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Molecules 2012, 17(9), 10928-10945; doi:10.3390/molecules170910928
Article

Systematic Study of the Physicochemical Properties of a Homologous Series of Aminobisphosphonates

1, 2, 3, 1, 1, 3, 1 and 1,*
1 School of Pharmacy, University of Eastern Finland, Biocenter Kuopio, P.O. Box 1627, FIN-70211 Kuopio, Finland 2 Laboratory of Inorganic Chemistry, Department of Chemistry, University of Helsinki, P.O. Box 55, FIN-00014 Helsinki, Finland 3 Department of Chemistry, University of Jyväskylä, P.O. Box 35, FIN-40014 Jyväskylä, Finland
* Author to whom correspondence should be addressed.
Received: 7 August 2012 / Revised: 4 September 2012 / Accepted: 5 September 2012 / Published: 12 September 2012
Download PDF [394 KB, 18 June 2014; original version 18 June 2014]

Abstract

Aminobisphosphonates, e.g., alendronate and neridronate, are a well known class of molecules used as drugs for various bone diseases. Although these molecules have been available for decades, a detailed understanding of their most important physicochemical properties under comparable conditions is lacking. In this study, ten aminobisphosphonates, H2N(CH2)nC(OH)[P(O)(OH)2]2, in which n = 2–5, 7–11 and 15 have been synthesized. Their aqueous solubility as a function of temperature and pH, pKa-values, thermal stability, IR absorptions, and NMR spectral data for bothliquid (1H, 13C, 31P-NMR) and solid state (13C, 15N and 31P-CPMAS NMR) were determined.
Keywords: bisphosphonates; aqueous solubility; pKa; physicochemical properties bisphosphonates; aqueous solubility; pKa; physicochemical properties
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.

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MDPI and ACS Style

Alanne, A.-L.; Hyvönen, H.; Lahtinen, M.; Ylisirniö, M.; Turhanen, P.; Kolehmainen, E.; Peräniemi, S.; Vepsäläinen, J. Systematic Study of the Physicochemical Properties of a Homologous Series of Aminobisphosphonates. Molecules 2012, 17, 10928-10945.

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