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2-クロロアデノシン水和物

2-クロロアデノシン水和物 化学構造式
146-77-0
CAS番号.
146-77-0
化学名:
2-クロロアデノシン水和物
别名:
2-クロロアデノシン水和物;抗生物質AT-265B;2-クロロアデノシン;9-[3α,4α-ジヒドロキシ-5β-(ヒドロキシメチル)テトラヒドロフラン-2β-イル]-2-クロロ-9H-プリン-6-アミン;6-アミノ-2-クロロ-9-(β-D-リボフラノシル)プリン水和物;6-アミノ-2-クロロプリンリボシド水和物;クロロアデノシン
英語化学名:
2-Chloroadenosine
英語别名:
CADO;Cl AS;Cl-Ado;2-CADO;CI-ADO;AT-265B;2-CL-ADO;NSC 36896;CHLOROADENOSINE;2-chloro-adenosin
CBNumber:
CB5398979
化学式:
C10H12ClN5O4
分子量:
301.69
MOL File:
146-77-0.mol

2-クロロアデノシン水和物 物理性質

融点 :
162 °C
沸点 :
591.8±60.0 °C(Predicted)
比重(密度) :
1.8359 (rough estimate)
屈折率 :
-50 ° (C=0.1, H2O)
貯蔵温度 :
Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
溶解性:
H2O: 10 mg/mL, clear, colorless
酸解離定数(Pka):
13.05±0.70(Predicted)
水溶解度 :
Soluble in water.
BRN :
43957
InChIKey:
BIXYYZIIJIXVFW-UUOKFMHZSA-N
CAS データベース:
146-77-0(CAS DataBase Reference)
NISTの化学物質情報:
Adenosine, 2-chloro-(146-77-0)

安全性情報

Sフレーズ  24/25
WGK Germany  3
RTECS 番号 AU7357550
HSコード  29349990
毒性 LD50 oral in mouse: > 100mg/kg

2-クロロアデノシン水和物 価格 もっと(31)

メーカー 製品番号 製品説明 CAS番号 包装 価格 更新時間 購入
富士フイルム和光純薬株式会社(wako) W01MPB02153755
2-Chloroadenosine
146-77-0 5mg ¥5000 2021-03-23 購入
富士フイルム和光純薬株式会社(wako) W01COBQA-9414 2-クロロアデノシン
2-Chloroadenosine
146-77-0 1g ¥6200 2021-03-23 購入
富士フイルム和光純薬株式会社(wako) W01COBQA-9414 2-クロロアデノシン
2-Chloroadenosine
146-77-0 5g ¥19800 2021-03-23 購入
富士フイルム和光純薬株式会社(wako) W01MPB02153755
2-Chloroadenosine
146-77-0 50mg ¥33400 2021-03-23 購入
東京化成工業 C2192 2-クロロアデノシン水和物 >98.0%(HPLC)(T)
2-Chloroadenosine Hydrate >98.0%(HPLC)(T)
146-77-0 1g ¥13900 2021-03-23 購入

2-クロロアデノシン水和物 化学特性,用途語,生産方法

外観

白色~ほとんど白色粉末~結晶

化学的特性

White to Off-White Crystalline Sold

使用

A selective A1-adenosine receptor agonist. Induces apoptosis

使用

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.

定義

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.

生物活性

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 .

薬理学

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.

純化方法

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-クロロアデノシン水和物 上流と下流の製品情報

原材料

準備製品


2-クロロアデノシン水和物 生産企業

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146-77-0(2-クロロアデノシン水和物)キーワード:


  • 146-77-0
  • 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>
  • 2-クロロアデノシン水和物
  • 抗生物質AT-265B
  • 2-クロロアデノシン
  • 9-[3α,4α-ジヒドロキシ-5β-(ヒドロキシメチル)テトラヒドロフラン-2β-イル]-2-クロロ-9H-プリン-6-アミン
  • 6-アミノ-2-クロロ-9-(β-D-リボフラノシル)プリン水和物
  • 6-アミノ-2-クロロプリンリボシド水和物
  • クロロアデノシン
  • ヌクレオシド,ヌクレオチド&関連試薬
  • ヌクレオシドと類似体
  • 生化学
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