85562-55-6

Basic information

• Product Name: 8-CHLORO-2'-DEOXYADENOSINE
• Synonyms: 8-CHLORO-2'-DEOXYADENOSINE;8-CL-DADO;8-Chloro-2'-deoxy-D-adenosine
• CAS NO: 85562-55-6
• Molecular Formula: C₁₀H₁₂ClN₅O₃
• Molecular Weight: 285.69
• Mol File: 85562-55-6.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 660°C at 760 mmHg
• Flash Point: 353°C
• Appearance: /
• Density: 2.03g/cm³
• Vapor Pressure: 2.56E-18mmHg at 25°C
• Refractive Index: 1.87
• CAS DataBase Reference: 8-CHLORO-2'-DEOXYADENOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: 8-CHLORO-2'-DEOXYADENOSINE(85562-55-6)
• EPA Substance Registry System: 8-CHLORO-2'-DEOXYADENOSINE(85562-55-6)

Safety Data

• Hazardous Substances Data: 85562-55-6(Hazardous Substances Data)

Usage

General Description

8-Chloro-2'-deoxyadenosine is a chemical compound that belongs to the class of nucleosides and nucleotides. It is a modified form of the nucleoside adenosine, with a chlorine atom attached to the 8 position of the adenine base. This modification gives the compound unique properties and potential pharmaceutical applications. 8-Chloro-2'-deoxyadenosine has been studied for its anti-cancer and antiviral properties, and it shows promise as a potential chemotherapeutic agent. It may also have potential applications in the treatment of certain viral infections. Overall, 8-Chloro-2'-deoxyadenosine is a valuable chemical compound with potential therapeutic applications in the fields of oncology and virology.

InChI:InChI=1/C10H12ClN5O3/c11-10-15-7-8(12)13-3-14-9(7)16(10)6-1-4(18)5(2-17)19-6/h3-6,17-18H,1-2H2,(H2,12,13,14)

Upstream product

• 116285-73-5 9-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-8-chloro-9H-purin-6-ylamine 
• 51549-32-7 3',5'-bis-O-[(tert-butyl)dimethylsilyl]-2'-deoxyadenosine 
• 958-09-8 2'-deoxy-D-adenosine 

Downstream Products

• 537697-47-5 N-[8-chloro-9-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-benzamide 
• 537697-48-6 N-(9-{5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-8-chloro-9H-purin-6-yl)-benzamide 

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.