+86-28-82633987
Product name: 2'-Deoxyguanosine monohydrate
Synonym name:
Catalogue No.: BP4232
Cas No.: 312693-72-4
Formula: C10H13N5O4
Mol Weight: 267.245
Botanical Source:
Type of Compound:
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Storage: Store in a well closed container, protected from air and light. Put into refrigerate or freeze for long term storage.
Whenever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20℃. Generally, these will be useable for up to two weeks.
The product could be supplied from milligrams to grams
Inquire for bulk scale.
For Reference Standard and R&D, Not for Human Use Directly.
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
139.2800
-1.4000
-1.4100
2.3500
.4300
.3100
Low
18.0800
3.6700
Yes
Yes
No
No
Yes
No
1.2
Yes
No
Yes
No
2'-Deoxyguanosine monohydrate (hereinafter referred to as 2'-dG), as an important nucleoside natural product, is widely found in the DNA molecules of organisms and plays a central role in the storage and transmission of genetic information. As a key component of deoxynucleosides, 2'-dG not only participates in nucleic acid construction but also plays an important role in cellular metabolism, signal transduction, and repair mechanisms. In recent years, with the rapid development of natural product pharmacology, 2'-dG, due to its unique chemical structure and biological activity, has gradually become a research hotspot, especially showing potential application value in anti-tumor, antiviral, and neuroprotective fields.
This review aims to systematically summarize the chemical structure and physicochemical properties of 2'-dG, plant origin and extraction methods, pharmacological activity and mechanism of action. Combining druggability parameters and pharmacokinetic characteristics, it explores the prospects and challenges of its clinical application, providing theoretical foundation and practical guidance for related research.
The chemical formula of 2'-deoxyguanosine monohydrate is C10H13N5O4· H2O, with a molecular weight of 267.24. Its core structure is formed by the connection of guanine bases and deoxyribose via β-N9 glycosidic bonds, and the hydrated form contains a molecule of crystalline water. In terms of molecular structure, the guanine ring is a nitrogen-containing heterocyclic structure with multiple hydrogen bond donors and acceptors, giving it strong polarity and hydrophilicity.
In terms of physicochemical properties, the LogP value of 2'-dG is -1.4, indicating strong hydrophilicity, with a water solubility of 2.35 mg/mL, making it suitable for biological utilization in aqueous phase systems. Its topological pole surface area (TPSA) is 139.28 Ų, indicating high molecular polarity, which affects membrane permeability and pharmacokinetic behavior. The blood-brain barrier has low permeability, suggesting its direct role in the central nervous system is limited. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. The Ames test value was 1.2, indicating a low genotoxicity risk and a solid safety foundation.
2'-Deoxyguanosine, as a nucleoside compound, is mainly found in the DNA of various organisms, with lower levels found in natural plants and usually obtained through biosynthetic pathways. Some plant tissues with high nucleotide content, such as certain seeds, spores, and young leaves, can contain trace amounts of 2'-dG. Since it mainly exists in a bound state within plants, direct extraction is quite difficult.
Common extraction methods include:
Currently, 2'-dG is mostly prepared industrially by chemical or biosynthetic methods to meet research and pharmaceutical needs.
As the basic nucleoside unit, 2'-deoxyguanosine itself performs various biological functions in the body. In recent years, research on its pharmacological activity has become increasingly in-depth, mainly focusing on the following aspects:
2'-dG acts as a precursor to DNA synthesis and participates in the cell proliferation process. Research has found that 2'-dG and its derivatives can influence tumor cell proliferation and apoptosis by regulating DNA synthesis and repair mechanisms. For example, 2'-dG can be replaced by certain nucleoside analogs, inducing DNA damage and promoting tumor cell apoptosis. Additionally, 2'-dG serves as a precursor molecule in certain drug designs, participating in the synthesis of antitumor drugs.
Nucleoside compounds are an important category of antiviral drugs. 2'-dG, as the deoxy form of guanine nucleoside, plays a key role in viral DNA synthesis. Related studies have shown that derivatives of 2'-dG can inhibit viral DNA polymerase activity and block viral replication, showing particular potential value in the treatment of DNA viruses such as herpes virus and hepatitis B virus.
Although 2'-dG itself has relatively low blood-brain barrier permeability, it plays a fundamental role in neuronal DNA repair and metabolism. Some studies show that 2'-dG and its metabolites can regulate oxidative stress responses in nerve cells, reduce nerve damage, and possess certain neuroprotective potential.
2'-dG participates in nucleic acid metabolism and affects the proliferation and function of immune cells. Its metabolites can regulate T cell activity and inflammatory responses, suggesting its potential application value in immunomodulation.
The biological effects of 2'-deoxyguanosine are mainly realized through the nucleic acid metabolic pathways in which it participates. Its key mechanisms include:
2'-dG, as an essential nucleoside for DNA synthesis, participates in the extension of DNA strands. It is catalyzed by deoxynucleoside kinase to 2'-deoxyguanosine triphosphate (dGTP), serving as the substrate for DNA polymerase and participating in DNA replication and repair processes. The balance of dGTP is crucial for cell cycle regulation and genomic stability.
2'-dG and its metabolites can regulate intracellular signaling pathways, such as controlling cell proliferation, differentiation, and apoptosis-related signaling molecules by affecting guanine nucleotide circulation. Additionally, changes in dGTP levels can affect cellular energy metabolism and redox status.
2'-dG-derived nucleoside analogs competitively inhibit viral DNA polymerase, blocking viral replication. Some nucleoside analogs can be incorporated into viral DNA strands, causing chain termination and exerting antiviral effects.
2'-dG and its metabolites influence immune responses by modulating nucleic acid receptors (such as the cGAS-STING pathway), modulating inflammatory factor expression, and participating in immune surveillance and anti-infective responses.
The druggability parameters of 2'-deoxyguanosine indicate that it has certain potential for drug development:
Pharmacokinetics, 2'-dG mainly enters cells via nucleoside transporters in the body, is then phosphorylated by deoxynucleoside kinases, and enters the nucleotide pool. Its metabolic pathways include deamination, methylation, and nucleotide degradation, ultimately excreted in urine. Due to its hydrophilicity and high polarity, oral bioavailability is limited, requiring improved delivery systems or derivative designs to enhance in vivo stability and targeting.
As a basic nucleoside unit, 2'-deoxyguanosine is not directly and widely used as a clinical drug, but it holds significant value in drug design and biomedical research. The future clinical application prospects are mainly reflected in the following aspects:
Nucleoside analogs based on the 2'-dG structure have become the foundation for various antitumor drugs. By improving its selectivity and cell uptake efficiency through structural modification, it is expected to develop novel, highly effective, and low-toxicity anticancer drugs.
2'-dG derivatives hold an important position in antiviral drugs, especially targeting DNA viruses. In the future, optimizing its pharmacokinetic properties can enhance antiviral activity and resistance, expanding clinical indications.
Although the intrinsic blood-brain barrier permeability of 2'-dG is limited, through nanocarrier or prodrug design, effective delivery to the central nervous system is expected to exert neuroprotective effects and promote neural repair.
The role of 2'-dG and its metabolites in immune regulation is gradually being recognized, and future therapeutic strategies for autoimmune diseases and chronic inflammation may be developed.
Changes in the content of 2'-dG and its metabolites are associated with various disease states and have potential as disease biomarkers, assisting in disease diagnosis and efficacy monitoring.
2'-Deoxyguanosine monohydrate, as a typical representative of nucleoside natural products, has a unique chemical structure and diverse biological functions. Its core role in DNA synthesis, repair, signal transduction, and immune regulation makes it an important target for pharmacological research and new drug development. Although it is still in the exploratory stage of clinical application, derivatives based on the 2'-dG structure have shown broad application prospects.
Future research should focus on deeply elucidating the molecular mechanisms of 2'-dG, optimizing its pharmacokinetic properties, developing highly efficient and safe derivatives and delivery systems, and promoting its clinical translation in anti-tumor, antiviral, neuroprotection, and immunomodulatory fields. Combining modern biotechnology and drug design concepts, 2'-dG is expected to become another important breakthrough in the field of natural product pharmacology.
Shenshuai
Wenjing
Hedandan
