1122-44-7

Usage

Uses

Used in Biotechnology and Molecular Biology:
5-IODOCYTOSINE is used as a building block for the synthesis of modified nucleic acids, which are crucial for the development of novel biotechnological tools and techniques. These modified nucleic acids can enhance the stability, specificity, and functionality of DNA and RNA molecules, leading to improved performance in various molecular biology applications.
Used in Drug Development:
In the pharmaceutical industry, 5-IODOCYTOSINE is used as a key component in the development of new drugs targeting various diseases. Its unique chemical properties allow for the creation of modified nucleic acids that can potentially interact with specific cellular targets, leading to the development of targeted therapeutics.
Used in Diagnostics:
5-IODOCYTOSINE can be employed in the development of diagnostic tools, such as molecular probes and sensors, due to its ability to form stable complexes with nucleic acids. These diagnostic tools can be used to detect and monitor various diseases at the molecular level, providing valuable information for disease management and treatment.
Used in Research:
In academic and research settings, 5-IODOCYTOSINE is used as a valuable reagent for studying the structure, function, and interactions of nucleic acids. Its unique properties enable researchers to gain insights into the molecular mechanisms underlying various biological processes, contributing to the advancement of scientific knowledge in the field of molecular biology.

InChI:InChI=1/C4H4IN3O/c5-2-1-7-4(9)8-3(2)6/h1H,(H3,6,7,8,9)

Upstream product

• 696-07-1 5-iodouracil 
• 71-30-7 Cytosine 

Downstream Products

• 197452-37-2 1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-L-erythro-pentofuranos-1-yl)-5-iodocytosine 
• 197452-38-3 1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-α-L-erythro-pentofuranos-1-yl)-5-iodocytosine 
• 199486-81-2 N-1-(p-toluenesulfonyl)cytosine 
• 255818-56-5 5-iodo-1-(5-O-benzoyl-2,3-dideoxy-2-fluoro-β-L-threo-pentofuranosyl)cytosine 
• 308847-79-2 5-vinylcytosine 
• 1055312-00-9 methyl 4-[(4-amino-5-iodo-2-oxopyrimidin-1(2H)-yl)methyl]benzoate 
• 1392268-09-5 (+/-)-[2-(5-iodocytosin-1-yl)thietane-3,3-diyl]dimethanediyl dibenzoate 
• 1432446-07-5 C₁₂H₇ClIN₃O 
• 1210877-78-3 1-(α-ferrocenylbenzyl)-5-iodocytosine 

Related news

On the temperature dependence of the two-dimensional condensation of 5-IODOCYTOSINE (cas 1122-44-7) at the mercury/electrolyte interface09/26/2019

By way of capacity-potential curves of 5-iodocytosine in th epotential range of the cathodic pit edge, the dependence of the critical degree of coverage of a two-dimensional condensed adsorption film on temperature was investigated. The Frumkin interaction coefficient determined from the critica...detailed

Relevant academic research and scientific papers

Investigation of 4-amino-5-alkynylpyrimidine-2(1H)-ones as anti-mycobacterial agents

In vitro anti-mycobacterial activities of novel 4-amino-5-alkynylpyrimidine-2(1H)-ones were investigated. 4-Amino-5-heptynylpyrimidine-2(1H)-one (3) and 4-amino-5-(2-phenylethynyl)pyrimidine-2(1H)-one (7) displayed potent in vitro activity against Mycobac

Artificial DNA made exclusively of nonnatural C-nucleosides with four types of nonnatural bases

We describe a new class of DNA-like oligomers made exclusively of nonnatural, stable C-nucleosides. The nucleosides comprise four types of nonnatural bases attached to a deoxyribose through an acetylene bond with the β-configuration. The artificial DNA fo

Crystalline supramolecular organic frameworksviahydrogen-bonding between nucleobases

We report a crystalline supramolecular framework assembled by H-bonding interactions between covalently fused monomers equipped with two guanine-cytosine nucleobase pairs.

Nucleobase-guanidiniocarbonyl-pyrrole conjugates as novel fluorimetric sensors for single stranded RNA

We demonstrate here for the first time that a guanidiniocarbonyl-pyrrole (GCP) unit can be applied for the fine recognition of single stranded RNA sequences-an intuitively unexpected result since so far binding of the GCP unit to ds-DNA or ds-RNA relied s

Synthesis of 5-/8-Halogenated or Ethynylated Lipophilic Nucleobases as Potential Synthetic Intermediates for Supramolecular Chemistry

A series of lipophilic nucleobases that are substituted at the 5- (pyrimidines) or 8- (purines) position with either a halogen atom or a terminal triple bond have been synthesized. The sequences and reactions studied in this work, which mainly comprise halogenation, alkylation, Sonogashira coupling, and trimethylsilylacetylene deprotection, have been carefully optimized, to reach the final compounds in the most straightforward and convenient way, with the highest possible purity and yield. These compounds include cytosine, isocytosine, and uracil derivatives as pyrimidine heterocycles, and guanine, isoguanine, and 2-aminoadenine derivatives as complementary purine bases. Variability was introduced at the N-1/N-9 positions of these pyrimidine/purine nucleobases, which were functionalized with alkyl or benzyl groups, as well as with protected amine or carboxylic acid substituents. The molecules prepared constitute a useful collection of synthetic intermediates for the field of chemical self-assembly. A series of lipophilic nucleobases substituted at the 5- (pyrimidines) or 8-position (purines) with either a halogen atom or a terminal triple bond have been synthesized. These molecules comprise a useful collection of synthetic intermediates for the field of chemical self-assembly.

New Imidazo[1,2-c]pyrimidin-5(6H)-Ones Derived from Cytosine: Synthesis, Structure, and Cytotoxic Activity

This work describes the synthesis of 8-iodoimidazo[1,2-c]pyrimidin-5(6H)-one 2 from 5-iodocytosine 1. This compound was subjected to Suzuki cross-coupling reaction with aryl and heteroarylboronic acids. After optimization, 10 products 3a-j were

X-ray crystal structures of halogen containing nucleobase derivatives in unsolvated and DMSO solvated forms

A series of halogenated nucleobase derivatives 1-4 is reported to yield solvent-free (2) and DMSO solvated crystals (1, 3, 4) on the crystallization from DMSO with one of them (4) containing an additional molecule of water. The molecular and crystal structures are described and comparatively discussed with reference to previous results on related compounds. The molecule of 1 is planar, molecules of 2 and 3 show syn alignment with reference to the heterocyclic ring and common C2′-endo conformation of the ribose residue, while 4 is also syn aligned but C4′-exo in the sugar conformation. The packing structures reveal typical aggregations created via networks of hydrogen bonds. These involve conventional N-H···N, N-H···O and O-H···O interactions between nucleobase and ribose units as well as solvent molecules, additionally supported by weak C-H···O contacts but excluding the participation of halogen···halogen interactions as well as halogen···heteroatom contacts in the supramolecular structure formation. Springer Science+Business Media, LLC 2009.

A Simple and Convenient Method for the Synthesis of 1-(2-Deoxy-2-fuoro-β-D-arabinofuranosyl)-5-iodocytosine

1-(2-Deoxy-2-fluoro-β-D-arabinofuranosyl)-5-iodocytosine (FIAC) is a pyrimidine nucleoside analog with activity against various herpes viruses. In this study, FIAC was conveniently synthesized by a substitution reaction between ((2R,3S,4S)-3-(benzoyloxy)-

Nanostructured Micelle Nanotubes Self-Assembled from Dinucleobase Monomers in Water

Despite the central importance of aqueous amphiphile assemblies in science and industry, the size and shape of these nano-objects is often difficult to control with accuracy owing to the non-directional nature of the hydrophobic interactions that sustain them. Here, using a bioinspired strategy that consists of programming an amphiphile with shielded directional Watson–Crick hydrogen-bonding functions, its self-assembly in water was guided toward a novel family of chiral micelle nanotubes with partially filled lipophilic pores of about 2 nm in diameter. Moreover, these tailored nanotubes are successfully demonstrated to extract and host molecules that are complementary in size and chemical affinity.

Dehalogenation of Halogenated Nucleobases and Nucleosides by Organoselenium Compounds

Halogenated nucleosides, such as 5-iodo-2′-deoxyuridine and 5-iodo-2′-deoxycytidine, are incorporated into the DNA of replicating cells to facilitate DNA single-strand breaks and intra- or interstrand crosslinks upon UV irradiation. In this work, it is shown that the naphthyl-based organoselenium compounds can mediate the dehalogenation of halogenated pyrimidine-based nucleosides, such as 5-X-2′-deoxyuridine and 5-X-2′-deoxycytidine (X=Br or I). The rate of deiodination was found to be significantly higher than that of the debromination for both nucleosides. Furthermore, the deiodination of iodo-cytidines was found to be faster than that of iodo-uridines. The initial rates of the deiodinations of 5-iodocytosine and 5-iodouracil indicated that the nature of the sugar moiety influences the kinetics of the deiodination. For both the nucleobases and nucleosides, the deiodination and debromination reactions follow a halogen-bond-mediated and addition/elimination pathway, respectively.