2-Chloroadenosine

한글명:2-Chloroadenosine

카스 번호146-77-0

상품명:2-Chloroadenosine

CBNumberCB5398979

분자식C10H12ClN5O4

포뮬러 무게301.69

MOL 파일146-77-0.mol

화학적 성질

녹는점	162 °C
끓는 점	591.8±60.0 °C(Predicted)
밀도	1.8359 (rough estimate)
굴절률	-50 ° (C=0.1, H2O)
저장 조건	Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
용해도	H₂O: 10 mg/mL, 투명, 무색
물리적 상태	고체
물리적 상태	단단한 모양
산도 계수 (pKa)	13.05±0.70(Predicted)
색상	흰색에서 황백색까지
수용성	물에 용해됩니다.
BRN	43957
InChIKey	BIXYYZIIJIXVFW-UUOKFMHZSA-N
CAS 데이터베이스	146-77-0(CAS DataBase Reference)
NIST	Adenosine, 2-chloro-(146-77-0)

위험 및 안전 성명

안전지침서

24/25

WGK 독일

RTECS 번호

AU7357550

HS 번호

29349990

독성

LD50 oral in mouse: > 100mg/kg

NFPA 704:

	0
3		0

그림문자(GHS)

2-Chloroadenosine 화학적 특성, 용도, 생산

화학적 성질
White to Off-White Crystalline Sold
용도
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.
정의
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.
생물학적 활성
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 .
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.
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.]

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