| Identification | Back Directory | [Name]
8-CHLOROADENOSINE | [CAS]
34408-14-5 | [Synonyms]
8-Cl-rA
8-CL-ADO
NSC354258
NSC-354258
NSC 354258
8-CHLOROADENOSINE
ADENOSINE, 8-CHLORO
8-Chloro-D-adenosine
8-CHLOROADENOSINE USP/EP/BP
6-Amino-8-chloropurine riboside
8Chloroadenosine,8 Chloroadenosine
2-(6-amino-8-chloropurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
2-(6-amino-8-chloro-9-purinyl)-5-(hydroxymethyl)oxolane-3,4-diol
8-Chloroadenosine, neoplastic and autoimmune agent anticancer agent | [Molecular Formula]
C10H12ClN5O4 | [MDL Number]
MFCD01076457 | [MOL File]
34408-14-5.mol | [Molecular Weight]
301.69 |
| Chemical Properties | Back Directory | [Melting point ]
189-191 °C | [Boiling point ]
707.4±70.0 °C(Predicted) | [density ]
2.19±0.1 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Store in freezer, under -20°C | [solubility ]
Soluble to 20 mM in water with gentle warming and to 100 mM in DMSO | [form ]
Crystalline solid. | [pka]
12.90±0.70(Predicted) | [color ]
White to off-white | [InChI]
InChI=1S/C10H12ClN5O4/c11-10-15-4-7(12)13-2-14-8(4)16(10)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,13,14)/t3-,5-,6-,9-/m1/s1 | [InChIKey]
MHDPPLULTMGBSI-UUOKFMHZSA-N | [SMILES]
OC[C@H]1O[C@@H](N2C3C(=C(N=CN=3)N)N=C2Cl)[C@H](O)[C@@H]1O |
| Hazard Information | Back Directory | [Description]
8-Chloroadenosine is a nucleoside analog; metabolized in vivo to 8-Chloro-ATP. Incorporates into RNA during transcription and inhibits RNA synthesis. Exhibits cytotoxicity in MM.1S, RPMI-8226 and U266 cancer cell lines; induces G2/M cell cycle arrest and mitotic catastrophe in A549 and H1299 cells.
| [Uses]
8-Chloroadenosine (cas# 34408-14-5) is a useful research chemical.8-Chloroadenosine is an analog of adenosine which depletes ATP and inhibits tumor growth in hematological malignancies as well as in lung and breast cancer cell lines. | [Biological Activity]
8-Chloroadenosine (8-Cl-Ado), an adenosine analog, is a potential antitumor drug that is currently in phase-I clinical trials for chronic lymphocytic leukemia (CLL). It has been reported that 8-Cl-Ado inhibits cancer cell growth and induces apoptosis in Granta, JeKo, Mino, and SP-53 MCL cell lines by inhibition of both DNA and RNA syntheses. In addition, 8-Cl-Ado induces autophagy in primary CLL cells5 and in MCF-7 and BT-474 breast cancer cells6. Research has shown that 8-Cl-Ado inhibits the proliferation and migration of SK-BR-3, MDA-MB-231, and MCF-7 breast cancer cells by targeting the RNA-editing enzyme ADAR1[1]. | [storage]
Store at -20°C | [References]
[1] Hong-Yue Ding. “8-Chloro-Adenosine Inhibits Proliferation of MDA-MB-231 and SK-BR-3 Breast Cancer Cells by Regulating ADAR1/p53 Signaling Pathway.” Cell Transplantation (2020): 963689720958656.
|
|
|