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Chemical Compound Review

Halmark     [(R)-cyano-(3- phenoxyphenyl)methyl] (2R)-2...

Synonyms: Asana, ESFENVALERATE, Sumi-alfa, Sumi-alpha, A alpha, ...
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Disease relevance of ESFENVALERATE

  • Two independent experimental strategies are employed: the ability of 12 monoclonal antibodies to recognize L cell transfectants bearing chimeric and mutant A alpha chains is assessed, and the amino acid sequences of A alpha chains expressed by immunoselected B lymphoma mutants are deduced [1].
  • The crystallographic structure of Neisseria gonorrhoeae pilin, which assembles into the multifunctional pilus adhesion and virulence factor, reveals an alpha-beta roll fold with a striking 85 A alpha-helical spine and an O-linked disaccharide [2].
  • Juveniles and young adult A alpha-/- mice are predisposed to spontaneous fatal abdominal hemorrhage, but long-term survival is variable and highly dependent on genetic background [3].
  • In this report we show that substituting alanines at all but five amino acids in the myelin basic protein (MBP) peptide Ac1-11 does not alter its ability to bind A alpha uA beta u (MHC class II molecules), to stimulate specific T cells and, surprisingly, to induce experimental autoimmune encephalomyelitis (EAE) in (PL/J x SJL/J)F1 mice [4].
  • Two families with hereditary renal amyloidosis were found to have a novel mutation in the fibrinogen A alpha chain gene [5].

Psychiatry related information on ESFENVALERATE

  • The role of A alpha chain is also implied by the permissiveness of E kappa alpha Aq beta but not Aq alpha Aq beta molecules in the deletion of V beta 6+ T cells [6].
  • Hyperphosphorylated tau, the major component of the paired helical filaments of Alzheimer's disease, was found to accumulate in the brains of mice in which the calcineurin A alpha gene was disrupted [calcineurin A alpha knockout (CNA alpha -/-)] [7].

High impact information on ESFENVALERATE

  • Mixed isotype (E alpha A beta and A alpha E beta) dimers are not found on Ia+ hematopoietic cells, although some pairs (e.g., E alpha A beta d) reach the membrane of transfected cells expressing only the two relevant class II genes [8].
  • We have now isolated and sequenced A alpha cDNA clones from five other mouse haplotypes: d, b, f, u, and q [9].
  • Regions of allelic hypervariability in the murine A alpha immune response gene [9].
  • The structure of one of these class II major histocompatibility complex molecules, A alpha, was recently deduced from sequence analysis of a cDNA clone produced from k haplotype mice [9].
  • The genes encoding the alpha- and beta-chains of the class II heterodimers, A alpha A beta and E alpha E beta, have recently been characterized at the molecular level, and certain cloned genes were shown to be functionally expressed after introduction into cells by DNA-mediated gene transfer [10].

Chemical compound and disease context of ESFENVALERATE


Biological context of ESFENVALERATE

  • These data on the effects of allelic variation on Ia levels provide a possible explanation for the strong linkage disequilibrium of A alpha and A beta genes and may account for the current molecular organization of the I region of the MHC [16].
  • The activation of T helper lymphocytes involves the recognition of class II major histocompatibility complex antigens, which are dimeric glycoproteins (of subunit composition A alpha A beta or E alpha E beta) expressed on the surfaces of macrophages and B lymphocytes [17].
  • All of the component chains of fibrinogen (A alpha, B beta, and gamma) are immunologically undetectable in the circulation of both neonatal and adult A alpha-/- mice, and blood samples fail to either clot or support platelet aggregation in vitro [3].
  • The combination of dissimilar alleles of the A alpha and A beta gene complexes, whose proteins contain homeo domain motifs, determines sexual development in the mushroom Coprinus cinereus [18].
  • To explore the role of the key coagulation factor, fibrinogen, in development, hemostasis, wound repair, and disease pathogenesis, we disrupted the fibrinogen A alpha chain gene in mice [3].

Anatomical context of ESFENVALERATE

  • Overt bleeding events develop shortly after birth in approximately 30% of A alpha-/- mice, most frequently in the peritoneal cavity, skin, and soft tissues around joints [3].
  • The periodic rupture of ovarian follicles in breeding-age A alpha-/- females does not appear to significantly diminish life expectancy relative to males; however, pregnancy uniformly results in fatal uterine bleeding around the tenth day of gestation [3].
  • T cell responses in calcineurin A alpha-deficient mice [19].
  • In this report, we have demonstrated that IFN-gamma and TNF-alpha increase expression of both the I-A and I-E region gene products on the surface of the myelomonocytic cell line WEHI-3, and that they mediate this increase via an increase in A alpha transcription [20].
  • By screening for inhibition of antigen presentation to NOD T cell hybridoma, we have selected a synthetic peptide, yTYTVHAAHAYTYt (small letters denote D amino acids), that efficiently blocks antigen presentation by the NOD class II MHC molecule A alpha g7A beta g7 (Ag7) in vitro [21].

Associations of ESFENVALERATE with other chemical compounds

  • Autoradiography of the display of EC-bound 125I on polyacrylamide gel showed the constitutive B beta- and gamma-chains of the fg molecule, with a partial loss of the A alpha-chain [22].
  • We have found that chymotrypsin A alpha is also inhibited by heparin cofactor II with a second-order rate constant value of 1.8 X 10(6) M-1 X min-1 at pH 8.0 and 25 degrees C. However, there was no measurable effect of heparin or dermatan sulfate on the rate of chymotrypsin inhibition [23].
  • Thus, CD11c/CD18 on tumor necrosis factor-stimulated neutrophils functions as a fibrinogen receptor that recognizes the sequence Gly-Pro-Arg in the N-terminal domain of the A alpha chain of fibrinogen [24].
  • Amino acid sequence analysis of the abnormal peptide indicated that A alpha proline-18, the second residue from the NH2-terminus of the fibrin alpha-chain, was replaced by leucine [25].
  • The basal level of lung cell gamma-FBG gene transcription was not accompanied by appreciable levels of A alpha and B beta chain gene transcription; however, nuclear run-on analysis suggested that the increase in lung cell FBG mRNAs in response to DEX +/- IL-6 was due to new transcription [26].

Gene context of ESFENVALERATE

  • Three of the four chains, A alpha, A beta and E beta, are controlled by loci in the I-A subregion, whereas the locus controlling the E alpha chain is located in the I-E subregion of the H-2 complex [27].
  • Mutants mice carrying targeted inactivations of both retinoic acid receptor (RAR) alpha and RAR gamma (A alpha/A gamma mutants) were analyzed at different embryonic stages, in order to establish the timing of appearance of defects that we previously observed during the fetal period [28].
  • The hindbrain of E8.5 A alpha/A gamma embryos shows a posterior expansion of rhombomere 3 and 4 (R3 and R4) markers, but fails to express kreisler, a normal marker of R5 and R6 [28].
  • At the nucleotide level Drosophila calcineurin A cDNA is 67 and 65% identical to human calcineurin A alpha and beta cDNAs, respectively [29].
  • CD4(+) alpha beta T cells from either normal C57BL/6 (B6) or MHC-II-deficient (A alpha(-/-) or A beta(-/-)) B6 donor mice engrafted into congenic immunodeficient RAG1(-/-) B6 hosts induced an aggressive inflammatory bowel disease (IBD) [30].

Analytical, diagnostic and therapeutic context of ESFENVALERATE

  • Functional sites on Ia molecules: a molecular dissection of A alpha immunogenicity [1].
  • Northern blot analyses indicated that one I-A-, I-E+ tumor strongly expressed A alpha, E alpha, and E beta mRNAs but possessed only a weak expression of A beta mRNA [31].
  • By immunoprecipitation and two-dimensional analysis of Ia molecules from F1 spleen cells, we could independently map the reactivities of the mAb as being determined by the A alpha or A beta chain [32].
  • In addition to FPB release, SDS-PAGE analysis of the time course of urokinase-mediated fibrinogenolysis indicates progressive proteolysis of both the A alpha- and B beta-chains of fibrinogen that occurs after FPB release is completed [33].
  • By separating the products of HNE digestion of fibrinogen using high performance liquid chromatography, identifying the immunoreactive fractions and subjecting them to amino acid analysis, the fragment was identified as A alpha 1-21, indicating an HNE cleavage site at the Val(A alpha 21)-Glu(A alpha 22) bond [34].


  1. Functional sites on Ia molecules: a molecular dissection of A alpha immunogenicity. Landais, D., Waltzinger, C., Beck, B.N., Staub, A., McKean, D.J., Benoist, C., Mathis, D. Cell (1986) [Pubmed]
  2. Structure of the fibre-forming protein pilin at 2.6 A resolution. Parge, H.E., Forest, K.T., Hickey, M.J., Christensen, D.A., Getzoff, E.D., Tainer, J.A. Nature (1995) [Pubmed]
  3. Resolution of spontaneous bleeding events but failure of pregnancy in fibrinogen-deficient mice. Suh, T.T., Holmbäck, K., Jensen, N.J., Daugherty, C.C., Small, K., Simon, D.I., Potter, S., Degen, J.L. Genes Dev. (1995) [Pubmed]
  4. A polyalanine peptide with only five native myelin basic protein residues induces autoimmune encephalomyelitis. Gautam, A.M., Pearson, C.I., Smilek, D.E., Steinman, L., McDevitt, H.O. J. Exp. Med. (1992) [Pubmed]
  5. Hereditary renal amyloidosis with a novel variant fibrinogen. Uemichi, T., Liepnieks, J.J., Benson, M.D. J. Clin. Invest. (1994) [Pubmed]
  6. MHC class II A alpha and E alpha molecules determine the clonal deletion of V beta 6+ T cells. Studies with recombinant and transgenic mice. Anderson, G.D., Banerjee, S., David, C.S. J. Immunol. (1989) [Pubmed]
  7. Cytoskeletal changes in the brains of mice lacking calcineurin A alpha. Kayyali, U.S., Zhang, W., Yee, A.G., Seidman, J.G., Potter, H. J. Neurochem. (1997) [Pubmed]
  8. Intracellular competition for component chains determines class II MHC cell surface phenotype. Sant, A.J., Germain, R.N. Cell (1989) [Pubmed]
  9. Regions of allelic hypervariability in the murine A alpha immune response gene. Benoist, C.O., Mathis, D.J., Kanter, M.R., Williams, V.E., McDevitt, H.O. Cell (1983) [Pubmed]
  10. Cell type-specific enhancer element associated with a mouse MHC gene, E beta. Gillies, S.D., Folsom, V., Tonegawa, S. Nature (1984) [Pubmed]
  11. A DNA binding protein regulated by IL-4 and by differentiation in B cells. Boothby, M., Gravallese, E., Liou, H.C., Glimcher, L.H. Science (1988) [Pubmed]
  12. Preliminary X-ray crystallographic study of cyanase from Escherichia coli. Kim, K.H., Honzatko, R.B., Little, R.M., Anderson, P.M. J. Mol. Biol. (1987) [Pubmed]
  13. Active site mapping of the serine proteases human leukocyte elastase, cathepsin G, porcine pancreatic elastase, rat mast cell proteases I and II. Bovine chymotrypsin A alpha, and Staphylococcus aureus protease V-8 using tripeptide thiobenzyl ester substrates. Harper, J.W., Cook, R.R., Roberts, C.J., McLaughlin, B.J., Powers, J.C. Biochemistry (1984) [Pubmed]
  14. Cyclosporin A/alpha interferon-induced autologous graft-versus-host disease following peripheral blood stem cell transplant for chronic myeloid leukaemia: a clinico-pathological study. Lim, S.H., Coleman, S., Bull, A., O'Callaghan, U., Evely, R., Booth, M. Bone Marrow Transplant. (1997) [Pubmed]
  15. Lack of enhancing effects of fenvalerate and esfenvalerate on induction of preneoplastic glutathione S-transferase placental form positive liver cell foci in rats. Hagiwara, A., Yamada, M., Hasegawa, R., Fukushima, S., Ito, N. Cancer Lett. (1990) [Pubmed]
  16. Influence of allelic polymorphism on the assembly and surface expression of class II MHC (Ia) molecules. Germain, R.N., Bentley, D.M., Quill, H. Cell (1985) [Pubmed]
  17. Functional expression of a transfected murine class II MHC gene. Germain, R.N., Norcross, M.A., Margulies, D.H. Nature (1983) [Pubmed]
  18. The combination of dissimilar alleles of the A alpha and A beta gene complexes, whose proteins contain homeo domain motifs, determines sexual development in the mushroom Coprinus cinereus. Kües, U., Richardson, W.V., Tymon, A.M., Mutasa, E.S., Göttgens, B., Gaubatz, S., Gregoriades, A., Casselton, L.A. Genes Dev. (1992) [Pubmed]
  19. T cell responses in calcineurin A alpha-deficient mice. Zhang, B.W., Zimmer, G., Chen, J., Ladd, D., Li, E., Alt, F.W., Wiederrecht, G., Cryan, J., O'Neill, E.A., Seidman, C.E., Abbas, A.K., Seidman, J.G. J. Exp. Med. (1996) [Pubmed]
  20. cis-acting sequences required for class II gene regulation by interferon gamma and tumor necrosis factor alpha in a murine macrophage cell line. Freund, Y.R., Dedrick, R.L., Jones, P.P. J. Exp. Med. (1990) [Pubmed]
  21. Prevention of autoimmune diabetes in non-obese diabetic mice by treatment with a class II major histocompatibility complex-blocking peptide. Hurtenbach, U., Lier, E., Adorini, L., Nagy, Z.A. J. Exp. Med. (1993) [Pubmed]
  22. Interaction between fibrinogen and cultured endothelial cells. Induction of migration and specific binding. Dejana, E., Languino, L.R., Polentarutti, N., Balconi, G., Ryckewaert, J.J., Larrieu, M.J., Donati, M.B., Mantovani, A., Marguerie, G. J. Clin. Invest. (1985) [Pubmed]
  23. Inhibition of chymotrypsin by heparin cofactor II. Church, F.C., Noyes, C.M., Griffith, M.J. Proc. Natl. Acad. Sci. U.S.A. (1985) [Pubmed]
  24. CD11c/CD18 on neutrophils recognizes a domain at the N terminus of the A alpha chain of fibrinogen. Loike, J.D., Sodeik, B., Cao, L., Leucona, S., Weitz, J.I., Detmers, P.A., Wright, S.D., Silverstein, S.C. Proc. Natl. Acad. Sci. U.S.A. (1991) [Pubmed]
  25. Fibrinogen Kyoto II, a new congenitally abnormal molecule, characterized by the replacement of A alpha proline-18 by leucine. Yoshida, N., Okuma, M., Hirata, H., Matsuda, M., Yamazumi, K., Asakura, S. Blood (1991) [Pubmed]
  26. Induction of fibrinogen biosynthesis and secretion from cultured pulmonary epithelial cells. Haidaris, P.J. Blood (1997) [Pubmed]
  27. Detection of CML determinants associated with H-2 controlled E beta and E alpha chains. Juretić, A., Nagy, Z.A., Klein, J. Nature (1981) [Pubmed]
  28. Roles of retinoic acid receptors in early embryonic morphogenesis and hindbrain patterning. Wendling, O., Ghyselinck, N.B., Chambon, P., Mark, M. Development (2001) [Pubmed]
  29. Molecular cloning and characterization of the genes encoding the two subunits of Drosophila melanogaster calcineurin. Guerini, D., Montell, C., Klee, C.B. J. Biol. Chem. (1992) [Pubmed]
  30. MHC-II-independent CD4+ T cells induce colitis in immunodeficient RAG-/- hosts. Trobonjaca, Z., Leithäuser, F., Möller, P., Bluethmann, H., Koezuka, Y., MacDonald, H.R., Reimann, J. J. Immunol. (2001) [Pubmed]
  31. Imbalanced MHC class II molecule expression at surface of murine B cell lymphomas. Zijlstra, M., Vasmel, W.L., Voormanns, M., de Goede, R.E., Schoenmakers, H.J., Nieland, J., Slater, R.M., Melief, C.J. J. Exp. Med. (1986) [Pubmed]
  32. Multiple functional sites on a single Ia molecule defined using T cell clones and antibodies with chain-determined specificity. Frelinger, J.G., Shigeta, M., Infante, A.J., Nelson, P.A., Pierres, M., Fathman, C.G. J. Exp. Med. (1984) [Pubmed]
  33. Urokinase has direct catalytic activity against fibrinogen and renders it less clottable by thrombin. Weitz, J.I., Leslie, B. J. Clin. Invest. (1990) [Pubmed]
  34. Development of an assay for in vivo human neutrophil elastase activity. Increased elastase activity in patients with alpha 1-proteinase inhibitor deficiency. Weitz, J.I., Landman, S.L., Crowley, K.A., Birken, S., Morgan, F.J. J. Clin. Invest. (1986) [Pubmed]
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