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Molecules 2015, 20(8), 14533-14551; doi:10.3390/molecules200814533

Prazosin-Conjugated Matrices Based on Biodegradable Polymers and α-Amino Acids—Synthesis, Characterization, and in Vitro Release Study

1
Department of Inorganic and Analytical Chemistry, Faculty of Pharmacy with the Laboratory Medicine Division, Medical University of Warsaw, Banacha 1, Warsaw 02-097, Poland
2
Department of Environmental Health Science, Faculty of Pharmacy with the Laboratory Medicine Division, Medical University of Warsaw, Banacha 1, Warsaw 02-097, Poland
*
Author to whom correspondence should be addressed.
Academic Editor: Maria Emília de Sousa
Received: 22 May 2015 / Revised: 24 July 2015 / Accepted: 5 August 2015 / Published: 12 August 2015
(This article belongs to the Section Medicinal Chemistry)
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Abstract

Novel and promising macromolecular conjugates of the α1-adrenergic blocker prazosin were directly synthesized by covalent incorporation of the drug to matrices composed of biodegradable polymers and α-amino acids for the development of a polymeric implantable drug delivery carrier. The cyto- and genotoxicity of the synthesized matrices were evaluated using a bacterial luminescence test, protozoan assay, and Salmonella typhimurium TA1535. A new urethane bond was formed between the hydroxyl end-groups of the synthesized polymer matrices and an amine group of prazosin, using 1,1′-carbonyldiimidazole (CDI) as a coupling agent. The structure of the polymeric conjugates was characterized by various spectroscopy techniques. A study of hydrogen nuclear magnetic resonance (1H-NMR) and differential scanning calorimetry (DSC) thermodiagrams indicated that the presence of prazosin pendant groups in the macromolecule structures increased the polymer’s rigidity alongside increasing glass transition temperature. It has been found that the kinetic release of prazosin from the obtained macromolecular conjugates, tested in vitro under different conditions, is strongly dependent on the physicochemical properties of polymeric matrices. Furthermore, the presence of a urethane bond in the macromolecular conjugates allowed for obtaining a relatively controlled release profile of the drug. The obtained results confirm that the pharmacokinetics of prazosin might be improved through the synthesis of polymeric conjugates containing biomedical polymers and α-amino acids in the macromolecule. View Full-Text
Keywords: controlled release/delivery; macromolecular drug delivery; biodegradable polymers; polymeric drug delivery system; prazosin; cytotoxicity controlled release/delivery; macromolecular drug delivery; biodegradable polymers; polymeric drug delivery system; prazosin; cytotoxicity
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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. (CC BY 4.0).

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MDPI and ACS Style

Oledzka, E.; Sawicka, A.; Sobczak, M.; Nalecz-Jawecki, G.; Skrzypczak, A.; Kolodziejski, W. Prazosin-Conjugated Matrices Based on Biodegradable Polymers and α-Amino Acids—Synthesis, Characterization, and in Vitro Release Study. Molecules 2015, 20, 14533-14551.

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