Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
119.3100
-.6325
-.6324
7.0545
.7919
.6533
High
28.7920
3.4842
No
Yes
No
No
Yes
No
1.2
Yes
No
Yes
No
2'-Deoxyadenosine monohydrate (CAS No.: 16373-93-6), as an important nucleoside natural product, holds broad research value in the fields of life sciences and pharmacology. As one of the fundamental building blocks of DNA, 2'-deoxyadenosine not only plays a key role in the storage and transmission of genetic information, but its derivatives and metabolites also exhibit significant biological activity across various biological processes. In recent years, with the deepening development of natural product pharmacology, the pharmacological effects, molecular mechanisms, and potential clinical applications of 2'-deoxyadenosine have gradually become research hotspots.
This review aims to systematically summarize the chemical structure and physicochemical properties, plant origin and extraction methods, pharmacological activity, and mechanism of action of 2'-deoxyadenosine monohydrate. Combining its druggability parameters and pharmacokinetic characteristics, it explores its application prospects in the treatment of related diseases, striving to provide theoretical support and research ideas for subsequent basic research and clinical translation.
The molecular formula of 2'-deoxyadenosine monohydrate is C10H13N5O3, with a molecular weight of 251.2460. Its structure is formed by the adenine base and 2'-deoxyribose bonded by β-N9 glycosidic bonds, forming a typical deoxynucleoside structure. Compared to ribose, the hydroxyl group at the 2' position is replaced by hydrogen, giving it greater chemical stability and specific biological functions.
In terms of physicochemical properties, the LogP value of 2'-deoxyadenosine monohydrate is -0.6325, indicating strong hydrophilicity, readily soluble in water (solubility about 7.0545 mg/mL), which is beneficial for absorption and distribution in the body. Its topological pole surface area (TPSA) is 119.3100 Ų, reflecting the molecule's presence of many polar groups, which may affect membrane permeability. Notably, this compound has a high blood-brain barrier penetration capability, suggesting potential advantages in the treatment of central nervous system diseases. Additionally, 2'-deoxyadenosine monohydrate did not exhibit hERG channel inhibitory activity, reducing the risk of cardiotoxicity; The Ames test result was 1.2, indicating low mutagenicity and good safety.
2'-Deoxyadenosine is a nucleoside compound widely present in the nuclei of various plants, especially in nucleic acid-rich plant tissues such as seeds, buds, and leaves. Common plants rich in 2'-deoxyadenosine include taxus spp., ginkgo biloba, and certain medicinal herbs.
The extraction method is mainly based on the crushing and extraction of plant tissues, with commonly used steps including:
In recent years, the application of emerging technologies such as ultrasound-assisted extraction and microwave-assisted extraction has significantly improved extraction efficiency and purity, providing technical support for large-scale preparation.
As a nucleoside compound, 2'-deoxyadenosine mainly exhibits pharmacological activity in regulating cellular metabolism, participating in DNA repair, and modulating immune responses. Numerous in vitro and in vivo studies have revealed its potential therapeutic effects across various disease models.
Anticancer activity: 2'-deoxyadenosine induces cancer cell apoptosis and inhibits tumor cell proliferation by interfering with DNA synthesis and repair processes. Some studies have shown that it can enhance the sensitivity of chemotherapy drugs and has synergistic anti-cancer effects.
Immune regulation: As an important substrate for immune cell metabolism, 2'-deoxyadenosine affects lymphocyte proliferation and differentiation, modulates inflammatory responses, and exhibits certain anti-inflammatory and immunomodulatory activities.
Neuroprotective effect: Its good blood-brain barrier penetration allows it to demonstrate potential neuroprotective effects in neurodegenerative diseases, possibly by regulating neuronal energy metabolism and reducing oxidative stress.
Antiviral activity: Some studies have shown that 2'-deoxyadenosine and its derivatives can inhibit viral nucleic acid synthesis and block viral replication, especially showing inhibitory effects in certain DNA virus infections.
The biological effects of 2'-deoxyadenosine mainly depend on its intracellular metabolic transformation and interactions with molecular targets. Its mechanisms of action include:
Nucleoside metabolism regulation: 2'-deoxyadenosine acts as a precursor to deoxynucleotides, participating in DNA synthesis and repair, influencing the cell cycle progression. Its metabolites regulate nucleotide pool balance, affecting cell proliferation and apoptosis.
Substrate competition between DNA polymerase and nuclease: By binding to DNA polymerase, 2'-deoxyadenosine can competitively inhibit DNA synthesis, causing DNA strand termination and inducing cell death.
Regulating cellular signaling pathways: 2'-Deoxyadenosine and its metabolites can affect various signaling pathways, such as MAPK and PI3K/Akt, regulating cell survival, proliferation, and metabolism.
Immune regulatory targets: By modulating the metabolic activities of T cells and B cells, it influences immune cell activation and the release of inflammatory mediators.
Neuroprotective mechanisms: May reduce oxidative damage to nerve cells by regulating mitochondrial function and antioxidant enzyme activity, thereby protecting neuronal survival.
From a druggability perspective, 2'-deoxyadenosine monohydrate exhibits good drug properties. It has a moderate molecular weight and high water solubility, which is beneficial for oral absorption and internal distribution. A negative LogP value indicates its hydrophilicity, which is beneficial for dissolution and transport in the blood. Although a high TPSA value may limit cell membrane permeability, its high blood-brain barrier permeability suggests its potential application advantages in the central nervous system.
In terms of safety, 2'-deoxyadenosine does not inhibit hERG channels, reducing the risk of cardiotoxicity. Ames trial results show that it has low mutagenicity and good safety, making it suitable for further clinical development.
Pharmacokinetic studies show that 2'-deoxyadenosine is rapidly uptaken and metabolized by cells in the body, mainly converted into active nucleotides through nucleoside kinase-mediated phosphorylation pathways. Its half-life is moderate, and its metabolic products are mainly excreted by the kidneys. The high permeability of the blood-brain barrier allows it to reach effective concentrations in brain tissue, giving it potential for treating central nervous system diseases.
Based on its unique pharmacological activity and good druggability, 2'-deoxyadenosine monohydrate shows broad clinical application prospects across multiple fields:
Antitumor therapy: As an adjunct chemotherapy drug, 2'-deoxyadenosine can enhance the efficacy of traditional drugs and reduce the development of resistance. In the future, structural modification can improve selectivity and stability, enabling the development of novel anticancer drugs.
Neurodegenerative diseases: Its excellent blood-brain barrier penetration and neuroprotective effects give it potential application value in neurodegenerative diseases such as Alzheimer's and Parkinson's.
Immune regulation and anti-inflammation: In autoimmune diseases and chronic inflammation, 2'-deoxyadenosine may play a therapeutic role by modulating immune cell function.
Antiviral therapy: Although research on DNA virus infection is still in its early stages, its potential should not be overlooked. In the future, drug design may be combined to optimize antiviral activity.
Future research should focus on in-depth analysis of metabolic pathways in vivo, optimization of drug delivery systems, and systematic evaluation of clinical safety and efficacy. Additionally, structural modification and derivative development based on 2'-deoxyadenosine will provide more possibilities for its clinical translation.
As an important natural nucleoside compound, 2'-deoxyadenosine monohydrate demonstrates potential in multiple fields such as anti-cancer, neuroprotection, immune regulation, and antiviral properties due to its unique chemical structure and good pharmacological activity. Its excellent druggability parameters and safety provide a solid foundation for clinical development. In the future, through multidisciplinary interdisciplinary research, it is expected that 2'-deoxyadenosine and its derivatives will be further revealed, becoming a new generation of highly efficient and safe therapeutic drugs, benefiting a wide range of patients.
