8-Chloroadenosine Chemical Properties

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

pka

12.90±0.70(Predicted)

form 

Crystalline solid.

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

8-Chloroadenosine Usage And Synthesis

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.

8-Chloroadenosine (34408-14-5)Related Product Information

• 2-Chloroadenosine
• 8-Chloroadenosine
• 2'-Deoxy-2-chloroadenosine
• 2-CHLOROADENOSINE HEMIHYDRATE,2-CHLOROADENOSINE HEMIDYDRATE
• 6-Deamino-6-chloroadenosine
• 6-CHLOROADENOSINE
• 8-CHLOROADENOSINE-5'-O-MONOPHOSPHATE SODIUM SALT,8-chloroadenosine-5’-monophosphate(8-cl-5’-amp),freeaci
• 8-CHLOROADENOSINE-5'-O-TRIPHOSPHATE SODIUM SALT,8-chloroadenosine-5’-triphosphate(8-cl-atp),sodiumsal
• 8-CHLOROADENOSINE-3',5'-CYCLIC MONOPHOSPHOROTHIOATE, SP-ISOMER SODIUM SALT
• 8-CHLOROADENOSINE-3',5'-CYCLIC MONOPHOSPHOROTHIOATE, RP-ISOMER SODIUM SALT
• 8-CHLORO-CAMP
• N-Cyclopentyl-2-chloroadenosine
• 2-CHLOROADENOSINE-3',5'-CYCLIC MONOPHOSPHATE SODIUM SALT,2-chloroadenosine-3’,5’-cyclicmonophosphate,sodiumsalt(2-cl-camp
• 2-Chloroadenosine 5’-Monophosphate
• 2-CHLOROADENOSINE, [8-14C]-
• 5'-Deoxy-5'-chloroadenosine
• (+)-5'-O-[[(S)-2-Amino-1-oxopropyl]aminosulfonyl]-2-chloroadenosine
• DIINOSINE PENTAPHOSPHATE