Buy 8-Chloroadenosine (BT-257340)

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8-Chloroadenosine

Catalog Number: BT-257340

CAS Number: 34408-14-5

Molecular Formula: C10H12ClN5O4

Molecular Weight: 301.69 g/mol

The product is for non-human research only. Not for therapeutic or veterinary use.

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Product Introduction

Description

8-Chloroadenosine is a chemical compound that belongs to the class of purine nucleosides. It is a modified form of adenosine, where the hydrogen atom at the 8th position of the purine ring is replaced by a chlorine atom. This modification alters the chemical and biological properties of adenosine, making 8-chloroadenosine a potent and selective agonist of the A1 adenosine receptor.

Properties

CAS Number

34408-14-5

Product Name

8-Chloroadenosine

IUPAC Name

(2R,3R,4S,5R)-2-(6-amino-8-chloropurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

Molecular Formula

C10H12ClN5O4

Molecular Weight

301.69 g/mol

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

InChI Key

MHDPPLULTMGBSI-UUOKFMHZSA-N

SMILES

C1=NC(=C2C(=N1)N(C(=N2)Cl)C3C(C(C(O3)CO)O)O)N

Solubility

Soluble in DMSO

Synonyms

8-Chloroadenosine; 8 Chloroadenosine; 8Chloroadenosine; NSC-354258; NSC 354258; NSC354258; 8-Cl-Ado; 8 Cl Ado; 8ClAdo

Canonical SMILES

C1=NC(=C2C(=N1)N(C(=N2)Cl)C3C(C(C(O3)CO)O)O)N

Isomeric SMILES

C1=NC(=C2C(=N1)N(C(=N2)Cl)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N

Method of Synthesis or Extraction

8-Chloroadenosine can be synthesized by several methods, including chlorination of adenosine, nucleophilic substitution of 8-bromo-adenosine, and direct synthesis from 8-chloroguanosine. The efficiency and yield of each method depend on the starting material, reaction conditions, and purification methods. Chlorination of adenosine is the most commonly used method, but it requires harsh conditions and produces low yields. Nucleophilic substitution of 8-bromo-adenosine is a milder method that yields higher purity and yields. Direct synthesis from 8-chloroguanosine is a more efficient method, but it requires specialized reagents and equipment. Environmental and safety considerations should be taken into account during the synthesis and handling of 8-chloroadenosine, as it is a hazardous and toxic substance.

Chemical Structure and Biological Activity

The chemical structure of 8-chloroadenosine consists of a purine ring, a ribose sugar, and a chlorine atom at the 8th position of the purine ring. The presence of the chlorine atom alters the electronic properties of the purine ring, making it more hydrophobic and less basic than adenosine. 8-Chloroadenosine selectively binds to the A1 adenosine receptor, a G protein-coupled receptor that is widely distributed in the brain, heart, and other organs. Binding of 8-chloroadenosine to the A1 receptor activates a signaling cascade that leads to inhibition of adenylate cyclase, reduction of cAMP levels, and modulation of ion channels and neurotransmitter release. The potency of 8-chloroadenosine as an A1 receptor agonist is higher than that of adenosine, making it a useful tool for studying the physiological and pathological roles of the A1 receptor.

Biological Effects

The biological effects of 8-chloroadenosine depend on the cell type, receptor expression, and concentration of the compound. In general, activation of the A1 receptor by 8-chloroadenosine leads to inhibition of neuronal excitability, reduction of heart rate and contractility, and modulation of immune and inflammatory responses. 8-Chloroadenosine has been shown to have potential therapeutic effects in various diseases, such as ischemia-reperfusion injury, epilepsy, pain, and inflammation. However, it also has potential toxic effects, such as induction of apoptosis, inhibition of cell proliferation, and disruption of mitochondrial function. The balance between the therapeutic and toxic effects of 8-chloroadenosine depends on the dose, duration, and route of administration, and should be carefully evaluated in preclinical and clinical studies.

Applications

8-Chloroadenosine has various applications in medical, environmental, and industrial research. In medical research, it is used as a tool compound to study the A1 receptor and its role in physiology and pathology. It is also being investigated as a potential therapeutic agent for various diseases, such as ischemic heart disease, epilepsy, and pain. In environmental research, 8-chloroadenosine is used as a marker for pollution and environmental contamination, as it is a metabolite of some pesticides and herbicides. It is also being studied for its potential role in pollution management and sustainability, as it can be used as a bioremediation agent for contaminated soils and water. In industrial research, 8-chloroadenosine is used as a starting material for the synthesis of other purine nucleosides and analogs, which have various applications in pharmaceuticals, agrochemicals, and materials science. Health and safety considerations should be taken into account during the handling and disposal of 8-chloroadenosine, as it is a hazardous and toxic substance.

Future Perspectives and Challenges

The use and study of 8-chloroadenosine face several limitations and challenges, such as its low solubility, stability, and bioavailability, as well as its potential toxic effects. Possible solutions and improvements include the development of more efficient and selective synthesis methods, the design of novel analogs with improved pharmacokinetic and pharmacodynamic properties, and the identification of new biological targets and pathways for 8-chloroadenosine. Future trends and prospects in the application of 8-chloroadenosine in scientific research include the integration of multidisciplinary approaches, such as computational modeling, high-throughput screening, and systems biology, to accelerate drug discovery and development.

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