Systematic Study of the Physicochemical Properties of a Homologous Series of Aminobisphosphonates

被引:32
作者
Alanne, Aino-Liisa [1 ]
Hyvonen, Helena [2 ]
Lahtinen, Manu [3 ]
Ylisirnio, Markku [1 ]
Turhanen, Petri [1 ]
Kolehmainen, Erkki [3 ]
Peraniemi, Sirpa [1 ]
Vepsalainen, Jouko [1 ]
机构
[1] Univ Eastern Finland, Sch Pharm, Bioctr Kuopio, FIN-70211 Kuopio, Finland
[2] Univ Helsinki, Dept Chem, Inorgan Chem Lab, FIN-00014 Helsinki, Finland
[3] Univ Jyvaskyla, Dept Chem, FIN-40014 Jyvaskyla, Finland
基金
芬兰科学院;
关键词
bisphosphonates; aqueous solubility; pKa; physicochemical properties; BISPHOSPHONATES; ACIDS; COORDINATION; DERIVATIVES; ALENDRONATE; CRYSTAL; GROWTH; AGENTS;
D O I
10.3390/molecules170910928
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
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, H2N(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 (H-1, C-13, P-31-NMR) and solid state (C-13, N-15 and P-31-CPMAS NMR) were determined.
引用
收藏
页码:10928 / 10945
页数:18
相关论文
共 30 条
[1]   Piperazinium and piperidinium trihydrogen 1-hydroxyethane-1,1-diphosphonates [J].
Afonin, EG ;
Aleksandrov, GG .
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2002, 72 (02) :221-225
[2]   Covalent Inhibition of Bacterial Quorum Sensing [J].
Amara, Neri ;
Mashiach, Roi ;
Amar, Dotan ;
Krief, Pnina ;
Spieser, Stephane A. H. ;
Bottomley, Matthew J. ;
Aharoni, Amir ;
Meijler, Michael M. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (30) :10610-10619
[3]  
[Anonymous], 1999, 4500 P PHOSPH 1 STAN
[4]  
Boichenko AP, 2009, CENT EUR J CHEM, V7, P8, DOI [10.2478/s11532-008-0099-z, 10.1109/PTC.2009.5282263]
[5]   Novel therapeutic agents for bone resorption. Part 1. Synthesis and protonation thermodynamics of poly(amido-amine)s containing bis-phosphonate residues [J].
Casolaro, Mario ;
Casolaro, Ilaria ;
Spreafico, Adriano ;
Capperucci, Caterina ;
Frediani, Bruno ;
Marcolongo, Roberto ;
Margiotta, Nicola ;
Ostuni, Rosa ;
Mendichi, Raniero ;
Samperi, Filippo ;
Ishii, Takehiko ;
Ito, Yoshihiro .
BIOMACROMOLECULES, 2006, 7 (12) :3417-3427
[6]   Herbicidal derivatives of aminomethylenebisphosphonic acid. Part IV. Hydroxyalkylidenebisphosphonates, iminomethylenebisphosphonates and ureidomethylenebisphosphonates [J].
Chuiko, AL ;
Lozinsky, MO ;
Jasicka-Misiak, I ;
Kafarski, P .
JOURNAL OF PLANT GROWTH REGULATION, 1999, 18 (04) :171-174
[7]   STRUCTURE OF 6-AMINO-1-HYDROXYHEXYLIDENEBIS(PHOSPHONIC ACID) [J].
COIRO, VM ;
LAMBA, D .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1989, 45 :446-448
[8]   1-Hydroxyalkane-1,1-diyldiphosphonates as potent chelating agents for metal ions. Potentiometric and spectroscopic studies of copper(II) coordination [J].
Dyba, M ;
JezowskaBojczuk, M ;
Kiss, E ;
Kiss, T ;
Kozlowski, H ;
Leroux, Y ;
ElManouni, D .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1996, (06) :1119-1123
[9]  
Fleisch H., 1995, BISPHOSPHONATES BONE
[10]   Mix-solvothermal syntheses, characterization, and properties of new zinc diphosphonates with Zn-O-P chains, layers, and 3D frameworks [J].
Fu, Ruibiao ;
Hu, Shengmin ;
Wu, Xintao .
CRYSTAL GROWTH & DESIGN, 2007, 7 (06) :1134-1144