8-Chloroadenosine
- CAS NO.:34408-14-5
- Empirical Formula: C10H12ClN5O4
- Molecular Weight: 301.69
- MDL number: MFCD01076457
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-07-02 08:55:11
What is 8-Chloroadenosine ?
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.
The Uses of 8-Chloroadenosine
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.
What are the applications of Application
8-Chloroadenosine is a cytotoxic metabolite of 8-Cl-cAMP
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.
Properties of 8-Chloroadenosine
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. |
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 |
Safety information for 8-Chloroadenosine
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H302:Acute toxicity,oral H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H332:Acute toxicity,inhalation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P280:Wear protective gloves/protective clothing/eye protection/face protection. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for 8-Chloroadenosine
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 |
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