68498-26-0

Basic information

• Product Name: 3,N(4)-ethenodeoxycytidine
• Synonyms: 3,N(4)-ethenodeoxycytidine
• CAS NO: 68498-26-0
• Molecular Formula: C₁₁H₁₃N₃O₄
• Molecular Weight: 251.2386
• Mol File: 68498-26-0.mol

Chemical Properties

• Boiling Point: 608.8°Cat760mmHg
• Flash Point: 322°C
• Appearance: /
• Density: 1.68g/cm³
• Vapor Pressure: 1.13E-15mmHg at 25°C
• Refractive Index: 1.747
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• CAS DataBase Reference: 3,N(4)-ethenodeoxycytidine(CAS DataBase Reference)
• NIST Chemistry Reference: 3,N(4)-ethenodeoxycytidine(68498-26-0)
• EPA Substance Registry System: 3,N(4)-ethenodeoxycytidine(68498-26-0)

Safety Data

• Hazardous Substances Data: 68498-26-0(Hazardous Substances Data)

Usage

Uses

Used in Medical Research:
3,N(4)-ethenodeoxycytidine is used as a biomarker for assessing oxidative stress in human white blood cells. Its presence indicates the level of oxidative damage to DNA, which can be a valuable indicator for researchers studying the effects of oxidative stress on human health and disease.
Used in Diagnostic Applications:
3,N(4)-ethenodeoxycytidine can be used as a diagnostic tool to identify and monitor oxidative stress-related conditions. By measuring the levels of this biomarker in patient samples, medical professionals can gain insights into the patient's oxidative stress status and make informed decisions regarding treatment and management strategies.
Used in Antioxidant Therapy Development:
3,N(4)-ethenodeoxycytidine can also be employed in the development of antioxidant therapies. By understanding the role of this biomarker in oxidative stress, researchers can design and test new antioxidants or interventions aimed at reducing oxidative damage and improving overall health.

InChI:InChI=1/C11H13N3O4/c15-6-8-7(16)5-10(18-8)14-3-1-9-12-2-4-13(9)11(14)17/h1-4,7-8,10,15-16H,5-6H2/t7-,8+,10+/m0/s1

Upstream product

• 55662-66-3 [13C⁴,15N₃]-3,N⁴-ethenocytosine 
• 951-77-9 2'-Deoxycytidine 
• 107-20-0 2-chloroethanal 
• 2065-75-0 2-Bromo-malonaldehyde 
• 3992-42-5 2'-deoxycytidine monohydrochloride 

Downstream Products

• 136851-95-1 5'-O-(4,4'-dimethoxytrityl)-3,N⁴-etheno-2'-deoxycytidine 

Relevant articles and documents

An aza-nucleoside, fragment-like inhibitor of the DNA repair enzyme alkyladenine glycosylase (AAG)

The DNA repair enzyme AAG has been shown in mice to promote tissue necrosis in response to ischaemic reperfusion or treatment with alkylating agents. A chemical probe inhibitor is required for investigations of the biological mechanism causing this phenomenon and as a lead for drugs that are potentially protective against tissue damage from organ failure and transplantation, and alkylative chemotherapy. Herein, we describe the rationale behind the choice of arylmethylpyrrolidines as appropriate aza-nucleoside mimics for an inhibitor followed by their synthesis and the first use of a microplate-based assay for quantification of their inhibition of AAG. We finally report the discovery of an imidazol-4-ylmethylpyrrolidine as a fragment-sized, weak inhibitor of AAG.

Synthesis of 8-(hydroxymethyl)-3,N4-etheno-2'-deoxycytidine, a potential carcinogenic glycidaldehyde adduct, and its site-specific incorporation into DNA oligonucleotides

The previously unreported glycidaldehyde adduct, 8-(hydroxymethyl)- 3,N4-etheno-2'-deoxycytidine (8-HM-εdC), has been synthesized for the first time by reaction of 2'-deoxycytidine with bromoacetaldehyde at pH 4.5, followed by reduction with sodium borohydride. The adduct was characterized by UV, MS, and NMR. The compound was stable to neutral and acidic conditions but not in alkaline solution. The corresponding phosphoramidite was synthesized in good yield from the intermediate, 3,N4-ethenocarbaldehyde-2'- deoxycytidine, using the standard methodology and site-specifically incorporated in both 15- and 25-met oligonucleotides, for studies on biochemical and biophysical properties. The resulting oligonucleotides were purified using HPLC, and the base composition was verified by HPLC after enzymatic digestion.

Addition of deoxyribose to guanine and modified DNA bases by Lactobacillus helveticus trans-N-deoxyribosylase

The use of bacterial trans-N-deoxyribosylase was evaluated as an alternative method for deoxyribosylation in the synthesis of deoxyribonucleosides containing potentially mutagenic adducts. A crude enzyme preparation was isolated from Lactobacillus helveticus and compared to Escherichia coli purine nucleoside phosphorylase. trans-N-deoxyribosylase was more regioselective than purine nucleoside phosphorylase in the deoxyribosylation of Gua at the N9 atom, as compared to N7, as demonstrated by NMR analysis of the product. 5,6,7,9-Tetrahydro-7-acetoxy-9- oxoimidazo[1,2-a]purine was efficiently deoxyribosylated by trans-N- deoxyribosylase but not at all by purine nucleoside phosphorylase. Other substrates for trans-N-deoxyribosylase were N2-(2-oxoethyl)Gua, pyrimido[1,2-a]purin-10(3H)-one, 1,N2-ε-Gua, N2,3ε-Gua, 3,N4-(-Cyt, 1,N6-ε-Ade, C8-methylGua, and C8-aminoGua, most of which gave the desired isomer (bond at the nitrogen corresponding to N9 in Gua) in good yield. Neither N7-alkylpurines nor C8-(arylamino)-substituted guanines were substrates. The approach offers a relatively convenient method of enzymatic preparation of many carcinogen-DNA adducts at the nucleoside level, for either use as standards or incorporation into oligonucleotides. trans-N- deoxyribosylase can also be used to remove deoxyribose from modified deoxyribonucleosides in the presence of excess Cyt.

Synthesis of 3,N4-Etheno, 3N4-Ethano, and 3-(2-Hydroxyethyl) Derivatives of 2'-Deoxycytidine and Their Incorporation into Oligomeric DNA

3,N4-Etheno, 3,N4-ethano, and 3-(2-hydroxyethyl)derivatives of 2'-deoxycytidine arise in mammalian DNA that has been exposed to the metabolic products of either vinyl chloride or the antitumor drug bis(chloroethyl)nitrosourea. These chemically-related adducts are thought to be associated with both mutagenesis and carcinogenesis. In this paper we report reliable syntheses of these deoxynucleosides and incorporation of the latter into oligodeoxynucleotides by the phosphoramidite route, using automated methods. It was found that 3-(2-hydroxyethyl)-2'-deoxycytidine is unstable in aqueous solution and undergoes an autoinduced hydrolysis to 3-(2-hydroxyethyl)-2'-deoxyuridine. The rate of this hydrolysis was found to be pH-dependent, having a maximum around pH 8, and a half-life of approximately 5 h. At higher or lower acidities, the reaction rate falls, indicating that the process involves a general acid-base catalysis. Thus in this case, oligomers were obtained that possessed 3-(2-hydroxyethyl)-2'-deoxyuridine residues, rather than the cytidine analogue. It is likely that the former represents the longer-lived species in DNA under physiological conditions. Representative oligomers containing these chemical lesions were analyzed by mass spectrometric and enzymatic degradation methods to confirm their structures.