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2-Chloradenosinhemihydrat Produkt Beschreibung

2-Chloroadenosine Struktur
146-77-0
CAS-Nr.
146-77-0
Bezeichnung:
2-Chloradenosinhemihydrat
Englisch Name:
2-Chloroadenosine
Synonyma:
CADO;Cl AS;Cl-Ado;2-CADO;CI-ADO;AT-265B;2-CL-ADO;NSC 36896;CHLOROADENOSINE;2-chloro-adenosin
CBNumber:
CB5398979
Summenformel:
C10H12ClN5O4
Molgewicht:
301.69
MOL-Datei:
146-77-0.mol

2-Chloradenosinhemihydrat Eigenschaften

Schmelzpunkt:
162 °C
Siedepunkt:
591.8±60.0 °C(Predicted)
Dichte
1.8359 (rough estimate)
Brechungsindex
-50 ° (C=0.1, H2O)
storage temp. 
Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
Löslichkeit
H2O: 10 mg/mL, clear, colorless
pka
13.05±0.70(Predicted)
Wasserlöslichkeit
Soluble in water.
BRN 
43957
InChIKey
BIXYYZIIJIXVFW-UUOKFMHZSA-N
CAS Datenbank
146-77-0(CAS DataBase Reference)
NIST chemische Informationen
Adenosine, 2-chloro-(146-77-0)

Sicherheit

S-Sätze: 24/25
WGK Germany  3
RTECS-Nr. AU7357550
HS Code  29349990
Toxizität LD50 oral in mouse: > 100mg/kg

2-Chloradenosinhemihydrat Chemische Eigenschaften,Einsatz,Produktion Methoden

Chemische Eigenschaften

White to Off-White Crystalline Sold

Verwenden

A selective A1-adenosine receptor agonist. Induces apoptosis

Verwenden

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.

Verwenden

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.

Biologische Aktivität

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.

Pharmakologie

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.

läuterung methode

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-Chloradenosinhemihydrat Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


2-Chloradenosinhemihydrat Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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146-77-0(2-Chloradenosinhemihydrat)Verwandte Suche:


  • 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>
  • Adenosine, 2-chloro-
  • 2-chloroadenosine fandachem
  • 2-Chloroadenosine USP/EP/BP
  • 146-77-0
  • 147-77-0
  • C10H12ClN5O4xH2O
  • C10H12ClN5O4
  • Nucleosides, Nucleotides, Oligonucleotides
  • Nucleoside Analogs
  • Biochemicals and Reagents
  • BioChemical
  • Adenosine
  • Adenosine receptor
  • 13C & 2H Sugars
  • Miscellaneous Biochemicals
  • Bases & Related Reagents
  • Carbohydrates & Derivatives
  • Heterocycles
  • Nucleotides
  • Biochemistry
  • Nucleosides and their analogs
  • Nucleosides, Nucleotides & Related Reagents
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