34408-14-5

34408-14-5 structure

Name: 8-Chloroadenosine
Chemical Name: 2-(6-amino-8-chloropurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
CAS Number: 34408-14-5
Molecular Formula: C₁₀H₁₂ClN₅O₄
Molecular Weight: 301.69
Catalog: Biochemical Nucleoside drugs Nucleoside intermediate
Create Date: 2018-09-11 19:52:28
Modify Date: 2024-01-11 14:58:12
8-Chloroadenosine (8-Cl-Ado), a unique ribonucleoside analog, depletes endogenous ATP that subsequently induces the phosphorylation and activation of AMPK. 8-Chloroadenosine induces autophagic cell death. 8-Chloroadenosine effectively inhibited in vivo tumor growth in mice[1].

Name	2-(6-amino-8-chloropurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
Synonyms	2-chloroadenosine Adenosine, 8-chloro- 8-Chloroadenosine N20C hydrochloride 8-chloro-adenosine

Description	8-Chloroadenosine (8-Cl-Ado), a unique ribonucleoside analog, depletes endogenous ATP that subsequently induces the phosphorylation and activation of AMPK. 8-Chloroadenosine induces autophagic cell death. 8-Chloroadenosine effectively inhibited in vivo tumor growth in mice[1].
Related Catalog	Signaling Pathways >> Epigenetics >> AMPK Research Areas >> Cancer Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> PI3K/Akt/mTOR >> AMPK
Target	AMPK
In Vitro	8-Chloroadenosine (8-Cl-Ado; 10 μM; 24-72 hours) induces an autophagic flux in both LC3B-II and p62 levels[1]. 8-Chloroadenosine (10 μM; 7-21 hours) induces phosphorylation of AMPK (Thr172) in a time-dependent manner in MCF-7 and BT-474 cells. Total AMPK protein levels were unchanged. 8-Chloroadenosine readily induces the phosphorylation of raptor Ser792 in MCF-7 cells. 8-Chloroadenosine (10 μM; 4-72 hours) induces ULK1 phosphorylation on Ser555 in MCF-7 and BT-474 cells[1]. 8-Chloroadenosine attenuates mTOR activity in breast cancer cells. 8-Chloroadenosine is independent of p53[1]. 8-Chloroadenosine (10 μM; 3 days) inhibits over 90% clonogenic survival in the MCF-7 breast cancer cell lines. The amount of apoptosis induction only reached ~30%[1]. 8-Chloroadenosine (10 μM) treatment results in a rapid depletion of ATP within 12-hours in T47D, SK-BR-3, and ZR-75-1 cells[1].
In Vivo	8-Chloroadenosine (25-100 mg/kg; IP; three times a week for 3 weeks) inhibits growth of both MCF-7 and BT-474 xenograft tumors with 100 mg/kg. 8-Chloroadenosine with 50 mg/kg dose does not affect the growth of the BT-474 xenograft tumors[1].
References	[1]. Christine M Stellrecht, et al. ATP directed agent, 8-chloro-adenosine, induces AMP activated protein kinase activity, leading to autophagic cell death in breast cancer cells. J Hematol Oncol. 2014 Mar 14;7:23.

Density	2.2±0.1 g/cm3
Boiling Point	707.4±70.0 °C at 760 mmHg
Molecular Formula	C₁₀H₁₂ClN₅O₄
Molecular Weight	301.69
Flash Point	381.6±35.7 °C
Exact Mass	301.057770
PSA	139.54000
LogP	-0.46
Vapour Pressure	0.0±2.4 mmHg at 25°C
Index of Refraction	1.912

HS Code	2934999090

4294-16-0

~0%

34408-14-5

1427459-38-8

Literature: US2013/72506 A1, ; Paragraph 0127 ;

58-61-7

~51%

34408-14-5

Literature: Journal of Organic Chemistry, , vol. 46, # 13 p. 2819 - 2823

HS Code	2934999090
Summary	2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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