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

doi:10.3390/molecules170910928

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

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

Aino-Liisa Alanne¹, Helena Hyvönen², Manu Lahtinen³, Markku Ylisirniö¹, Petri Turhanen¹, Erkki Kolehmainen³, Sirpa Peräniemi¹ and Jouko Vepsäläinen^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; in revised form: 4 September 2012 / Accepted: 5 September 2012 / Published: 12 September 2012

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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, pK_a-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

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Cite This Article

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.

AMA 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(9):10928-10945.

Chicago/Turabian Style

Alanne, Aino-Liisa; Hyvönen, Helena; Lahtinen, Manu; Ylisirniö, Markku; Turhanen, Petri; Kolehmainen, Erkki; Peräniemi, Sirpa; Vepsäläinen, Jouko. 2012. "Systematic Study of the Physicochemical Properties of a Homologous Series of Aminobisphosphonates." Molecules 17, no. 9: 10928-10945.

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