35
Views
6
CrossRef citations to date
0
Altmetric
Original Articles

Comparative Study of Hydrophobicity Parameters of Novel 5′‐Carbamates of Zidovudine

&
Pages 2195-2209 | Received 03 Jan 2005, Accepted 02 Apr 2005, Published online: 06 Feb 2007
 

Abstract

The lipophilic character of a series of 5′‐carbamates of zidovudina has been studied. The lipophilicity was measured by means of reversed‐phase thin layer chromatography (RP‐TLC) and reversed‐phase high performance liquid chromatography (RP‐HPLC) techniques giving the corresponding RMw and log k′w parameters, respectively. These values were compared with those obtained by the classical shake flask methodology. RP‐TLC assays were performed on the basis of thermodynamically true RM values, and buffer pH's 7.4 and 12.03 were chosen to determine the influence of the pH on the lipophilicity of the studied compounds. In addition, the influence of the organic modifier was studied in RP‐TLC, showing the superiority of methanol as compared with acetone as the organic modifier, and physicochemical reasons have been discussed. Based on RP‐TLC results, RP‐HPLC studies were carried out using methanol and buffer pH 7.4 as mobile phase. Chromatographic data (RMw and log k′w) proved to be reliable parameters for describing the lipophilic properties of the test compounds.

Acknowledgments

The authors gratefully acknowledge the Agencia Córdoba Ciencia, the FONCYT, the Secretaría de Ciencia y Técnica de la Universidad Nacional de Córdoba (SECYT‐UNC), and the Consejo Nacional de Investigaciones Científicas y Tecnológicas (CONICET) of Argentina for financial support. The authors also wish to express their sincere thanks to L. Alassia (FILAXIS Laboratories, Buenos Aires, Argentina) for supplying zidovudina and thymidine. M.A.R. acknowledges receipt of a fellowship granted by SECYT‐UNC.

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:

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:

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.