7-Deaza-2'-deoxy-7-iodoadenosine
[CAS# 166247-63-8]

Identification

• Classification: Biochemical >> Nucleoside drugs
• Name: 7-Deaza-2'-deoxy-7-iodoadenosine
• Synonyms: 7-(2-Deoxy-beta-D-erythro-pentofuranosyl)-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-4-amine
• Molecular Formula: C₁₁H₁₃IN₄O₃
• Molecular Weight: 376.15
• CAS Registry Number: 166247-63-8
• EC Number: 881-340-4
• SMILES: C1[C@@H]([C@H](O[C@H]1N2C=C(C3=C(N=CN=C32)N)I)CO)O

Properties

• Solubility: Very slightly soluble (0.71 g/L) (25 °C), Calc.^*
• Density: 2.35±0.1 g/cm³ (20 °C 760 Torr), Calc.^*
• Index of Refraction: 1.882, Calc.^*
• Boiling Point: 657.4±55.0 °C (760 mmHg), Calc.^*
• Flash Point: 351.4±31.5 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety 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
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

7-Deaza-2'-deoxy-7-iodoadenosine is a modified purine nucleoside that is structurally related to adenosine, a naturally occurring nucleoside involved in numerous biological processes, including energy transfer, signal transduction, and the regulation of blood flow. This compound has been utilized in the study of nucleoside analogs and their potential therapeutic applications, particularly in antiviral and anticancer research.

The modification of the purine ring structure, specifically the incorporation of a deaza group at the 7-position of the adenine base, enhances the pharmacological properties of the molecule by altering its interactions with enzymes involved in nucleic acid metabolism. The introduction of a 7-iodo group further enhances its stability and reactivity in biological systems, potentially improving its bioactivity in certain therapeutic contexts.

7-Deaza-2'-deoxy-7-iodoadenosine has been evaluated in the context of nucleoside analogs for the treatment of viral infections and cancer. The 2'-deoxy modification ensures that it is incorporated into DNA rather than RNA, making it particularly relevant in the development of antiviral therapies targeting DNA viruses. It may also exhibit properties that can be exploited in cancer treatment by interfering with DNA replication and repair mechanisms.

In experimental settings, 7-Deaza-2'-deoxy-7-iodoadenosine has been used to explore the mechanisms by which nucleoside analogs can inhibit viral replication and cellular division. Studies have shown that its incorporation into viral or cancer cell DNA can result in chain termination or mutagenic effects, making it a candidate for further investigation in drug development programs.

Given its modifications, 7-Deaza-2'-deoxy-7-iodoadenosine is also studied for its potential as a molecular probe to better understand purine metabolism and the interactions between nucleosides and cellular enzymes. However, while its chemical properties are well-characterized, clinical applications are limited at present, and it remains a compound primarily used in laboratory research.

In summary, 7-Deaza-2'-deoxy-7-iodoadenosine is a useful chemical entity in the development of nucleoside analog-based therapies, with potential applications in antiviral and anticancer treatments, although further research and clinical trials are needed to fully establish its therapeutic efficacy.

References

2016. New small molecule inhibitors of histone methyl transferase DOT1L with a nitrile as a non-traditional replacement for heavy halogen atoms. Bioorganic & Medicinal Chemistry Letters, 26(18).
DOI: 10.1016/j.bmcl.2016.07.041