8-Bromoadenosine

Names

[ Name ]:
8-Bromoadenosine

[Synonym ]:
8-Br-A
8-Bromoadenine-9-β-D-ribofuranoside
8-Bromoadenosine
(2R,3R,4S,5R)-2-(6-Amino-8-bromo-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
Adenosine, 8-bromo-
8-BROMO-D-ADENOSINE
6-AMINO-8-BROMOPURINE RIBOSIDE
8-bromo-adenosine
MFCD00005733
EINECS 220-959-0

Biological Activity

[Description]:

8-Bromoadenosine is an adenosine analog. Adenosine analogs mostly act as smooth muscle vasodilators and have also been shown to inhibit cancer progression. Its popular products are adenosine phosphate, Acadesine (HY-13417), Clofarabine (HY-A0005), Fludarabine phosphate (HY-B0028) and Vidarabine (HY-B0277)[1].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Cell Cycle/DNA Damage >> Nucleoside Antimetabolite/Analog

[References]

[1]. Man S, et al. Potential and promising anticancer drugs from adenosine and its analogs. Drug Discov Today. 2021 Jun;26(6):1490-1500.

Chemical & Physical Properties

[ Density]:
2.5±0.1 g/cm3

[ Boiling Point ]:
717.7±70.0 °C at 760 mmHg

[ Melting Point ]:
210-212 °C (dec.)(lit.)

[ Molecular Formula ]:
C₁₀H₁₂BrN₅O₄

[ Molecular Weight ]:
346.14

[ Flash Point ]:
387.8±35.7 °C

[ Exact Mass ]:
345.007263

[ PSA ]:
139.54000

[ LogP ]:
-0.30

[ Vapour Pressure ]:
0.0±2.4 mmHg at 25°C

[ Index of Refraction ]:
1.941

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36-S24/25-S22

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

Synthetic Route

Click to get detail synthetic route

Articles

PKA signaling drives mammary tumorigenesis through Src.

Oncogene 34(9) , 1160-73, (2015)

Protein kinase A (PKA) hyperactivation causes hereditary endocrine neoplasias; however, its role in sporadic epithelial cancers is unknown. Here, we show that heightened PKA activity in the mammary ep...

ADAM12-directed ectodomain shedding of E-cadherin potentiates trophoblast fusion.

Cell Death Differ. 22 , 1970-84, (2015)

Trophoblasts, placental cells of epithelial lineage, undergo extensive differentiation to form the cellular components of the placenta. Trophoblast progenitor cell differentiation into the multinuclea...

Prostaglandin E2 Inhibits NLRP3 Inflammasome Activation through EP4 Receptor and Intracellular Cyclic AMP in Human Macrophages.

J. Immunol. 194 , 5472-87, (2015)

PGE2 is a potent lipid mediator involved in maintaining homeostasis but also promotion of acute inflammation or immune suppression in chronic inflammation and cancer. Nucleotide-binding domain, leucin...