compound has been shown to induce apoptosis in several cell types either via activation of adenosine receptors or via intracellular metabolism. However, the molecular mechanisms of 2-CAdo-induced apoptosis are unclear. Here, we analyzed the effects of 2-CAdo in the leukemia cell line EHEB. 2-CAdo was found to induce apoptosis in EHEB cells, as shown by caspase-3 activation, DNA fragmentation, poly(ADP-ribose) polymerase (PARP) cleavage and phosphatidylserine exposure. Cytotoxicity of 2-CAdo was completely suppressed by 5-iodotubercidin, an adenosine kinase inhibitor, indicating that apoptosis induced by 2-CAdo was the result of its intracellular metabolism. Accordingly, we found that 2-CAdo was efficiently converted into 2-chloroATP. In parallel, a decrease of intracellular ATP concentration as well as a general inhibition of macromolecular synthesis, involving DNA, RNA and protein synthesis, was observed. Moreover, 2-CAdo induced cytochrome c release into the cytosol, indicating activation of the intrinsic pathway of apoptosis. This was found associated with a decline in Mcl-1 protein level and p53-independent. Inhibition of AMP deaminase by coformycin markedly prevented ATP depletion, and also significantly reduced 2-CAdo cytotoxicity and caspase-3 activation. In conclusion, our data show that intracellular metabolism of 2-CAdo can lead to activation of the intrinsic pathway of apoptosis and that ATP depletion, in addition to the accumulation of the triphosphate analogue, contributes to 2-CAdo-induced apoptosis.

storage

Store at +4°C

Purification Methods

Purify 2-chloroadenosine by recrystallisation from H2O (~1% in cold), and it has max at 264 nm (pH 1 and 7) and 265 nm (pH 13) in H2O. [Brown & Weliky J Org Chem 23 125 1958, Schaeffer & Thomas J Am Chem Soc 80 3738 1958, IR: Davoll & Lewy J Am Chem Soc 74 1563 1952, Beilstein 26 III/IV 3725.]

2-Chloroadenosine Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 2-Chloroadenosine manufacturers

Xinxiang Aurora Biotechnology Co.,Ltd.
Product
2-chloroadenosine 146-77-0
Price
US $0.00/Kg
Min. Order
1Kg
Purity
98%
Supply Ability
20Ton
Release date
2024-10-31
Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
2-Chloroadenosine 146-77-0
Price
US $120.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
10ton
Release date
2024-05-22
WUHAN FORTUNA CHEMICAL CO., LTD
Product
2-Chloroadenosine 146-77-0
Price
US $0.00/Kg/Bag
Min. Order
1KG
Purity
98%min HPLC
Supply Ability
100KGS
Release date
2021-07-03

146-77-0, 2-ChloroadenosineRelated Search:

2-Chloroadenosine 2'-Deoxy-2-chloroadenosine 6-AMINO-2-CHLOROPURINE RIBOSIDE HEMIHYDRATE,2-CHLOROADENOSINE HEMIDYDRATE,2-CHLOROADENOSINE HEMIHYDRATE 2-Amino-6-chloropurine-9-riboside 6-Deamino-6-chloroadenosine 8-Chloroadenosine 2-Chloropurine Purine Adenine 2-CHLORO-9-(2,3-O-ISOPROPYLIDENE-BETA-D-RIBOFURANOSYL)ADENINE (+)-5'-O-[[(S)-2-Amino-1-oxopropyl]aminosulfonyl]-2-chloroadenosine N-Cyclopentyl-2-chloroadenosine 2-CHLORO-9-(2-3-O-ISOPROPYLIDENE-BETA-D-RIBOFURANOSYLURONIC ACID)ADENINE 5'-sulfamoyl-2-chloroadenosine 2'-MECCPA 2-CHLOROADENOSINE, [8-3H]- 2-CHLOROADENOSINE, [8-14C]- 2-CHLOROADENOSINE-3',5'-CYCLIC MONOPHOSPHATE SODIUM SALT,2-chloroadenosine-3’,5’-cyclicmonophosphate,sodiumsalt(2-cl-camp

  • 2-CADO 6-Amino-2-chloropurine Riboside 6-Amino-2-chloro-9-(beta-D-ribofuranosyl)purine
  • (2R,3R,4S,5R)-2-(6-aMino-2-chloro-9H-purin-9-yl)-5-(hydroxyMethyl)tetrahydrofuran-3,4-diol
  • (2R,3R,4S,5R)-2-(6-aMino-2-chloro-9H-purin-9-yl)-5-(hydroxyMethyl)oxolane-3,4-diol
  • 2-Chloroadenosine≥ 98% (HPLC)
  • 2-chloro-adenosin
  • Cl AS
  • Cl-Ado
  • 2-chloropurine riboside
  • 6-AMINO-2-CHLOROPURINE RIBOSIDE
  • 2-CL-ADO
  • 2-CHLOROADENOSINE
  • 2-CHLORO-D-ADENOSINE
  • 2-CADO
  • CHLOROADENOSINE
  • Regadenoson Impurity 5
  • 2-Cl-Ado / 2-CADO
  • 2-CADO,6-Amino-2-chloropurine riboside
  • 6-Amino-2-chloropurine Ribosid
  • 6-amino-2-chloro-9-(beta-d-ribofuranosyl)purine
  • 2-Chloroadenosine Hydrate
  • 2-CHLOROADENOSINE (6-AMINO-2-CHLOROPURINE RIBOSIDE)
  • 9-[3α,4α-Dihydroxy-5β-(hydroxymethyl)tetrahydrofuran-2β-yl]-2-chloro-9H-purine-6-amine
  • Antibiotic AT-265B
  • AT-265B
  • CI-ADO
  • CADO
  • 6-Amino-2-chloropuri
  • NSC 36896
  • 2-chloroadenine nucleoside
  • 2-Chloroadenosine Hydrate&gt
  • Adenosine, 2-chloro-
  • 2-Chloroadenosine USP/EP/BP
  • 2-Cl-Ar
  • 2-Chloroadenosine,ADA inhibitor,antimalarial agent, metabolite of cladribine GL100647
  • Nicotinamide nucleoside impurities
  • (3R, 4S, 5R)-2-(6-amino-2-chloro-9H-purin-9yl)-5-(hydroxymethyl) tetrahydrofuran-3, 4-diol
  • 2-Chloroadenosine,98%
  • 146-77-0
  • 147-77-0
  • C10H12ClN5O4xH2O
  • C10H12ClN5O4
  • Nucleosides, Nucleotides, Oligonucleotides
  • Nucleoside Analogs
  • Biochemicals and Reagents
  • BioChemical
  • Adenosine
  • Adenosine receptor
  • 13C & 2H Sugars
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