organothiophosphorus compounds


Summary: Compounds containing carbon-phosphorus bonds in which the phosphorus component is also bonded to one or more sulfur atoms. Many of these compounds function as CHOLINERGIC AGENTS and as INSECTICIDES.

Top Publications

  1. Li L, Salto Tellez M, Tan C, Whiteman M, Moore P. GYY4137, a novel hydrogen sulfide-releasing molecule, protects against endotoxic shock in the rat. Free Radic Biol Med. 2009;47:103-13 pubmed publisher
    ..These results suggest an anti-inflammatory effect of GYY4137. The possibility that GYY4137 and other slow-releasing H(2)S donors exert anti-inflammatory activity in other models of inflammation and in humans warrants further study. ..
  2. Perry M, Hui C, Whiteman M, Wood M, Adcock I, Kirkham P, et al. Hydrogen sulfide inhibits proliferation and release of IL-8 from human airway smooth muscle cells. Am J Respir Cell Mol Biol. 2011;45:746-52 pubmed publisher
    ..Therefore, regulation of H(2)S may represent a novel approach to controlling ASM proliferation and cytokine release that is found in patients with asthma. ..
  3. Snodgrass G, Gore J, Abel C, Jackson R. Acephate resistance in populations of the tarnished plant bug (Heteroptera: Miridae) from the Mississippi River Delta. J Econ Entomol. 2009;102:699-707 pubmed
    ..New insecticides in different classes are badly needed for control of tarnished plant bugs in cotton in the mid-South. ..
  4. Battu R, Sahoo S, Jyot G. Persistence of acephate and cypermethrin on cotton leaves, cottonseed, lint and soil. Bull Environ Contam Toxicol. 2009;82:124-8 pubmed publisher
    ..Interestingly, none of the samples of cottonseed, lint and soil showed presence of acephate or cypermethrin at the detection limit of 0.02 mg kg(-1) at first pick of the harvest time of the crop. ..
  5. Chuanjiang T, Dahui L, Xinzhong Z, Shanshan C, Lijuan F, Xiuying P, et al. Residue analysis of acephate and its metabolite methamidophos in open field and greenhouse pakchoi (Brassica campestris L.) by gas chromatography-tandem mass spectrometry. Environ Monit Assess. 2010;165:685-92 pubmed publisher
    ..While in the open-field pakchoi, >90% of total methamidophos was found to be the metabolite of acephate. ..
  6. Lee Z, Zhou J, Chen C, Zhao Y, Tan C, Li L, et al. The slow-releasing hydrogen sulfide donor, GYY4137, exhibits novel anti-cancer effects in vitro and in vivo. PLoS ONE. 2011;6:e21077 pubmed publisher
    ..We also propose that a combination of apoptosis and cell cycle arrest contributes to this effect and that H?S donors should be investigated further as potential anti-cancer agents. ..
  7. Wang L, Wang G, Li S, Jiang J. Luteibacter jiangsuensis sp. nov.: a methamidophos-degrading bacterium isolated from a methamidophos-manufacturing factory. Curr Microbiol. 2011;62:289-95 pubmed publisher
    ..nov. is proposed. The type strain is JW-64-1(T) (=CGMCC 1.10133(T) = DSM 22396(T)). ..
  8. Li L, Whiteman M, Guan Y, Neo K, Cheng Y, Lee S, et al. Characterization of a novel, water-soluble hydrogen sulfide-releasing molecule (GYY4137): new insights into the biology of hydrogen sulfide. Circulation. 2008;117:2351-60 pubmed publisher
    ..GYY4137 is likely to prove useful in the study of the many and varied biological effects of H(2)S. GYY4137 may also prove of therapeutic value in cardiovascular disease. ..
  9. Chai L, Wong M, Mohd Tahir N, Hansen H. Degradation and mineralization kinetics of acephate in humid tropic soils of Malaysia. Chemosphere. 2010;79:434-40 pubmed publisher
    ..Sandy soils with low microbial activity are more prone to acephate leaching than clay soils rich in humic matter. ..

More Information


  1. Otto T, Kasten S, Kovaleva E, Liu Z, BUCHMAN G, Tolosa M, et al. Purification and characterization of functional human paraoxonase-1 expressed in Trichoplusia ni larvae. Chem Biol Interact. 2010;187:388-92 pubmed publisher
    ..Insect production of HuPON1 may provide a source for both in vitro enzymatic and crystallographic studies and in vivo stability and anti-nerve agent efficacy testing. ..
  2. Wang L, Wen Y, Guo X, Wang G, Li S, Jiang J. Degradation of methamidophos by Hyphomicrobium species MAP-1 and the biochemical degradation pathway. Biodegradation. 2010;21:513-23 pubmed publisher
    ..Finally, S-methyl dihydrogen thiophosphate and methyl dihydrogen phosphate are likely transformed into phosphoric acid...
  3. Garrett N, Whiteman M, Moger J. Imaging the uptake of gold nanoshells in live cells using plasmon resonance enhanced four wave mixing microscopy. Opt Express. 2011;19:17563-74 pubmed publisher
    ..67% to 11.47%. The most important factor affecting uptake in this study was found to be the rate of H2S release, with rapid-release from NaHS resulting in significantly greater uptake. ..
  4. Whiteman M, Li L, Rose P, Tan C, Parkinson D, Moore P. The effect of hydrogen sulfide donors on lipopolysaccharide-induced formation of inflammatory mediators in macrophages. Antioxid Redox Signal. 2010;12:1147-54 pubmed publisher
    ..This study may also explain some of the apparent discrepancies in the literature regarding the pro- versus antiinflammatory role of H(2)S. ..
  5. Yu F, Zhao J, Tang C, Geng B. [Effect of synthesized GYY4137, a slowly releasing hydrogen sulfide donor, on cell viability and distribution of hydrogen sulfide in mice]. Beijing Da Xue Xue Bao Yi Xue Ban. 2010;42:493-7 pubmed
  6. Farag A, Radwan A, Eweidah M, ElMazoudy R, El Sebae A. Evaluation of male-mediated reproductive toxic effects of methamidophos in the mouse. Andrologia. 2012;44:116-24 pubmed publisher
    ..The current study demonstrated adverse effects of male methamidophos exposure on pregnancy outcome with effects on sperm parameters at 2 and 3 mg kg(-1) day(-1) . ..
  7. Fuseini G, Ebsworth P, Jones S, Knight D. The efficacy of ACTELLIC 50 EC, pirimiphos methyl, for indoor residual spraying in Ahafo, Ghana: area of high vector resistance to pyrethroids and organochlorines. J Med Entomol. 2011;48:437-40 pubmed
    ..Therefore, it is recommended for use in IRS programs in this part of Ghana, where there is high vector resistance to most of the insecticides. ..
  8. Blasco C, Vazquez Roig P, Onghena M, Masia A, Pico Y. Analysis of insecticides in honey by liquid chromatography-ion trap-mass spectrometry: comparison of different extraction procedures. J Chromatogr A. 2011;1218:4892-901 pubmed publisher
    ..Results obtained applying the four extraction techniques to real honey samples are analogous. ..
  9. Pourmirza A. Local variation in susceptibility of Colorado potato beetle (Coleoptera: Chrysomelidae) to insecticide. J Econ Entomol. 2005;98:2176-80 pubmed
    ..The glass jar and filter paper testing methods are simple and sensitive test techniques for measuring susceptibility of Colorado potato beetle adults and larvae to phosalone, respectively. ..
  10. Farag A, Eweidah M, Tayel S, el Sebae A. Developmental toxicity of acephate by gavage in mice. Reprod Toxicol. 2000;14:241-5 pubmed
    ..No visceral malformations were observed. On the basis of the present results acephate showed maternal and developmental toxicity at 28 mg/kg/day. ..
  11. Kolaczinski J, Fanello C, Herve J, Conway D, Carnevale P, Curtis C. Experimental and molecular genetic analysis of the impact of pyrethroid and non-pyrethroid insecticide impregnated bednets for mosquito control in an area of pyrethroid resistance. Bull Entomol Res. 2000;90:125-32 pubmed
  12. Wu M, Deng J, Tsai W, Ger J, Wong S, Li H. Food poisoning due to methamidophos-contaminated vegetables. J Toxicol Clin Toxicol. 2001;39:333-6 pubmed
    ..3 ppm. Since methamidophos is normally applied to vegetables during planting, improper selection and/or overuse of pesticide or improper harvest times may explain the occurrence of these high residue levels of methamidophos. ..
  13. Koch D, Lu C, Fisker Andersen J, Jolley L, Fenske R. Temporal association of children's pesticide exposure and agricultural spraying: report of a longitudinal biological monitoring study. Environ Health Perspect. 2002;110:829-33 pubmed
  14. Barr D, Bravo R, Weerasekera G, Caltabiano L, Whitehead R, Olsson A, et al. Concentrations of dialkyl phosphate metabolites of organophosphorus pesticides in the U.S. population. Environ Health Perspect. 2004;112:186-200 pubmed
    ..These data will be important in evaluating the impact of organophosphorus pesticide exposure in the U.S. population and the effectiveness of regulatory actions. ..
  15. Lai K, Stolowich N, Wild J. Characterization of P-S bond hydrolysis in organophosphorothioate pesticides by organophosphorus hydrolase. Arch Biochem Biophys. 1995;318:59-64 pubmed
    ..Phosphorothiolate esters, such as demeton-S, provided noncompetitive inhibition for paraoxon (a P-O triester) hydrolysis, suggesting that the binding of these two different classes of substrates was not identical. ..
  16. Wallace J, Dicay M, McKnight W, Martin G. Hydrogen sulfide enhances ulcer healing in rats. FASEB J. 2007;21:4070-6 pubmed
    ..The results further suggest that drugs releasing hydrogen sulfide could be employed to accelerate healing of gastric ulcers, and possibly of other wounds. ..
  17. Bravo R, Caltabiano L, Weerasekera G, Whitehead R, Fernandez C, Needham L, et al. Measurement of dialkyl phosphate metabolites of organophosphorus pesticides in human urine using lyophilization with gas chromatography-tandem mass spectrometry and isotope dilution quantification. J Expo Anal Environ Epidemiol. 2004;14:249-59 pubmed
    ..Use of this method with approximately 1100 urine samples collected from pregnant women and children indicate that the low limits of detection allow this method to be used in general population studies. ..
  18. Harnly M, McLaughlin R, Bradman A, Anderson M, Gunier R. Correlating agricultural use of organophosphates with outdoor air concentrations: a particular concern for children. Environ Health Perspect. 2005;113:1184-9 pubmed
    ..Agricultural applications of organophosphates and their oxon products may have substantial volatization and off-field movement and are a probable source of exposures of public health concern. ..
  19. Pennetier C, Corbel V, Boko P, Odjo A, N Guessan R, Lapied B, et al. Synergy between repellents and non-pyrethroid insecticides strongly extends the efficacy of treated nets against Anopheles gambiae. Malar J. 2007;6:38 pubmed
    ..The residual efficacy and the inhibition of blood feeding conferred by these mixtures were assessed against Anopheles gambiae mosquitoes...
  20. Miyata K, Tamamushi R, Tsunoda H, Ohkubo A, Seio K, Sekine M. Synthesis and triplex formation of oligonucleotides containing 8-thioxodeoxyadenosine. Org Lett. 2009;11:605-8 pubmed publisher
    ..Consequently, it was found that s(8)dA exhibited much stronger hybridization ability than dC under neutral conditions when four s(8)dA bases were arranged in a consecutive sequence. ..
  21. Bajgar J. Protective effect of reversible cholinesterase inhibitors (tacrine, pyridostigmine) and eqbuche against VX poisoning and brain acetylcholinesterase inhibition in rats. Acta Medica (Hradec Kralove). 2008;51:223-8 pubmed
    ..Tacrine alone or in other combinations has had no better prophylactic effect in comparison with these combinations containing pyridostigmine. Equine butyrylcholinesterase, also protected against VX poisoning very effectively. ..
  22. Siegwart M, Monteiro L, Maugin S, Olivares J, Malfitano Carvalho S, Sauphanor B. Tools for resistance monitoring in oriental fruit moth (Lepidoptera: Tortricidae) and first assessment in Brazilian populations. J Econ Entomol. 2011;104:636-45 pubmed
    ..These biological and molecular characterizations of adaptive response to insecticides in C. molesta provide tools for early detection of insecticide resistance in field populations of this pest. ..
  23. Liang M, Fan K, Pan Y, Jiang H, Wang F, Yang D, et al. Fe3O4 magnetic nanoparticle peroxidase mimetic-based colorimetric assay for the rapid detection of organophosphorus pesticide and nerve agent. Anal Chem. 2013;85:308-12 pubmed publisher
  24. Pennetier C, Costantini C, Corbel V, Licciardi S, Dabire R, Lapied B, et al. Mixture for controlling insecticide-resistant malaria vectors. Emerg Infect Dis. 2008;14:1707-14 pubmed publisher
    ..Mixing repellents and organophosphates on bed nets could be used to control insecticide-resistant malaria vectors if residual activity of the mixture is extended and safety is verified. ..
  25. Kongtip P, Changfuang S, Yoosook W, Chantanakul S, Sujirarat D. Ethion exposure and biological monitoring in vegetable farmers. J Med Assoc Thai. 2011;94:286-94 pubmed
    ..001. The modified method provided a reliable result and the urinary DEP during work shifts was found to be a reliable biomarker of ethion exposure. ..
  26. Sporty J, Lemire S, Jakubowski E, Renner J, Evans R, Williams R, et al. Immunomagnetic separation and quantification of butyrylcholinesterase nerve agent adducts in human serum. Anal Chem. 2010;82:6593-600 pubmed publisher
  27. Qi L, Zuo G, Cheng Z, Zhu H, Li S. Oxidative degradation of chemical warfare agents in water by bleaching powder. Water Sci Technol. 2012;66:1377-83 pubmed publisher
    ..Oxidative degradation of VX could finally generate O-ethyl methylphosphonate acid (EMPA), sulfonic acids, SO(4)(2-) and NO(3)(-) ions. GD would be converted into non-toxic pinacolyl methylphosphonate via nucleophilic substitution. ..
  28. John H, Mikler J, Worek F, Thiermann H. Reversed-phase ion-pair chromatography-diode array detection of the bispyridinium compound MB327: plasma analysis of a potential novel antidote for the treatment of organophosphorus poisoning. Drug Test Anal. 2016;8:154-63 pubmed publisher
    ..Finally, the RPIPC-DAD procedure was applied to samples from an in vivo study of swine. ..
  29. Mena F, Azzopardi M, Pfennig S, Ruepert C, Tedengren M, Castillo L, et al. Use of cholinesterase activity as a biomarker of pesticide exposure used on Costa Rican banana plantations in the native tropical fish Astyanax aeneus (Günther, 1860). J Environ Biol. 2014;35:35-42 pubmed
  30. Savi G, Piacentini K, Bortolotto T, Scussel V. Degradation of bifenthrin and pirimiphos-methyl residues in stored wheat grains (Triticum aestivum L.) by ozonation. Food Chem. 2016;203:246-251 pubmed publisher
    ..1, 301.1 and 319.2) were identified by LC-MS. O3 is a strong oxidizer that has shown the potential to reduce pesticide residues in stored grain in order to ensure food quality and safety. ..
  31. Malekmohammadi M, Galehdari H. Target site insensitivity mutations in the AChE enzyme confer resistance to organophosphorous insecticides in Leptinotarsa decemlineata (Say). Pestic Biochem Physiol. 2016;126:85-91 pubmed publisher
    ..Site-directed mutagenesis and protein expression experiments are needed for a more complete evaluation. ..
  32. Güngördü A. Comparative toxicity of methidathion and glyphosate on early life stages of three amphibian species: Pelophylax ridibundus, Pseudepidalea viridis, and Xenopus laevis. Aquat Toxicol. 2013;140-141:220-8 pubmed publisher
    ..laevis. The selected biomarker enzymes AChE, CaE, and GST are useful in understanding the toxic mechanisms of these pesticides in anuran tadpoles as early warning indicators. ..
  33. Mashauri F, Manjurano A, Kinung hi S, Martine J, Lyimo E, Kishamawe C, et al. Indoor residual spraying with micro-encapsulated pirimiphos-methyl (Actellic® 300CS) against malaria vectors in the Lake Victoria basin, Tanzania. PLoS ONE. 2017;12:e0176982 pubmed publisher
    ..P-methyl 300 CShas a long residual efficacy on sprayed wall surfaces and therefore it is effective in controlling principal malaria vectors of An. gambiae s.l and An. funestus which rest on wall surfaces after and before feeding. ..
  34. Peng P, Ye X. O,O-dimethylthiophosphonosulfenyl bromide-silver triflate: a new powerful promoter system for the preactivation of thioglycosides. Org Biomol Chem. 2011;9:616-22 pubmed publisher
    ..The usefulness of this new promoter is illustrated by a successful iterative one-pot oligosaccharide assembly...
  35. Attademo A, Cabagna Zenklusen M, Lajmanovich R, Peltzer P, Junges C, Bassó A. B-esterase activities and blood cell morphology in the frog Leptodactylus chaquensis (Amphibia: Leptodactylidae) on rice agroecosystems from Santa Fe Province (Argentina). Ecotoxicology. 2011;20:274-82 pubmed publisher
  36. Xu S, Liu Y, Tai H, Zhu J, Ding H, Lee R. Synthesis of transferrin (Tf) conjugated liposomes via Staudinger ligation. Int J Pharm. 2011;404:205-10 pubmed publisher
    ..Pharmacokinetic parameters indicated that these liposomes retained long circulating properties relative to the free drug. In summary, Staudinger ligation is an effective method for the synthesis of receptor targeted liposomes. ..
  37. Zhang D, Li B, Zhang X, Zhang Z, Wang W, Liu F. Phoxim Microcapsules Prepared with Polyurea and Urea-Formaldehyde Resins Differ in Photostability and Insecticidal Activity. J Agric Food Chem. 2016;64:2841-6 pubmed publisher
    ..These experiments indicated that it is crucial to select the appropriate wall materials for pesticide microcapsules on the basis of application sites and physicochemical properties of pesticide active ingredients. ..
  38. Gill S, Rizvi F, Khan M, Khan A. Toxic effects of cypermethrin and methamidophos on bovine corpus luteal cells and progesterone production. Exp Toxicol Pathol. 2011;63:131-5 pubmed publisher
    ..Cypermethrin exhibited more adverse toxic changes in viable cell counts, progesterone production and histological findings as compared to methamidophos. ..
  39. Ding Q, Huang X, Wu J. Facile synthesis of benzothiazoles via cascade reactions of 2-iodoanilines, acid chlorides and Lawesson's reagent. J Comb Chem. 2009;11:1047-9 pubmed publisher
  40. Katos A, Conti M, Moran T, Gordon R, Doctor B, Sciuto A, et al. Abdominal bloating and irritable bowel syndrome like symptoms following microinstillation inhalation exposure to chemical warfare nerve agent VX in guinea pigs. Toxicol Ind Health. 2007;23:231-40 pubmed
    ..These results suggest that microinstillatipn inhalation VX exposure induces gastrointestinal disturbances similar to that of irritable bowel syndrome and bloating. ..
  41. Liu X, Luo Z, Zheng J, Xiong B. Effects of waterborne acephate exposure on antioxidant responses and acetylcholinesterase activities in Synechogobius hasta. Environ Toxicol. 2013;28:42-50 pubmed publisher
  42. Reeves T, Wales M, Grimsley J, Li P, Cerasoli D, Wild J. Balancing the stability and the catalytic specificities of OP hydrolases with enhanced V-agent activities. Protein Eng Des Sel. 2008;21:405-12 pubmed publisher
    ..This study describes the first rationally designed, stability/activity balance for an OPH enzyme with a legitimate V-agent activity, and its crystal structure. ..
  43. Han S, Li J, Xi H, Xu D, Zuo Y, Zhang J. Photocatalytic decomposition of acephate in irradiated TiO2 suspensions. J Hazard Mater. 2009;163:1165-72 pubmed publisher
    ..About 100% sulfur atoms are transformed into SO(4)(2-) in 180 min, however; only 3% nitrogen atoms and 2% phosphorus atoms were transformed into NO(3)(-) and PO(4)(3-). ..
  44. Kanamori Kataoka M, Seto Y. Paraoxonase activity against nerve gases measured by capillary electrophoresis and characterization of human serum paraoxonase (PON1) polymorphism in the coding region (Q192R). Anal Biochem. 2009;385:94-100 pubmed publisher
    ..PON1 hydrolyzed sarin and soman more effectively than paraoxon. ..
  45. Okumu F, Mbeyela E, Lingamba G, Moore J, Ntamatungiro A, Kavishe D, et al. Comparative field evaluation of combinations of long-lasting insecticide treated nets and indoor residual spraying, relative to either method alone, for malaria prevention in an area where the main vector is Anopheles arabiensis. Parasit Vectors. 2013;6:46 pubmed publisher
  46. Ahmadkhaniha R, Samadi N, Salimi M, Sarkhail P, Rastkari N. Simultaneous determination of parathion, malathion, diazinon, and pirimiphos methyl in dried medicinal plants using solid-phase microextraction fibre coated with single-walled carbon nanotubes. ScientificWorldJournal. 2012;2012:627607 pubmed publisher
    ..The developed method was successfully applied to determine target organophosphorus pesticides in real samples. ..
  47. Choi J, Yu J, Yang D, Ra K, Kim K, Hong G, et al. Acetylthiocholine (ATC)--cleaving cholinesterase (ChE) activity as a potential biomarker of pesticide exposure in the Manila clam, Ruditapes philippinarum, of Korea. Mar Environ Res. 2011;71:162-8 pubmed publisher
    ..These results suggest that ChE activity in R. philippinarum is a potential biomarker for assessing organophosphorous pesticide contamination in coastal environments...
  48. Zhao Q, Lu Q, Yu Q, Feng Y. Dispersive microextraction based on "magnetic water" coupled to gas chromatography/mass spectrometry for the fast determination of organophosphorus pesticides in cold-pressed vegetable oils. J Agric Food Chem. 2013;61:5397-403 pubmed publisher
    ..2% and 6.5%, respectively. Finally, the established "magnetic water" microextraction method was successfully applied for the determination of pesticide residues in several kinds of cold-pressed vegetable oils. ..
  49. Lima C, Ribeiro Carvalho A, Filgueiras C, Manhães A, Meyer A, Abreu Villaca Y. Exposure to methamidophos at adulthood elicits depressive-like behavior in mice. Neurotoxicology. 2009;30:471-8 pubmed publisher
    ..There were no correlations between acetylcholinesterase activity and behavioral measures. Our results indicate that methamidophos at doses below the threshold for systemic toxicity induces depressive-like behavior in adult mice. ..
  50. Quintero A, Caselles M, Ettiene G, de Colmenares N, Ramírez T, Medina D. Monitoring of organophosphorus pesticide residues in vegetables of agricultural area in Venezuela. Bull Environ Contam Toxicol. 2008;81:393-6 pubmed publisher
    ..Methamidophos was founded in the vegetables in the rank of 6.3%-65.5%. The results show that 16.7% of the samples tested have residues higher than the maximum limits permitted. ..
  51. Li H, Guo J, Ping H, Liu L, Zhang M, Guan F, et al. Visual detection of organophosphorus pesticides represented by mathamidophos using Au nanoparticles as colorimetric probe. Talanta. 2011;87:93-9 pubmed publisher
    ..The proposed colorimetric assay exhibits good reproducibility and accuracy, providing a simple and rapid method for the analysis of organophosphorus pesticides...
  52. Whangsuk W, Dubbs J, Sallabhan R, Somsongkul K, Mongkolsuk S, Loprasert S. ChpR is a chlorpyrifos-responsive transcription regulator in Sinorhizobium meliloti. J Mol Microbiol Biotechnol. 2010;18:141-7 pubmed publisher
    ..Both the ChpR transcription factor and chpA promoter constitute a good candidate system for genetic-based biosensor development. ..
  53. Wang F, Shi Z, Tong R, Xu X. Dynamics of phoxim residues in green onion and soil as influenced by arbuscular mycorrhizal fungi. J Hazard Mater. 2011;185:112-6 pubmed publisher
    ..Our results indicate a promising potential of AM fungi for the control of organophosphate residues in vegetables, as well as for the phytoremediation of organophosphorus pesticide-contaminated soil. ..