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

phosphanium     phosphanium

Synonyms: phosphonium, phosphorus(1+), AC1NUTBC, AGN-PC-0CPT0S, AC1NUTB9, ...
 
 
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 phosphanium

 

High impact information on phosphanium

 

Chemical compound and disease context of phosphanium

 

Biological context of phosphanium

 

Anatomical context of phosphanium

 

Associations of phosphanium with other chemical compounds

  • Membrane potential difference (Em) (mV), determined as the distribution of [14C]tetraphenyl phosphonium ion was -28 mV in control cells and -42 mV in valinomycin-treated cells (p less than 0.05) [21].
  • 1. Replacement of choline by the phosphonium analogue does not affect the growth rate of P815Y, NIL, 3T3, and SV40/3T3 cells in culture [22].
  • For the first time, suppressive activity against T. cruzi is reported for a 7-aminoquinoline, a phosphonium salt, and TAC pamoate; The biological model is believed to be able to serve as a means of identifying other new "leads* in seeking drugs broadly effective against T=ruzi infections in man [23].
  • 2. The temperature-dependence of the 31P n.m.r. (nuclear-magnetic-resonance) linewidths of the phosphate resonances of sonicated vesicles of distearoyl phosphatidylcholine and the phosphonium analogue are similar [24].
  • The reaction of the phosphonium ylide with 8-phenylmenthyl cinnamate followed by the hydrolysis of the resulting enol ether 4a afforded (3R,4S)-4-(diphenylphosphinyl)-3-phenylcycloheptanone (3R,4S)-5a as the major isomer [25].
 

Gene context of phosphanium

  • We also present data which demonstrate that other organic cations which contain aromatic rings, a minimal degree of lipophilicity (log P> -1) and carry a delocalized (Rho 123) or shielded (triphenylmethyl phosphonium) positive charge, also accumulate to a greater degree in MDR- vs MDR+ cells [26].
  • Various phosphonium salts possessing single or double alkyl chains of various lengths (C10 to C18) were prepared as cationic biocides, and their antimicrobial activities against 11 typical strains of microorganisms including methicillin-resistant Staphylococcus aureus (MRSA) were evaluated [27].
  • The smr gene was subcloned and expressed in S. aureus and E. coli and its ability to confer the multidrug resistant phenotype was demonstrated for two different lipophilic cation classes: phosphonium derivatives and quarternary amines [28].
  • PH4 of Petunia Is an R2R3 MYB Protein That Activates Vacuolar Acidification through Interactions with Basic-Helix-Loop-Helix Transcription Factors of the Anthocyanin Pathway [7].
  • In contrast, quaternary ammonium and phosphonium salts gave excellent ESI spectra, particularly in the positive ion mode [29].
 

Analytical, diagnostic and therapeutic context of phosphanium

  • MALDI/PSD analysis of glycopeptides converted to their acetyl phosphonium derivatives is an effective alternative to electron capture dissociation, as illustrated by the positioning of up to three GalNac residues along the full tandem repeat peptide sequence derived from the MUC 5AC mucin [30].
  • CONCLUSION: The high tumor accumulation and sensitivity to the phase of tumor development suggest the potential use of radiolabeled phosphonium analogs for in vivo tumor staging and as a tool for investigating tumor evolution [2].
  • 18F-Labeled p-fluorobenzyl triphenyl phosphonium cation (18F-FBnTP) is a member of a new class of positron-emitting lipophilic cations that may act as myocardial perfusion PET tracers [20].
  • Titration of the chemical shift of the phosphonium phosphorus reflects a group on the protein that has a pKa value of less than or equal to 5, which from the refined X-ray structure (D.R. Davies, personal communication) of the site is assigned to Asp-97L [31].
  • The catalytic activity of phosphonium salts towards cyclic carbonate synthesis from propylene oxide and CO(2) has been enormously enhanced by their immobilization onto silica that itself has no catalytic activity [32].

References

  1. Membrane potential in anaerobically growing Staphylococcus aureus and its relationship to gentamicin uptake. Mates, S.M., Patel, L., Kaback, H.R., Miller, M.H. Antimicrob. Agents Chemother. (1983) [Pubmed]
  2. Preferential accumulation of (3)H-tetraphenylphosphonium in non-small cell lung carcinoma in mice: comparison with (99m)Tc-MIBI. Madar, I., Weiss, L., Izbicki, G. J. Nucl. Med. (2002) [Pubmed]
  3. 1H NMR visible lipids are induced by phosphonium salts and 5-fluorouracil in human breast cancer cells. Cooper, W.A., Bartier, W.A., Rideout, D.C., Delikatny, E.J. Magnetic resonance in medicine : official journal of the Society of Magnetic Resonance in Medicine / Society of Magnetic Resonance in Medicine. (2001) [Pubmed]
  4. Novel phosphonium salts display in vitro and in vivo cytotoxic activity against human ovarian cancer cell lines. Manetta, A., Gamboa, G., Nasseri, A., Podnos, Y.D., Emma, D., Dorion, G., Rawlings, L., Carpenter, P.M., Bustamante, A., Patel, J., Rideout, D. Gynecol. Oncol. (1996) [Pubmed]
  5. Acute dermal toxicity of two quarternary organophosphonium salts in the rabbit. Dunn, B.J., Nichols, C.W., Gad, S.C. Toxicology (1982) [Pubmed]
  6. Calcium movement and membrane potential changes in the early phase of neutrophil activation by phorbol myristate acetate: a study with ion-selective electrodes. Mottola, C., Romeo, D. J. Cell Biol. (1982) [Pubmed]
  7. PH4 of Petunia Is an R2R3 MYB Protein That Activates Vacuolar Acidification through Interactions with Basic-Helix-Loop-Helix Transcription Factors of the Anthocyanin Pathway. Quattrocchio, F., Verweij, W., Kroon, A., Spelt, C., Mol, J., Koes, R. Plant Cell (2006) [Pubmed]
  8. On the enzymic mechanism of oxidative phosphorylation. Green, D.E., Vande Zande, H. Proc. Natl. Acad. Sci. U.S.A. (1982) [Pubmed]
  9. Investigation of the microheterogeneity and aglycone specificity-conferring residues of black cherry prunasin hydrolases. Zhou, J., Hartmann, S., Shepherd, B.K., Poulton, J.E. Plant Physiol. (2002) [Pubmed]
  10. The phosphonium ion efflux system of Escherichia coli: relationship to the ethidium efflux system and energetic studies. Midgley, M. J. Gen. Microbiol. (1986) [Pubmed]
  11. Mechanism of inhibition of FaDu hypopharyngeal carcinoma cell growth by tetraphenylphosphonium chloride. Rideout, D., Bustamante, A., Patel, J. Int. J. Cancer (1994) [Pubmed]
  12. Time-dependent binding of paramagnetic and fluorescent hydrophobic ions to the acetylcholine receptor from Torpedo. Hartsel, S.C., Moore, C.R., Raines, D.E., Cafiso, D.S. Biochemistry (1987) [Pubmed]
  13. Syntheses of halogenated ethenyl isocyanide chromium complexes as organometallic precursor molecules for ethenyl and ethynyl isocyanides. Balbo-Block, M., Bartel, C., Lentz, D., Preugschat, D. Chemistry (Weinheim an der Bergstrasse, Germany) (2001) [Pubmed]
  14. Chemistry and biology of the 2 beta-alkyl-3 beta-phenyl analogues of cocaine: subnanomolar affinity ligands that suggest a new pharmacophore model at the C-2 position. Kozikowski, A.P., Eddine Saiah, M.K., Johnson, K.M., Bergmann, J.S. J. Med. Chem. (1995) [Pubmed]
  15. Cardioselective ammonium, phosphonium, and sulfonium analogues of alpha-tocopherol and ascorbic acid that inhibit in vitro and ex vivo lipid peroxidation and scavenge superoxide radicals. Grisar, J.M., Marciniak, G., Bolkenius, F.N., Verne-Mismer, J., Wagner, E.R. J. Med. Chem. (1995) [Pubmed]
  16. A new strategy to screen molecular imaging probe uptake in cell culture without radiolabeling using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Cheng, Z., Winant, R.C., Gambhir, S.S. J. Nucl. Med. (2005) [Pubmed]
  17. Enhanced uptake of [11C]TPMP in canine brain tumor: a PET study. Madar, I., Anderson, J.H., Szabo, Z., Scheffel, U., Kao, P.F., Ravert, H.T., Dannals, R.F. J. Nucl. Med. (1999) [Pubmed]
  18. Induction of magnetic resonance-visible lipid in a transformed human breast cell line by tetraphenylphosphonium chloride. Roman, S.K., Jeitner, T.M., Hancock, R., Cooper, W.A., Rideout, D.C., Delikatny, E.J. Int. J. Cancer (1997) [Pubmed]
  19. Tetraphenylphosphonium as a novel molecular probe for imaging tumors. Min, J.J., Biswal, S., Deroose, C., Gambhir, S.S. J. Nucl. Med. (2004) [Pubmed]
  20. Characterization of uptake of the new PET imaging compound 18F-fluorobenzyl triphenyl phosphonium in dog myocardium. Madar, I., Ravert, H.T., Du, Y., Hilton, J., Volokh, L., Dannals, R.F., Frost, J.J., Hare, J.M. J. Nucl. Med. (2006) [Pubmed]
  21. Evidence for a channel for the electrogenic transport of chloride ion in the rat hepatocyte. Bear, C.E., Petrunka, C.N., Strasberg, S.M. Hepatology (1985) [Pubmed]
  22. The metabolism of the phosphonium analogue of choline in cultured cells. A useful nuclear-magnetic-resonance probe for membrane phosphatidylcholine. Sim, E., Pasternak, C.A. Biochem. J. (1976) [Pubmed]
  23. In search of anti-Trypanosoma cruzi drugs: new leads from a mouse model. Kinnamon, K.E., Steck, E.A., Hanson, W.L., Chapman, W.L. J. Med. Chem. (1977) [Pubmed]
  24. Physical studies on phosphonium phosphatidylcholine. A unique [31P]phosphorus nuclear-magnetic-resonance probe for model and biological membranes. Sim, E., Cullis, P.R., Richards, R.E. Biochem. J. (1975) [Pubmed]
  25. Diastereoselective tandem Michael-intramolecular Wittig reactions of a cyclic phosphonium ylide with 8-phenylmenthyl enoates. Nagao, T., Suenaga, T., Ichihashi, T., Fujimoto, T., Yamamoto, I., Kakehi, A., Iriye, R. J. Org. Chem. (2001) [Pubmed]
  26. Accumulation of simple organic cations correlates with differential cytotoxicity in multidrug-resistant and -sensitive human and rodent cells. Lampidis, T.J., Shi, Y.F., Calderon, C.L., Kolonias, D., Tapiero, H., Savaraj, N. Leukemia (1997) [Pubmed]
  27. Synthesis and antimicrobial activity of dimethyl- and trimethyl-substituted phosphonium salts with alkyl chains of various lengths. Kanazawa, A., Ikeda, T., Endo, T. Antimicrob. Agents Chemother. (1994) [Pubmed]
  28. A staphylococcal multidrug resistance gene product is a member of a new protein family. Grinius, L., Dreguniene, G., Goldberg, E.B., Liao, C.H., Projan, S.J. Plasmid (1992) [Pubmed]
  29. Evaluation of counterions for electrospray ionization mass spectral analysis of a highly sulfated carbohydrate, sucrose octasulfate. Gunay, N.S., Tadano-Aritomi, K., Toida, T., Ishizuka, I., Linhardt, R.J. Anal. Chem. (2003) [Pubmed]
  30. Localization of the O-glycosylated sites in peptides by fixed-charge derivatization with a phosphonium group. Czeszak, X., Morelle, W., Ricart, G., Tétaert, D., Lemoine, J. Anal. Chem. (2004) [Pubmed]
  31. A combined proton and phosphorus-31 nuclear magnetic resonance investigation of the combining site of M603, a phosphocholine-binding myeloma protein. Gettins, P., Pótter, M., Leatherbarrow, R.J., Dwek, R.A. Biochemistry (1982) [Pubmed]
  32. Synergistic hybrid catalyst for cyclic carbonate synthesis: Remarkable acceleration caused by immobilization of homogeneous catalyst on silica. Takahashi, T., Watahiki, T., Kitazume, S., Yasuda, H., Sakakura, T. Chem. Commun. (Camb.) (2006) [Pubmed]
 
WikiGenes - Universities