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Nucleoside analogue information


The antiviral drug aciclovir (bottom), a nucleoside analogue that functions by mimicking guanosine (top)

Nucleoside analogues are structural analogues of a nucleoside, which normally contain a nucleobase and a sugar. Nucleotide analogues are analogues of a nucleotide, which normally has one to three phosphates linked to a nucleoside. Both types of compounds can deviate from what they mimick in a number of ways, as changes can be made to any of the constituent parts (nucleobase, sugar, phosphate).[1] They are related to nucleic acid analogues.

Nucleoside and nucleotide analogues can be used in therapeutic drugs, including a range of antiviral products used to prevent viral replication in infected cells. The most commonly used is acyclovir.

Nucleotide and nucleoside analogues can also be found naturally. Examples include ddhCTP (3ʹ-deoxy-3′,4ʹdidehydro-CTP) produced by the human antiviral protein viperin[2] and sinefungin (a S-Adenosyl methionine analogue) produced by some Streptomyces.[3]

  1. ^ Seley-Radtke, KL; Yates, MK (June 2018). "The evolution of nucleoside analogue antivirals: A review for chemists and non-chemists. Part 1: Early structural modifications to the nucleoside scaffold". Antiviral Research. 154: 66–86. doi:10.1016/j.antiviral.2018.04.004. PMC 6396324. PMID 29649496.
  2. ^ Gizzi AS, Grove TL, Arnold JJ, Jose J, Jangra RK, Garforth SJ, et al. (June 2018). "A naturally occurring antiviral ribonucleotide encoded by the human genome". Nature. 558 (7711). Springer Science and Business Media LLC: 610–614. Bibcode:2018Natur.558..610G. doi:10.1038/s41586-018-0238-4. PMC 6026066. PMID 29925952.
  3. ^ Vedel, M; Lawrence, F; Robert-Gero, M; Lederer, E (14 November 1978). "The antifungal antibiotic sinefungin as a very active inhibitor of methyltransferases and of the transformation of chick embryo fibroblasts by Rous sarcoma virus". Biochemical and Biophysical Research Communications. 85 (1): 371–6. doi:10.1016/s0006-291x(78)80052-7. PMID 217377.

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Nucleoside analogue

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in all cases. Nucleoside analogues may also be used to treat viral infections. For example, azidothymidine (AZT) is a nucleoside analogue used to prevent...

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alternative nucleoside/nucleotide analogues that correctly bind to RNA are used. This is achieved by using a different backbone sugar. These analogues include...

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categorized into three classes—nucleoside active site inhibitors (NIs), non-nucleoside allosteric inhibitors, and pyrophosphate analogues. Subsequently, all three...

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Aciclovir

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observed. It appears to be safe during breastfeeding. Aciclovir is a nucleoside analogue that mimics guanosine. It works by decreasing the production of the...

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List of antiviral drugs

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PMID 25387551. Gish RG (January 2006). "Treating HCV with ribavirin analogues and ribavirin-like molecules". The Journal of Antimicrobial Chemotherapy...

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(AZT), is also a nucleoside analogue. An improved knowledge of the action of reverse transcriptase has led to better nucleoside analogues to treat HIV infections...

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Penciclovir

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Penciclovir is a guanosine analogue antiviral drug used for the treatment of various herpesvirus infections. It is a nucleoside analogue which exhibits low toxicity...

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Blasticidin S

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treatment with the antibiotic. Blasticidin S is a nucleoside analogue antibiotic, resembling the nucleoside cytidine. Blasticidin works against human cells...

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Fialuridine

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1-(2-deoxy-2-fluoro-1-D-arabinofuranosyl)-5-iodouracil (FIAU), is a nucleoside analogue that was investigated as a potential therapy for hepatitis B virus...

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Nucleic acid analogue

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artificial nucleotides featured 2 fused aromatic rings. Several nucleoside analogues are used as antiviral or anticancer agents. The viral polymerase...

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Deuremidevir

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Deuremidevir, also known as VV116, is an nucleoside analogue antiviral drug. It is administrated through oral tablets, which contain the hydrobromide...

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Cordyceps militaris

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the pharmacologically active compound cordycepin. Cordycepin is a nucleoside analogue of adenosine-differing by only a single hydroxyl group. It has been...

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Sorivudine

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Sorivudine (INN), is a nucleoside analogue antiviral drug, marketed under trade names such as Usevir (Nippon Shoji, Eisai) and Brovavir (BMS). It is used...

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Idoxuridine

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Idoxuridine is an anti-herpesvirus antiviral drug. It is a nucleoside analogue, a modified form of deoxyuridine, similar enough to be incorporated into...

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Feline infectious peritonitis

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271–281 Dickinson et al 2020. Antiviral treatment using the adenosine nucleoside analogue GS‐441524 in cats with clinically diagnosed neurological feline infectious...

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Ticagrelor

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useful before surgery or if side effects occur. Ticagrelor is a nucleoside analogue: the cyclopentane ring is similar to the sugar ribose, and the nitrogen...

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Nucleobase

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2-amino-6-(2-thienyl)purine and pyrrole-2-carbaldehyde. In medicine, several nucleoside analogues are used as anticancer and antiviral agents. The viral polymerase...

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Hepatitis

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(pegylated interferon) and the oral nucleoside analogues. Lamivudine was the first approved oral nucleoside analogue. While effective and potent, lamivudine...

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Troxacitabine

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Troxacitabine (brand name Troxatyl) is a nucleoside analogue with anticancer activity. Its use is being studied in patients with refractory lymphoproliferative...

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Thymidine

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Jean-Pierre (2008). "LdT (telbivudine) as a potent and specific nucleoside analogue (Tyzeka™, Sebivo™) for the treatment of chronic hepatitis B". Collection...

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Massive parallel sequencing

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“virtual Terminators”, which are unblocked terminators with a second nucleoside analogue that acts as an inhibitor. These terminators have the appropriate...

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Pyrimidine analogue

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Floxuridine (FUDR) 6-azauracil (6-AU) Nucleoside analogues Cytarabine (Cytosine arabinoside) Gemcitabine Nucleotide analogues Pyrimidine Fluorouracil Floxuridine...

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Nucleotide

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of nucleotides. A purified nucleoside is protected to create a phosphoramidite, which can then be used to obtain analogues not found in nature and/or...

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