Next Article in Journal
Asymmetric Ruthenium(II) and Osmium(II) Complexes with New Bidentate Polyquinoline Ligands. Synthesis and NMR Characterization
Next Article in Special Issue
Biological Actions of Artemisinin: Insights from Medicinal Chemistry Studies
Previous Article in Journal
Reductive Heck Reactions of N-Methyl-substituted Tricyclic Imides
Previous Article in Special Issue
Ancient Chinese Methods Are Remarkably Effective for the Preparation of Artemisinin-Rich Extracts of Qing Hao with Potent Antimalarial Activity
Molecules 2010, 15(3), 1309-1323; doi:10.3390/molecules15031309
Review

Stereodynamic Investigation of Labile Stereogenic Centres in Dihydroartemisinin

1,* , 1,* , 1, 1, 1, 2
,
2 and 2
Received: 1 January 2010 / Revised: 25 January 2010 / Accepted: 4 March 2010 / Published: 5 March 2010
Download PDF [379 KB, uploaded 18 June 2014]

Abstract

Since its identification in the early 1970s, artemisinin, as well as semi-synthetic derivatives and synthetic trioxanes, have been used in malaria therapy. Reduction of artemisinin by NaBH4 produced dihydroartemisinin (DHA), and yielded a new stereochemically labile centre at C-10, which, in turn, provided two interconverting lactol hemiacetal epimers (namely a and b), whose rate of interconversion depends on buffer, pH, and solvent polarity. Since interconversion of the two epimers occurred on a chromatographic time-scale, this prompted a thorough investigation of the phenomenon as a crucial requisite of any analytical method aimed at quantitating this family of drugs. In this critical review we discuss the current importance of the on-column epimerization of DHA in the development of analytical methods aimed at quantifying the drug, with the purpose of identifying the optimal conditions to minimize on-column epimerization while achieving the best selectivity and efficiency of the overall separation.
Keywords: Dihydroartemisinin (DHA); on-column epimerization; cryo-HPLC; dynamic HPLC (DHPLC); computer simulation Dihydroartemisinin (DHA); on-column epimerization; cryo-HPLC; dynamic HPLC (DHPLC); computer simulation
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote
MDPI and ACS Style

D’Acquarica, I.; Gasparrini, F.; Kotoni, D.; Pierini, M.; Villani, C.; Cabri, W.; Di Mattia, M.; Giorgi, F. Stereodynamic Investigation of Labile Stereogenic Centres in Dihydroartemisinin. Molecules 2010, 15, 1309-1323.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here

Comments

Cited By

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert