Advanced search
Publication Cover
Future Medicinal Chemistry Volume 7, 2015 - Issue 13
Submit an article Journal homepage
206
Views
1
CrossRef citations to date
0
Altmetric
Preliminary Communication

Design, Synthesis and Cellular Metabolism Study of 4′-Selenonucleosides

Jinha Yu1 Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul151–742, KoreaView further author information
,
Pramod K Sahu1 Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul151–742, KoreaView further author information
,
Gyudong Kim1 Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul151–742, KoreaView further author information
,
Shuhao Qu1 Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul151–742, KoreaView further author information
,
Yoojin Choi1 Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul151–742, KoreaView further author information
,
Jayoung Song1 Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul151–742, KoreaView further author information
,
Sang Kook Lee1 Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul151–742, KoreaView further author information
,
Minsoo Noh1 Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul151–742, KoreaView further author information
,
Sunghyouk Park1 Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul151–742, KoreaView further author information
&
Lak Shin Jeong1 Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul151–742, KoreaCorrespondence[email protected]
View further author information
 show all
Pages 1643-1655 | Published online: 24 Sep 2015

References

  • Jordheim LP , DurantelD, ZoulimF, DumontetC. Advances in the development of nucleoside and nucleotide analogues for cancer and viral diseases. Nat. Rev. Drug Discov.12 (6), 447–464 (2013).
  • De Clercq E . Antiviral drugs in current clinical use. J. Clin. Virol.30 (2), 115–133 (2004).
  • Marquez VE , ChoiY, CominMJet al. Understanding how the herpes thymidine kinase orchestrates optimal sugar and nucleobase conformations to accommodate its substrate at the active site: a chemical approach. J. Am. Chem. Soc.127 (43), 15145–15150 (2005).
  • Marquez VE , Ben-KasusT, BarchiJJJr, GreenKM, NicklausMC, AgbariaR. Experimental and structural evidence that herpes 1 kinase and cellular DNA polymerase(s) discriminate on the basis of sugar pucker. J. Am. Chem. Soc.126 (2), 543–549 (2004).
  • Jeong LS , ToshDK, KimHOet al. First synthesis of 4′-selenonucleosides showing unusual Southern conformation. Org. Lett.10 (2), 209–212 (2008).
  • Tosh DK , ChoiWJ, KimHOet al. Stereoselective synthesis and conformational study of novel 2′,3′-didehydro-2′,3′-dideoxy-4′-selenonucleosides. J. Org. Chem.73 (11), 4259–4262 (2008).
  • Jeong LS , ChoiYN, ToshDK, ChoiWJ, KimHO, ChoiJ. Design and synthesis of novel 2′,3′-dideoxy-4′-selenonucleosides as potential antiviral agents. Bioorg. Med. Chem.16 (23), 9891–9897 (2008).
  • Jeong LS , ToshDK, ChoiWJet al. Discovery of a new template for anticancer agents: 2′-deoxy-2′-fluoro-4′-selenoarabinofuranosyl-cytosine (2′-F-4′-seleno-ara-C). J. Med. Chem.52 (17), 5303–5306 (2009).
  • Alexander V , ChoiWJ, ChunJet al. A new DNA building block, 4′-selenothymidine: synthesis and modification to 4′-seleno-AZT as a potential anti-HIV agent. Org. Lett.12 (10), 2242–2245 (2010).
  • Yu J , KimJH, LeeHWet al. New RNA purine building blocks, 4′-selenopurine nucleosides: first synthesis and unusual mixture of sugar puckerings. Chem. A Eur. J.19 (18), 5528–5532 (2013).
  • Kim J-H , YuJ, AlexanderVet al. Structure–activity relationships of 2′-modified-4′-selenoarabinofuranosyl-pyrimidines as anticancer agents. Eur. J. Med. Chem.83, 208–225 (2014).
  • Sahu PK , KimG, YuJet al. Stereoselective synthesis of 4′-selenonucleosides via seleno-Michael reaction as potent antiviral agents. Org. Lett.16 (21), 5796–5799 (2014).
  • Lee SK , HeoYH, SteeleeVE, PezzutoJM. Induction of apoptosis by 1,4-phenylenebis(methylene)selenocyanate in cultured human colon cancer cells. Anticancer Res.22 (1A), 97–102 (2002).
  • Nasr M , LitterstC, McGowanJ. Computer-assisted structure-activity correlations of dideoxynucleoside analogs as potential anti-HIV drugs. Antiviral Res.14 (3), 125–148 (1989).
  • Hao Z , CooneyDA, FarquharDet al. Potent DNA chain termination activity and selective inhibition of human immunodeficiency virus reverse transcriptase by 2′,3′-dideoxyuridne-5′-monophosphate. Mol. Pharm.37 (2), 157–163 (1990).
  • Sastry JK , NehetePN, KhanSet al. Membrane-permeable dideoxyuridine 5′-monophosphate analogue inhibits human immunodeficiency virus infection. Mol. Pharm.41 (3), 441–445 (1992).

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.