Structural requirements for bisphosphonate binding on hydroxyapatite: NMR study of bisphosphonate partial esters.

@article{Puljula2015StructuralRF,
  title={Structural requirements for bisphosphonate binding on hydroxyapatite: NMR study of bisphosphonate partial esters.},
  author={Elina Puljula and Petri A. Turhanen and Jouko Veps{\"a}l{\"a}inen and Maelle Monteil and Marc Lecouvey and Janne Weisell},
  journal={ACS medicinal chemistry letters},
  year={2015},
  volume={6 4},
  pages={
          397-401
        }
}
Eighteen different bisphosphonates, including four clinically used bisphosphonate acids and their phosphoesters, were studied to evaluate how the bisphosphonate structure affects binding to bone. Bisphosphonates with weak bone affinity, such as clodronate, could not bind to hydroxyapatite after the addition of one ester group. Medronate retained its ability to bind after the addition of one ester group, and hydroxy-bisphosphonates could bind even after the addition of two ester groups. Thus… 

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References

SHOWING 1-10 OF 34 REFERENCES
Differences between bisphosphonates in binding affinities for hydroxyapatite.
TLDR
There are substantial differences among BPs in their binding to HAP, which may be exploited in the development of biomaterials and may also partly explain the extent of their relative skeletal retention and persistence of biological effects observed in both animal and clinical studies.
NMR investigations of the static and dynamic structures of bisphosphonates on human bone: a molecular model.
TLDR
The results of an investigation of the binding of a series of bisphosphonate drugs to human bone using 2H, 13C, 15N, and 31P nuclear magnetic resonance spectroscopy show that the bisph phosphonate groups bind irrotationally to bone, displacing orthophosphate from the bone mineral matrix.
Structure-activity relationships of various bisphosphonates
TLDR
Taking into account all factors, 1-hydroxypentylidene-1,1-bisphosphonate and AHPrBP seem to be the most active compounds to inhibit bone resorption.
An update on the pharmacology of bisphosphonates and analogues with lower bone affinity
It has become clear that the pharmacological characteristics of nitrogen-containing bisphosphonates (NBPs) are the result of both their ability to inhibit farnesyl diphosphate synthase in osteoclasts
Bisphosphonate prodrugs: synthesis and in vitro evaluation of novel acyloxyalkyl esters of clodronic acid.
TLDR
In human serum, the stability of pivaloyloxymethyl esters was comparable to their stability in phosphate buffer (pH 7.4), which suggests that their degradation in human serum is mostly due to the chemical hydrolysis.
Solid‐state NMR of bisphosphonates adsorbed on hydroxyapatite
Solid‐state 31P and 13C magic angle spinning (MAS) NMR spectra were used to characterize pure bisphosphonates and also bisphosphonates adsorbed on hydroxyapatite. Four geminal bisphosphonates,
Bisphosphonate protonation states, conformations, and dynamics on bone mineral probed by solid-state NMR without isotope enrichment.
  • M. S. Ironside, M. Duer, D. Reid, S. Byard
  • Chemistry
    European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V
  • 2010
...
...