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Chemical Compound Review

Isobutyrate     2-methylpropanoic acid

Synonyms: Isobutanoate, i-butyrate, iso-Butyrate, i-Butyric acid, AGN-PC-0091P6, ...
 
 
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Disease relevance of isobutyric acid

 

High impact information on isobutyric acid

  • All the peptides, except one, were acylated at the N terminus with different hydrophobic acids--e.g., isobutyric acid (Ibu) or 1-naphthylacetic acid (Nac) in order to study the effect of N-terminal acylation on the antagonistic activity [6].
  • Acetate was more selective for GPR43, whereas butyrate and isobutyrate were more active on GPR41 [7].
  • Among C4-C16 fatty acids, MACS1 preferentially utilizes octanoate, whereas isobutyrate is the most preferred fatty acid among C2-C6 fatty acids for Sa protein [8].
  • On examination, the biological activities of insulin and insulin-like growth factor I in the patient's cultured fibroblasts, insulin sensitivity of amino isobutyric acid uptake and thymidine incorporation was decreased, but insulin-like growth factor I action was normal [9].
  • System Nb activity can be monitored by assaying Na(+)-dependent [3H]glutamine uptake in the presence of 2 mM concentrations of both 2-(methylamino) isobutyric acid and threonine to block uptake by systems A and ASC, respectively [10].
 

Chemical compound and disease context of isobutyric acid

 

Biological context of isobutyric acid

 

Anatomical context of isobutyric acid

 

Associations of isobutyric acid with other chemical compounds

 

Gene context of isobutyric acid

  • Stimulatory effects of PDGF occurred at concentrations of 2 ng/ml, with maximal stimulation up to 5-fold of the control value for amino isobutyric acid and glucose uptake and up to 8- to 10-fold for thymidine incorporation [28].
  • The active metabolite desisobutyryl-ciclesonide (des-CIC) is derived from ciclesonide by esterase cleavage of isobutyrate at the C21 position [29].
  • Na(+)-dependent amino isobutyric acid transport by two neuroblastoma cell lines with and without amplification of the oncogene N-myc is studied [30].
  • Acetate and isobutyrate did not induce tTG expression or growth suppression at concentrations up to 8 mM [31].
  • After one hour incubation with interleukin-1 beta (IL-1 beta), the uptake of alpha-(methylamino) isobutyric acid (MeAIB) by human osteoarthritic synovial cells appeared significantly increased [32].
 

Analytical, diagnostic and therapeutic context of isobutyric acid

  • The oligosaccharide-lipids were treated with dilute acid to liberate the water-soluble oligosaccharides and these oligosaccharides could then be separated into seven or eight distinct radioactive peaks by paper chromatography in isobutyric acid/NH4OH/H2betaO (57/4/39) [33].
  • The mean cortical blood to brain transfer constant (Ki) for 14C-amino isobutyric acid (AIB) was significantly greater at 3 and 6 h of reperfusion, 2.5 times the mean values of controls (p less than 0.05) (2.5 microliter g-1 min-1 and 1.0 microliters g-1 min-1 respectively), but had returned to control values after reperfusion for 24 h [34].
  • During the degradation of isobutyrate by the co-culture, isobutyrate was isomerized to butyrate, which was then oxidized [35].
  • Reversed-phase high-performance liquid chromatography (RP-HPLC) using alpha-hydroxy isobutyric acid (alpha-HIBA) as an eluent on reversed-phase column modified to cation exchanger has been reported to achieve the separation [36].
  • The supernatant was analyzed for acetate, proprionate, butyrate, isobutyrate, valerate, and isovalerate concentrations by use of gas chromatography [37].

References

  1. Nonactin biosynthesis: disruption of the polyketide synthase genes, nonKJ, in Streptomyces griseus leads to an overall 96 decrease in macrotetrolide production, yet a net increase in nonactin analogues which incorporate isobutyrate. Walczak, R.J., Nelson, M.E., Priestley, N.D. J. Am. Chem. Soc. (2001) [Pubmed]
  2. Effects of carbon sources on chemical composition of cell envelopes of Pseudomonas aeruginosa in association with polymyxin resistance. Gilleland, H.E., Conrad, R.S. Antimicrob. Agents Chemother. (1980) [Pubmed]
  3. Interconversion of valine and leucine by Clostridium sporogenes. Monticello, D.J., Costilow, R.N. J. Bacteriol. (1982) [Pubmed]
  4. Maternal-fetal exchange during protein malnutrition in the rat. Placental transfer of alpha-amino isobutyric acid. Rosso, P. J. Nutr. (1977) [Pubmed]
  5. Evidence for clostridial implication in necrotizing enterocolitis through bacterial fermentation in a gnotobiotic quail model. Waligora-Dupriet, A.J., Dugay, A., Auzeil, N., Huerre, M., Butel, M.J. Pediatr. Res. (2005) [Pubmed]
  6. Synthesis and biological activities of highly potent antagonists of growth hormone-releasing hormone. Zarandi, M., Horvath, J.E., Halmos, G., Pinski, J., Nagy, A., Groot, K., Rekasi, Z., Schally, A.V. Proc. Natl. Acad. Sci. U.S.A. (1994) [Pubmed]
  7. Functional characterization of human receptors for short chain fatty acids and their role in polymorphonuclear cell activation. Le Poul, E., Loison, C., Struyf, S., Springael, J.Y., Lannoy, V., Decobecq, M.E., Brezillon, S., Dupriez, V., Vassart, G., Van Damme, J., Parmentier, M., Detheux, M. J. Biol. Chem. (2003) [Pubmed]
  8. Molecular identification and characterization of two medium-chain acyl-CoA synthetases, MACS1 and the Sa gene product. Fujino, T., Takei, Y.A., Sone, H., Ioka, R.X., Kamataki, A., Magoori, K., Takahashi, S., Sakai, J., Yamamoto, T.T. J. Biol. Chem. (2001) [Pubmed]
  9. A mutation (Trp1193-->Leu1193) in the tyrosine kinase domain of the insulin receptor associated with type A syndrome of insulin resistance. Iwanishi, M., Haruta, T., Takata, Y., Ishibashi, O., Sasaoka, T., Egawa, K., Imamura, T., Naitou, K., Itazu, T., Kobayashi, M. Diabetologia (1993) [Pubmed]
  10. Identification of a system N-like Na(+)-dependent glutamine transport activity in rat brain neurons. Tamarappoo, B.K., Raizada, M.K., Kilberg, M.S. J. Neurochem. (1997) [Pubmed]
  11. Production of branched-chain volatile fatty acids by certain anaerobic bacteria. Allison, M.J. Appl. Environ. Microbiol. (1978) [Pubmed]
  12. Pseudomonas sp. strain HBP1 Prp degrades 2-isopropylphenol (ortho-cumenol) via meta cleavage. Reichlin, F., Kohler, H.P. Appl. Environ. Microbiol. (1994) [Pubmed]
  13. Induction of mucosal and systemic antibody specific for SeMF3 of Streptococcus equi by intranasal vaccination using a sucrose acetate isobutyrate based delivery system. Nally, J.E., Artiushin, S., Sheoran, A.S., Burns, P.J., Simon, B., Gilley, R.M., Gibson, J., Sullivan, S., Timoney, J.F. Vaccine (2000) [Pubmed]
  14. Crystallization of butyrate kinase 2 from Thermotoga maritima mediated by vapor diffusion of acetic acid. Diao, J., Cooper, D.R., Sanders, D.A., Hasson, M.S. Acta Crystallogr. D Biol. Crystallogr. (2003) [Pubmed]
  15. Biosynthesis of lasalocid A. Metabolic interrelationships of carboxylic acid precursors and polyether antibiotics. Sherman, M.M., Yue, S., Hutchinson, C.R. J. Antibiot. (1986) [Pubmed]
  16. Gluconeogenesis in isolated intact lamb liver cells. Effects of glucagon and butyrate. Clark, M.G., Filsell, O.H., Jarrett, I.G. Biochem. J. (1976) [Pubmed]
  17. Effect of maternal dietary restriction on fetal growth and placental transfer of alpha-amino isobutyric acid in rats. Ahokas, R.A., Lahaye, E.B., Anderson, G.D., Lipshitz, J. J. Nutr. (1981) [Pubmed]
  18. Transient loss of plasmid-mediated mercuric ion resistance after stress in Pseudomonas aeruginosa. Calcott, P.H. Appl. Environ. Microbiol. (1981) [Pubmed]
  19. Placental blood flow and transfer of nutrient analogs in large, average, and small guinea pig littermates. Saintonge, J., Rosso, P. Pediatr. Res. (1981) [Pubmed]
  20. Influence of vascular flow on amino acid transport across frog small intestine. Parsons, D.S., Sanderson, I.R. J. Physiol. (Lond.) (1980) [Pubmed]
  21. Neutral amino acid uptake by the isolated perfused sheep choroid plexus. Preston, J.E., Segal, M.B., Walley, G.J., Zlokovic, B.V. J. Physiol. (Lond.) (1989) [Pubmed]
  22. A transient increase in amino acid transport modulated by insulin in differentiating muscle cells. Farfel, Z., Karlish, S., Prives, J. J. Cell. Physiol. (1979) [Pubmed]
  23. Tigliane-type phorbols stimulate human melanocyte proliferation: potentially safer agents for melanocyte culture. Cela, A., Leong, I., Krueger, J. J. Invest. Dermatol. (1991) [Pubmed]
  24. On the ability of galactose to influence hexose and amino acid uptake by isolated rat brain capillaries. Segal, S., Hwang, S.M. J. Neurochem. (1983) [Pubmed]
  25. Glutamine transport in mouse cerebral astrocytes. Nagaraja, T.N., Brookes, N. J. Neurochem. (1996) [Pubmed]
  26. Bisfunction of propionic acid on purified rat liver beta-ureidopropionase. Kikugawa, M., Fujimoto, S., Mizota, C., Tamaki, N. FEBS Lett. (1988) [Pubmed]
  27. Inhibition of the glycine cleavage system by branched-chain amino acid metabolites. Kølvraa, S. Pediatr. Res. (1979) [Pubmed]
  28. The effects of platelet-derived growth factor in cultured microvessel endothelial cells. Bar, R.S., Boes, M., Booth, B.A., Dake, B.L., Henley, S., Hart, M.N. Endocrinology (1989) [Pubmed]
  29. In vitro and in vivo anti-inflammatory activity of the new glucocorticoid ciclesonide. Stoeck, M., Riedel, R., Hochhaus, G., Häfner, D., Masso, J.M., Schmidt, B., Hatzelmann, A., Marx, D., Bundschuh, D.S. J. Pharmacol. Exp. Ther. (2004) [Pubmed]
  30. Na(+)-dependent AIB transport by neuroblastoma cells. del Castillo-Olivares, A., Medina, M.A. FEBS Lett. (1992) [Pubmed]
  31. Induction of tissue transglutaminase expression by propionate and n-butyrate in colon cancer cell lines. Fukuda, K. J. Nutr. Biochem. (1999) [Pubmed]
  32. Stimulation of alpha-(methylamino) isobutyric acid uptake by interleukin-1 in human synovial cells. Involvement of a cAMP dependent pathway. LeMaire, V., Aussel, C., Hernvann, A., Launay, J.M., Ekindjian, O.G. Eur. Cytokine Netw. (1994) [Pubmed]
  33. Glycoprotein biosynthesis in plants. Demonstration of lipid-linked oligosaccharides of mannose and N-acetylglucosamine. Forsee, W.T., Elbein, A.D. J. Biol. Chem. (1975) [Pubmed]
  34. Transient blood-brain barrier permeability following profound temporary global ischaemia: an experimental study using 14C-AIB. Dobbin, J., Crockard, H.A., Ross-Russell, R. J. Cereb. Blood Flow Metab. (1989) [Pubmed]
  35. Syntrophothermus lipocalidus gen. nov., sp. nov., a novel thermophilic, syntrophic, fatty-acid-oxidizing anaerobe which utilizes isobutyrate. Sekiguchi, Y., Kamagata, Y., Nakamura, K., Ohashi, A., Harada, H. Int. J. Syst. Evol. Microbiol. (2000) [Pubmed]
  36. Separation and determination of lanthanides, thorium and uranium using a dual gradient in reversed-phase liquid chromatography. Raut, N.M., Jaison, P.G., Aggarwal, S.K. Journal of chromatography. A. (2004) [Pubmed]
  37. Gastrointestinal volatile fatty acid concentrations and pH in cats. Brosey, B.P., Hill, R.C., Scott, K.C. Am. J. Vet. Res. (2000) [Pubmed]
 
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