Methylenediphosphonic Acid Research Articles

Phosphonato complexes of platinum(II): Kinetics of formation and phosphorus-31 NMR characterization studies

Reactions of cis-diamminedichloroplatinum(II) with phosphonoformic acid (PFA), phosphonoacetic acid (PAA), and methylenediphosphonic acid (MDP) yield various phosphonatoplatinum(II) chelates which were characterized by phosphorus-31 NMR spectroscopy. The P-31 resonances for the chelates appear at 6–12 ppm downfield as compared to the uncomplexed ligands. All complexes exhibit monoprotic acidic behavior in the pH range 2–10. The chemical shift-pH profiles yielded acidity constants, 1.0 × 10 −4, 1.5 × 10 −4, and 1.3 × 10 −6 M −1, for the PFA, PAA, and MDP chelates. In addition to the monomeric chelate, MDP formed a bridged diplatinum(II,II) complex when it reacted with cis-Pt (NH 3) 2(H 2O) 2 2+. The P-31 resonance for this binuclear complex appears at 22 ppm downfield from the unreacted ligand. Rate data for the complexation reactions of the phosphonate ligands with the dichloroplatinum complex are consistent with a mechanism in which a monodentate complex is formed initially through rate-limiting aquation process of the platinum complex, followed by a rapid chelation. For the PFA and PAA complexes, initial binding sites are the carboxylato oxygens. Implications of the various binding modes of the phosphonates in relationship to their antiviral activities are discussed.

ChemInform Abstract: Preparation and Crystal Structures of New Platinum/Phosphonate Complexes.

AbstractThe Pt complexes (I) and (II) are prepared by reaction of the corresponding dichlorodiamine‐Pt(II) complexes with trisodium phosphonoformate or methylene diphosphonic acid, in the cases of (Ib) and (II) after chloride abstraction with AgNO3.

Indirect spectrophotometric determination of BIDA, DISIDA, DTPA and MDP in labelled compounds

N-(4-(n-butyl)-acetanilide)iminodiacetic acid (BIDA), N-(2,6-diisopropylacetanilide)iminodiacetic acid (DISIDA), diethylenetriaminepentaacetic acid (DTPA) and methylene diphosphonic acid (MDP) are used in labelling kits. The contents of BIDA, DISIDA or MDP of the 99mTc-labelled compounds can be determined (indirectly) spectrophotometrically with copper, eriochrome cyanine R (ECC) and dodecylethyldimethylammonium bromide (DEDA) in a sodium barbital buffered system at pH 8.5. The calibration curves obey Beer's Law from 0 to 40 μg/25 mL for BIDA and DISIDA, 0 to 60 μg/25 mL for DTPA and 0 to 100 μg/10 mL for MDP.

Iminobis(Methylenediphosphonic) acid

When formamide was reacted with phosphorous acid and phosphorus trichloride, the formation of iminobis(methylenediphosphonic) acid was detected.

Reaction of pyrophosphites with carboxylate esters

Reaction of formates with tetraalkyl pyrophosphites in the presence of boron trifluoride gives alkoxy(aryloxy)methylenediphosphonic acids.

Complexometric titration of thorium with methylene diphosphonic acid: Application to the determination of methylene diphosphonic acid in labelling kits

Methylene diphosphonic acid (MDP) is used as a selective titrimetric reagent for thorium. In the presence of trans-1,2- diaminocyclohexane- N, N, N′, N′-tetraacetic acid (DCTA) a soluble binuclear ternary complex, Th 2 (DCTA) 2 (MDP) is formed. The titration is carried out with MDP in a slightly acidic medium, buffered with ethylenediamine (EDA), using methylthymol blue as indicator. For the determination of MDP in labelling kits, two 5 mL aliquots of thorium nitrate solution (4 mM) are respectively titrated with 2.000 mM MDP and the MDP solution prepared from the labelling kit.

α CÉTOPHOSPHONATES ET ESTERS CYCLIQUES D'HYDROXYMÉTHYLÈNES DIPHOSPHONATES SYNTHESES, STRUCTURES ET HYDROLYSE

Abstract Synthesis of symmetrical diesters derived from hydroxy methylene diphosphonic acids 1 to 8 is described either in one step or via the corresponding α ketophosphonate 1a to 8a. Study of the diphosphonates (1 to 6) → phosphate-phosphonates (1b to 6b) isomerization has been realized. Results related to peculiar cases in connection with nonsymmetrical esters 10, 11, 17 and study of the hydrolysis reaction of diphosphonates are presented.

ATP analogues and other phosphate compounds as gorging stimulants for Rhodnius prolixus

Five analogues of ATP and six other non-nucleotide compounds with phosphate groups were tested as gorging stimulants for second-instar larvae of Rhodnius prolixus to determine the importance of the phosphate chain. Only molecules with terminal phosphate groups were potent. Insertion of an imido group (5′-Adenylylimidodiphosphate, AMP-PNP) or a methylene group (β, γ-Methylene adenosine 5′-triphosphate, AMP-PCP) between the β and γ phosphates of ATP reduced the potency compared to ATP by ratios of 1.8 and 25.5, respectively. Substituting ribose (Adenosine 5′-diphosphoribose, AMP-PR) for the γ phosphate group or an amidate or a sulphate group (Adenosine 5′-phosphoramidate, AMP-N; Adenosine 5′-phosphosulphate, AMP-S) for the β and γ phosphate groups of ATP resulted in a complete loss of stimulatory activity. Some non-nucleotide phosphate compounds were potent phagostimulants. Pyrophosphate with an ED 50 of 64 μM had a potency ratio compared with ATP of 1:17. Methylene diphosphonic acid (ED 50 680 μM) and even single phosphate ions (ED 50 2.5 mM) had substantial potency. Two isomers of phosphoglyceric acid differ greatly in their ability to stimulate gorging; 2-PGA was active (ED 50 160 μM) whereas 3-PGA had almost no activity. A summary of known phagostimulants to R. prolixus supports the hypothesis that ATP-like gorging stimulants act by forming a temporary binding to 3 sites on a receptor protein in the membrane of the chemosensory cell. The amino group on C 6 of adenine, the OH group on C 2 of ribose and the terminal phosphate group(s) determine potency, presumably by determining binding affinity. However, only the phosphate group appears essential to the chemosensory process.

Effects of acute administration of ethane hydroxydiphosphonate (EHDP) on skeletal scintigraphy with technetium-99m methylene diphosphonic acid (Tc-MDP) in the rat.

A study has been performed in the rat to assess the effect of EHDP on the distribution of 99Tcm-labelled MDP used for skeletal imaging. Profound alterations in bone, kidney and blood levels were observed. These observations cast doubt on the value of bone scans for monitoring the therapeutic effect of diphosphonates.

Kinetics of dissolution of calcium hydroxyapatite: IV. The effect of some biologically important inhibitors

A model describing the kinetics of dissolution of calcium hydroxyapatite, Ca 10(PO 4) 6(OH) 2, microcrystals in aqueous solution is presented. In this model the rate-controlling step is formation of dissolution nuclei, the lateral growth rate of which depends on the concentration of hydrogen ions. This dependence on hydrogen ion concentration is explained by hydrogen ion catalysis of the exchange of phosphate between the crystal surface and the solution. According to this model, the rate of dissolution should be practically zero when the size of a critical dissolution nucleus is comparable to the ratio of the surface area to the number of inhibitor units adsorbed to the crystal surface. A simple model for Langmuir adsorption of inhibitors onto crystals, taking into account the protolytic forms of the inhibitor in the solution and on the crystal surface is presented. The effects of pyrophosphoric acid, 1-hydroxy-ethylidene-1, 1-diphosphonic acid, methylene diphosphonic acid, 3-phosphoglyceric acid, 3-phosphoserine, 3-amino-1,1,3-propanetricarboxylic acid (γ-carboxyglutamic acid) and phosphoethanolamine on the rate of dissolution of calcium hydroxyapatite crystals in aqueous syspension at pH = 6.8 and pH = 7.2 have been studied.

The determination of methylene diphosphonic acid in lyophilized radiopharmaceuticals

The determination of methylene diphosphonic acid in lyophilized radiopharmaceuticals

Determination of Methylenediphosphonic Acid by Ion-Pairing High Pressure Liquid Chromatography with Refractive Index Detection

Determination of Methylenediphosphonic Acid by Ion-Pairing High Pressure Liquid Chromatography with Refractive Index Detection

E.S.R. spectra of X-irradiated methylene diphosphonic acid III.

(1979). E.S.R. spectra of X-irradiated methylene diphosphonic acid III. Molecular Physics: Vol. 37, No. 5, pp. 1649-1653.

Inhibition of hypersensitivity of delayed and immediate types in guinea pigs by methylenediphosphonic acid

The effect of subcutaneous injection of the immunosuppressive agent methylene-diphosphonic acid (MDPA) on hypersensitivity of delayed and immediate types (HDT and HIT) was studied in guinea pigs. Administration of MDPA to the animals in a dose of 30 μg/g was found to inhibit HDT and HIT by 60–80% compared with the control.

Synthesis and characterization of straight-chain oligomers of methylenediphosphonic acid

Synthesis and characterization of straight-chain oligomers of methylenediphosphonic acid

Structural investigations of methylenediphosphonic acids. 2. The molecular and crystal structure of propane-1,3-diphosphonic acid

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTStructural investigations of methylenediphosphonic acids. 2. The molecular and crystal structure of propane-1,3-diphosphonic acidE. Gebert, A. H. Reis Jr., M. E. Druyan, S. W. Peterson, G. W. Mason, and D. F. PeppardCite this: J. Phys. Chem. 1977, 81, 5, 471–475Publication Date (Print):March 1, 1977Publication History Published online1 May 2002Published inissue 1 March 1977https://doi.org/10.1021/j100520a020RIGHTS & PERMISSIONSArticle Views78Altmetric-Citations17LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (656 KB) Supporting Info (1)»Supporting Information Supporting Information Get e-Alerts

E.S.R. spectra of X-irradiated methylene diphosphonic acid

The E.S.R. spectra of phosphorus-centred radicals formed in the X-irradiation of single crystals of methylene diphosphonic acid are reported. The radicals are identified as phosphoranyl radicals, (HO)2(O)P-CH2-P(OH)3 and the tricoordinated species OP(OH)2, (HO)2(O)P-CH2-P(O)(OH). In the last radical coupling from the second 31P nucleus is also observed. Attempts are made to correlate the direction cosines of the 31P couplings with the X-ray crystallographic data.

Comparison of 99mTc-labeled phosphate and phosphonate agents for skeletal imaging

The use of 99mTc-labeled phosphate and phosphonate compounds in place of 18F, 85Sr, and 87Sr for bone scintigraphy has become commonplace throughout the world in a relatively short time. The labeling of polyphosphate with 99mTc 4 years ago, followed rapidly by the introduction of 99mTc-labeled pyrophosphate for skeletal imaging, must therefore be regarded as a major contribution to the practice of diagnostic nuclear medicine. The markedly reduced patient radiation exposure and concomitant increase in photon detection efficiency derived from the more favorable physical decay characteristics of 99mTc led to increased sensitivity and resolution and in turn to improved diagnostic efficacy. The subsequent clinical use of the phosphonate complex 99mTc-HEDP represented a further modification of the same basic approach. Current clinical trials with 99mTc-labeled methylene diphosphonic acid (MDP), which appears to demonstrate enhanced biologic properties for scintigraphy of the osseous structures, is the latest example in this series of refinements. This article compares the technetium-labeled agents already in clinical use and, using animal data, contrasts them with several new multifunctional phosphonates and the novel inorganic compound sodium imidodiphosphate (IDP). In addition, an attempt is made to clarify the conflicting evidence in the nuclear medicine literature regarding the relationship between polyphosphate chain length and skeletal uptake.

Full anhydrization of methylenediphosphonic acid and of phosphoric acids by a carbodiimide

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTFull anhydrization of methylenediphosphonic acid and of phosphoric acids by a carbodiimideThomas. Glonek, John R. Van Wazer, and Terrell C. MyersCite this: Inorg. Chem. 1975, 14, 7, 1597–1602Publication Date (Print):July 1, 1975Publication History Published online1 May 2002Published inissue 1 July 1975https://doi.org/10.1021/ic50149a032RIGHTS & PERMISSIONSArticle Views75Altmetric-Citations11LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (778 KB) Get e-Alerts Get e-Alerts

E.S.R. spectra of X-irradiated methylene diphosphonic acid

E.S.R. spectra of X-irradiated methylene diphosphonic acid