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Chiodo F, Marradi M, Calvo J, et al. Glycosystems in nanotechnology: Gold glyconanoparticles as carrier for anti-HIV prodrugs. Beilstein J Org Chem. 2014;10:1339-46doi: 10.3762/bjoc.10.136.
Chiodo, F., Marradi, M., Calvo, J., Yuste, E., & Penadés, S. (2014). Glycosystems in nanotechnology: Gold glyconanoparticles as carrier for anti-HIV prodrugs. Beilstein journal of organic chemistry, 101339-46. https://doi.org/10.3762/bjoc.10.136
Chiodo, Fabrizio, et al. "Glycosystems in nanotechnology: Gold glyconanoparticles as carrier for anti-HIV prodrugs." Beilstein journal of organic chemistry vol. 10 (2014): 1339-46. doi: https://doi.org/10.3762/bjoc.10.136
Chiodo F, Marradi M, Calvo J, Yuste E, Penadés S. Glycosystems in nanotechnology: Gold glyconanoparticles as carrier for anti-HIV prodrugs. Beilstein J Org Chem. 2014 Jun 12;10:1339-46. doi: 10.3762/bjoc.10.136. eCollection 2014. PMID: 24991287; PMCID: PMC4077455.
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Beilstein J Org Chem. 2014 Jun 12;10:1339-46. doi: 10.3762/bjoc.10.136. eCollection 2014.

Glycosystems in nanotechnology: Gold glyconanoparticles as carrier for anti-HIV prodrugs.

Beilstein journal of organic chemistry

Fabrizio Chiodo, Marco Marradi, Javier Calvo, Eloisa Yuste, Soledad Penadés

Affiliations

  1. Laboratory of GlycoNanotechnology, Biofunctional Nanomaterials Unit, CIC biomaGUNE, Paseo Miramón 182, 20009, San Sebastián, Spain.
  2. Laboratory of GlycoNanotechnology, Biofunctional Nanomaterials Unit, CIC biomaGUNE, Paseo Miramón 182, 20009, San Sebastián, Spain ; Networking Research Center on Bioengineering, Biomaterials and Nanomedicine (CIBER-BBN), Paseo Miramón 182, 20009, San Sebastián, Spain.
  3. Technological Platform of Mass Spectrometry, CIC biomaGUNE, Paseo Miramón 182, 20009, San Sebastián, Spain.
  4. AIDS Research Unit, Institut d'Investigacions Biomediques August Pi i Sunyer, Barcelona, Spain ; HIVACAT, Barcelona, Spain.

PMID: 24991287 PMCID: PMC4077455 DOI: 10.3762/bjoc.10.136

Abstract

The therapeutic approach for the treatment of HIV infection is based on the highly active antiretroviral therapy (HAART), a cocktail of antiretroviral drugs. Notwithstanding HAART has shown different drawbacks like toxic side effects and the emergence of viral multidrug resistance. Nanotechnology offers new tools to improve HIV drug treatment and prevention. In this scenario, gold nanoparticles are an interesting chemical tool to design and prepare smart and efficient drug-delivery systems. Here we describe the preparation and antiviral activity of carbohydrate-coated gold nanoparticles loaded with anti-HIV prodrug candidates. The nucleoside reverse transcriptase inhibitors abacavir and lamivudine have been converted to the corresponding thiol-ending ester derivatives and then conjugated to ~3 nm glucose-coated gold nanoparticles by means of "thiol-for-thiol" ligand place exchange reactions. The drugs-containing glyconanoparticles were characterized and the pH-mediated release of the drug from the nanoparticle has been determined. The antiviral activity was tested by evaluating the replication of NL4-3 HIV in TZM-bl infected cells. The proof-of-principle presented in this work aims to introduce gold glyconanoparticles as a new multifunctional drug-delivery system in the therapy against HIV.

Keywords: HAART; HIV; drug-delivery system; gold glyconanoparticles; multivalent glycosystems; reverse transcriptase inhibitors

References

  1. Chemistry. 2009 Sep 28;15(38):9874-88 - PubMed
  2. Adv Drug Deliv Rev. 2013 Nov;65(13-14):1803-15 - PubMed
  3. Lancet. 2007 Mar 3;369(9563):787-797 - PubMed
  4. Antimicrob Agents Chemother. 2002 Jun;46(6):1896-905 - PubMed
  5. Chemistry. 2003 May 9;9(9):1909-21 - PubMed
  6. Biomater Sci. 2013 Jun 7;1(6):658-668 - PubMed
  7. Science. 2008 May 9;320(5877):760-4 - PubMed
  8. Methods Enzymol. 2012;509:21-40 - PubMed
  9. Adv Carbohydr Chem Biochem. 2010;64:211-90 - PubMed
  10. Biomaterials. 2013 Aug;34(26):6202-28 - PubMed
  11. ACS Nano. 2012 Feb 28;6(2):1565-77 - PubMed
  12. Science. 2010 Sep 3;329(5996):1168-74 - PubMed
  13. Bioorg Med Chem. 2011 Jun 1;19(11):3527-39 - PubMed
  14. J Virol. 2000 Sep;74(18):8358-67 - PubMed
  15. Chem Commun (Camb). 2004 Dec 21;(24):2848-9 - PubMed
  16. Nanoscale. 2013 Apr 7;5(7):2756-64 - PubMed
  17. Curr Opin Pharmacol. 2010 Oct;10(5):507-15 - PubMed
  18. Bioorg Med Chem Lett. 2010 May 1;20(9):2718-21 - PubMed
  19. Chem Soc Rev. 2009 Jun;38(6):1759-82 - PubMed
  20. Chembiochem. 2009 Jul 20;10(11):1806-9 - PubMed
  21. PLoS One. 2013 Aug 27;8(8):e73027 - PubMed
  22. Small. 2014 Jul 9;10(13):2602-10 - PubMed
  23. J Nanobiotechnology. 2005 Jun 29;3:6 - PubMed
  24. J Virol. 1998 Apr;72(4):2855-64 - PubMed
  25. J Virol. 2008 Dec;82(24):12585-8 - PubMed
  26. N Engl J Med. 2003 Dec 11;349(24):2283-5 - PubMed
  27. Nanomedicine (Lond). 2012 May;7(5):651-62 - PubMed
  28. Chem Soc Rev. 2013 Jun 7;42(11):4728-45 - PubMed
  29. IEEE Trans Nanobioscience. 2007 Dec;6(4):275-81 - PubMed
  30. Science. 2004 Mar 19;303(5665):1818-22 - PubMed
  31. J Mol Biol. 2011 Jul 29;410(5):798-810 - PubMed
  32. Drugs. 2011 Mar 5;71(4):387-414 - PubMed
  33. J Control Release. 2010 Nov 20;148(1):122-127 - PubMed
  34. J Am Chem Soc. 2008 Jun 4;130(22):6896-7 - PubMed
  35. Nanomedicine. 2013 Jan;9(1):28-38 - PubMed
  36. Chem Soc Rev. 2012 Mar 21;41(6):2256-82 - PubMed
  37. Bioconjug Chem. 2012 Apr 18;23(4):814-25 - PubMed

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