Volume 11 Issue 3
Jun.  2021
Turn off MathJax
Article Contents
Monika Zielińska, Ewa Chmielewska, Tomasz Buchwald, Adam Voelkel, Paweł Kafarski. Determination of bisphosphonates anti-resorptive properties based on three forms of ceramic materials: Sorption and release process evaluation[J]. Journal of Pharmaceutical Analysis, 2021, 11(3): 364-373. doi: 10.1016/j.jpha.2020.07.011
Citation: Monika Zielińska, Ewa Chmielewska, Tomasz Buchwald, Adam Voelkel, Paweł Kafarski. Determination of bisphosphonates anti-resorptive properties based on three forms of ceramic materials: Sorption and release process evaluation[J]. Journal of Pharmaceutical Analysis, 2021, 11(3): 364-373. doi: 10.1016/j.jpha.2020.07.011

Determination of bisphosphonates anti-resorptive properties based on three forms of ceramic materials: Sorption and release process evaluation

doi: 10.1016/j.jpha.2020.07.011
Funds:

This work was supported by the Ministry of Science and Higher Education grants and subsidy of the Ministry of Science and Higher Education.

  • Received Date: Apr. 15, 2020
  • Accepted Date: Jul. 31, 2020
  • Rev Recd Date: Jul. 31, 2020
  • Available Online: Jan. 24, 2022
  • Publish Date: Jun. 15, 2021
  • There is a strong need to search for more effective compounds with bone anti-resorptive properties, which will cause fewer complications than commonly used bisphosphonates. To achieve this goal, it is necessary to search for new techniques to characterize the interactions between bone and drug. By studying their interaction with hydroxyapatite (HA), this study used three forms of ceramic materials, two of which are bone-stimulating materials, to assess the suitability of new active substances with anti-resorptive properties. In this study, three methods based on HA in loose form, polycaprolactone/HA (a polymer-ceramic materials containing HA), and polymer-ceramic monolithic in-needle extraction (MINE) device (a polymer inert skeleton), respectively, were used. The affinity of risedronate (a standard compound) and sixteen aminomethylenebisphosphonates (new compounds with potential antiresorptive properties) to HA was defined according to the above-mentioned methods. Ten monolithic materials based on 2-hydroxyethyl methacrylate/ethylene dimethacrylate are prepared and studied, of which one was selected for more-detailed further research. Simulated body fluids containing bisphosphonates were passed through the MINE device. In this way, sorption–desorption of bisphosphonates was evaluated using this MINE device. The paper presents the advantages and disadvantages of each technique and its suitability for assessing new active substances. All three methods allow for the selection of several compounds with potentially higher anti-resorptive properties than risedronate, in hope that it reflects their higher bone affinity and release ability.
  • loading
  • G.H. Nancollas, R. Tang, R.J. Phipps, et al., Novel insights into actions of bisphosphonates on bone: Differences in interactions with hydroxyapatite, Bone 38 (2006) 617-627. https://doi.org/10.1016/j.bone.2005.05.003
    R. Graham, R. Russell, Bisphosphonates: The first 40 years, Bone, 49 (2011) 2-19. https://doi.org/10.1016/j.bone.2011.04.022
    R.G.G Russell, N.B. Watts, et al., Mechanisms of action of bisphosphonates: similarities and differences and their potential influence on clinical efficacy, Osteoporos Int., 19 (2008) 733-759. https://doi.org/10.1007/s00198-007-0540-8
    F. Errassifi, S. Sarda, A. Barroug et al., Infrared, Raman and NMR investigations of risedronate adsorption on nanocrystalline apatites, J. Colloid Interface Sci. 420 (2014) 101-111. https://doi.org/10.1016/j.jcis.2014.01.017
    R.G.G. Russell, Z. Xia, J.E. Dunford, et al., Bisphosphonates An Update on Mechanisms of Action and How These Relate to Clinical Efficacy, Ann N Y Acad Sci. 1117 (2007) 209-257. https://doi.org/10.1196/annals.1402.089
    M.A. Lawson, Z. Xia, B.L. Barnett et al., Differences Between Bisphosphonates in Binding Affinities for Hydroxyapatite, J Biomed Mater Res B Appl Biomater. 92 (2010) 149-155. https://doi.org/10.1002/jbm.b.31500
    M. Pietrzynska, R. Tomczak, K. Jezierska, et al., Polymer-ceramic Monolithic In-Needle Extraction (MINE) device: preparation and examination of drug affinity, Mater. Sci. Eng. C 68 (2016) 70-77. https://doi.org/10.1016/j.msec.2016.05.097
    M. Pietrzynska, J. Zembrzuska, R.Tomczak, et al., Experimental and in silico investigations of organic phosphates and phosphonates sorption on polymer-ceramic monolithic materials and hydroxyapatite, Eur. J. Pharmaceut. Sci. 93 (2016) 295-303. https://doi.org/10.1016/j.ejps.2016.08.033
    J. Krenkova, N.A. Lacher, F. Svec, Control of Selectivity via Nanochemistry: Monolithic Capillary Column Containing Hydroxyapatite Nanoparticles for Separation of Proteins and Enrichment of Phosphopeptides, Anal. Chem. 82 (2010) 8335-8341. https://doi.org/10.1021/ac1018815
    E. Chmielewska, K. Kempińska, J. Wietrzyk, et al, Novel Bisphosphonates and Their Use, Int Pat Appl WO2015159153 (A1) ― 2015-10-22
    E. Matczak-Jon, K. Slepokura, P. Kafarski, Solid state and solution behaviour of N-(2-pyridyl)- and N-(4-methyl-2-pyridyl)aminomethane-1,1-diphosphonic acids, J. Mol. Struct. 782 (2006) 81-93. https://doi.org/10.1016/j.molstruc.2005.07.004
    E. Matczak-Jon, W. Sawka-Dobrowolska, P. Kafarski, et al., Molecular organization and solution properties of N-substituted aminomethane-1,1-diphosphonic acids, New J. Chem. 25 (2001) 1447-1457. https://doi.org/10.1039/B102282M
    S. Ghosh, J.M. Chan,C. R. Lea, et al., Effects of Bisphosphonates on the Growth of Entamoeba histolytica and Plasmodium Species in Vitro and in Vivo, J. Med Chem. 47 (1) (2004) 175-187. https://doi.org/10.1021/jm030084x
    E. Matczak-Jon, K. Slepokura, P.Kafarski, [(5-Bromo-pyridinium-2- ylamino)(phosphono)meth-yl]phospho-nate, Acta Crystallogr. C. 62 (2006) 132-135. https://doi.org/10.1107/S0108270106002423
    E. Matczak-Jon, K. Slepokura, Conformations and resulting hydrogen-bonded networks of hydrogen{phosphono[(pyridin-1-ium-3-yl)amino]methyl}phosphonate and related 2-chloro and 6-chloro derivatives, Acta Crystallogr. C. 67 (2011) 450-456. https://doi.org/10.1107/s0108270111040650
    L. Widler, K.A. Jaeggi, M. Glatt et al. Highly Potent Geminal Bisphosphonates. From Pamidronate Disodium (Aredia) to Zoledronic Acid (Zometa), J. Med. Chem. 45 (2002) 3721-3738. https://doi.org/10.1021/jm020819i
    W. Goldeman, A. Nasulewicz-Goldeman, Synthesis and antiproliferative activity of aromatic and aliphatic bis[aminomethylidene(bisphosphonic)] acidsBioorg. Med. Chem. Lett. 24 (2014)) 3475-3479. https://doi.org/10.1016/j.bmcl.2014.05.071
    E. Chmielewska, Z. Mazur, K. Kempinska, et al., N-Arylaminomethylenebisphosphonates bearing fluorine atoms: Synthesis and antiosteoporotic activity, Phosphorus Sulfur Silicon Relat. Elem. 190 (2015) 2164-2172. https://doi.org/10.1080/10426507.2015.1085046
    E. Matczak-Jon, K. Slepokura, B. Kurzak, X-ray evidence for the relationship between pyridyl side chain basicity and the Z/E preferences of 5-halogen substituted (pyridin-2-yl)aminomethane-1,1- diphosphonic acids; implications for metal ions coordination in solution, Arkivoc. 4 (2012) 167-185. https://doi.org/10.3998/ark.5550190.0013.412
    K. Azzaoui, M. Berrabah, E. Mejdoubi et al. Use of hydroxylapatite composite membranes for analysis of bisphenol A, Res. Chem. Intermed, 40 (2014) 2621-2628. https://doi.org/10.1007/s11164-013-1115-2
    M. Pietrzynska, M. Czerwinski, A. Voelkel, Poly(vinyl alcohol)/hydroxyapatite monolithic in-needle extraction (MINE) device: preparation and examination of drug affinity, Eur. J. Pharm. Sci. 105 (2017)195-202. https://doi.org/10.1016/j.ejps.2017.05.040
    D.B. Rorabacher, Statistical treatment for rejection of deviant values: critical values of Dixon's "Q" parameter and related subrange ratios at the 95% confidence level, Anal. Chem. 63 (1991) 139-146. https://doi.org/10.1021/ac00002a010
    P. Petruczynik, P. Kafarski, M. Psurski, et al., Three-Component Reaction of Diamines with Triethyl Orthoformate and Diethyl Phosphite and Anti-Proliferative and Antiosteoporotic Activities of the Products, Molecules 25(6) (2020) 1424. https://doi.org/10.3390/molecules25061424
    Z. Okulus, T. Buchwald, M. Szybowicz, et al., Study of a new resin-based composites containing hydroxyapatite filler using Raman and infrared spectroscopy, Mater. Chem. Phys. 145 (2014) 304-312. 10.1016/j.matchemphys.2014.02.012
    M.J. Rogers, J.C. Crockett, F.P. Coxon, et al., Biochemical and molecular mechanisms of action of bisphosphonates, Bone 49 (2011) 34-41. https://doi.org/10.1016/j.bone.2010.11.008
    M. Pietrzynska, A. Voelkel, K. Bielicka-Daszkiewicz, Preparation and examination of Monolithic In-Needle Extraction (MINE) device for the direct analysis of liquid samples, Anal. Chim. Acta 776 (2013) 50-56. https://doi.org/10.1016/j.aca.2013.03.022
    M. Pietrzynska, A. Voelkel, Optimization of the in-needle extraction device for the direct flow of the liquid sample through the sorbent layer, Talanta 129 (2014) 392-397. https://doi.org/10.1016/j.talanta.2014.06.026
    V. Kumar, R. Kant Sinha, Bisphosphonate related osteonecrosis of the jaw: An update, J. Maxillofac. Oral. Surg. 13 (2014) 386-393. https://doi.org/10.1007/s12663-013-0564-x
    C. Walter, B. Al-Nawas, N. Frickhofen, et al., Prevalence of bisphosphonate associated osteonecrosis of the jaws in multiple myeloma patients, Head & Face Med. 6 (2010) 6-11. https://doi.org/10.1186/1746-160X-6-11
  • 加载中

Catalog

    通讯作者: 陈斌, bchen63@163.com
    • 1. 

      沈阳化工大学材料科学与工程学院 沈阳 110142

    1. 本站搜索
    2. 百度学术搜索
    3. 万方数据库搜索
    4. CNKI搜索

    Article Metrics

    Article views (66) PDF downloads(1) Cited by()
    Proportional views
    Related

    /

    DownLoad:  Full-Size Img  PowerPoint
    Return
    Return