105784-83-6

Basic information

• Product Name: 5-IODO-2',3'-DIDEOXYURIDINE
• Synonyms: 5-IODO-2',3'-DIDEOXYURIDINE;2',3'-DIDEOXY-5-IODOURIDINE;5-I-ddU;5-Iodo-2',3'-Dideoxy-D-Uridine
• CAS NO: 105784-83-6
• Molecular Formula: C₉H₁₁IN₂O₄
• Molecular Weight: 338.1
• Mol File: 105784-83-6.mol

Chemical Properties

• Melting Point: 176 °C (dec.)(lit.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 2.02g/cm³
• Storage Temp.: 2-8°C
• PKA: 7.94±0.10(Predicted)
• BRN: 5956836
• CAS DataBase Reference: 5-IODO-2',3'-DIDEOXYURIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-IODO-2',3'-DIDEOXYURIDINE(105784-83-6)
• EPA Substance Registry System: 5-IODO-2',3'-DIDEOXYURIDINE(105784-83-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 8-9
• Hazardous Substances Data: 105784-83-6(Hazardous Substances Data)

Usage

Uses

Used in Research and Development:
5-IODO-2',3'-DIDEOXYURIDINE is used as a research tool for [application type] in the fields of [application reason] antiviral and anticancer studies. Its unique chemical properties allow for the development of new therapeutic strategies and a better understanding of the underlying mechanisms of these diseases.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 5-IODO-2',3'-DIDEOXYURIDINE is used as a key component in the preparation of fluorescence-tagged chain-terminating reagents, such as T-526, for rapid DNA sequencing. This application aids in the development of new drugs and therapies by providing valuable insights into the genetic makeup of viruses and cancer cells.
Used in Diagnostics:
5-IODO-2',3'-DIDEOXYURIDINE is also utilized in the development of diagnostic tools and tests for the detection and monitoring of viral and cancer-related conditions. Its incorporation into fluorescence-tagged reagents enables rapid and accurate identification of specific genetic markers, contributing to the early diagnosis and treatment of these diseases.

Upstream product

• 5983-09-5 2',3'-Dideoxyuridine 
• 5983-09-5 2',3'-Dideoxyuridine 
• 3056-15-3 3',5'-di-O-(methanesulfonyl)-2'-deoxyuridine 
• 951-78-0 2'-deoxyuridine 
• 681821-72-7 2',3'-dideoxy-5-iodo-6-methoxyuridine 
• 5974-93-6 2',3'-dideoxy-2',3'-didehydrouridine 
• 3056-16-4 1-(3,5-anhydro-2-deoxy-β-D-threo-pentofuranosyl)uracil 

Downstream Products

• 1393815-12-7 3'-O-acetyl-5-(2-(4-ethynylphenyl)ethynyl)-2'-deoxycytidine 
• 1393815-10-5 3'-O-acetyl-5-(2-(4-ethynylphenyl)ethynyl)-2'-deoxyuridine 
• 114748-60-6 2,2,2-Trifluoro-N-{3-[1-((S)-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-prop-2-ynyl}-acetamide 
• 114748-60-6 5-(3-Trifluoroacetamido-1-propynyl)-2',3'-dideoxy-uridine 

Relevant articles and documents

Inhibition of Mycobacterium tuberculosis, Mycobacterium bovis, and Mycobacterium avium by novel dideoxy nucleosides

The prevalence of tuberculosis (TB) and mutidrug-resistant tuberculosis (MDR-TB) has been increasing, leading to serious infections, high mortality, and a global health threat. Here, we report the identification of a novel class of dideoxy nucleosides as potent and selective inhibitors of Mycobacterium bovis, Mycobacterium tuberculosis, and drug-resistant Mycobacterium tuberculosis. A series of 5-acetylenic derivatives of 2′,3′-dideoxyuridine (3-8) and 3′-fluoro-2′,3′-dideoxyuridine (22-27) were synthesized and tested for their antimycobacterial activity against M. bovis, M. tuberculosis, and M. avium. 2′,3′-Dideoxyuridine possessing 5-decynyl, 5-dodecynyl, 5-tridecynyl, and 5-tetradecynyl substituents (4-7) exhibited the highest antimycobacterial activity against all three mycobacteria. In contrast, in the 3′-fluoro-2′,3′-dideoxyuridine series, a 5-tetradecynyl analogue (26) displayed the most potent activity against these mycobacteria. Among other derivatives, 5-bromo-2′,3′-dideoxycytidine (11), 5-methyl-2′,3′-dideoxycytidine (12), and 5-chloro-4-thio-2′, 3′-dideoxyuridine (19) exhibited modest inhibition of M. bovis and M. tuberculosis. In the series of dideoxy derivatives of adenosine, guanosine, and purines, 2-amino-6-mercaptoethyl-9-(2,3-dideoxy-β-D-glyceropentofuranosyl) purine (32) and 2-amino-4-fluoro-7-(2,3-dideoxy-β-D-glyceropentofuranosyl) pyrrolo[2,3-d]-pyrimidine (35) were the most efficacious against M. bovis and M. tuberculosis, and M. avium, respectively.

Discovery of a New Family of Inhibitors of Human Cytomegalovirus (HCMV) Based upon Lipophilic Alkyl Furano Pyrimidine Dideoxy Nucleosides: Action via a Novel Non-Nucleosidic Mechanism

Following our discovery of the potent anti-varicella zoster virus action of lipophilic alkyl furano pyrimidine 2′-deoxynucleosides, we now report that 2′,3′-dideoxy sugar analogues are devoid of anti-VZV activity but are potent and selective inhibitors of human cytomegalovirus (HCMV). The present compounds are active in vitro at ca. 1 μM with cytotoxicity only above 200 μM. Importantly, we have discovered that the new agents do not act as nucleoside analogues, despite their nucleosidic structure, and time of addition studies revealed that the compounds may inhibit HCMV at an event in the replication cycle of the virus that precedes DNA synthesis. They represent new leads in the discovery of improved therapies for HCMV, particularly in view of their novel mechanism of action.

Cyanine dye activating group with improved coupling selectivity

Activating groups for cyanine dyes used to label chain terminators in nucleotide sequencing, based on N-hydroxyphthalimide, are disclosed. From these activating groups, activated dyes of the present Invention are prepared which react with the derivitized nucleotide chain terminators to give a labeled chain terminator of the present Invention. The activating groups of the present Invention allow the dye-chain terminator reaction to occur at a much higher yield and with much greater selectivity for the mono-substituted product, compared with the prior art.

Alkynylamino-nucleotides

Alkynylamino-nucleotides and labeled alkynylaminonucleotides useful, for example, as chain terminating substrates for DNA sequencing are provided along with several key intermediates and processes for their preparation. For some applications, longer, hydrophilic linkers are provided.

Method of gene mapping

The method described characterizes each DNA segment to be mapped by cleaving it to produce DNA fragments which are then end labeled with a reporter(s) specific to the end nucleotides of each fragment. The labeled fragments are again cleaved to produce short fragments which are separated according to size. The short fragments are analyzed as to report identify and size which is indicative of the character of each fragment. By derivatizing the cleaved ends of the primary cleaved fragments, the labeling may be delayed until the second cleavage. Prior to the labeling the derivatized fragments, all underivatized fragments are removed, the derivatized fragments being immobilized.

Alkynylamino-nucleotides

Alkynylamino-nucleotides and labeled alkynylamino-nucleotides useful, for example, as chain terminating substrates for DNA sequencing are provided along with several key intermediates and processes for their preparation.