phosphines

Summary

Summary: Inorganic or organic compounds derived from phosphine (PH3) by the replacement of H atoms. (From Grant & Hackh's Chemical Dictionary, 5th ed)

Top Publications

  1. Opit G, Phillips T, Aikins M, Hasan M. Phosphine resistance in Tribolium castaneum and Rhyzopertha dominica from stored wheat in Oklahoma. J Econ Entomol. 2012;105:1107-14 pubmed
  2. Schlipalius D, Valmas N, Tuck A, Jagadeesan R, Ma L, Kaur R, et al. A core metabolic enzyme mediates resistance to phosphine gas. Science. 2012;338:807-10 pubmed publisher
    ..Mutation of DLD in C. elegans increases arsenite sensitivity. This specific vulnerability may be exploited to control phosphine-resistant insects and safeguard food security...
  3. Kim D, Kim H, Le U, Jiang S, Kim H, Lee K, et al. Evaluation of a mitochondrial voltage sensor, (18F-fluoropentyl)triphenylphosphonium cation, in a rat myocardial infarction model. J Nucl Med. 2012;53:1779-85 pubmed publisher
    ..The purpose of this study was to develop and evaluate ((18)F-fluoropentyl)triphenylphosphonium salt ((18)F-FPTP) as a myocardial PET agent...
  4. Nayak M, Holloway J, Emery R, Pavic H, Bartlet J, Collins P. Strong resistance to phosphine in the rusty grain beetle, Cryptolestes ferrugineus (Stephens) (Coleoptera: Laemophloeidae): its characterisation, a rapid assay for diagnosis and its distribution in Australia. Pest Manag Sci. 2013;69:48-53 pubmed publisher
    ..The aim was to characterise this resistance, to develop a rapid bioassay for its diagnosis to support pest management and to document the distribution of resistance in Australia in 2007-2011...
  5. Jagadeesan R, Collins P, Daglish G, Ebert P, Schlipalius D. Phosphine resistance in the rust red flour beetle, Tribolium castaneum (Coleoptera: Tenebrionidae): inheritance, gene interactions and fitness costs. PLoS ONE. 2012;7:e31582 pubmed publisher
    ..The results from this work will inform phosphine resistance management strategies and provide a basis for the identification of the resistance genes...
  6. Mau Y, Collins P, Daglish G, Nayak M, Pavic H, Ebert P. The rph1 gene is a common contributor to the evolution of phosphine resistance in independent field isolates of Rhyzopertha dominica. PLoS ONE. 2012;7:e31541 pubmed publisher
    ..Despite the capacity of phosphine to disrupt a wide range of enzymes and biological processes, it is remarkable that the initial step in the selection of resistance is so similar in isolated outbreaks...
  7. Li S, Wang H, Xian M, Whorton A. Identification of protein nitrosothiols using phosphine-mediated selective reduction. Nitric Oxide. 2012;26:20-6 pubmed publisher
  8. Bechtold E, Reisz J, Klomsiri C, Tsang A, Wright M, Poole L, et al. Water-soluble triarylphosphines as biomarkers for protein S-nitrosation. ACS Chem Biol. 2010;5:405-14 pubmed publisher
    ..This work provides a new means for detecting and quantifying S-nitrosated species in solution and suggests that phosphines may be useful tools for understanding the complex physiological roles of S-nitrosation and its implications in ..
  9. Schlipalius D, Chen W, Collins P, Nguyen T, Reilly P, Ebert P. Gene interactions constrain the course of evolution of phosphine resistance in the lesser grain borer, Rhyzopertha dominica. Heredity (Edinb). 2008;100:506-16 pubmed publisher
    ..A lack of visible fitness cost associated with alleles at either locus suggests that the resistance phenotype will persist in the field. ..

More Information

Publications67

  1. Cowen B, Miller S. Enantioselective [3+2]-cycloadditions catalyzed by a protected, multifunctional phosphine-containing alpha-amino acid. J Am Chem Soc. 2007;129:10988-9 pubmed
  2. Pavan F, Poelhsitz G, do Nascimento F, Leite S, Batista A, Deflon V, et al. Ruthenium (II) phosphine/picolinate complexes as antimycobacterial agents. Eur J Med Chem. 2010;45:598-601 pubmed publisher
    ..78 and 0.26 microg/mL, respectively. The results are comparable to or better than "first line" or "second line" drugs commonly used in the treatment of TB. ..
  3. Zhang J, Li S, Zhang D, Wang H, Whorton A, Xian M. Reductive ligation mediated one-step disulfide formation of S-nitrosothiols. Org Lett. 2010;12:4208-11 pubmed publisher
    ..This reaction can be used to design new biosensors of S-nitrosated proteins. ..
  4. Lin F, Hoyt H, van Halbeek H, Bergman R, Bertozzi C. Mechanistic investigation of the staudinger ligation. J Am Chem Soc. 2005;127:2686-95 pubmed
    The Staudinger ligation of azides and phosphines has found widespread use in the field of chemical biology, but the mechanism of the transformation has not been characterized in detail...
  5. Pimentel M, Faroni L, Tótola M, Guedes R. Phosphine resistance, respiration rate and fitness consequences in stored-product insects. Pest Manag Sci. 2007;63:876-81 pubmed
    ..Thus, management strategies based on the interruption of phosphine fumigation may result in reestablishment of susceptibility, and shows good potential for more effective management of phosphine-resistant populations...
  6. Tran Y, Kwon O. Phosphine-catalyzed [4 + 2] annulation: synthesis of cyclohexenes. J Am Chem Soc. 2007;129:12632-3 pubmed
  7. Wang Z, Castellano S, Kinderman S, Argueta C, Beshir A, Fenteany G, et al. Diversity through a branched reaction pathway: generation of multicyclic scaffolds and identification of antimigratory agents. Chemistry. 2011;17:649-54 pubmed publisher
    ..From this library, several molecules were identified that inhibit the migration and invasion of breast cancer cells and may serve as leads for the development of antimetastatic agents...
  8. Stump G, Wallace A, Regan C, Lynch J. In vivo antiarrhythmic and cardiac electrophysiologic effects of a novel diphenylphosphine oxide IKur blocker (2-isopropyl-5-methylcyclohexyl) diphenylphosphine oxide. J Pharmacol Exp Ther. 2005;315:1362-7 pubmed
    ..1%). These findings support the approach of atrial selective modulation of refractoriness through block of IKur for the development of potentially safer and more effective atrial antiarrhythmic agents...
  9. Wang H, Xian M. Chemical methods to detect S-nitrosation. Curr Opin Chem Biol. 2011;15:32-7 pubmed publisher
    ..In this review we summarize recent developments of the methods to detect S-nitrosation. Our focus is on the methods which can be used to directly conjugate the site(s) of S-nitrosation...
  10. Reisz J, Klorig E, Wright M, King S. Reductive phosphine-mediated ligation of nitroxyl (HNO). Org Lett. 2009;11:2719-21 pubmed publisher
    ..These results define new HNO reactivity and provide the basis of new HNO detection methods...
  11. Schlipalius D, Cheng Q, Reilly P, Collins P, Ebert P. Genetic linkage analysis of the lesser grain borer Rhyzopertha dominica identifies two loci that confer high-level resistance to the fumigant phosphine. Genetics. 2002;161:773-82 pubmed
    ..91 cM (1.1 Mbp) of the DNA markers...
  12. Rajendran S, Gunasekaran N. The response of phosphine-resistant lesser grain borer Rhyzopertha dominica and rice weevil Sitophilus oryzae in mixed-age cultures to varying concentrations of phosphine. Pest Manag Sci. 2002;58:277-81 pubmed
    ..The results indicate that application of phosphine in rising concentrations is more effective than in constant or falling concentrations...
  13. Niu X, Geng J, Wang X, Wang C, Gu X, Edwards M, et al. Temporal and spatial distributions of phosphine in Taihu Lake, China. Sci Total Environ. 2004;323:169-78 pubmed
    ..The local average values of the phosphine concentrations were from 21550 to 563,100 pg/kg. Its highest value was 919,238 pg/kg at 6# site (Zhihu harbor), a severely polluted sampling site...
  14. Linsmeier C, Wallman L, Faxius L, Schouenborg J, Bjursten L, Danielsen N. Soft tissue reactions evoked by implanted gallium phosphide. Biomaterials. 2008;29:4598-604 pubmed publisher
    ..Taken together, our results show that the biocompatible properties of GaP are worse than those of the well-documented biomaterial Ti...
  15. Du Y, Zhang X, Tu D, Zhao N, Liu Y, Xiao H, et al. Molecular determinants of Kv1.5 channel block by diphenyl phosphine oxide-1. J Mol Cell Cardiol. 2010;48:1111-20 pubmed publisher
    ..5 channel blockers AVE0118 and S0100176. Block of Kv1.5 by DPO-1 was significantly reduced in the presence of Kvbeta1.3...
  16. Pandit S, Zlochiver S, Filgueiras Rama D, Mironov S, Yamazaki M, Ennis S, et al. Targeting atrioventricular differences in ion channel properties for terminating acute atrial fibrillation in pigs. Cardiovasc Res. 2011;89:843-51 pubmed publisher
    ..The goal was to terminate atrial fibrillation (AF) by targeting atrioventricular differences in ionic properties...
  17. Feng Z, Song X, Yu Z. Seasonal and spatial distribution of matrix-bound phosphine and its relationship with the environment in the Changjiang River Estuary, China. Mar Pollut Bull. 2008;56:1630-6 pubmed publisher
  18. Cruz D, Wang Z, Kibbie J, Modlin R, Kwon O. Diversity through phosphine catalysis identifies octahydro-1,6-naphthyridin-4-ones as activators of endothelium-driven immunity. Proc Natl Acad Sci U S A. 2011;108:6769-74 pubmed publisher
  19. Hällström W, Mårtensson T, Prinz C, Gustavsson P, Montelius L, Samuelson L, et al. Gallium phosphide nanowires as a substrate for cultured neurons. Nano Lett. 2007;7:2960-5 pubmed
    ..The cells interacted closely with the nanostructures, and cells penetrated by hundreds of wires were observed as well as wire bending due to forces exerted by the cells...
  20. Sriramurthy V, Kwon O. Diphosphine-catalyzed mixed double-Michael reaction: a unified synthesis of indolines, dihydropyrrolopyridines, benzimidazolines, tetrahydroquinolines, tetrahydroisoquinolines, dihydrobenzo-1,4-oxazines, and dihydrobenzo-3,1-oxazines. Org Lett. 2010;12:1084-7 pubmed publisher
    ..The benzannulated N-heterocycles were isolated in excellent yields under mild metal-free conditions; they were purified without the need for aqueous workups...
  21. Henry C, Kwon O. Phosphine-catalyzed synthesis of highly functionalized coumarins. Org Lett. 2007;9:3069-72 pubmed
    ..This nitronate was subjected to efficient face-, regio-, and exo-selective 1,3-dipolar cycloadditions to provide tetracyclic coumarin derivatives...
  22. Collins P, Daglish G, Bengston M, Lambkin T, Pavic H. Genetics of resistance to phosphine in Rhyzopertha dominica (Coleoptera: Bostrichidae). J Econ Entomol. 2002;95:862-9 pubmed
    ..There was also evidence of a minor dominant gene present in approximately 5% of Strong-R individuals...
  23. Gorin D, Toste F. Relativistic effects in homogeneous gold catalysis. Nature. 2007;446:395-403 pubmed
    ..This Review draws on experimental and computational data to present our current understanding of homogeneous gold catalysis, focusing on previously unexplored reactivity and its application to the development of new methodology...
  24. Tucker J, Moore D, Ramsey M, Kato P, Langlois R, Burroughs B, et al. Multi-endpoint biological monitoring of phosphine workers. Mutat Res. 2003;536:7-14 pubmed
    ..The results are most easily interpreted as supporting the effectiveness of the personal protective equipment that is now worn by the workers but which was not employed prior to and during the earlier studies...
  25. Hale J, Butler J, Gelfanova V, You J, Knierman M. A simplified procedure for the reduction and alkylation of cysteine residues in proteins prior to proteolytic digestion and mass spectral analysis. Anal Biochem. 2004;333:174-81 pubmed
    ..Elimination of the need for desalting of samples after reaction raised the possibility of automation of the procedure for liquid samples, which is difficult with conventional reduction and alkylation chemistries...
  26. Atkinson K, Cowley M, Elliott P, Duckett S, Green G, López Serrano J, et al. Spontaneous transfer of parahydrogen derived spin order to pyridine at low magnetic field. J Am Chem Soc. 2009;131:13362-8 pubmed publisher
  27. Gandin V, Fernandes A, Rigobello M, Dani B, Sorrentino F, Tisato F, et al. Cancer cell death induced by phosphine gold(I) compounds targeting thioredoxin reductase. Biochem Pharmacol. 2010;79:90-101 pubmed publisher
    ..Pharmacodynamic studies in human ovarian cancer cells allowed for the correlation of intracellular drug accumulation with TrxR inhibition that leads to the induction of apoptosis via the mitochondrial pathway...
  28. Pepelko B, Seckar J, Harp P, Kim J, Gray D, Anderson E. Worker exposure standard for phosphine gas. Risk Anal. 2004;24:1201-13 pubmed
    ..Collectively, these findings support the occupational exposure limits of 0.3 ppm (8-hour TWA) and 1 ppm (STEL) established in the updated applicator's manuals for phosphine-generating products, which recently received approval from OPP...
  29. Okolie N, Aligbe J, Osakue E. Phostoxin-induced biochemical and pathomorphological changes in rabbits. Indian J Exp Biol. 2004;42:1096-9 pubmed
    ..Histological examination of the tissues revealed pronounced degenerative changes in liver, heart and kidney...
  30. Regan C, Wallace A, Cresswell H, Atkins C, Lynch J. In vivo cardiac electrophysiologic effects of a novel diphenylphosphine oxide IKur blocker, (2-Isopropyl-5-methylcyclohexyl) diphenylphosphine oxide, in rat and nonhuman primate. J Pharmacol Exp Ther. 2006;316:727-32 pubmed
    ..Moreover, the selective increase in atrial refractoriness in primate supports the concept of I(Kur) blockade as an approach for the development of atrial-specific antiarrhythmic agents...
  31. Kuczynski B, Reo N. Evidence that plasmalogen is protective against oxidative stress in the rat brain. Neurochem Res. 2006;31:639-56 pubmed
    ..Our data suggest a high basal [PlsEtn], or the capacity to synthesize new ethanolamine lipids (particularly PlsEtn) may protect against PH(3) toxicity...
  32. Song X, Morrison R, Feng Z, Liu D, Harrison J, Yu Z. Matrix-bound phosphine in sediments from Lake Illawarra, New South Wales, Australia. Mar Pollut Bull. 2011;62:1744-50 pubmed publisher
    ..It was confirmed that high MBP concentrations are indicative of a phosphorus rich environment. The results tend to support the premise that MBP is generated by microbial attack on OP under anaerobic conditions...
  33. Fan Y, Kwon O. Diversity-oriented synthesis based on the DPPP-catalyzed mixed double-Michael reactions of electron-deficient acetylenes and ?-amino alcohols. Molecules. 2011;16:3802-25 pubmed publisher
    ..We synthesized 36 of these 60 oxazolidines in enantiomerically pure form from proteinogenic amino acid-derived ?-amino alcohols...
  34. Zheng W, Chu Y, Yin Q, Xu L, Yang C, Zhang W, et al. Crucial effect of the first CXXC motif of human QSOX 1b on the activity to different substrates. J Biochem. 2011;149:293-300 pubmed publisher
  35. Reisz J, Zink C, King S. Rapid and selective nitroxyl (HNO) trapping by phosphines: kinetics and new aqueous ligations for HNO detection and quantitation. J Am Chem Soc. 2011;133:11675-85 pubmed publisher
    ..We now report a kinetic analysis for the trapping of HNO by phosphines, ligations of enzyme-generated HNO, and compatibility studies illustrating the selectivity of phosphines for HNO ..
  36. Hsu C, Chi B, Liu M, Li J, Chen C, Chen R. Phosphine-induced oxidative damage in rats: role of glutathione. Toxicology. 2002;179:1-8 pubmed
  37. Hsu C, Chi B, Casida J. Melatonin reduces phosphine-induced lipid and DNA oxidation in vitro and in vivo in rat brain. J Pineal Res. 2002;32:53-8 pubmed
    ..It is concluded that melatonin, probably because of its free radical scavenging ability, confers marked protection against PH(3)-induced oxidative toxicity in brain...
  38. Guo H, Xu Q, Kwon O. Phosphine-promoted [3 + 3] annulations of aziridines with allenoates: facile entry into highly functionalized tetrahydropyridines. J Am Chem Soc. 2009;131:6318-9 pubmed publisher
    ..Notably, these reactions are the first reported examples of aziridines as reaction partners in nucleophilic phosphine-catalyzed transformations...
  39. Stauffer S, Hartwig J. Fluorescence resonance energy transfer (FRET) as a high-throughput assay for coupling reactions. Arylation of amines as a case study. J Am Chem Soc. 2003;125:6977-85 pubmed
    ..Reactions with K(3)PO(4) base in aqueous mixtures of polar and nonpolar organic solvents were shown to be appropriate for the amination chemistry...
  40. Perez Navero J, Ibarra de la Rosa I, Frías Pérez M, Arroyo Marín M, Pérez Jorge P. [Fatal poisoning by accidental inhalation of aluminium phosphide]. An Pediatr (Barc). 2009;71:427-31 pubmed publisher
  41. Feng Z, Song X, Yu Z. Distribution characteristics of matrix-bound phosphine along the coast of China and possible environmental controls. Chemosphere. 2008;73:519-25 pubmed publisher
  42. do Nascimento F, Von Poelhsitz G, Pavan F, Sato D, Leite C, Selistre de Araujo H, et al. Synthesis, characterization, X-ray structure and in vitro antimycobacterial and antitumoral activities of Ru(II) phosphine/diimine complexes containing the "SpymMe2" ligand, SpymMe2=4,6-dimethyl-2-mercaptopyrimidine. J Inorg Biochem. 2008;102:1783-9 pubmed publisher
    ..Complexes 1 and 2 also showed promising antitumor activity, with IC(50) values of 0.46+/-0.02 and 0.43+/-0.08microM, respectively, against MDA-MB-231 breast tumor cells...
  43. Daglish G, Kopittke R, Cameron M, Pavic H. Predicting mortality of phosphine-resistant adults of Sitophilus oryzae (L) (Coleoptera: Curculionidae) in relation to changing phosphine concentration. Pest Manag Sci. 2004;60:655-9 pubmed
    ..This approach could simplify the prediction of efficacy of typical fumigations in which concentrations tend to rise and then fall over a period of days...
  44. Rajendran S, Parveen H, Begum K, Chethana R. Influence of phosphine on hatching of Cryptolestes ferrugineus (Coleoptera: Cucujidae), Lasioderma serricorne (Coleoptera: Anobiidae) and Oryzaephilus surinamensis (Coleoptera: Silvanidae). Pest Manag Sci. 2004;60:1114-8 pubmed
    ..Developmental delay was, however, not evident in susceptible strains of C ferrugineus, L serricorne and O surinamensis that were exposed to phosphine for 24 h...
  45. Creech G, Kwon O. Alcohol-assisted phosphine catalysis: one-step syntheses of dihydropyrones from aldehydes and allenoates. Org Lett. 2008;10:429-32 pubmed publisher
    ..This method provides an efficient, one-step route toward disubstituted dihydropyrones from simple, stable starting materials...
  46. Cline D, Redding S, Brohawn S, Psathas J, Schneider J, Thorpe C. New water-soluble phosphines as reductants of peptide and protein disulfide bonds: reactivity and membrane permeability. Biochemistry. 2004;43:15195-203 pubmed
    ..The effectiveness of all four phosphines relative to DTT has been determined using model disulfides, including a fluorescent disulfide-containing peptide ..
  47. Cha on U, Valmas N, Collins P, Reilly P, Hammock B, Ebert P. Disruption of iron homeostasis increases phosphine toxicity in Caenorhabditis elegans. Toxicol Sci. 2007;96:194-201 pubmed
    ..This study identifies similarities between phosphine toxicity and iron overload and demonstrates that phosphine can trigger iron release from storage proteins, increasing lipid peroxidation, leading to cell injury and/or cell death...
  48. Lorini I, Collins P, Daglish G, Nayak M, Pavic H. Detection and characterisation of strong resistance to phosphine in Brazilian Rhyzopertha dominica (F.) (Coleoptera: Bostrychidae). Pest Manag Sci. 2007;63:358-64 pubmed
    ..The present research indicates that widespread phosphine resistance may be developing in Brazil. Fumigation practices should be monitored and resistance management plans implemented to alleviate further resistance development...
  49. Bosanac T, Wilcox C. Precipiton reagents: precipiton phosphines for solution-phase reductions. Org Lett. 2004;6:2321-4 pubmed
    structure: see text] [structure: see text] [structure: see text] Several Precipiton phosphines were prepared and employed in the Staudinger reaction and in the reduction of secondary ozonides...
  50. Daglish G, Collins P, Pavic H, Kopittke R. Effects of time and concentration on mortality of phosphine-resistant Sitophilus oryzae (L) fumigated with phosphine. Pest Manag Sci. 2002;58:1015-21 pubmed
    ..Limited data on the Chinese resistant strain supported this finding. Twenty-three days exposure at 0.02 mg litre-1 had no effect on mixed-age cultures of this strain, but there were no survivors after 5 days exposure to 1 mg litre-1...
  51. Ralle M, Lutsenko S, Blackburn N. X-ray absorption spectroscopy of the copper chaperone HAH1 reveals a linear two-coordinate Cu(I) center capable of adduct formation with exogenous thiols and phosphines. J Biol Chem. 2003;278:23163-70 pubmed
    ..The implications of these findings for mechanisms of copper transport are discussed...
  52. Pavan F, Poelhsitz G, Barbosa M, Leite S, Batista A, Ellena J, et al. Ruthenium(II) phosphine/diimine/picolinate complexes: inorganic compounds as agents against tuberculosis. Eur J Med Chem. 2011;46:5099-107 pubmed publisher
    ..Also, all compounds showed significant intracellular inhibition and the compound SCAR05 showed a better activity than rifampin and SQ109. This is the first report of activity against in vitro infection of ruthenium compounds...
  53. Wassenaar J, Jansen E, van Zeist W, Bickelhaupt F, Siegler M, Spek A, et al. Catalyst selection based on intermediate stability measured by mass spectrometry. Nat Chem. 2010;2:417-21 pubmed publisher
    ..We demonstrate this concept in the palladium-catalysed allylic alkylation reaction using diphosphine and IndolPhos ligands and support our results with high-level density functional theory calculations...
  54. Sriramurthy V, Barcan G, Kwon O. Bisphosphine-catalyzed mixed double-Michael reactions: asymmetric synthesis of oxazolidines, thiazolidines, and pyrrolidines. J Am Chem Soc. 2007;129:12928-9 pubmed
  55. Han X, Wang Y, Zhong F, Lu Y. Enantioselective [3 + 2] cycloaddition of allenes to acrylates catalyzed by dipeptide-derived phosphines: facile creation of functionalized cyclopentenes containing quaternary stereogenic centers. J Am Chem Soc. 2011;133:1726-9 pubmed publisher
    A new family of dipeptide-based chiral phosphines was designed and prepared...
  56. Saxon E, Bertozzi C. Cell surface engineering by a modified Staudinger reaction. Science. 2000;287:2007-10 pubmed
    ..The tremendous selectivity of the transformation should permit its execution within a cell's interior, offering new possibilities for probing intracellular interactions...
  57. Zhu X, Lan J, Kwon O. An expedient phosphine-catalyzed [4 + 2] annulation: synthesis of highly functionalized tetrahydropyridines. J Am Chem Soc. 2003;125:4716-7 pubmed
  58. Shoup T, Elmaleh D, Brownell A, Zhu A, Guerrero J, Fischman A. Evaluation of (4-[18F]Fluorophenyl)triphenylphosphonium ion. A potential myocardial blood flow agent for PET. Mol Imaging Biol. 2011;13:511-517 pubmed publisher
    ..The lipophilic cationic compound, (4-[¹?F]fluorophenyl)triphenylphosphonium ion (¹?F-FTPP) was synthesized and evaluated as a potential positron emission tomography (PET) myocardial perfusion agent...