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South African Journal of Chemistry

On-line version ISSN 1996-840X
Print version ISSN 0379-4350

S.Afr.j.chem. (Online) vol.63  Durban  2010




The synthesis of substituted piperazine-cholesterol conjugates for use as components of nucleic acid transfection lipoplexes*



Rafique Ul IslamI, II; Myron M. JohnsonI, II; Raushaan MohammedI; Justin HeanII; Patrick ArbuthnotII; Charles B. de KoningI, **; Willem A.L. van OtterloI, **

IMolecular Sciences Institute, School of Chemistry, University of the Witwatersrand, Private Bag 3, WITS 2050, South Africa
IIAntiviral Gene Therapy Research Unit, School of Pathology, University of the Witwatersrand Medical School, Private Bag 3, WITS 2050, South Africa




A small library of cholesterol-piperazine conjugates were synthesized by the reaction of cholesteryl chloroformate with a set of substituted piperazines in dichloromethane at room temperature. The conjugates, all obtained in good to excellent yields, were synthesized to be key components of nucleic acid transfection lipoplexes.

Keywords: Piperazine, cholesterol, conjugates, transfection, cationic lipoplexes



Full text available only in PDF format.



This material is based upon work supported financially by the National Research Foundation (NRF GUN 68339, 65495, 2053652 and IRDP of the NRF), Pretoria. Any opinion, findings and conclusions or recommendations expressed in this material are those of the authors and therefore the NRF does not accept any liability in regard thereto. This work was also supported by funding under the Sixth Research Framework Programme of the European Union, Project RIGHT (LSHB-CT-2004-005276), from CANSA, ESASTAP the South African Poliomyelitis Research Foundation and by the University of the Witwatersrand. We also gratefully acknowledge Mr R. Mampa for providing the NMR service and Dr A. Dinsmore and Mrs M. Ferreira for supplying some LRMS spectroscopy results. Ms J. Schneider and Ms M. Ismail from the Mass Spectroscopy Service, University of Dortmund and Max Planck Institute for Molecular Physiology, Dortmund, Germany, are thanked for performing the HRMS on the compounds 6a-q, 7, 9 and 11.


References and Notes

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Received 8 May 2010
Revised 25 June 2010
Accepted 6 July 2010



* This paper was submitted upon invitation to invited speakers (CdK) at the South African Chemical Institute's 11th Frank Warren Conference, January 2010, in Pietermaritzburg, KwaZulu-Natal, South Africa.
** To whom correspondence should be addressed. E-mail: de Koning ( van Otterlo (

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