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Chemical Compound Review

PHENYLUREA     phenylurea

Synonyms: Monophenylurea, Phenyl-urea, N-Phenylurea, Stabilizer VH, SureCN54471, ...
 
 
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Disease relevance of phenylurea

 

High impact information on phenylurea

  • In vitro enzyme assays showed that the gene product of one heterologously expressed P450 cDNA (CYP71A10) specifically catalyzed the metabolism of phenylurea herbicides, converting four herbicides of this class (fluometuron, linuron, chlortoluron, and diuron) into more polar compounds [6].
  • A phenylurea series of chemical inhibitors of XIAP was recently generated by our laboratories (Schimmer, A. D., Welsh, K., Pinilla, C., Bonneau, M., Wang, Z., Pedersen, I. M., Scott, F. L., Glinsky, G. V., Scudiero, D. A., Sausville, E., Salvesen, G., Nefzi, A., Ostresh, J. M., Houghten, R. A., and Reed, J. C. (2004) Cancer Cell 5, 25-35) [7].
  • Phenylurea-based XIAP antagonists induced apoptosis (defined by annexin V staining) prior to mitochondrial membrane depolarization, in contrast to cytotoxic anticancer drugs [7].
  • Apoptosis induced by active phenylurea-based compounds was blocked by chemical inhibitors of caspases, with inhibitors of downstream effector caspases displaying more effective suppression than inhibitors of upstream initiator caspases [7].
  • The Jerusalem artichoke (Helianthus tuberosus) xenobiotic inducible cytochrome P450, CYP76B1, catalyzes rapid oxidative dealkylation of various phenylurea herbicides to yield nonphytotoxic metabolites [8].
 

Chemical compound and disease context of phenylurea

 

Biological context of phenylurea

  • In the molecular structure of the hA(3) receptor, two residues, Ser243 (TM6) and Ser271 (TM7), create a hydrophilic region, which seems to permit a better accommodation of the phenylurea series into this putative hA(3) binding site than the phenylacetyl series [11].
  • Effect of phenylurea herbicides on soil microbial communities estimated by analysis of 16S rRNA gene fingerprints and community-level physiological profiles [12].
  • The present study focuses on kinetics and mechanistic aspects of the transformation of phenylurea herbicides induced by well-defined excited triplet states, which have been chosen to model DOM triplet states having oxidative character [13].
  • The imprinting effect of the originated specific binding sites for the selective recognition of phenylurea herbicides was clearly demonstrated [14].
  • During method development of U.S. Environmental Protection Agency (EPA) Methods 526 (for unstable semivolatile compounds) and 532 (for phenylurea pesticides), a number of studies were conducted to identify compatible microbial inhibitors [15].
 

Anatomical context of phenylurea

 

Associations of phenylurea with other chemical compounds

 

Gene context of phenylurea

  • Induction of antioxidant enzyme activities by a phenylurea derivative, EDU [22].
  • The potency of 3,4-DCAc androgen receptor binding was compared with that of several phenylurea compounds [23].
  • The inhibitory efficiency of the phenylurea series on wheat and spinach pieces led to the conclusion that some extrachloroplastic factors seemed to limit the accessibility of the D1-protein target [24].
  • Effect of intramonolayer hydrogen bonding of carboxyl groups in self-assembled monolayers on a single force with phenylurea on an AFM probe tip [25].
  • The individual hydrogen-bonding force between the phenylurea-modified tip and the binary mixed SAMs with various fractions of MHA was evaluated by repetitive force measurements and their statistical analyses by an autocorrelation method [25].
 

Analytical, diagnostic and therapeutic context of phenylurea

  • Pulse radiolysis experiments allowed limitation of the reduction potential of phenylurea(.+) within 2.22 V versus the normal hydrogen electrode (NHE)< E degrees (phenylurea(.+)/phenylurea)<2.43 V versus NHE [26].
  • Metabolism of the phenylurea herbicide isoproturon by Sphingomonas sp. strain SRS2 was significantly enhanced when the strain was grown in coculture with a soil bacterium (designated strain SRS1) [27].
  • Mixed immunosorbent for selective on-line trace enrichment and liquid chromatography of phenylurea herbicides in environmental waters [28].
  • High-performance liquid chromatographic (HPLC) separations of eighteen phenylurea pesticides were investigated using both reversed-phase and normal-phase systems [29].
  • New strategies for the determination of phenylurea pesticides by gas chromatography with hot splitless inlet systems [30].

References

  1. Degradation of substituted phenylurea herbicides by Arthrobacter globiformis strain D47 and characterization of a plasmid-associated hydrolase gene, puhA. Turnbull, G.A., Ousley, M., Walker, A., Shaw, E., Morgan, J.A. Appl. Environ. Microbiol. (2001) [Pubmed]
  2. Isolation from agricultural soil and characterization of a Sphingomonas sp. able to mineralize the phenylurea herbicide isoproturon. Sørensen, S.R., Ronen, Z., Aamand, J. Appl. Environ. Microbiol. (2001) [Pubmed]
  3. Sequences of the cDNAs encoding the heavy- and light-chain Fab region of an antibody to the phenylurea herbicide diuron. Bell, C.W., Scholthof, K.B., Zhang, G., Karu, A.E. Gene (1995) [Pubmed]
  4. Influence of UV irradiation on the toxicity of phenylurea herbicides using Microtox test. Bonnemoy, F., Lavédrine, B., Boulkamh, A. Chemosphere (2004) [Pubmed]
  5. Recovery of Nostoc muscorum previously exposed to some triazine and phenylurea herbicides. Abou-Waly, H., Shabana, E.F. Bulletin of environmental contamination and toxicology. (1993) [Pubmed]
  6. Expression of a soybean cytochrome P450 monooxygenase cDNA in yeast and tobacco enhances the metabolism of phenylurea herbicides. Siminszky, B., Corbin, F.T., Ward, E.R., Fleischmann, T.J., Dewey, R.E. Proc. Natl. Acad. Sci. U.S.A. (1999) [Pubmed]
  7. Cellular, biochemical, and genetic analysis of mechanism of small molecule IAP inhibitors. Wang, Z., Cuddy, M., Samuel, T., Welsh, K., Schimmer, A., Hanaii, F., Houghten, R., Pinilla, C., Reed, J.C. J. Biol. Chem. (2004) [Pubmed]
  8. Engineering herbicide metabolism in tobacco and Arabidopsis with CYP76B1, a cytochrome P450 enzyme from Jerusalem artichoke. Didierjean, L., Gondet, L., Perkins, R., Lau, S.M., Schaller, H., O'Keefe, D.P., Werck-Reichhart, D. Plant Physiol. (2002) [Pubmed]
  9. Biotransformation of phenylurea herbicides by a soil bacterial strain, Arthrobacter sp. N2: structure, ecotoxicity and fate of diuron metabolite with soil fungi. Tixier, C., Sancelme, M., Aït-Aïssa, S., Widehem, P., Bonnemoy, F., Cuer, A., Truffaut, N., Veschambre, H. Chemosphere (2002) [Pubmed]
  10. Transformation of the insecticide teflubenzuron by microorganisms. Finkelstein, Z.I., Baskunov, B.P., Rietjens, I.M., Boersma, M.G., Vervoort, J., Golovleva, L.A. Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes. (2001) [Pubmed]
  11. Pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine derivatives as adenosine receptor antagonists. Influence of the N5 substituent on the affinity at the human A 3 and A 2B adenosine receptor subtypes: a molecular modeling investigation. Pastorin, G., Da Ros, T., Spalluto, G., Deflorian, F., Moro, S., Cacciari, B., Baraldi, P.G., Gessi, S., Varani, K., Borea, P.A. J. Med. Chem. (2003) [Pubmed]
  12. Effect of phenylurea herbicides on soil microbial communities estimated by analysis of 16S rRNA gene fingerprints and community-level physiological profiles. el Fantroussi, S., Verschuere, L., Verstraete, W., Top, E.M. Appl. Environ. Microbiol. (1999) [Pubmed]
  13. Aqueous oxidation of phenylurea herbicides by triplet aromatic ketones. Canonica, S., Hellrung, B., M??ller, P., Wirz, J. Environ. Sci. Technol. (2006) [Pubmed]
  14. Selective high performance liquid chromatography imprinted-stationary phases for the screening of phenylurea herbicides in vegetable samples. Tamayo, F.G., Martin-Esteban, A. Journal of chromatography. A. (2005) [Pubmed]
  15. Microbial inhibitors for U.S. EPA drinking water methods for the determination of organic compounds. Winslow, S.D., Pepich, B.V., Bassett, M.V., Wendelken, S.C., Munch, D.J., Sinclair, J.L. Environ. Sci. Technol. (2001) [Pubmed]
  16. Biomimetic approach to biomembrane models studies: medium influence on the interaction kinetics of some phenylurea derivatives herbicides. Librando, V., Sarpietro, M.G., Minniti, Z., Micieli, D., Castelli, F. Environ. Sci. Technol. (2006) [Pubmed]
  17. Effects of tail-like substituents on the binding of competitive inhibitors to the Q(B) site of photosystem II. Reifler, M.J., Szalai, V.A., Peterson, C.N., Brudvig, G.W. J. Mol. Recognit. (2001) [Pubmed]
  18. A new fluorescent PET chemosensor for fluoride ions. Kim, S.K., Yoon, J. Chem. Commun. (Camb.) (2002) [Pubmed]
  19. High-performance liquid chromatographic determination of phenylureas by photochemically-induced fluorescence detection. Muñoz de la Peña, A., Mahedero, M.C., Bautista-Sánchez, A. Journal of chromatography. A. (2002) [Pubmed]
  20. Frentizole therapy of thrombocytopenia in systemic lupus erythematosus and refractory idiopathic thrombocytopenic purpura. O'Duffy, J.D., Colgan, J.P., Phyliky, R.L., Ferguson, R.H. Mayo Clin. Proc. (1980) [Pubmed]
  21. Analysis of carbamate and phenylurea pesticide residues in fruit juices by solid-phase microextraction and liquid chromatography-mass spectrometry. Sagratini, G., Mañes, J., Giardiná, D., Damiani, P., Picó, Y. Journal of chromatography. A (2007) [Pubmed]
  22. Induction of antioxidant enzyme activities by a phenylurea derivative, EDU. Stevens, T.M., Boswell, G.A., Adler, R., Ackerman, N.R., Kerr, J.S. Toxicol. Appl. Pharmacol. (1988) [Pubmed]
  23. Application of an androgen receptor assay for the characterisation of the androgenic or antiandrogenic activity of various phenylurea herbicides and their derivatives. Bauer, E.R., Meyer, H.H., Stahlschmidt-Allner, P., Sauerwein, H. The Analyst. (1998) [Pubmed]
  24. Photosynthesis inhibition by phenylureas: a QSAR approach. Arnaud, L., Taillandier, G., Kaouadji, M., Ravanel, P., Tissut, M. Ecotoxicol. Environ. Saf. (1994) [Pubmed]
  25. Effect of intramonolayer hydrogen bonding of carboxyl groups in self-assembled monolayers on a single force with phenylurea on an AFM probe tip. Kado, S., Murakami, T., Kimura, K. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry. (2006) [Pubmed]
  26. Mechanisms of direct and TiO2-photocatalysed UV degradation of phenylurea herbicides. Canle López, M., Fernández, M.I., Rodríguez, S., Santaballa, J.A., Steenken, S., Vulliet, E. Chemphyschem : a European journal of chemical physics and physical chemistry. (2005) [Pubmed]
  27. Growth in coculture stimulates metabolism of the phenylurea herbicide isoproturon by Sphingomonas sp. strain SRS2. Sørensen, S.R., Ronen, Z., Aamand, J. Appl. Environ. Microbiol. (2002) [Pubmed]
  28. Mixed immunosorbent for selective on-line trace enrichment and liquid chromatography of phenylurea herbicides in environmental waters. Martin-Esteban, A., Fernández, P., Stevenson, D., Cámara, C. The Analyst. (1997) [Pubmed]
  29. Determination of phenylurea pesticides by high-performance liquid chromatography with UV and photoconductivity detectors in series. Walters, S.M., Westerby, B.C., Gilvydis, D.M. J. Chromatogr. (1984) [Pubmed]
  30. New strategies for the determination of phenylurea pesticides by gas chromatography with hot splitless inlet systems. Gennaro, M.C., Marengo, E., Gianotti, V., Maurino, V. Journal of chromatography. A. (2001) [Pubmed]
 
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