Disease relevance of phosphanium

• The electrical potential (delta psi) across the cytoplasmic membranes of Staphylococcus aureus cells growing under aerobic and anaerobic conditions was determined by measuring the equilibrium distribution of [3H]tetraphenyl phosphonium [1].
• Here, we extend our studies of phosphonium cations to nonbrain tumors and characterize the biodistribution and tumor specificity of (3)H-tetraphenylphosphonium ((3)H-TPP) in non-small cell lung carcinoma in mice [2].
• 1H NMR visible lipids are induced by phosphonium salts and 5-fluorouracil in human breast cancer cells [3].
• Novel phosphonium salts display in vitro and in vivo cytotoxic activity against human ovarian cancer cell lines [4].
• Tetrabutyl phosphonium chloride and tetrabutyl phosphonium bromide were evaluated for their potential to cause primary dermal irritation and acute dermal toxicity in rabbits [5].

High impact information on phosphanium

• To quantitate calcium movements and membrane potential changes in stimulated neutrophils, we have measured net fluxes of Ca2+ and of the lipophilic cation tetraphenyl phosphonium by a very sensitive ion-selective electrode system [6].
• Stimulation of neutrophils after attainment of steady-state accumulation of tetraphenyl phosphonium (resting potential of -67 mV) results in a marked depolarization, with a lag period of approximately 60 s [6].
• PH4 encodes a MYB domain protein that is expressed in the petal epidermis and that can interact, like AN2, with AN1 and the related BHLH protein JAF13 in yeast two-hybrid assays [7].
• The reactive species in a phosphoryl ester in substrate-level phosphorylation and phosphonium ion of orthophosphate in oxidative phosphorylation [8].
• Such behavior was also shown by recombinant AH1, PH2, and PH4 proteins after expression in Pichia pastoris [9].

Chemical compound and disease context of phosphanium

• The phosphonium ion efflux system of Escherichia coli: relationship to the ethidium efflux system and energetic studies [10].

Biological context of phosphanium

• Cationic phosphonium salts that inhibit carcinoma cell growth through antimitochondrial effects might be used to treat solid tumors without the risk of secondary tumors associated with agents affecting nuclear DNA [11].
• These results strongly suggest that the binding sites for the phosphonium ion (and the high-affinity histrionicotoxin blocking site) are accessible only through the aqueous phase [12].
• The unstable phosphorane 5, which is formed on reaction of 4b with trimethylphosphane, decomposed thermally and on hydrolysis yielding pentacarbonyl(1,2-difluoroethenyl isocyanide)chromium (6) [13].
• Wittig reaction of 6 with the appropriate phosphorane and hydrogenation delivered the final products [14].
• 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 [15].

Anatomical context of phosphanium

• In addition, MALDI-TOF-MS was used to screen a library of 8 phosphonium cations and subsequently rank their ability to penetrate membranes and accumulate in cells [16].
• In vitro studies have demonstrated the membrane potential-dependent enhanced uptake of phosphonium salts, including [3H]triphenylmethylphosphonium (TPMP), into mitochondria of carcinoma and glioma-derived tumor cells, suggesting the potential use of phosphonium salts as tracers for tumor imaging [17].
• Proton magnetic resonance spectroscopy (1H MRS) and DNA flow cytometry were used to monitor the effects of the cationic lipophilic phosphonium salt and potential antineoplastic agent tetraphenylphosphonium chloride (TPP) on the transformed human breast cell line HBL-100 [18].
• Mitochondrial membrane potential (DeltaPsim)-dependent enhanced uptake of phosphonium salts, including (3)H-tetraphenylphosphonium ((3)H-TPP), in tumor cells, suggests the potential use of phosphonium salts as tracers for tumor imaging [19].
• Characterization of uptake of the new PET imaging compound 18F-fluorobenzyl triphenyl phosphonium in dog myocardium [20].

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