The world's first wiki where authorship really matters (Nature Genetics, 2008). Due credit and reputation for authors. Imagine a global collaborative knowledge base for original thoughts. Search thousands of articles and collaborate with scientists around the globe.

wikigene or wiki gene protein drug chemical gene disease author authorship tracking collaborative publishing evolutionary knowledge reputation system wiki2.0 global collaboration genes proteins drugs chemicals diseases compound
Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
Chemical Compound Review

AG-D-73488     dihydroxy-oxo-phosphanium

Synonyms: CHEBI:44976, LTBB003363, CTK0H5070, AKOS015903593, FT-0688176, ...
Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

Disease relevance of dihydroxy-oxo-phosphanium


Psychiatry related information on dihydroxy-oxo-phosphanium

  • This method of monolayer formation contrasts the requirement for heating and long reaction times found to be necessary to form phosphonate monolayers on other metal oxide substrates, such as titanium and silicon [6].

High impact information on dihydroxy-oxo-phosphanium

  • Using the hippocampal slice preparation, we now report that the phosphonic acid derivative of baclofen, phaclofen, is a remarkably selective antagonist of both the postsynaptic action of baclofen and the bicuculline-resistant action of GABA, and that it selectively abolishes the slow inhibitory postsynaptic potential in pyramidal cells [7].
  • The x-ray structures of three esterase-like catalytic antibodies identified by screening for catalytic activity the entire hybridoma repertoire, elicited in response to a phosphonate transition state analog (TSA) hapten, were analyzed [8].
  • The three-dimensional structure of an unusually active hydrolytic antibody with a phosphonate transition state analog (hapten) bound to the active site has been solved to 2.5 A resolution [9].
  • Immunization with a phosphonate monoester transition-state analog of cocaine provided monoclonal antibodies capable of catalyzing the hydrolysis of the cocaine benzoyl ester group [10].
  • An antibody generated against a neutral phosphonate diester transition-state analog was found to catalyze the aminoacylation of the 3'-hydroxyl group of thymidine with an alanyl ester [11].

Chemical compound and disease context of dihydroxy-oxo-phosphanium


Biological context of dihydroxy-oxo-phosphanium

  • The IC50 for the amide was 4.4 x 10(-4) mol fraction and for the phosphonate was 1.6 x 10(-5) mol fraction [17].
  • This work shows that these ligands exhibit excellent enantioselectivity in rhodium-catalyzed asymmetric hydrogenation of alpha,beta-unsaturated phosphonic acid derivatives [18].
  • Other recognizable gene clusters include many involved in catabolic activities such as protocatechuate utilization and phosphonate degradation [19].
  • A keto analog of PALA, 4,5-dicarboxy-2-ketopentyl phosphonate, also binds tightly to the catalytic subunit and induces a very similar conformational change, whereas an alcohol analog, 4,5-dicarboxy-2-hydroxypentyl phosphonate, does not bind tightly, indicating the critical importance of an unhindered carbonyl group with trigonal geometry [20].
  • The kinetics of binding and dissociation of stable phosphonate analogs of the tetrahedral intermediate (Alberg, D., and Bartlett, P.A. (1989) J. Am. Chem. Soc. 111, 2337) were also examined [21].

Anatomical context of dihydroxy-oxo-phosphanium

  • The crystal structure of human neutrophil cathepsin G, complexed with the peptidyl phosphonate inhibitor Suc-Val-Pro-PheP-(OPh)2, has been determined to a resolution of 1.8 A using Patterson search techniques [22].
  • One such novel phosphonate quinoxalinedione derivative and competitive AMPA antagonist ZK200775 exhibited a surprisingly long therapeutic time window of >4 h after permanent occlusion of the middle cerebral artery in rats and was devoid of renal toxicity [23].
  • Most of the nucleophilic reactivity of B cells measured by formation of covalent adducts of a hapten amidino phosphonate diester was attributed to micro and kappa/lambda subunits of the B cell receptor [24].
  • The majority of CD4(+) T cells repopulating the intestinal mucosa following PMPA therapy were CD29(hi) and CD11ahi [25].
  • Phosphonate 9-[2-(phosphomethoxypropyl]adenine (PMPA) treatment led to a moderate suppression of intestinal viral loads and repopulation of intestinal mucosa by predominantly activated memory CD4(+) T-helper cells [25].

Associations of dihydroxy-oxo-phosphanium with other chemical compounds

  • An antibody generated against a neutral phosphonate diester transition-state (TS not equal to) analog catalyzes the formation of an amide bond between a phenylalanyl amino group and an acyl azide derived from L-alanine [26].
  • Antibodies elicited against a phosphonate transition-state analogue were found to catalyze hydrolysis of a nonbioactive chloramphenicol monoester as a prodrug at a significantly higher rate above the uncatalyzed background reaction to regenerate chloramphenicol as a parent molecule [27].
  • Inhibition of fibroblast growth factor-2-induced vascular tumor formation by the acyclic nucleoside phosphonate cidofovir [28].
  • The phosphonate compound 2-aminoethylphosphonate is present as a component of complex carbohydrates on the surface membrane of many trypanosomatids including glycosylinositolphospholipids of Trypanosoma cruzi [29].
  • The finding that phosphonate modification at each of the 536 and 564 sites can promote interaction with the Grb2 adaptor protein indicates that the intramolecular interactions fostered by post-translational modifications of tyrosine are not energetically strong and susceptible to intermolecular competition [30].

Gene context of dihydroxy-oxo-phosphanium

  • (S, S)-3-Cyclohexyl-2-[[5-(2, 4-difluorophenyl)-2-[(phosphonomethyl)amino]pent-4-ynoyl]amino] propio nic acid (47), an arylacetylene amino phosphonate dipeptide, was found to inhibit ECE-1 and NEP with IC50 values of 14 nM and 2 microM, respectively [31].
  • The selectivity of CYP2C8 in catalyzing phosphonate O-deethylation indicates that coadministration of drugs that are metabolized by the same enzyme requires careful consideration [32].
  • Thus, the phosphonate moiety in this analog represents an important new lead in the development of FPGS inhibitors [33].
  • On the basis of mutational analysis, the genes for phosphonate uptake and degradation in Escherichia coli were shown to be organized in a 10.9-kb operon of 14 genes (named phnC to phnP) and induced by phosphate (P(i)) starvation [Metcalf and Wanner (1993) J Bacteriol 175: 3430-3442] [34].
  • 3-(3-Actamide-1-benzyl-2-ethylindolyl-5-oxy)propane phosphonic acid (LY311727), a potent inhibitor of human group IIA PLA2, strongly inhibits GV-PLA2 with an IC50 value of about 36 nM which is comparable to its inhibition of group IIA PLA2 [35].

Analytical, diagnostic and therapeutic context of dihydroxy-oxo-phosphanium


  1. Inhibition of a class C beta-lactamase by a specific phosphonate monoester. Pratt, R.F. Science (1989) [Pubmed]
  2. Radiopharmaceutical therapy of 5T33 murine myeloma by sequential treatment with samarium-153 ethylenediaminetetramethylene phosphonate, melphalan, and bone marrow transplantation. Turner, J.H., Claringbold, P.G., Manning, L.S., O'Donoghue, H.L., Berger, J.D., Glancy, R.J. J. Natl. Cancer Inst. (1993) [Pubmed]
  3. A genetic approach to the generation of antibodies with enhanced catalytic activities. Lesley, S.A., Patten, P.A., Schultz, P.G. Proc. Natl. Acad. Sci. U.S.A. (1993) [Pubmed]
  4. Inhibition of acquired immunodeficiency syndrome virus by oligodeoxynucleoside methylphosphonates. Sarin, P.S., Agrawal, S., Civeira, M.P., Goodchild, J., Ikeuchi, T., Zamecnik, P.C. Proc. Natl. Acad. Sci. U.S.A. (1988) [Pubmed]
  5. A phase I study of samarium-153 ethylenediaminetetramethylene phosphonate therapy for disseminated skeletal metastases. Turner, J.H., Claringbold, P.G., Hetherington, E.L., Sorby, P., Martindale, A.A. J. Clin. Oncol. (1989) [Pubmed]
  6. Formation of self-assembled monolayers of alkylphosphonic acid on the native oxide surface of SS316L. Raman, A., Dubey, M., Gouzman, I., Gawalt, E.S. Langmuir : the ACS journal of surfaces and colloids. (2006) [Pubmed]
  7. A physiological role for GABAB receptors in the central nervous system. Dutar, P., Nicoll, R.A. Nature (1988) [Pubmed]
  8. Structural convergence in the active sites of a family of catalytic antibodies. Charbonnier, J.B., Golinelli-Pimpaneau, B., Gigant, B., Tawfik, D.S., Chap, R., Schindler, D.G., Kim, S.H., Green, B.S., Eshhar, Z., Knossow, M. Science (1997) [Pubmed]
  9. Crystal structure of a catalytic antibody with a serine protease active site. Zhou, G.W., Guo, J., Huang, W., Fletterick, R.J., Scanlan, T.S. Science (1994) [Pubmed]
  10. Antibody-catalyzed degradation of cocaine. Landry, D.W., Zhao, K., Yang, G.X., Glickman, M., Georgiadis, T.M. Science (1993) [Pubmed]
  11. An efficient antibody-catalyzed aminoacylation reaction. Jacobsen, J.R., Prudent, J.R., Kochersperger, L., Yonkovich, S., Schultz, P.G. Science (1992) [Pubmed]
  12. Potent inhibition of hemangioma formation in rats by the acyclic nucleoside phosphonate analogue cidofovir. Liekens, S., Andrei, G., Vandeputte, M., De Clercq, E., Neyts, J. Cancer Res. (1998) [Pubmed]
  13. Investigations concerning the mode of action of 3,4-dihydroxybutyl-1-phosphonate on Escherichia coli. Cheng, P.J., Nunn, W.D., Tyhach, R.J., Goldstein, S.L., Engel, R., Tropp, B.E. J. Biol. Chem. (1975) [Pubmed]
  14. A phosphonate monoester hydrolase from Burkholderia caryophilli PG2982 is useful as a conditional lethal gene in plants. Dotson, S.B., Lanahan, M.B., Smith, A.G., Kishore, G.M. Plant J. (1996) [Pubmed]
  15. Identification and Characterization of Single Chain Anti-cocaine Catalytic Antibodies. McKenzie, K.M., Mee, J.M., Rogers, C.J., Hixon, M.S., Kaufmann, G.F., Janda, K.D. J. Mol. Biol. (2007) [Pubmed]
  16. The synthesis and antiviral properties of acyclic nucleoside analogues with a phosphonomethoxy fragment in the side chain. Khandazhinskaya, A., Yasko, M., Shirokova, E. Current medicinal chemistry. (2006) [Pubmed]
  17. Critical role of a hydrogen bond in the interaction of phospholipase A2 with transition-state and substrate analogues. Yu, L., Dennis, E.A. Proc. Natl. Acad. Sci. U.S.A. (1991) [Pubmed]
  18. Asymmetric hydrogenation of alpha,beta-unsaturated phosphonates with Rh-BisP* and Rh-MiniPHOS catalysts: scope and mechanism of the reaction. Gridnev, I.D., Yasutake, M., Imamoto, T., Beletskaya, I.P. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
  19. The complete sequence of the 1,683-kb pSymB megaplasmid from the N2-fixing endosymbiont Sinorhizobium meliloti. Finan, T.M., Weidner, S., Wong, K., Buhrmester, J., Chain, P., Vorhölter, F.J., Hernandez-Lucas, I., Becker, A., Cowie, A., Gouzy, J., Golding, B., Pühler, A. Proc. Natl. Acad. Sci. U.S.A. (2001) [Pubmed]
  20. Evidence from 13C NMR for protonation of carbamyl-P and N-(phosphonacetyl)-L-aspartate in the active site of aspartate transcarbamylase. Roberts, M.F., Opella, S.J., Schaffer, M.H., Phillips, H.M., Stark, G.R. J. Biol. Chem. (1976) [Pubmed]
  21. "Kinetic competence" of the 5-enolpyruvoylshikimate-3-phosphate synthase tetrahedral intermediate. Anderson, K.S., Johnson, K.A. J. Biol. Chem. (1990) [Pubmed]
  22. The 1.8 A crystal structure of human cathepsin G in complex with Suc-Val-Pro-PheP-(OPh)2: a Janus-faced proteinase with two opposite specificities. Hof, P., Mayr, I., Huber, R., Korzus, E., Potempa, J., Travis, J., Powers, J.C., Bode, W. EMBO J. (1996) [Pubmed]
  23. ZK200775: a phosphonate quinoxalinedione AMPA antagonist for neuroprotection in stroke and trauma. Turski, L., Huth, A., Sheardown, M., McDonald, F., Neuhaus, R., Schneider, H.H., Dirnagl, U., Wiegand, F., Jacobsen, P., Ottow, E. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
  24. Ontogeny of proteolytic immunity: IgM serine proteases. Planque, S., Bangale, Y., Song, X.T., Karle, S., Taguchi, H., Poindexter, B., Bick, R., Edmundson, A., Nishiyama, Y., Paul, S. J. Biol. Chem. (2004) [Pubmed]
  25. Activated memory CD4(+) T helper cells repopulate the intestine early following antiretroviral therapy of simian immunodeficiency virus-infected rhesus macaques but exhibit a decreased potential to produce interleukin-2. Mattapallil, J.J., Smit-McBride, Z., Dailey, P., Dandekar, S. J. Virol. (1999) [Pubmed]
  26. Antibody catalysis of peptide bond formation. Jacobsen, J.R., Schultz, P.G. Proc. Natl. Acad. Sci. U.S.A. (1994) [Pubmed]
  27. Prodrug activation via catalytic antibodies. Miyashita, H., Karaki, Y., Kikuchi, M., Fujii, I. Proc. Natl. Acad. Sci. U.S.A. (1993) [Pubmed]
  28. Inhibition of fibroblast growth factor-2-induced vascular tumor formation by the acyclic nucleoside phosphonate cidofovir. Liekens, S., Neyts, J., De Clercq, E., Verbeken, E., Ribatti, D., Presta, M. Cancer Res. (2001) [Pubmed]
  29. Properties of phosphoenolpyruvate mutase, the first enzyme in the aminoethylphosphonate biosynthetic pathway in Trypanosoma cruzi. Sarkar, M., Hamilton, C.J., Fairlamb, A.H. J. Biol. Chem. (2003) [Pubmed]
  30. The role of C-terminal tyrosine phosphorylation in the regulation of SHP-1 explored via expressed protein ligation. Zhang, Z., Shen, K., Lu, W., Cole, P.A. J. Biol. Chem. (2003) [Pubmed]
  31. Design and synthesis of potent, selective inhibitors of endothelin-converting enzyme. Wallace, E.M., Moliterni, J.A., Moskal, M.A., Neubert, A.D., Marcopulos, N., Stamford, L.B., Trapani, A.J., Savage, P., Chou, M., Jeng, A.Y. J. Med. Chem. (1998) [Pubmed]
  32. Phosphonate O-deethylation of [4-(4-bromo-2-cyano-phenylcarbamoyl) benzyl]-phosphonic acid diethyl ester, a lipoprotein lipase-promoting agent, catalyzed by cytochrome P450 2C8 and 3A4 in human liver microsomes. Morioka, Y., Otsu, M., Naito, S., Imai, T. Drug Metab. Dispos. (2002) [Pubmed]
  33. Mechanism-based inhibition of human folylpolyglutamate synthetase: design, synthesis, and biochemical characterization of a phosphapeptide mimic of the tetrahedral intermediate. Tsukamoto, T., Haile, W.H., McGuire, J.J., Coward, J.K. Arch. Biochem. Biophys. (1998) [Pubmed]
  34. Phosphate-independent expression of the carbon-phosphorus lyase activity of Escherichia coli. Yakovleva, G.M., Kim, S.K., Wanner, B.L. Appl. Microbiol. Biotechnol. (1998) [Pubmed]
  35. Expression and characterization of human group V phospholipase A2. Chen, Y., Dennis, E.A. Biochim. Biophys. Acta (1998) [Pubmed]
  36. Specific marrow ablation before marrow transplantation using an aminophosphonic acid conjugate 166Ho-EDTMP. Appelbaum, F.R., Brown, P.A., Sandmaier, B.M., Storb, R., Fisher, D.R., Shulman, H.M., Graham, T.C., Schuening, F.G., Deeg, H.J., Bianco, J.A. Blood (1992) [Pubmed]
  37. A new approach to the synthesis of the 5'-deoxy-5'-methylphosphonate linked thymidine oligonucleotide analogues. Szabó, T., Kers, A., Stawinski, J. Nucleic Acids Res. (1995) [Pubmed]
  38. Synthesis and enzymatic properties of deoxyribooligonucleotides containing methyl and phenylphosphonate linkages. Agarwal, K.L., Riftina, F. Nucleic Acids Res. (1979) [Pubmed]
  39. New approach to oligonucleotide microarrays using zirconium phosphonate-modified surfaces. Nonglaton, G., Benitez, I.O., Guisle, I., Pipelier, M., Léger, J., Dubreuil, D., Tellier, C., Talham, D.R., Bujoli, B. J. Am. Chem. Soc. (2004) [Pubmed]
  40. Inhibition mode of a bisubstrate inhibitor of KDO8P synthase: a frequency-selective REDOR solid-state and solution NMR characterization. Kaustov, L., Kababya, S., Belakhov, V., Baasov, T., Shoham, Y., Schmidt, A. J. Am. Chem. Soc. (2003) [Pubmed]
WikiGenes - Universities