Synthesis of 1-hydroxy-1,1-bisphosphonates as ligands for MOFs
Petri A. Turhanen
University of Eastern Finland, School of Pharmacy, Biocenter Kuopio, P.O. Box 1627, FIN- 70211, Kuopio, FINLAND.
petri.turhanen@uef.fi
Pyrophosphates, which have P-O-P structure, are crucial for life and can be found naturally e.g. in mammalian cells. Bisphosphonates (BPs) are analogues of pyrophosphate, having stable P-C-P backbone instead of chemically and enzymatically unstable P-O-P bridge as in pyrophosphates. BPs have been used for various purposes during over 50 years lifetime. Initially BPs were used as water softeners by inhibiting the crystallization of calcium and magnesium salts, but nowadays they are mainly known as drugs for the treatment of various bone diseases like osteoporosis and Paget`s disease.¹
Our group has very strong experience related to the synthesis of different kind of 1-hydroxy-1,1-bisphosphonates and various studies related to medicinal use and non-medicinal area have been done until these days. As an examples, we have reported novel applications for BPs: 1) method for collecting metals from water solutions using insoluble BP², 2) bisphosphonate-based solid phase method for effective removal of chromium(III) from aqueous solutions and tannery effluents³, 3) novel approach to the non-herbicidal effects of BPs on the plant growth⁴ and 4) first bisphosphonate hydrogelators as potential composers of biocompatible gels.⁵ Recently, collaboration with Prof. Konstantinos Demadis and his group (Univ. Crete) has led to novel findings related to methods for controlled release of BPs. It is very clear that the potential of BPs in new fields is unquestionable.
Below can seen the most common method to prepare1-hydroxy-1,1-bisphosphonates, which is very useful also in large scale syntheses. There are some other methods to prepare 1-hydroxy-1,1-bisphosphonates and these will be discussed in the presentation.
References:
[1] (a) R. Graham, G. Russell, Bone 2011, 49, 2−19; (b) W.M. Abdou, A.A. Shaddy, ARKIVOC, 2009, 143.
[2] a) P.A. Turhanen, J.J. Vepsäläinen, S. Peräniemi, Sci. Rep. 2015, 5, 8992. b) P. Turhanen, S. Peräniemi, J. Vepsäläinen, Patent WO2012131170 (A1).
[3] A-L. Alanne, M. Tuikka, K. Tõnsuaadu, M. Ylisirniö, L. Hämäläinen, P. Turhanen, J. Vepsäläinen, S. Peräniemi, RSC Adv., 2013, 3, 14132.
[4] A-L. Alanne, S. Peräniemi, P. Turhanen, M. Tuomainen, J. Vepsäläinen, A. Tervahauta, Chemosphere, 2014, 95, 266.
[5] A-L. Alanne, M. Lahtinen, M. Löfman, P. Turhanen, E. Kolehmainen, J. Vepsäläinen, E. Sievänen, J. Mater. Chem B., 2013, 1, 6201.
[6] (a) K. E. Papathanasiou, P. Turhanen, S. I. Brckner, E. Brunner and K. D. Demadis, Sci. Rep., 2017, 7, 4743. b) M. Vassaki, K.E. Papathanasiou, C. Hadjicharalambous, D. Chandrinou, P. Turhanen, D. Choquesillo-Lazarte, K.D. Demadis, Chem. Comm., 2020, 56, 5166-5169.