8-Bromoadenosine
[CAS# 2946-39-6]

Identification

• Classification: Biochemical >> Nucleoside drugs >> Nucleoside intermediate
• Name: 8-Bromoadenosine
• Synonyms: (2R,3R,4S,5R)-2-(6-amino-8-bromopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• Protein Sequence: N
• Molecular Formula: C₁₀H₁₂BrN₅O₄
• Molecular Weight: 346.14
• CAS Registry Number: 2946-39-6
• EC Number: 220-959-0
• SMILES: C1=NC(=C2C(=N1)N(C(=N2)Br)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N

Properties

• Density: 2.5±0.1 g/cm³, Calc.^*
• Melting point: 210 � 212 ºC (decomp.) (Expl.)
• Index of Refraction: 1.941, Calc.^*
• Boiling Point: 717.7±70.0 ºC (760 mmHg), Calc.^*
• Flash Point: 387.8±35.7 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

8-Bromoadenosine is a synthetic analog of adenosine, a purine nucleoside that plays crucial roles in cellular processes, including energy transfer, signal transduction, and regulation of various metabolic pathways. The chemical formula for 8-bromoadenosine is C10H12BrN5O3, and it is characterized by the bromine atom substituted at the 8-position of the adenine ring.

The discovery of 8-bromoadenosine arose from the ongoing study of nucleoside analogs and their potential applications in biological research. These analogs are often used to investigate the roles of purine nucleosides in various biological systems, as they can mimic or inhibit the action of natural nucleosides while offering modified chemical structures that may yield unique pharmacological properties. The introduction of halogen substituents, like the bromine in 8-bromoadenosine, is a common strategy to alter the reactivity and biological activity of the parent molecule.

8-Bromoadenosine is primarily used in biochemical and pharmacological studies to explore the effects of purine nucleosides on cellular processes. It has been shown to act as a substrate for enzymes that interact with adenosine, such as adenosine deaminase, and is used in research investigating the metabolic pathways involving adenosine. The modification of the adenosine molecule with a bromine atom at the 8-position can affect the binding properties and enzymatic processing, making it a useful tool for studying purine metabolism and signaling.

One notable application of 8-bromoadenosine is its use in the study of adenosine receptors. Adenosine receptors are involved in a wide range of physiological processes, including neurotransmission, immune response, and cardiovascular function. By utilizing 8-bromoadenosine, researchers can probe the interactions between adenosine and its receptors, particularly in understanding the binding affinities of various adenosine receptor subtypes. This has implications for drug development, particularly in targeting adenosine receptors for the treatment of conditions like asthma, chronic pain, and neurological disorders.

Additionally, 8-bromoadenosine is used in studies that aim to understand the role of purine nucleosides in DNA and RNA synthesis. The compound can be incorporated into cellular DNA or RNA, allowing researchers to study its effects on nucleic acid metabolism and the potential for introducing modifications into genetic material. This application is particularly useful in the context of cancer research, where understanding the impact of nucleoside analogs on DNA replication and repair can help develop new therapeutic strategies.

In conclusion, 8-bromoadenosine is a synthetic purine nucleoside analog that has found significant use in biochemical and pharmacological research. Its applications in studying adenosine receptor interactions, purine metabolism, and nucleic acid synthesis have made it a valuable tool in understanding cellular processes. By modifying the natural adenosine structure with a bromine atom at the 8-position, 8-bromoadenosine provides a means to investigate the specific biological roles of adenosine and its derivatives.

References

1971. Synthesis of 8-bromoadenosine 5'-(α-D-glucopyranosyl diphosphate). Bulletin of the Academy of Sciences of the USSR, Division of chemical science, 20(6).
DOI: 10.1007/bf00855377

2020. Monitoring of uncaging processes by designing photolytical reactions. Photochemical & photobiological sciences: Official journal of the European Photochemistry Association and the European Society for Photobiology, 19(10).
DOI: 10.1039/d0pp00169d

2022. Different Mechanisms of DNA Radiosensitization by 8-Bromoadenosine and 2'-Deoxy-2'-fluorocytidine Observed on DNA Origami Nanoframe Supports. The Journal of Physical Chemistry Letters, 13(16).
DOI: 10.1021/acs.jpclett.2c00584