Product name: Deoxycytidine
Synonym name: Deoxyribose cytidine;Cytosine deoxyribonucleoside; Cytosine deoxyriboside
Catalogue No.: BP4233
Cas No.: 951-77-9
Formula: C9H13N3O4
Mol Weight: 227.22
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℃
110.6000
-1.7199
-1.7204
14.1122
.5195
.9400
High
12.8507
3.5062
Yes
Yes
No
No
Yes
No
0.9
No
Yes
Yes
No
2'-Deoxycytidine (CAS No. 951-77-9) is an important pyrimidine 2'-deoxyribonucleoside with cytosine as a nucleobase in its structure. As one of the fundamental building blocks of DNA synthesis, 2'-deoxycytidine plays a key role in nucleic acid metabolism, biosynthesis, and maintenance of cellular function. It is widely present in various organisms, including mice, Saccharomyces cerevisiae, E. coli, and humans, demonstrating its importance in the metabolic networks of different species. In recent years, with the deepening of research on nucleic acid drugs and antitumor drugs, the pharmacological characteristics and mechanisms of 2'-deoxycytidine and its derivatives have gradually become research hotspots in the field of natural product pharmacology.
This paper aims to systematically review the chemical structure and physicochemical properties of 2'-deoxycytidine, plant origin and extraction methods, pharmacological activity and mechanism of action, druggability evaluation and pharmacokinetic characteristics, and to look forward to its potential for clinical application. By integrating the latest research progress, it strives to provide comprehensive and in-depth reference materials for researchers in related fields.
The molecular formula of 2'-deoxycytidine is C9H13N3O4, with a molecular weight of 227.2200. Its structure consists of a cytosine nucleobase connected to 2'-deoxyribose via β-N1-glycosidic bonds. Unlike cytidine, the ribose ring of 2'-deoxycytidine lacks a hydroxyl group at the 2' position, giving it unique chemical stability and bioactivity.
In terms of physicochemical properties, the LogP value of 2'-deoxycytidine was -1.7199, indicating strong hydrophilicity and easy solubility in water (about 14.1122 mg/mL). Its polar surface area (TPSA) is 110.6 Ų, indicating that the molecule has high polarity and hydrogen bond donor/acceptor capacity, which is beneficial for binding to biomacromolecules. The high permeability of the blood-brain barrier suggests it may cross the central nervous system barrier and has potential neuropharmacological applications. The hERG inhibitory test result was negative, indicating a low risk of cardiotoxicity; The Ames test value was 0.9, indicating a relatively low genotoxicity risk.
2'-Deoxycytidine mainly exists as a nucleic acid metabolite in various organisms, with low levels found in natural plants and usually obtained through biosynthetic pathways. Its main sources include plant tissues rich in nucleic acids and microbial fermentation products. Traditional extraction methods mostly rely on nucleic acid hydrolysis, combining enzymatic hydrolysis or acid-base hydrolysis to degrade nucleic acids into monomer nucleosides, which are then purified and separated by high-performance liquid chromatography (HPLC).
In recent years, with the development of biotechnology, microbial fermentation has become an effective method for obtaining high-purity 2'-deoxycytidine. By genetically modifying microorganisms such as Saccharomyces cerevisiae and E. coli to enhance their nucleoside biosynthesis capacity, large-scale production is achieved. In addition, the application of modern separation technologies such as supercritical fluid extraction and membrane separation has also significantly improved extraction efficiency and purity.
As a precursor for DNA synthesis, 2'-deoxycytidine mainly exhibits pharmacological activity in regulating cell proliferation, gene expression, and metabolic homeostasis. In antitumor research, derivatives of 2'-deoxycytidine, such as cytarabine, are widely used in the treatment of leukemia and lymphoma, demonstrating significant cytotoxicity and antiproliferative effects.
Basic research shows that 2'-deoxycytidine itself is involved in DNA repair and replication, and can influence the course of the cell cycle. Its abnormal metabolic pathways in tumor cells have become an important entry point for targeted therapy. In addition, the potential role of 2'-deoxycytidine in immune regulation and neuroprotection is gradually being revealed. For example, in certain neurodegenerative disease models, metabolic abnormalities of 2'-deoxycytidine are associated with pathological progression, suggesting it may serve as a biomarker or therapeutic target.
The main mechanism of action of 2'-deoxycytidine involves its role as a substrate for DNA synthesis in nucleic acid metabolism. Within cells, it is phosphorylated by nucleoside kinase to 2'-deoxycytidine monophosphate (dCMP), which is further converted into diphosphate and triphosphate forms for DNA polymerase synthesis. This process is regulated by various enzymes, including deoxynucleotide kinase, nucleotide kinase, and nucleotide reductase.
Additionally, 2'-deoxycytidine and its metabolites can regulate DNA methylation status and influence gene expression regulation. Its role in cell signaling is also gradually being recognized, especially in regulating apoptosis and stress responses. Molecular targets mainly include DNA polymerase, nucleotide metabolases, and related regulatory proteins.
In the antitumor mechanism, derivatives of 2'-deoxycytidine incorporate DNA strands, induce chain termination and DNA damage, and activate the cell apoptosis pathway. Additionally, its inhibitory effect on DNA repair enzymes enhances tumor cells' sensitivity to chemotherapy drugs.
From the perspective of druggability parameters, 2'-deoxycytidine has good water solubility and low lipid solubility (LogP -1.7199), which is beneficial for oral absorption and internal distribution. Its higher polar surface area (TPSA 110.6) helps bind enzymes and receptors but may limit its transmembrane diffusion rate.
High blood-brain barrier permeability suggests its potential application value in central nervous system diseases. Negative hERG channel suppression indicates better cardiac safety and reduced risk of arrhythmias. Ames test results showed low genotoxicity and met drug safety requirements.
Pharmacokinetics, 2'-deoxycytidine is mainly metabolized in the body through nucleoside kinase-mediated phosphorylation, has a short half-life, and requires optimized administration or structural modification to improve stability and bioavailability. Its metabolites and excretion pathways are clearly defined, which is beneficial for clinical dose adjustment and toxicological monitoring.
As a key intermediate in nucleic acid metabolism, 2'-deoxycytidine has mature applications in anti-tumor and antiviral fields, with huge future development potential. Due to its excellent druggability and safety, 2'-deoxycytidine bulks and their structurally modified derivatives are expected to play a greater role in precision medicine, gene therapy, and neurological disease treatment.
With advances in nucleic acid drug technology, the design of nucleoside analogs related to 2'-deoxycytidine will become more diverse, with significantly improved targeting and selectivity. In addition, the combined application of immunotherapy and nanocarrier delivery technology will broaden its clinical indications and improve treatment efficacy.
Future research should focus on deeply elucidating the molecular mechanisms of 2'-deoxycytidine, optimizing its pharmacokinetic characteristics, and exploring its potential value in central nervous system diseases and immune regulation. At the same time, it strengthens its safety evaluation and clinical translational research to promote its smooth transition from basic research to clinical application.
2'-Deoxycytidine, as a fundamental and key pyrimidine 2'-deoxyribonucleoside, plays an irreplaceable role in living organisms. Its unique chemical structure and physicochemical properties endow it with a wide range of biological functions and pharmacological activities. Through a systematic review of its pharmacological mechanisms, druggability, and clinical application prospects, this paper provides important references for the field of natural product pharmacology.
In the future, with continuous advances in biotechnology and medicinal chemistry, 2'-deoxycytidine and its derivatives will show broader application prospects in disease treatment and precision medicine, driving the pharmacology of natural products to deeper levels.
