Curr Health Sci J, vol. 38, no. 4, 2012

Characterization of a tosylated cholesteryl derivative

[Original paper]

SIMONA CRISTINA RIZEA(1), CATALINA IONESCU(1),VERONIQUE BARRAGAN-MONTERO(2),J. NEAMTU(1)

 
(1) Faculty of Pharmacy, University of Medicine and Pharmacy Craiova;
(2) Equipe SyGReM, Institut des Biomolécules Max Mousseron, Universite Montpellier 2, France


Abstract:

Purpose. This study presents the synthesis of 11-cholesteryloxy-3,6,9-trioxaundecyl-1-p-toluenesulfonate and its detailed structural characterization. Bearing a p-toluenesulfonyl group, it is a very versatile compound that can be used in the synthesis of a wide variety of derivatives that can be incorporated in liposomes, with various applications in modern drug delivery systems. Material/Methods.  The compound has been prepared in a sequence of three reactions, using cholesterol as starting compound. After purification, the tosylated product has been analysed by 1H, 13C NMR and mass spectrometry.  Results. The performed analysis confirmed the structure of the desired derivative. Conclusions.11-cholesteryloxy-3,6,9-trioxaundecyl-1-p-toluenesulfonate has been successfully obtained as a pure compound in 58.26 % overall yield  starting from cholesterol.


Keywords:
liposomes, ligands, cholesterol, NMR analysis, mass spectrometry



Corresponding:
Simona Cristina Rizea, PhD Student, Faculty of Pharmacy, University of Medicine and Pharmacy Craiova,Str. Petru Rares nr. 2-4 Craiova 200349,Dolj, RomAnia, e-mail: mondeasimona@yahoo.com


DOI 10.12865/CHSJ.38.04.08 - Download PDF