32387-56-7

Basic information

• Product Name: 5-CHLORO-2'-DEOXYCYTIDINE
• Synonyms: 5-CHLORO-2'-DEOXYCYTIDINE;Cytochlor
• CAS NO: 32387-56-7
• Molecular Formula: C₉H₁₂ClN₃O₄
• Molecular Weight: 261.66228
• Product Categories: Miscellaneous Biochemicals
• Mol File: 32387-56-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 497.9°Cat760mmHg
• Flash Point: 254.9°C
• Appearance: /
• Density: 1.86g/cm³
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5-CHLORO-2'-DEOXYCYTIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CHLORO-2'-DEOXYCYTIDINE(32387-56-7)
• EPA Substance Registry System: 5-CHLORO-2'-DEOXYCYTIDINE(32387-56-7)

Safety Data

• Hazardous Substances Data: 32387-56-7(Hazardous Substances Data)

Usage

Uses

5-Chloro-2’-deoxycytidine is a good markers to detect myeloperoxidase (MPO) activity in biological fluids. Possible radiosensitizing agent for cancer treatment.

Upstream product

• 951-77-9 2'-Deoxycytidine 

Downstream Products

• 1356140-66-3 4-N-acetyl-5-chloro-5'-O-(4,4'-dimethoxytrityl)-deoxycytidine 
• 1356140-67-4 4-N-acetyl-5-chloro-5'-O-(4,4'-dimethoxytrityl)-deoxycytidine 3'-(2-cyanoethyl N,N-diisopropylphosphoramidite) 

Relevant articles and documents

Ability of hypochlorous acid and N -chloramines to chlorinate DNA and its constituents

Myeloperoxidase is a heme enzyme released by activated phagocytes that is responsible for the generation of the strong oxidant hypochlorous acid (HOCl). Although HOCl has potent bactericidal properties and plays an important role in the human immune system, this oxidant also causes damage to tissues, particularly under inflammatory conditions. There is a strong link between chronic inflammation and the incidence of many cancers, which may be associated with the ability of HOCl and related oxidants such as N-chloramines to damage DNA. However, in contrast to HOCl, little is known about the reactivity of N-chloramines with DNA and its constituents. In this study, we examine the ability of HOCl and various N-chloramines to form chlorinated base products on nucleosides, nucleotides, DNA, and in cellular systems. Experiments were performed with N-chloramines formed on Nα-acetyl-histidine (His-C), Nα-acetyl-lysine (Lys-C), glycine (Gly-C), taurine (Tau-C), and ammonia (Mono-C). Treatment of DNA and related materials with HOCl and His-C resulted in the formation of 5-chloro-2'-deoxycytidine (5CldC), 8-chloro-2'-deoxyadenosine (8CldA) and 8-chloro-2'-deoxyguanosine (8CldG). With the nucleosides, 8CldG was the favored product in each case, and HOCl was the most efficient chlorinating agent. 5Cl(d)C was the most abundant product on exposure of the nucleotides and DNA to HOCl and His-C, with only low levels of chlorinated products observed with Lys-C, Gly-C, Tau-C, and Mono-C. 5CldC was also formed on exposure of smooth muscle cells to either HOCl or His-C. Cellular RNA was also a target for HOCl and His-C, with evidence for the formation of 5-chloro-cytidine (5ClC). This study shows that HOCl and the model N-chloramine, His-C, are able to chlorinate cellular genetic material, which may play a role in the development of various inflammatory cancers.

Highly efficient method for C-5 halogenation of pyrimidine-based nucleosides in ionic liquids

A novel, highly efficient, convenient, and benign methodology for C-5 halogenation of pyrimidine-based nucleosides has been developed using N-halosuccinimides as halogenating reagents without using any catalyst in ionic liquid medium. The ionic liquids were successfully recovered and reused for all the reactions. Georg Thieme Verlag Stuttgart.

New Procedure for the Chlorination of Pyrimidine and Purine Nucleosides

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