Systematic study of the physicochemical properties of a homologous series of aminobisphosphonates

Molecules. 2012 Sep 12;17(9):10928-45. doi: 10.3390/molecules170910928.

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, H(2)N(CH2)(n)C(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 both liquid (1)H, (13)C, (31)P-NMR and solid state(13)C, (15)N and (31)P-CPMAS NMR) were determined.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alendronate / chemistry*
  • Diphosphonates / chemical synthesis*
  • Diphosphonates / chemistry*
  • Hydrogen-Ion Concentration
  • Magnetic Resonance Spectroscopy
  • Solubility
  • Temperature
  • Water / chemistry

Substances

  • Diphosphonates
  • Water
  • 6-amino-1-hydroxyhexane-1,1-diphosphonate
  • Alendronate