15176-29-1 Usage
Description
5-Ethyl-2'-deoxyuridine is a nucleoside analog with potential applications in various fields due to its unique chemical properties. It is a modified form of the naturally occurring nucleoside, deoxyuridine, with an additional ethyl group attached to the 5' position. This modification may influence its interactions with biological systems and contribute to its potential uses.
Uses
Used in Pharmaceutical Industry:
5-Ethyl-2'-deoxyuridine is used as a modulator for enhancing the antitumor action and pharmacokinetics of 5-Fluorouracil (F596000), a potent antineoplastic agent in clinical use. By modulating the activity and distribution of 5-Fluorouracil, it may improve the efficacy of cancer treatments and reduce side effects.
Used in Antiallergic Applications:
5-Ethyl-2'-deoxyuridine is used as an antiallergic agent, potentially helping to alleviate symptoms associated with allergic reactions. Its specific mechanism of action in this context may involve the modulation of immune responses or the inhibition of certain cellular processes involved in allergy development.
Used as a Mast Cell Degranulation Inhibitor:
In the field of immunology and allergy treatment, 5-Ethyl-2'-deoxyuridine is used as a mast cell degranulation inhibitor. Mast cell degranulation is a process that releases histamine and other inflammatory mediators, leading to allergic symptoms. By inhibiting this process, 5-Ethyl-2'-deoxyuridine may help to reduce the severity of allergic reactions.
Used as an Angiogenesis Blocker:
In the context of cancer therapy, 5-Ethyl-2'-deoxyuridine is used as an angiogenesis blocker. Angiogenesis is the process by which new blood vessels form, and it is often a critical factor in tumor growth and metastasis. By blocking angiogenesis, 5-Ethyl-2'-deoxyuridine may help to limit the growth and spread of cancerous cells.
Used in Edoxudine Production:
5-Ethyl-2'-deoxyuridine is also used in the production of Edoxudine, a compound with solid chemical properties. Edoxudine has been found to modulate both the antitumor action and pharmacokinetics of 5-Fluorouracil, further emphasizing the potential utility of 5-Ethyl-2'-deoxyuridine in the development of novel cancer treatments.
Biochem/physiol Actions
5-Ethyl-2′-deoxyuridine (EUdR) is used as a 5-fluorouracil (FU) modulator. EtdUrd may be used to enhance the therapeutic index of 5-FU by reducing the catabolism, prolonging the plasma and intratumoral concentrations of 5-FU, and offering protection to normal organs by increasing the endogenous uridine levels.
Check Digit Verification of cas no
The CAS Registry Mumber 15176-29-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,5,1,7 and 6 respectively; the second part has 2 digits, 2 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 15176-29:
(7*1)+(6*5)+(5*1)+(4*7)+(3*6)+(2*2)+(1*9)=101
101 % 10 = 1
So 15176-29-1 is a valid CAS Registry Number.
15176-29-1Relevant articles and documents
Importance of 3′-hydroxyl group of the nucleosides for the reactivity of thymidine phosphorylase from Escherichia coli
Hatano, Akihiko,Harano, Aiko,Kirihara, Masayuki
, p. 232 - 233 (2006)
Thymidine phosphorylase in phosphate buffer catalyzed the conversion of thymidine to unnatural nucleosides. The 3′-OH, but not the 5′-OH of ribosyl moiety is necessary to be recognized as a substrate. Thus 3′-deoxythymidine could not convert to 5-fluorouracil-2′,3′- dideoxyribose. However, 5′-deoxythymidine was converted to 5-fluorouracil-2′,5′-dideoxyribose. Copyright
Letter: Synthesis of C-5 substituted pyrimidine nucleosides via organopalladium intermediates.
Bergstrom,Ruth
, p. 1587 - 1589 (1976)
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One-pot approach to functional nucleosides possessing a fluorescent group using nucleobase-exchange reaction by thymidine phosphorylase
Hatano, Akihiko,Kurosu, Masayuki,Yonaha, Susumu,Okada, Munehiro,Uehara, Sanae
, p. 6900 - 6905 (2013/10/08)
Herein, we describe β-selective coupling between a modified uracil and a deoxyribose to produce functionalized nucleosides catalyzed by thymidine phosphorylase derived from Escherichia coli. This enzyme mediates nucleobase-exchange reactions to convert unnatural nucleosides possessing a large functional group such as a fluorescent molecule, coumarin or pyrene, linked via an alkyl chain at the C5 position of uracil. 5-(Coumarin-7-oxyhex-5- yn)uracil (C4U) displayed 57.2% conversion at 40% DMSO concentration in 1.0 mM phosphate buffer pH 6.8 to transfer thymidine to an unnatural nucleoside with C4U as the base. In the case of using 5-(pyren-1-methyloxyhex-5-yn)uracil (P4U) as the substrate, TP also could catalyse the reaction to generate a product with a very large functional group at 50% DMSO concentration (21.6% conversion). We carried out docking simulations using MF myPrest for the modified uracil bound to the active site of TP. The uracil moiety of the substrate binds to the active site of TP, with the fluorescent moiety linked to the C5 position of the nucleobase located outside the surface of the enzyme. As a consequence, the bulky fluorescent moiety binding to uracil has little influence on the coupling reaction.
Nucleoside analogue phosphates for topical use
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, (2008/06/13)
Compositions for topical use in herpes virus infections comprising anti-herpes nucleoside analogue phosphate esters, such as acyclovir monophosphate, acyclovir diphosphate, and acyclovir triphosphate which show increased activity against native strains of herpes virus as well as against resistant strains, particularly thymidine kinase negative strains of virus. Also disclosed are methods for treatment of herpes infections with nucleoside phosphates. Anti-herpes nucleoside analogues phosphate esters include the phosphoramidates and phosphothiorates, as well as polyphosphates comprising C and S bridging atoms.
