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Chemical Compound Review

oxomethyl     methanone

Synonyms: Formyl, Formyl radical, HCO(.), CHEBI:29327, AC1L3WFO, ...
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Disease relevance of methanone


Psychiatry related information on methanone


High impact information on methanone

  • The formyl group is held by a novel hydrogen bonding network, involving His9 on the bottom of the groove, and the side chain of the P1 methionine is lodged in the B pocket [9].
  • The identification of other members of this family, including receptors for the chemokines IL-8 and Mip-1/Rantes, thrombin, formyl peptide, and platelet activating factor, provide new tools for understanding structure-function relationships relevant to the inflammatory process [10].
  • Receptors, including those for the Fc end of the immunoglobulin G (ref. 1), the C3b component of complement, formyl peptides and plant lectins have been identified on the surface of neutrophils [11].
  • In this study, we isolated formyltransferase (fmt) mutant strains of L. monocytogenes that lacked the ability to add formyl groups to nascent polypeptides [12].
  • Tumor necrosis factor alpha, granulocyte colony-stimulating factor, granulocyte/macrophage colony-stimulating factor, and formyl peptide were each found to cause a twofold increase in expression of CD14 on the surface of polymorphonuclear leukocytes (PMN) [13].

Chemical compound and disease context of methanone

  • N10-Formyltetrahydrofolate is the formyl donor for glycinamide ribotide transformylase in Escherichia coli [14].
  • It is well established that formyl peptide chemoattractants can activate a phospholipase C in leukocytes via a pertussis toxin (PT)-sensitive guanine nucleotide regulatory (G) protein [15].
  • These results demonstrate that the NH2-terminal formyl peptides produced by E. coli, of which formyl-methionyl-leucyl-phenylalanine appears to be the major component, are the peptide mediators responsible for leukocyte chemotactic activity in the bacterial culture extracts [16].
  • The pool of intracellular formyl peptide receptors localized to the specific granule-enriched fraction appeared functionally coupled to a cosedimenting G-protein in experiments demonstrating modulation of high affinity N-formylmethionylleucyl[3H]phenylalanine binding by guanosine 5'-(3-O-thio)triphosphate or pertussis toxin [17].
  • In dibutyryl-cAMP-differentiated HL-60 cells, histamine H1 and formyl peptide receptors mediate increases in the cytosolic Ca2+ concentration ([Ca2+]i) via pertussis toxin-sensitive G proteins of the Gi family [18].

Biological context of methanone

  • Thus, it appears that large changes in cytosolic free calcium are not necessary for formyl peptide-induced polymorphonuclear leukocyte chemotaxis [19].
  • The binding site comprises C668 and G715 located in a groove accommodating the methionyl side-chain, R700, in the vicinity of the formyl group, Y701 and K702 close to the acyl bond between fMet and tRNA(f)(Met), and the surface lined with residues K702-S660, along which the acceptor arm of the initiator tRNA spans in the direction 3' to 5' [20].
  • Binding of both 125I-labeled and tetramethylrhodamine-labeled formyl peptide increases in response to treatment of the culture with polar compounds that induce cell differentiation [21].
  • Stimulation of the human neutrophil respiratory burst by formyl peptides is primed by a protein kinase inhibitor, staurosporine [22].
  • We investigated signaling pathways downstream of G protein-coupled receptors (GPCRs) that are relevant to alpha4beta1 integrin affinity up-regulation using formyl peptide receptor-transfected U937 cells stimulated with fMLP or stromal-derived factor-1alpha and human peripheral blood monocytes stimulated with multiple chemokines or chemoattractants [23].

Anatomical context of methanone


Associations of methanone with other chemical compounds

  • We examined the role of intracellular and extracellular calcium on the ability of human polymorphonuclear leukocytes to migrate chemotactically and reexpress (or recycle) formyl peptide receptors when challenged with the synthetic chemotactic peptide, N-formyl-methionyl-leucyl-phenylalanine (FMLP) [19].
  • When either MCT or HCO was fed in the absence of cholesterol, there was little effect on receptor-dependent LDL transport but a 36-43% increase in LDL-cholesterol production [29].
  • The PAF receptor antagonist, L-652,731, blocked responses (O2-. production and enzyme release) of rat neutrophils stimulated with PAF but did not block responses triggered by immune complexes, formyl chemotactic peptide or opsonized zymosan particles [30].
  • Preincubation of neutrophils with 400 ng/ml component I and 1,600 ng/ml component II of botulinum C2 toxin for 30 min almost completely inhibited the formyl peptide-stimulated polymerization of G-actin and at the same time decreased the amount of F-actin in unstimulated neutrophils by an average of approximately 30% [31].
  • The def gene could be inactivated if the fmt gene was also inactivated, or if biosynthesis of N10-formyl-tetrahydrofolate, the formyl donor in methionyl-tRNA(i) transformylation, was blocked by trimethoprim [32].

Gene context of methanone

  • Recent studies have proposed a functional link between annexin 1 (ANXA1), an endogenous anti-inflammatory mediator, and receptors of the formyl-peptide family [33].
  • These findings prompted us to identify the structural requirement for formyl peptide ligand binding by delineation of the primary structure of the rabbit FPR [34].
  • Furthermore, CRAMP induced the chemotaxis of human embryonic kidney 293 cells transfected with either FPRL1 or mouse formyl peptide receptor-2, the mouse homologue of FPRL1, but not by untransfected parental human embryonic kidney 293 cells, confirming the use of FPRL1/mouse formyl peptide receptor-2 by CRAMP [35].
  • We conclude that formyl peptide receptors are coupled to three MAPK cascades by Gi proteins [36].
  • Human neutrophil Fc gamma RIIIB and formyl peptide receptors are functionally linked during formyl-methionyl-leucyl-phenylalanine-induced chemotaxis [37].

Analytical, diagnostic and therapeutic context of methanone


  1. CD8 T cell detection of bacterial infection: sniffing for formyl peptides derived from Mycobacterium tuberculosis. Lauvau, G., Pamer, E.G. J. Exp. Med. (2001) [Pubmed]
  2. Cryopreservable neutrophil surrogates. Stored cytoplasts from human polymorphonuclear leukocytes retain chemotactic, phagocytic, and microbicidal function. Malawista, S.E., Van Blaricom, G., Breitenstein, M.G. J. Clin. Invest. (1989) [Pubmed]
  3. Expression of Escherichia coli methionyl-tRNA formyltransferase in Saccharomyces cerevisiae leads to formylation of the cytoplasmic initiator tRNA and possibly to initiation of protein synthesis with formylmethionine. Ramesh, V., Köhrer, C., RajBhandary, U.L. Mol. Cell. Biol. (2002) [Pubmed]
  4. Binding of formyl peptides to Walker 256 carcinosarcoma cells and the chemotactic response of these cells. Rayner, D.C., Orr, F.W., Shiu, R.P. Cancer Res. (1985) [Pubmed]
  5. Induction of actin polymerization in permeabilized neutrophils. Role of ATP. Redmond, T., Tardif, M., Zigmond, S.H. J. Biol. Chem. (1994) [Pubmed]
  6. Chemotactic-like receptors and Abeta peptide induced responses in Alzheimer's disease. Lorton, D., Schaller, J., Lala, A., De Nardin, E. Neurobiol. Aging (2000) [Pubmed]
  7. Hindfoot containment orthosis for management of bone and soft-tissue defects of the heel. Johnson, J.E., Rudzki, J.R., Janisse, E., Janisse, D.J., Valdez, R.R., Hanel, D.P., Gould, J.S. Foot & ankle international / American Orthopaedic Foot and Ankle Society [and] Swiss Foot and Ankle Society. (2005) [Pubmed]
  8. Using the Internet to deliver health care value. MacStravic, S. Health marketing quarterly. (2001) [Pubmed]
  9. H2-M3, a full-service class Ib histocompatibility antigen. Lindahl, K.F., Byers, D.E., Dabhi, V.M., Hovik, R., Jones, E.P., Smith, G.P., Wang, C.R., Xiao, H., Yoshino, M. Annu. Rev. Immunol. (1997) [Pubmed]
  10. C5A anaphylatoxin and its seven transmembrane-segment receptor. Gerard, C., Gerard, N.P. Annu. Rev. Immunol. (1994) [Pubmed]
  11. Receptors for concanavalin A cluster at the front of polarized neutrophils. Weinbaum, D.L., Sullivan, J.A., Mandell, G.L. Nature (1980) [Pubmed]
  12. H2-M3-restricted CD8+ T cells are not required for MHC class Ib-restricted immunity against Listeria monocytogenes. D'Orazio, S.E., Shaw, C.A., Starnbach, M.N. J. Exp. Med. (2006) [Pubmed]
  13. Activation of the adhesive capacity of CR3 on neutrophils by endotoxin: dependence on lipopolysaccharide binding protein and CD14. Wright, S.D., Ramos, R.A., Hermanowski-Vosatka, A., Rockwell, P., Detmers, P.A. J. Exp. Med. (1991) [Pubmed]
  14. N10-Formyltetrahydrofolate is the formyl donor for glycinamide ribotide transformylase in Escherichia coli. Dev, I.K., Harvey, R.J. J. Biol. Chem. (1978) [Pubmed]
  15. Role of a guanine nucleotide regulatory protein in the activation of phospholipase C by different chemoattractants. Verghese, M.W., Charles, L., Jakoi, L., Dillon, S.B., Snyderman, R. J. Immunol. (1987) [Pubmed]
  16. Purification and identification of formyl-methionyl-leucyl-phenylalanine as the major peptide neutrophil chemotactic factor produced by Escherichia coli. Marasco, W.A., Phan, S.H., Krutzsch, H., Showell, H.J., Feltner, D.E., Nairn, R., Becker, E.L., Ward, P.A. J. Biol. Chem. (1984) [Pubmed]
  17. Subcellular localization of Gi alpha in human neutrophils. Rotrosen, D., Gallin, J.I., Spiegel, A.M., Malech, H.L. J. Biol. Chem. (1988) [Pubmed]
  18. The H1 receptor agonist 2-(3-chlorophenyl)histamine activates Gi proteins in HL-60 cells through a mechanism that is independent of known histamine receptor subtypes. Seifert, R., Hagelüken, A., Höer, A., Höer, D., Grünbaum, L., Offermanns, S., Schwaner, I., Zingel, V., Schunack, W., Schultz, G. Mol. Pharmacol. (1994) [Pubmed]
  19. Formyl peptide-induced chemotaxis of human polymorphonuclear leukocytes does not require either marked changes in cytosolic calcium or specific granule discharge. Role of formyl peptide receptor reexpression (or recycling). Perez, H.D., Elfman, F., Marder, S., Lobo, E., Ives, H.E. J. Clin. Invest. (1989) [Pubmed]
  20. Mapping the fMet-tRNA(f)(Met) binding site of initiation factor IF2. Guenneugues, M., Caserta, E., Brandi, L., Spurio, R., Meunier, S., Pon, C.L., Boelens, R., Gualerzi, C.O. EMBO J. (2000) [Pubmed]
  21. A subpopulation of cultured human promyelocytic leukemia cells (HL-60) displays the formyl peptide chemotactic receptor. Niedel, J., Kahane, I., Lachman, L., Cuatrecasas, P. Proc. Natl. Acad. Sci. U.S.A. (1980) [Pubmed]
  22. Stimulation of the human neutrophil respiratory burst by formyl peptides is primed by a protein kinase inhibitor, staurosporine. Combadière, C., el Benna, J., Pedruzzi, E., Hakim, J., Périanin, A. Blood (1993) [Pubmed]
  23. Phospholipase C, calcium, and calmodulin are critical for {alpha}4{beta}1 integrin affinity up-regulation and monocyte arrest triggered by chemoattractants. Hyduk, S.J., Chan, J.R., Duffy, S.T., Chen, M., Peterson, M.D., Waddell, T.K., Digby, G.C., Szaszi, K., Kapus, A., Cybulsky, M.I. Blood (2007) [Pubmed]
  24. Mitochondrial N-formylmethionyl proteins as chemoattractants for neutrophils. Carp, H. J. Exp. Med. (1982) [Pubmed]
  25. Bacterial chemotactic oligopeptides and the intestinal mucosal barrier. Ferry, D.M., Butt, T.J., Broom, M.F., Hunter, J., Chadwick, V.S. Gastroenterology (1989) [Pubmed]
  26. Spasmogenic activity of chemotactic N-formylated oligopeptides: identity of structure--function relationships for chemotactic and spasmogenic activities. Marasco, W.A., Fantone, J.C., Ward, P.A. Proc. Natl. Acad. Sci. U.S.A. (1982) [Pubmed]
  27. Human neutrophils contain an intracellular pool of putative receptors for the chemoattractant N-formyl-methionyl-leucyl-phenylalanine. Fletcher, M.P., Gallin, J.I. Blood (1983) [Pubmed]
  28. Rho GEF Lsc is required for normal polarization, migration, and adhesion of formyl-peptide-stimulated neutrophils. Francis, S.A., Shen, X., Young, J.B., Kaul, P., Lerner, D.J. Blood (2006) [Pubmed]
  29. Mechanisms by which saturated triacylglycerols elevate the plasma low density lipoprotein-cholesterol concentration in hamsters. Differential effects of fatty acid chain length. Woollett, L.A., Spady, D.K., Dietschy, J.M. J. Clin. Invest. (1989) [Pubmed]
  30. Evidence for the role of platelet-activating factor in immune complex vasculitis in the rat. Warren, J.S., Mandel, D.M., Johnson, K.J., Ward, P.A. J. Clin. Invest. (1989) [Pubmed]
  31. Influence of botulinum C2 toxin on F-actin and N-formyl peptide receptor dynamics in human neutrophils. Norgauer, J., Just, I., Aktories, K., Sklar, L.A. J. Cell Biol. (1989) [Pubmed]
  32. Genetic characterization of polypeptide deformylase, a distinctive enzyme of eubacterial translation. Mazel, D., Pochet, S., Marlière, P. EMBO J. (1994) [Pubmed]
  33. The annexin 1 receptor(s): is the plot unravelling? Perretti, M. Trends Pharmacol. Sci. (2003) [Pubmed]
  34. The rabbit neutrophil N-formyl peptide receptor. cDNA cloning, expression, and structure/function implications. Ye, R.D., Quehenberger, O., Thomas, K.M., Navarro, J., Cavanagh, S.L., Prossnitz, E.R., Cochrane, C.G. J. Immunol. (1993) [Pubmed]
  35. Mouse cathelin-related antimicrobial peptide chemoattracts leukocytes using formyl peptide receptor-like 1/mouse formyl peptide receptor-like 2 as the receptor and acts as an immune adjuvant. Kurosaka, K., Chen, Q., Yarovinsky, F., Oppenheim, J.J., Yang, D. J. Immunol. (2005) [Pubmed]
  36. Formyl peptide receptors are coupled to multiple mitogen-activated protein kinase cascades by distinct signal transduction pathways: role in activation of reduced nicotinamide adenine dinucleotide oxidase. Rane, M.J., Carrithers, S.L., Arthur, J.M., Klein, J.B., McLeish, K.R. J. Immunol. (1997) [Pubmed]
  37. Human neutrophil Fc gamma RIIIB and formyl peptide receptors are functionally linked during formyl-methionyl-leucyl-phenylalanine-induced chemotaxis. Kew, R.R., Grimaldi, C.M., Furie, M.B., Fleit, H.B. J. Immunol. (1992) [Pubmed]
  38. Evidence that a formyl-substituted iron porphyrin is the prosthetic group of myeloperoxidase: magnetic circular dichroism similarity of the peroxidase to Spirographis heme-reconstituted myoglobin. Sono, M., Bracete, A.M., Huff, A.M., Ikeda-Saito, M., Dawson, J.H. Proc. Natl. Acad. Sci. U.S.A. (1991) [Pubmed]
  39. Cytotoxic effect of 7alpha-hydroxy-4-cholesten-3-one on HepG2 cells: hypothetical role of acetaldehyde-modified delta4-3-ketosteroid-5beta-reductase (the 37-kd-liver protein) in the pathogenesis of alcoholic liver injury in the rat. Lin, R.C., Fillenwarth, M.J., Du, X. Hepatology (1998) [Pubmed]
  40. Neutrophil aggregation is beta 2-integrin- and L-selectin-dependent in blood and isolated cells. Simon, S.I., Chambers, J.D., Butcher, E., Sklar, L.A. J. Immunol. (1992) [Pubmed]
  41. Signal transduction by the formyl peptide receptor. Studies using chimeric receptors and site-directed mutagenesis define a novel domain for interaction with G-proteins. Amatruda, T.T., Dragas-Graonic, S., Holmes, R., Perez, H.D. J. Biol. Chem. (1995) [Pubmed]
  42. Characterization of the plasma membrane bound GTPase from rabbit neutrophils. I. Evidence for an Ni-like protein coupled to the formyl peptide, C5a, and leukotriene B4 chemotaxis receptors. Feltner, D.E., Smith, R.H., Marasco, W.A. J. Immunol. (1986) [Pubmed]
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