Synthesis of a cholesteryl-HEG phosphoramidite derivative and its application to lipid-conjugates of the anti-HIV 5'TGGGAG³' Hotoda's sequence

Molecules. 2012 Oct 22;17(10):12378-92. doi: 10.3390/molecules171012378.

Abstract

A novel phosphoramidite derivative of cholesterol, with an ether-linked hexaethylene glycol (HEG) spacer arm, has been obtained through simple and reproducible solid phase modified oligonucleotide synthesis manipulations. This building block and the known phosphoramidite derivative of 3b-(2-hydroxyethoxy)cholesterol have been exploited in standard oligonucleotide synthesis protocols for the preparation of 5'- conjugates of the G-quadruplex-forming ⁵'TGGGAG³' oligomer, known as the Hotoda's sequence, to produce new potential anti-HIV agents.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-HIV Agents / chemical synthesis*
  • Anti-HIV Agents / chemistry
  • Anti-HIV Agents / pharmacology*
  • Base Sequence
  • Cholesterol Esters / chemical synthesis*
  • Cholesterol Esters / chemistry*
  • Chromatography, High Pressure Liquid
  • Ethylene Glycols / chemical synthesis*
  • Ethylene Glycols / chemistry
  • G-Quadruplexes*
  • HIV / drug effects*
  • Organophosphorus Compounds / chemical synthesis*
  • Organophosphorus Compounds / chemistry

Substances

  • Anti-HIV Agents
  • Cholesterol Esters
  • Ethylene Glycols
  • Organophosphorus Compounds
  • phosphoramidite
  • hexaethylene glycol