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The Scientific World Journal
Volume 2014, Article ID 803789, 6 pages
http://dx.doi.org/10.1155/2014/803789
Research Article

The Influence of pH and Temperature on the Stability of N-[(Piperidine)methylene]daunorubicin Hydrochloride and a Comparison of the Stability of Daunorubicin and Its Four New Amidine Derivatives in Aqueous Solutions

1Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Poznan University of Medical Sciences, 6 Grunwaldzka Street, 60-780 Poznań, Poland
2Department of Oncological Surgery II, Greater Poland Cancer Centre, 15 Garbary Street, 61-688 Poznań, Poland
3Department of Modified Antibiotics, Institute of Biotechnology and Antibiotics, 5 Starościńska Street, 02-515 Warsaw, Poland

Received 29 August 2013; Accepted 24 December 2013; Published 6 February 2014

Academic Editors: A. Nokhodchi, M. Ozyazici, and C. Pichon

Copyright © 2014 Mikołaj Piekarski et al. 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.

Abstract

The influence of pH and temperature on the stability of N-[(piperidine)methylene]daunorubicin hydrochloride (PPD) was investigated. Degradation was studied using an HPLC method. Specific acid-base catalysis of PPD involves hydrolysis of protonated molecules of PPD catalyzed by hydrogen ions and spontaneous hydrolysis under the influence of water zwitterions, unprotonated molecules, and monoanions of PPD. The thermodynamic parameters of these reactions, energy, enthalpy, and entropy, were calculated. Also, the stability of daunorubicin and its new amidine derivatives (piperidine, morpholine, pyrrolidine, and hexahydroazepin-1-yl) in aqueous solutions was compared and discussed.