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Chemical Compound Review

1,4-Butanolide     oxolan-2-one

Synonyms: BLON, BUTYROLACTONE, Butyrylactone, butyrolactonL, gamma-BL, ...
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Disease relevance of gamma-Butyrolactone


Psychiatry related information on gamma-Butyrolactone

  • It inhibited spontaneous locomotor activity (LMA) in rodents, reversed the gamma-butyrolactone (GBL) induced accumulation of rat striatal DOPA and inhibited brain DA neuronal firing, all suggestive of direct DA autoreceptor agonist activity [6].
  • In Experiment 1, Gbl caused a dose-related decrease in lever pressing during a fixed-interval reinforcement schedule [7].

High impact information on gamma-Butyrolactone


Chemical compound and disease context of gamma-Butyrolactone


Biological context of gamma-Butyrolactone

  • DNase I protection assays mapped the SpbR-binding site in the papR1 promoter to a sequence homologous to other known butyrolactone autoregulatory elements [11].
  • Remarkably, the functional distribution of SCP1 genes somewhat resembles that of the chromosome: predicted gene products/functions include ECF sigma factors, antibiotic biosynthesis, a gamma-butyrolactone signalling system, members of the actinomycete-specific Wbl class of regulatory proteins and 14 secreted proteins [17].
  • RESULTS: DNA sequencing has shown that the tylosin biosynthetic gene cluster, within which four open reading frames utilise the rare TTA codon, contains at least five candidate regulatory genes, one of which (tylP) encodes a gamma-butyrolactone signal receptor for which tylQ is a probable target [18].
  • Effects of gamma-hydroxybutrate and gamma-butyrolactone on cerebral energy metabolism during exposure and recovery from hypoxemia-oligemia [19].
  • Derivatives of gamma-butyrolactone (GBL) substituted on the alpha- and/or gamma-positions were synthesized and tested for their effects on behavior in mice, on the electroencephalographs and blood pressure of paralyzed-ventilated guinea pigs, and on electrical activity of incubated hippocampal slices [20].

Anatomical context of gamma-Butyrolactone


Associations of gamma-Butyrolactone with other chemical compounds

  • In order of increasing ring size, Delta H degrees (acid) = 368.7 +/- 2., 369.4 +/- 2.2, 367.3 +/- 2.2, and 368.3 +/- 2.2 kcal/mol and BDE = 99.4 +/- 2.3, 94.8 +/- 2.3, 89.2 +/- 2.3, and 92.8 +/- 2.4 kcal/mol for beta-propiolactone, gamma-butyrolactone, delta-valerolactone, and epsilon-caprolactone, respectively [26].
  • Lithium, alsterpaullone or valproate, three independent glycogen synthase kinase-3 inhibitors, but not butyrolactone 1, an inhibitor of cyclin-dependent protein kinases, induced mitochondrial clustering in association with tau dephosphorylation [27].
  • The increase in DOPA output after intraperitoneal administration of haloperidol or gamma-butyrolactone and the decrease in DOPA output after intraperitoneal administration of apomorphine are in excellent agreement with results of postmortem studies, in which a decarboxylase inhibitor was used to measure the activity of tyrosine hydroxylase [28].
  • Treatment with sulfatase or beta-glucuronidase plus saccharic acid 1,4-lactone did not change the retention time of the metabolite [29].
  • Furthermore, pretreatment with bromocriptine and L-dopa blocked both the increase in serum PRL concentration and the decrease in anterior pituitary DA content induced by alpha-methyltyrosine and gamma-butyrolactone [30].

Gene context of gamma-Butyrolactone


Analytical, diagnostic and therapeutic context of gamma-Butyrolactone


  1. PI factor, a novel type quorum-sensing inducer elicits pimaricin production in Streptomyces natalensis. Recio, E., Colinas, A., Rumbero, A., Aparicio, J.F., Martín, J.F. J. Biol. Chem. (2004) [Pubmed]
  2. Influence of various agents on the development of brain edema in the rat following microembolism. Protective effect of gamma-butyrolactone. Bralet, J., Beley, P., Bralet, A.M., Beley, A. Stroke (1979) [Pubmed]
  3. Synergistic potentiation of halopoderidol-induced catalepsy by gamma-butyrolactone. Olianas, M.C., De Montis, M.G., Mulas, G., Tagliamonte, A. J. Neurochem. (1976) [Pubmed]
  4. fMRI of generalized absence status epilepticus in conscious marmoset monkeys reveals corticothalamic activation. Tenney, J.R., Marshall, P.C., King, J.A., Ferris, C.F. Epilepsia (2004) [Pubmed]
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  6. Dopamine autoreceptor agonists as potential antipsychotics. 3.6-Propyl-4,5,5a,6,7,8-hexahydrothiazolo[4,5-f]quinolin-2-amine. Caprathe, B.W., Jaen, J.C., Wise, L.D., Heffner, T.G., Pugsley, T.A., Meltzer, L.T., Parvez, M. J. Med. Chem. (1991) [Pubmed]
  7. Gamma-butyrolactone's discriminability and effect on low rates of lever pressing by rats: alone and in combination with D-amphetamine and naloxone. McIntire, K.D., Cleary, J., Weinfurter, S. Pharmacol. Biochem. Behav. (1988) [Pubmed]
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  9. Transmitter metabolism in substantia nigra after inhibition of dopaminergic neurones by butyrolactone. Hefti, F., Lienhart, R., Lichtensteiger, W. Nature (1976) [Pubmed]
  10. Regulation of cyclin-dependent kinase 5 and casein kinase 1 by metabotropic glutamate receptors. Liu, F., Ma, X.H., Ule, J., Bibb, J.A., Nishi, A., DeMaggio, A.J., Yan, Z., Nairn, A.C., Greengard, P. Proc. Natl. Acad. Sci. U.S.A. (2001) [Pubmed]
  11. Pleiotropic functions of a Streptomyces pristinaespiralis autoregulator receptor in development, antibiotic biosynthesis, and expression of a superoxide dismutase. Folcher, M., Gaillard, H., Nguyen, L.T., Nguyen, K.T., Lacroix, P., Bamas-Jacques, N., Rinkel, M., Thompson, C.J. J. Biol. Chem. (2001) [Pubmed]
  12. A-factor as a microbial hormone that controls cellular differentiation and secondary metabolism in Streptomyces griseus. Horinouchi, S., Beppu, T. Mol. Microbiol. (1994) [Pubmed]
  13. Regulation of tylosin production and morphological differentiation in Streptomyces fradiae by TylP, a deduced gamma-butyrolactone receptor. Stratigopoulos, G., Gandecha, A.R., Cundliffe, E. Mol. Microbiol. (2002) [Pubmed]
  14. A single amino acid substitution in region 1.2 of the principal sigma factor of Streptomyces coelicolor A3(2) results in pleiotropic loss of antibiotic production. Aigle, B., Wietzorrek, A., Takano, E., Bibb, M.J. Mol. Microbiol. (2000) [Pubmed]
  15. A complex role for the gamma-butyrolactone SCB1 in regulating antibiotic production in Streptomyces coelicolor A3(2). Takano, E., Chakraburtty, R., Nihira, T., Yamada, Y., Bibb, M.J. Mol. Microbiol. (2001) [Pubmed]
  16. Tolerance to the effects of baclofen and gamma-butyrolactone on locomotor activity and dopaminergic neurons in the mouse. Gianutsos, G., Moore, K.E. J. Pharmacol. Exp. Ther. (1978) [Pubmed]
  17. SCP1, a 356,023 bp linear plasmid adapted to the ecology and developmental biology of its host, Streptomyces coelicolor A3(2). Bentley, S.D., Brown, S., Murphy, L.D., Harris, D.E., Quail, M.A., Parkhill, J., Barrell, B.G., McCormick, J.R., Santamaria, R.I., Losick, R., Yamasaki, M., Kinashi, H., Chen, C.W., Chandra, G., Jakimowicz, D., Kieser, H.M., Kieser, T., Chater, K.F. Mol. Microbiol. (2004) [Pubmed]
  18. Multiple regulatory genes in the tylosin biosynthetic cluster of Streptomyces fradiae. Bate, N., Butler, A.R., Gandecha, A.R., Cundliffe, E. Chem. Biol. (1999) [Pubmed]
  19. Effects of gamma-hydroxybutrate and gamma-butyrolactone on cerebral energy metabolism during exposure and recovery from hypoxemia-oligemia. MacMillan, V. Stroke (1980) [Pubmed]
  20. Anticonvulsant properties of alpha, gamma, and alpha, gamma-substituted gamma-butyrolactones. Klunk, W.E., Covey, D.F., Ferrendelli, J.A. Mol. Pharmacol. (1982) [Pubmed]
  21. 3,4-dihydroxyphenylacetic acid (DOPAC) and the rat mesolimbic dopaminergic pathway: drug effects and evidence for somatodendritic mechanisms. Beart, P.M., Gundlach, A.L. Br. J. Pharmacol. (1980) [Pubmed]
  22. Caffeine mimics dopamine receptor agonists without stimulation of dopamine receptors. Watanabe, H., Uramoto, H. Neuropharmacology (1986) [Pubmed]
  23. Developmental differences in dopamine synthesis inhibition by (+/-)-7-OH-DPAT. Anderson, S.L., Dumont, N.L., Teicher, M.H. Naunyn Schmiedebergs Arch. Pharmacol. (1997) [Pubmed]
  24. Endothelial cell formation of focal adhesions on hydrophilic plasma polymers. Sanborn, S.L., Murugesan, G., Marchant, R.E., Kottke-Marchant, K. Biomaterials (2002) [Pubmed]
  25. Effect of low dose gamma-butyrolactone therapy on forebrain neuronal ischemia in the unrestrained, awake rat. Lavyne, M.H., Hariri, R.J., Tankosic, T., Babiak, T. Neurosurgery (1983) [Pubmed]
  26. Conformation-dependent reaction thermochemistry: study of lactones and lactone enolates in the gas phase. Karty, J.M., Janaway, G.A., Brauman, J.I. J. Am. Chem. Soc. (2002) [Pubmed]
  27. Role of tau phosphorylation by glycogen synthase kinase-3beta in the regulation of organelle transport. Tatebayashi, Y., Haque, N., Tung, Y.C., Iqbal, K., Grundke-Iqbal, I. J. Cell. Sci. (2004) [Pubmed]
  28. Use of microdialysis for monitoring tyrosine hydroxylase activity in the brain of conscious rats. Westerink, B.H., De Vries, J.B., Duran, R. J. Neurochem. (1990) [Pubmed]
  29. Characterization of a glucuronide metabolite of 4-(methyl-nitrosamino)-1-(3-pyridyl)-1-butanone (NNK) and its dose-dependent excretion in the urine of mice and rats. Morse, M.A., Eklind, K.I., Toussaint, M., Amin, S.G., Chung, F.L. Carcinogenesis (1990) [Pubmed]
  30. Pharmacological manipulation of anterior pituitary dopamine content in the male rat: relationship to serum prolactin concentration and lysosomal enzyme activity. Demarest, K.T., Riegle, G.D., Moore, K.E. Endocrinology (1984) [Pubmed]
  31. Reduced tyrosine hydroxylase and GTP cyclohydrolase mRNA expression, tyrosine hydroxylase activity, and associated neurochemical alterations in Nurr1-null heterozygous mice. Eells, J.B., Misler, J.A., Nikodem, V.M. Brain Res. Bull. (2006) [Pubmed]
  32. Induction of apoptosis in cancer cells by tumor necrosis factor and butyrolactone, an inhibitor of cyclin-dependent kinases. Belizário, J.E., Sherwood, S., Beçak, W. Braz. J. Med. Biol. Res. (1999) [Pubmed]
  33. Prominent induction of cyclin B1 in G2/M renal cancer cells with butyrolactone 1. Kasuya, Y., Hosaka, Y., Matsushima, H., Goto, T., Kitamura, T., Okuyama, A. International journal of urology : official journal of the Japanese Urological Association. (2003) [Pubmed]
  34. Effects of pantolactone and butyrolactone on the pleiotropic phenotypes of lon mutants and on thermal induction of the SOS phenomena in a tif mutant of Escherichia coli K12. Nakayama, H., Nakayama, K., Nakayama, R., Kato, Y. Arch. Microbiol. (1982) [Pubmed]
  35. Purification and molecular cloning of a butyrolactone autoregulator receptor from Streptomyces virginiae. Okamoto, S., Nihira, T., Kataoka, H., Suzuki, A., Yamada, Y. J. Biol. Chem. (1992) [Pubmed]
  36. An investigation of the relationship between the dopaminergic and electroencephalographic effects of gamma-butyrolactone. Snead, O.C. Neuropharmacology (1982) [Pubmed]
  37. Chiral separation of gamma-butyrolactone derivatives by gas chromatography on 2,3-di-O-methyl-6-O-tert.-butyldimethylsilyl-beta-cyclodextrin. Ramos, M.d.a. .C., Teixeira, L.H., de Aquino Neto, F.R., Barreiro, E.J., Rodrigues, C.R., Fraga, C.A. Journal of chromatography. A. (2003) [Pubmed]
  38. Control of growth, secondary metabolism and sporulation in Streptomyces venezuelae ISP5230 by jadW(1), a member of the afsA family of gamma-butyrolactone regulatory genes. Wang, L., Vining, L.C. Microbiology (Reading, Engl.) (2003) [Pubmed]
  39. Cloning and characterization of a gene encoding the gamma-butyrolactone autoregulator receptor from Streptomyces clavuligerus. Kim, H.S., Lee, Y.J., Lee, C.K., Choi, S.U., Yeo, S.H., Hwang, Y.I., Yu, T.S., Kinoshita, H., Nihira, T. Arch. Microbiol. (2004) [Pubmed]
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