66376-36-1Relevant articles and documents
The molecular structure of 4-amino 1-hydroxy butylidene-1 bisphosphonic acid (AHBBPA); an uncommon anhydrous hydroxybisphosphonic acid
Ohanessian, Jacqueline,Avenel, Daniele,El Manouni, Driss,Benramdane, Mounya
, p. 99 - 110 (1997)
The molecular structure of an anhydrous hydroxybisphosphonic acid was determined by X-ray diffraction techniques and compared to the corresponding hydrated crystalline form. The hydrogen bond network and intermolecular interactions show that the polar bisphosphonic group undergoes a rotation to accomodate a different distribution in the hydrophobic/polar zones observed in the crystal packing, while the rest of the amino side chain connected to the functional carbon atom has identical conformation.
Synthesis of silver nanoparticles for the dual delivery of doxorubicin and alendronate to cancer cells
Benyettou,Rezgui,Ravaux,Jaber,Blumer,Jouiad,Motte,Olsen,Platas-Iglesias,Magzoub,Trabolsi
, p. 7237 - 7245 (2015)
We present the synthesis of a silver nanoparticle (AgNP) based drug-delivery system that achieves the simultaneous intracellular delivery of doxorubicin (Dox) and alendronate (Ald) and improves the anticancer therapeutic indices of both drugs. Water, under microwave irradiation, was used as the sole reducing agent in the size-controlled, bisphosphonate-mediated synthesis of stabilized AgNPs. AgNPs were coated with the bisphosphonate Ald, which templated nanoparticle formation and served as a site for drug attachment. The unreacted primary ammonium group of Ald remained free and was subsequently functionalized with either Rhodamine B (RhB), through amide formation, or Dox, through imine formation. The RhB-conjugated NPs (RhB-Ald@AgNPs) were studied in HeLa cell culture. Experiments involving the selective inhibition of cell membrane receptors were monitored by confocal fluorescence microscopy and established that macropinocytosis and clathrin-mediated endocytosis were the main mechanisms of cellular uptake. The imine linker of the Dox-modified nanoparticles (Dox-Ald@AgNPs) was exploited for acid-mediated intracellular release of Dox. We found that Dox-Ald@AgNPs had significantly greater anti-cancer activity in vitro than either Ald or Dox alone. Ald@AgNPs can accommodate the attachment of other drugs as well as targeting agents and therefore constitute a general platform for drug delivery.
Biocompatible organic coatings based on bisphosphonic acid RGD‐derivatives for PEO‐modified titanium implants
Danilko, Ksenia V.,Dyakonov, Grigory S.,Farrakhov, Ruzil G.,Galimshina, Zulfia R.,Gil'fanova, Guzel U.,Lukina, Elena S.,Mukaeva, Veta R.,Parfenov, Evgeny V.,Parfenova, Lyudmila V.
, (2020/01/13)
Currently, significant attention is attracted to the problem of the development of the specific architecture and composition of the surface layer in order to control the biocompatibility of implants made of titanium and its alloys. The titanium surface properties can be tuned both by creating an inorganic sublayer with the desired morphology and by organic top coating contributing to bioactivity. In this work, we developed a composite biologically active coatings based on hybrid molecules obtained by chemical crosslinking of amino acid bisphosphonates with a linear tripeptide RGD, in combination with inorganic porous sublayer created on titanium by plasma electrolytic oxidation (PEO). After the addition of organic molecules, the PEO coated surface gets nobler, but corrosion currents increase. In vitro studies on proliferation and viability of fibroblasts, mesenchymal stem cells and osteoblastlike cells showed the significant dependence of the molecule bioactivity on the structure of bisphosphonate anchor and the linker. Several RGDmodified bisphosphonates of β–alanine, γ–aminobutyric and ε–aminocaproic acids with BMPS or SMCC linkers can be recommended as promising candidates for further in vivo research.
Novel bisphosphonates with antiresorptive effect in bone mineralization and osteoclastogenesis
Savino, Salvatore,Toscano, Annamaria,Purgatorio, Rosa,Profilo, Emanuela,Laghezza, Antonio,Tortorella, Paolo,Angelelli, Mariacristina,Cellamarea, Saverio,Scala, Rosa,Tricarico, Domenico,Thomas Marobbio, Carlo Marya,Perna, Filippo,Vitale, Paola,Agamennone, Mariangela,Dimiccoli, Vincenzo,Tolomeo, Anna,Scilimati, Antonio
, p. 184 - 200 (2018/09/18)
Bisphosphonates such as zoledronic, alendronic and risedronic acids are a class of drugs clinically used to prevent bone density loss and osteoporosis. Novel P-C-P bisphosphonates were synthesized for targeting human farnesyl pyrophosphate synthase (hFPPS) and human geranylgeranyl pyrophosphate synthase (hGGPPS), key enzymes of the mevalonate pathway, and capable of anti-proliferative action on a number of cell lines (PC3, MG63, MC3T3, RAW 264.7, J774A.1, bone marrow cells and their co-colture with PC3) involved in bone homeostasis, bone formation and death. Among sixteen compounds, [1-hydroxy-2-(pyrimidin-2-ylamino)ethane-1,1-diyl]bis(phosphonic acid) (10) was effective in reducing PC3 and RAW 264.7 cell number in crystal-violet and cell-dehydrogenase activity assays at 100 μM concentration. 10 reduced differentiated osteoclasts number similarly with zoledronic acid in osteoclastogenesis assay. At nanomolar concentrations, 10 was more effective than zoledronic acid in inducing mineralization in MC3T3 and murine bone marrow cells. Further, 10 significantly inhibited the activity of hFPPS showing an IC50 of 0.31 μM and a remarkable hydroxyapatite binding of 90%. Docking calculations were performed identifying putative interactions between some representative novel bisphosphonates and both hFPPS and hGGPPS. Then, 10 was found to behave similarly or even better than zoledronic acid as a anti-resorptive agent.
Functional Micelles for Hard Tissue Targeted Delivery of Chemicals
-
, (2016/12/16)
Compositions and methods for targeting agents to hard tissue are provided.
