5-Iodo-2'-deoxycytidine
[CAS# 611-53-0]

Identification

• Classification: Biochemical >> Nucleoside drugs >> Deoxynucleotides and their analogues
• Name: 5-Iodo-2'-deoxycytidine
• Synonyms: 4-Amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidin-2-one; 5-IdC
• Molecular Formula: C₉H₁₂IN₃O₄
• Molecular Weight: 353.11
• CAS Registry Number: 611-53-0
• EC Number: 210-269-8
• SMILES: C1[C@@H]([C@H](O[C@H]1N2C=C(C(=NC2=O)N)I)CO)O

Properties

• Density: 2.4±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.815, Calc.^*
• Boiling Point: 522.1±60.0 °C (760 mmHg), Calc.^*
• Flash Point: 269.6±32.9 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302
• Safety Statements: P264-P270-P301+P317-P330-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

5-Iodo-2'-deoxycytidine is a synthetic nucleoside analog primarily used in molecular biology and medicinal chemistry. It is a derivative of 2'-deoxycytidine, where the hydrogen atom at the 5-position of the pyrimidine ring is replaced with an iodine atom. This modification allows it to interfere with DNA synthesis and replication processes, making it useful in various applications.

The synthesis of 5-iodo-2'-deoxycytidine was first reported in the early 1970s. As a nucleoside analog, it was designed to explore the potential of halogenated compounds in inhibiting viral replication and cell proliferation, particularly in cancer therapy. It is closely related to other halogenated nucleosides that have shown potential in chemotherapy and antiviral treatments.

5-Iodo-2'-deoxycytidine has demonstrated antiviral properties, particularly against DNA viruses. The iodine substitution at the 5-position of the pyrimidine ring influences the incorporation of the nucleoside into viral DNA, inhibiting viral replication. It has been studied for its effects on viruses such as herpes simplex virus (HSV) and human cytomegalovirus (HCMV).

As a nucleoside analog, 5-iodo-2'-deoxycytidine is also studied for its potential in cancer treatment. It can be incorporated into the DNA of rapidly dividing cancer cells, disrupting DNA replication and inducing cytotoxicity. By interfering with the DNA replication machinery, it inhibits cell proliferation and promotes apoptosis, making it a candidate for chemotherapy, particularly in the treatment of solid tumors.

5-Iodo-2'-deoxycytidine is a substrate for the enzyme deoxycitidine kinase, which phosphorylates it to its active triphosphate form. This active form is then incorporated into the DNA during replication. The halogenated base alters the structure of the DNA and inhibits the function of DNA polymerases, leading to DNA damage and cellular death. This mechanism is particularly effective in rapidly dividing cells, such as cancer cells or virus-infected cells.

Beyond its direct therapeutic potential, 5-iodo-2'-deoxycytidine is used in research, particularly in studies of nucleic acid metabolism and DNA replication. Its incorporation into DNA and the subsequent effects on cellular processes make it a valuable tool for studying DNA replication, repair, and cell cycle regulation.

In conclusion, 5-iodo-2'-deoxycytidine is a halogenated nucleoside analog with applications in antiviral therapy, cancer treatment, and molecular research. Its ability to inhibit DNA replication makes it an important compound for both therapeutic and investigative purposes, particularly in oncology and virology.

References

1961. Preparation of 5-iodo-2'-deoxycytidine. Biochemical Pharmacology, 8(2).
DOI: 10.1016/0006-2952(61)90109-5

1998. Efficacy of select antivirals against Cryptosporidium parvum in vitro. FEMS Microbiology Letters, 168(1).
DOI: 10.1016/s0378-1097(98)00419-4

2018. New Synthetic Route to CY5-Labeled 2'-Deoxycytidine-5'-Triphosphates Using Sonogashira Reaction. Russian Journal of Bioorganic Chemistry, 44(2).
DOI: 10.1134/s1068162018020103