Product name: 2'-Desoxyuridine
Synonym name: Deoxyribose uracil; Deoxyuridine;Uracil deoxyriboside
Catalogue No.: BP4234
Cas No.: 951-78-0
Formula: C₉H₁₂N₂O₅
Mol Weight: 228.204
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℃

Introduction/Overview

2'-Deoxyuridine (2'-Desoxyuridine, abbreviated as dUrd) is a pyrimidine class of 2'-deoxyribonucleoside, structurally formed by the bond between a uracil base and 2'-deoxyribose via a β-N1-glycosidic bond. As an important intermediate in nucleic acid metabolism, 2'-deoxyuridine plays a key role in DNA synthesis and repair. It is metabolically active in various organisms, including mice, Saccharomyces cerevisiae, E. coli, and humans, demonstrating broad biological significance. In recent years, as nucleoside compounds have been increasingly applied in anti-tumor, antiviral, and gene therapy, the research value of 2'-deoxyuridine as a fundamental nucleoside structural unit has become increasingly prominent. This paper aims to systematically review the chemical structure and physicochemical properties, sources and extraction methods, pharmacological activity, mechanism of action, druggability evaluation, and clinical application prospects of 2'-deoxyuridine, hoping to provide reference and inspiration for research in related fields.

Chemical structure and physicochemical properties

The chemical formula of 2'-deoxyuridine is C9H12N2O5, with a molecular weight of 228.2040. Its structure consists of uracil bases and 2'-deoxyribose. Unlike uridine, it lacks a hydroxyl (-OH) group at the 2' position of its ribose ring, giving it higher chemical stability and different biological functions. The CAS number of this compound is 951-78-0.

In terms of physicochemical properties, 2'-deoxyuridine exhibits high water solubility (about 38.29 mg/mL), with a LogP value of -1.5163, indicating strong hydrophilicity, easily soluble in water but poorly soluble in fat-soluble solvents. The polar surface area (TPSA) is 104.55 Ų, reflecting its high molecular polarity, which has an important impact on its binding to biomacromolecules. The high penetration of the blood-brain barrier suggests that it may have certain biological activity in the central nervous system. Additionally, the hERG channel inhibition test results were negative, indicating a low risk of cardiotoxicity. The Ames test value was 1.8, indicating a low genotoxicity risk and good safety.

Plant Origins and Extraction Methods

2'-Deoxyuridine mainly exists as a nucleic acid metabolite in various organisms, and is not directly present in plants as a secondary metabolite in nature. Its main source is the degradation products of DNA within biological cells, or through biosynthetic pathways catalyzed by uridine through deoxidase.

Although 2'-deoxyuridine itself is not directly extracted from plants, it can be obtained through hydrolysis and purification steps in some nucleic acid-rich plant tissues. Common extraction methods include:

1. Cell or tissue hydrolysis: Hydrolyzing nucleic acids in plant cells under acidic or alkaline conditions, releasing nucleosides and their derivatives.
2. Solvent extraction: Extracting water-soluble nucleoside compounds using water or buffer.
3. Chromatographic purification: Extracts are separated and purified using high-performance liquid chromatography (HPLC), ion exchange chromatography, or affinity chromatography techniques to obtain high-purity 2'-deoxyuridine.

In addition, modern biotechnological methods such as microbial fermentation and enzymatic catalytic synthesis are widely used in the industrial production of 2'-deoxyuridine, especially in drug synthesis and nucleic acid research.

Pharmacological activity research

As a precursor and metabolic intermediate in DNA synthesis, 2'-deoxyuridine exhibits multiple pharmacological activities, mainly reflected in the following aspects:

1. Antitumor activity
   2'-Deoxyuridine itself is not a direct antitumor drug, but its metabolites and analogs play an important role in antitumor drug development. For example, 5-fluoro-2'-deoxyuridine (5-FdUrd) is a widely used anti-metabolic anticancer drug that inhibits tumor cell proliferation by incorporating DNA. Research into the metabolic pathway of 2'-deoxyuridine provides a theoretical basis for the design of such drugs.

2. Antiviral effects
   Nucleoside compounds are widely used in antiviral therapy. The structure of 2'-deoxyuridine provides a template for developing nucleoside analogs for designing inhibitors targeting viral DNA polymerase, thereby indirectly exerting antiviral effects.

3. DNA repair and gene stability
   2'-Deoxyuridine participates in base substitution and synthesis during DNA repair, maintaining genome stability. Metabolic abnormalities may lead to DNA damage accumulation, which in turn triggers hereditary diseases or cancer.

4. Neuroprotective effects
   Due to its good blood-brain barrier penetration, some studies have focused on the potential applications of 2'-deoxyuridine and its derivatives in neurological diseases, such as the treatment and neuroprotection of neurodegenerative diseases.

Mechanism of action and molecular targets

The biological function of 2'-deoxyuridine mainly depends on its role in nucleic acid metabolism, with specific mechanisms including:

1. Role in nucleotide metabolism pathways
   2'-Deoxyuridine is phosphorylated by nucleotide kinase to produce 2'-deoxyuridine monophosphate (dUMP), which is then converted to thymidine (dTMP) by thymidine synthase, providing the essential nucleotide for DNA synthesis. This process is crucial for cell proliferation and DNA repair.

2. Interactions with DNA polymerase
   As a precursor to DNA synthesis, the metabolites of 2'-deoxyuridine can be recognized by DNA polymerase and incorporated into DNA strands, affecting the accuracy of DNA replication and repair.

3. Regulates thymidine synthase (TS) activity
   The metabolite dUMP of 2'-deoxyuridine is the substrate of TS, which catalyzes the conversion of dUMP to dTMP, which is the only intracellular thymidine synthesis pathway. TS is a target for various antitumor drugs, and the metabolic state of 2'-deoxyuridine affects TS activity and drug sensitivity.

4. Involved in DNA damage responses
   During DNA damage repair, the metabolic regulation of 2'-deoxyuridine maintains base balance, prevents mutation accumulation, and ensures genome stability.

Druggability evaluation and pharmacokinetics

2'-Deoxyuridine has good druggability parameters:

• Moderate molecular weight (228.2040), compliant with Lipinski's rule, favorable for oral absorption.
• The LogP value was -1.5163, indicating strong hydrophilicity, which facilitates distribution and dissolution in the body.
• TPSA is 104.55 Ų, suitable for cell membrane penetration, especially due to its high blood-brain barrier penetration, suggesting its potential for central nervous system diseases.
• No hERG channel suppression, reducing the risk of cardiotoxicity.
• Ames test value is 1.8, indicating low genotoxicity and good safety.

Pharmacokinetics, 2'-deoxyuridine is mainly metabolized in the body through nucleotide kinases and nucleotide metabolizers, with a fast half-life and good bioavailability. Its water solubility and polarity make it widely distributed in the blood, but its high metabolic rate limits its use as a drug alone. Through structural modification and drug carrier technology, its stability and targeting ability can be improved.

Prospects and outlooks for clinical applications

Although 2'-deoxyuridine itself has not yet been widely used as a standalone drug, as a nucleoside metabolic center molecule, it holds significant clinical potential in multiple fields:

1. The foundation of anti-tumor drug development
   The metabolic pathway of 2'-deoxyuridine provides a theoretical basis for the design of antimetabolic drugs, especially in the design of thymidine synthase inhibitors and DNA-incorporated drugs.

2. Gene therapy and nucleic acid drug carriers
   As a nucleoside structural unit, 2'-deoxyuridine holds significant value in the synthesis and modification of nucleic acid drugs and is expected to be used in emerging therapeutic technologies such as gene editing and RNA interference.

3. Treatment of neurological diseases
   Its excellent blood-brain barrier penetration makes it and its derivatives promising for neuroprotection and the treatment of neurodegenerative diseases.

4. Biomarkers and metabolic monitoring
   Changes in the concentration of 2'-deoxyuridine and its metabolites in vivo can serve as markers of abnormal DNA metabolism, used for the diagnosis and efficacy monitoring of cancer, genetic diseases, and metabolic diseases.

Future research should focus on structural optimization, pharmacokinetic improvements, and targeted delivery technology development for 2'-deoxyuridine to enhance its clinical value. At the same time, in-depth analysis of its mechanisms in cellular metabolic networks will drive innovative development of nucleoside drugs.

Conclusion

2'-Deoxyuridine, as a pyrimidine 2'-deoxyribonucleoside, plays an irreplaceable role in nucleic acid metabolism and cell biology. Its excellent physicochemical properties and biological activity make it an important foundation for the development of nucleoside drugs. Although it is not yet widely used as a standalone drug, in-depth research into its metabolic pathways and mechanisms of action provides valuable theoretical and practical foundations for fields such as anti-tumor, antiviral, and neuroprotective treatments. In the future, with the development of biotechnology and medicinal chemistry, 2'-deoxyuridine and its derivatives are expected to play a greater role in clinical treatment and become an important component of the new generation of nucleoside drugs.