Tetrasodium carbonyldiphosphonate. Synthesis, reactions, and spectral properties

Quimby, Oscar T.; Prentice, J. B.; Nicholson, D. Allan

doi:10.1021/jo01287a104

Cited by 42 publications

(16 citation statements)

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“…Dichloromethylenediphosphonic acid was synthesized as described by Quimby et al (1967) and difluoromethylenediphosphonic acid was synthesized as described by Blackburn et al (1981 a). Adenosine 5'-(0,T-dichloromethylene)triphosphonate (AMP-PCC12P) and adenosine 5'-(p,y-difluoromethylene)triphosphonate (AMP-PCF2P) (Blackburn et al, 1981b) were obtained by activation of AMP with carbonyldiimidazole followed by addition of dichloro-or difluoromethylenediphosphonic acid respectively.…”

Section: Pharmacological Studiesmentioning

confidence: 99%

Pharmacological effects of isopolar phosphonate analogues of ATP on P₂‐purinoceptors in guinea‐pig taenia coli and urinary bladder

Cusack

Hourani

Loizou

et al. 1987

British J Pharmacology

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1Isopolar methylene phosphonate analogues ofadenosine triphosphate (ATP) were synthesized and tested on the guinea-pig isolated taenia coli (where ATP causes relaxation) and urinary bladder (where ATP causes contraction), to see if restoration of the electronegativity of the methylene linkage would enhance pharmacological potency. The compounds used were the dichloromethylene and difluoromethylene analogues of adenosine 5'-(P,y-methylene)triphosphonate (AMP-PCP), L-adenosine 5'-(P,y-methylene)triphosphonate (L-AMP-PCP) and 2-methylthioadenosine 5'-(f,y-methylene)-triphosphonate (2-methylthio-AMP-PCP). 2 The order ofpotency of the analogues depended on the tissue, and was independent of the nature of the purine or ribose moieties. None of the analogues was degraded by ectonucleotidases on either tissue. 3 In the taenia coli the order of potency for relaxation was difluoromethylene > dichloromethylene > methylene, and this reflected the order ofelectronegativity of the analogues. The isopolar analogues of L-AMP-PCP were inactive in the taenia coli. 4 In the bladder the order of potency for contraction was difluoromethylene> methylene> dichloromethylene, suggesting that electronegativity is of lesser importance here. The isopolar analogues of L-AMP-PCP were active in this tissue. 5 The differences between the two tissues in the order of potency for these non-degradable analogues supports suggestions that P2-purinoceptors in the taenia coli (P2y) are different from those in the bladder (P2X). The isopolar analogues of L-AMP-PCP, like L-AMP-PCP itself, were selective agonists at the P2x-purinoceptor.

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Section: Pharmacological Studiesmentioning

confidence: 99%

Pharmacological effects of isopolar phosphonate analogues of ATP on P₂‐purinoceptors in guinea‐pig taenia coli and urinary bladder

Cusack

Hourani

Loizou

et al. 1987

British J Pharmacology

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“…A bisdialkylphosphonomethyl-dialkylphosphate was first mentioned by Quimby [4] as isopropyl ester. It was considered as an intermediate in the reaction of sodium diisopropyl phosphite with phosgene in toluene for the synthesis of tetrasodium carbonyldiphosphonate, but it has not been isolated in a pure state.…”

Section: Resultsmentioning

confidence: 99%

Convenient synthesis of bisphosphonomethylphosphoric acid

Gagnard

Leydet

Barragan

et al. 2003

Heteroatom Chemistry

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“…Medronate and clodronate were from Sigma (St. Louis, MO, USA). Oxidronate was synthesized to order (Quimby et al 1967). Etidronate, PPi, PFA, amino acids, and other compounds were purchased from Wako Pure Chemical Industries (Osaka, Japan).…”

Section: Mice and Reagentsmentioning

confidence: 99%

Inhibition of Phosphate Transporters Ameliorates the Inflammatory and Necrotic Side Effects of the Nitrogen-Containing Bisphosphonate Zoledronate in Mice

Okada

Kiyama

Sato

et al. 2013

Tohoku J. Exp. Med.

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Bisphosphonates (BPs) are pyrophosphate analogs. They are widely used against enhanced boneresorption in various diseases. Nitrogen-containing BPs (N-BPs) exhibit strong anti-bone-resorptive effects but have inflammatory and necrotic side effects. The non-nitrogen-containing BPs (non-N-BPs) etidronate and clodronate lack such side effects, but their anti-bone-resorptive effects are weak. In mice, etidronate and clodronate reduce the inflammatory/necrotic effects of N-BPs, even those of zoledronate, the N-BP with the strongest anti-bone-resorptive effect yet reported and the highest risk of inflammation/necrosis. Here, to explore the mechanisms underlying this protection, we used a mouse model in which a single reagent or a mixture of two reagents was injected subcutaneously into ear-pinnas. These reagents included zoledronate, four non-N-BPs, pyrophosphate, and inhibitors of various organic-anion-transporters. Pyrophosphate and two of the four non-N-BPs (not etidronate or clodronate) had inflammatory/necrotic effects. These effects were reduced by etidronate and clodronate, but not by phosphonoformate, an inhibitor of two of the three known phosphate-transporter families. Phosphonoformate reduced the inflammatory/necrotic effects of zoledronate, but not those of pyrophosphate or of non-N-BPs. Conversely, pyrophosphate, at non-inflammatory/necrotic concentrations, reduced the inflammatory/necrotic effects of non-N-BPs, but not those of zoledronate. The efficacies of the protective effects against the inflammatory/ necrotic effects of zoledronate were clodronate > etidronate > phosphonoformate. These findings suggest that (i) the N-BP zoledronate may enter soft-tissue cells via phosphonoformate-inhibitable phosphatetransporters, (ii) other phosphate-transporters may carry pyrophosphate and inflammatory/necrotic non-N-BPs into such cells, and (iii) etidronate and clodronate inhibit all these transporters, and they ameliorate the side effects of zoledronate by inhibiting phosphonoformate-inhibitable phosphatetransporters.

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Tetrasodium carbonyldiphosphonate. Synthesis, reactions, and spectral properties

Cited by 42 publications

References 0 publications

Pharmacological effects of isopolar phosphonate analogues of ATP on P₂‐purinoceptors in guinea‐pig taenia coli and urinary bladder

Pharmacological effects of isopolar phosphonate analogues of ATP on P₂‐purinoceptors in guinea‐pig taenia coli and urinary bladder

Convenient synthesis of bisphosphonomethylphosphoric acid

Inhibition of Phosphate Transporters Ameliorates the Inflammatory and Necrotic Side Effects of the Nitrogen-Containing Bisphosphonate Zoledronate in Mice

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Tetrasodium carbonyldiphosphonate. Synthesis, reactions, and spectral properties

Cited by 42 publications

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Pharmacological effects of isopolar phosphonate analogues of ATP on P2‐purinoceptors in guinea‐pig taenia coli and urinary bladder

Pharmacological effects of isopolar phosphonate analogues of ATP on P2‐purinoceptors in guinea‐pig taenia coli and urinary bladder

Convenient synthesis of bisphosphonomethylphosphoric acid

Inhibition of Phosphate Transporters Ameliorates the Inflammatory and Necrotic Side Effects of the Nitrogen-Containing Bisphosphonate Zoledronate in Mice

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Pharmacological effects of isopolar phosphonate analogues of ATP on P₂‐purinoceptors in guinea‐pig taenia coli and urinary bladder

Pharmacological effects of isopolar phosphonate analogues of ATP on P₂‐purinoceptors in guinea‐pig taenia coli and urinary bladder