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Chemical Compound Review

butyrate     butanoate

Synonyms: butanate, propylformate, N-Butyrate, n-butanoate, BUTYRIC_ACID, ...
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Disease relevance of butanoic acid

  • A more acute effect of suppression of EBV release was observed in a second model of 12-o-tetradecanoyl phorbol-13-acetate and n-butyrate induction of EBV in 37 degrees C-cultured P3HR-1 cells [1].
  • K562 is an established human erythroleukemia cell line, inducible for hemoglobin synthesis by a variety of compounds including n-butyrate [2].
  • Similar repeating units were detected in hamster cells that were nonpermissive for human adenovirus and in cells pretreated with n-butyrate [3].
  • Thus, n-butyrate can influence the expression of multiple genes in this hepatoblastoma cell through its actions on events that appear to be posttranscriptional [4].
  • Kinetics of Ii synthesis, processing, and turnover in n-butyrate-treated Burkitt's lymphoma cell lines which express or do not express class II antigens and in hairy leukemic cells [5].
 

High impact information on butanoic acid

  • A positive serologic response was defined by the recognition of an antigenic polypeptide, p40, in n-butyrate-treated BC-1 cells and by the absence of p40 recognition in untreated BC-1 cells or EBV-infected, KSHV-negative cells [6].
  • Treatment of MAE cell clones with 1.0 mM n-butyrate stops cell proliferation reversibly and causes an increased synthesis of alpha D and pi (or pi') globin polypeptide chains [7].
  • Effect of n-butyrate on DNA synthesis in chick fibroblasts and HeLa cells [8].
  • Nuclei from n-butyrate-treated HeLa cells remain inactive in control cytosol; control nuclei are strongly inhibited by cytosol from treated cells [8].
  • BACKGROUND & AIMS: Among substrates available to the colonic mucosa, n-butyrate from bacterial origin represents a major fuel [9].
 

Chemical compound and disease context of butanoic acid

 

Biological context of butanoic acid

  • The short-chain fatty acid n-butyrate (10 mM), on its own, accounted for 86% of the total oxygen consumption and suppressed oxidation of endogenous fuel by 82% [15].
  • The metabolic effect of these agents on n-butyrate and glucose oxidation in human colonocytes is unknown [16].
  • The effects produced by n-butyrate could, therefore, be the result of lengthening the G1 phase of the cell cycle or a modification of histones affecting transcription during virus activation [17].
  • Studies with synchronized cultures showed that n-butyrate delayed the onset of DNA synthesis, characteristic of the S phase, and inhibited histone deacetylation in log-phase cells [17].
  • n-Butyrate, a short-chain aliphatic carboxylic acid with pleiotropic actions, is present at high concentrations in the portal circulation and thus may play an important role in the regulation of specific gene expression in the mammalian liver [4].
 

Anatomical context of butanoic acid

  • It is suggested that failure of fatty-acid (n-butyrate) oxidation in UC is an expression of an energy-deficiency disease of the colonic mucosa [18].
  • Cell quiescence induced by serum deprivation (3T3 cells) or by addition of n-butyrate (L1210) results in cell arrest at a state which, judged by RNA content, is similar to that of G1A of exponentially growing cells [19].
  • Four stages were examined: epithelial cells derived on plastic from intestinal culture and grown as a cell clone, the same cells grown on connective tissue support, primary epithelial explants grown on fibroblasts with a laminin base, and primary epithelial explants grown on fibroblasts and laminin with n-butyrate added to the incubation medium [20].
  • Novel mode of interference with nuclear factor of activated T-cells regulation in T-cells by the bacterial metabolite n-butyrate [21].
  • Biosynthesis of heparin. Effects of n-butyrate on cultured mast cells [22].
 

Associations of butanoic acid with other chemical compounds

 

Gene context of butanoic acid

 

Analytical, diagnostic and therapeutic context of butanoic acid

References

  1. Inhibition of Epstein-Barr virus (EBV) release from the P3HR-1 Burkitt's lymphoma cell line by a monoclonal antibody against a 200,000 dalton EBV membrane antigen. Sairenji, T., Reisert, P.S., Spiro, R.C., Connolly, T., Humphreys, R.E. J. Exp. Med. (1985) [Pubmed]
  2. K562 human erythroleukemia cell variants resistant to growth inhibition by butyrate have deficient histone acetylation. Ohlsson-Wilhelm, B.M., Farley, B.A., Kosciolek, B., La Bella, S., Rowley, P.T. Am. J. Hum. Genet. (1984) [Pubmed]
  3. Adenovirus chromatin structure at different stages of infection. Daniell, E., Groff, D.E., Fedor, M.J. Mol. Cell. Biol. (1981) [Pubmed]
  4. n-Butyrate induces plasminogen activator inhibitor type 1 messenger RNA in cultured Hep G2 cells. Smith, T.J., Piscatelli, J.J., Andersen, V., Wang, H.S., Lance, P. Hepatology (1996) [Pubmed]
  5. Kinetics of Ii synthesis, processing, and turnover in n-butyrate-treated Burkitt's lymphoma cell lines which express or do not express class II antigens and in hairy leukemic cells. Spiro, R.C., Sairenji, T., Humphreys, R.E. J. Immunol. (1985) [Pubmed]
  6. Antibodies to butyrate-inducible antigens of Kaposi's sarcoma-associated herpesvirus in patients with HIV-1 infection. Miller, G., Rigsby, M.O., Heston, L., Grogan, E., Sun, R., Metroka, C., Levy, J.A., Gao, S.J., Chang, Y., Moore, P. N. Engl. J. Med. (1996) [Pubmed]
  7. Isolation and transformation of primary mesenchymal cells of the chick embryo. Keane, R.W., Lindblad, P.C., Pierik, L.T., Ingram, V.M. Cell (1979) [Pubmed]
  8. Effect of n-butyrate on DNA synthesis in chick fibroblasts and HeLa cells. Hagopian, H.K., Riggs, M.G., Swartz, L.A., Ingram, V.M. Cell (1977) [Pubmed]
  9. Effect of germfree state on the capacities of isolated rat colonocytes to metabolize n-butyrate, glucose, and glutamine. Cherbuy, C., Darcy-Vrillon, B., Morel, M.T., Pégorier, J.P., Duée, P.H. Gastroenterology (1995) [Pubmed]
  10. Effect of sodium n-butyrate on induction of prostaglandin synthase activity in cloned mastocytoma P-815 2-E-6 cells. Koshihara, Y., Kawamura, M., Senshu, T., Murota, S. Biochem. J. (1981) [Pubmed]
  11. Modulation of the HSV-TK/ganciclovir bystander effect by n-butyrate in glioblastoma: correlation with gap-junction intercellular communication. Robe, P.A., Jolois, O., N'Guyen, M., Princen, F., Malgrange, B., Merville, M.P., Bours, V. Int. J. Oncol. (2004) [Pubmed]
  12. Supplementation of enteral nutrition with butyrate leads to increased portal efflux of amino acids in growing pigs with short bowel syndrome. Welters, C.F., Deutz, N.E., Dejong, C.H., Soeters, P.B., Heineman, E. J. Pediatr. Surg. (1996) [Pubmed]
  13. Inhibition of human endothelial cell proliferation in vitro in response to n-butyrate and propionate. Tse, C.S., Williams, D.M. J. Periodont. Res. (1992) [Pubmed]
  14. Nitric oxide effect on colonocyte metabolism: co-action of sulfides and peroxide. Roediger, W.E., Babidge, W.J. Mol. Cell. Biochem. (2000) [Pubmed]
  15. Utilization of nutrients by isolated epithelial cells of the rat colon. Roediger, W.E. Gastroenterology (1982) [Pubmed]
  16. Reducing sulfur compounds of the colon impair colonocyte nutrition: implications for ulcerative colitis. Roediger, W.E., Duncan, A., Kapaniris, O., Millard, S. Gastroenterology (1993) [Pubmed]
  17. Cell cycle-specific enhancement of type C virus activation by sodium n-butyrate. Long, C.W., Suk, W.A., Snead, R.M., Christensen, W.L. Cancer Res. (1980) [Pubmed]
  18. The colonic epithelium in ulcerative colitis: an energy-deficiency disease? Roediger, W.E. Lancet (1980) [Pubmed]
  19. Subcompartments of the G1 phase of cell cycle detected by flow cytometry. Darzynkiewicz, Z., Sharpless, T., Staiano-Coico, L., Melamed, M.R. Proc. Natl. Acad. Sci. U.S.A. (1980) [Pubmed]
  20. Human fetal enterocytes in vitro: modulation of the phenotype by extracellular matrix. Sanderson, I.R., Ezzell, R.M., Kedinger, M., Erlanger, M., Xu, Z.X., Pringault, E., Leon-Robine, S., Louvard, D., Walker, W.A. Proc. Natl. Acad. Sci. U.S.A. (1996) [Pubmed]
  21. Novel mode of interference with nuclear factor of activated T-cells regulation in T-cells by the bacterial metabolite n-butyrate. Diakos, C., Prieschl, E.E., Saemann, M., Novotny, V., Bohmig, G., Csonga, R., Baumruker, T., Zlabinger, G.J. J. Biol. Chem. (2002) [Pubmed]
  22. Biosynthesis of heparin. Effects of n-butyrate on cultured mast cells. Jacobsson, K.G., Riesenfeld, J., Lindahl, U. J. Biol. Chem. (1985) [Pubmed]
  23. n-Butyrate effects thyroid hormone stimulation of prolactin production and mRNA levels in GH1 cells. Stanley, F., Samuels, H.H. J. Biol. Chem. (1984) [Pubmed]
  24. n-Butyrate increases the level of thyroid hormone nuclear receptor in non-pituitary cultured cells. Mitsuhashi, T., Uchimura, H., Takaku, F. J. Biol. Chem. (1987) [Pubmed]
  25. Effect of L-glutamine and n-butyrate on the restitution of rat colonic mucosa after acid induced injury. Scheppach, W., Dusel, G., Kuhn, T., Loges, C., Karch, H., Bartram, H.P., Richter, F., Christl, S.U., Kasper, H. Gut (1996) [Pubmed]
  26. Protein kinase C-independent activation of the Epstein-Barr virus lytic cycle. Gradoville, L., Kwa, D., El-Guindy, A., Miller, G. J. Virol. (2002) [Pubmed]
  27. In vivo butyrylcholinesterase activity is not increased in Alzheimer's disease synapses. Kuhl, D.E., Koeppe, R.A., Snyder, S.E., Minoshima, S., Frey, K.A., Kilbourn, M.R. Ann. Neurol. (2006) [Pubmed]
  28. p21 Waf1/Cip1 can protect human colon carcinoma cells against p53-dependent and p53-independent apoptosis induced by natural chemopreventive and therapeutic agents. Mahyar-Roemer, M., Roemer, K. Oncogene (2001) [Pubmed]
  29. Retinoblastoma protein is required for efficient colorectal carcinoma cell apoptosis by histone deacetylase inhibitors in the absence of p21Waf. Wagner, S., Roemer, K. Biochem. Pharmacol. (2005) [Pubmed]
  30. n-butyrate reduces the expression of beta-galactoside alpha 2,6-sialyltransferase in Hep G2 cells. Shah, S., Lance, P., Smith, T.J., Berenson, C.S., Cohen, S.A., Horvath, P.J., Lau, J.T., Baumann, H. J. Biol. Chem. (1992) [Pubmed]
  31. N-Butyrate incubation of immature chicken erythrocytes preferentially enhances the solubility of beta A chromatin. Ferenz, C.R., Nelson, D.A. Nucleic Acids Res. (1985) [Pubmed]
  32. Targeting glycosylation pathways and the cell cycle: sugar-dependent activity of butyrate-carbohydrate cancer prodrugs. Sampathkumar, S.G., Jones, M.B., Meledeo, M.A., Campbell, C.T., Choi, S.S., Hida, K., Gomutputra, P., Sheh, A., Gilmartin, T., Head, S.R., Yarema, K.J. Chem. Biol. (2006) [Pubmed]
 
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