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Chemical Compound Review

sebacate     decanedioic acid

Synonyms: Sebacinsaure, Sebacinsaeure, n-Decanedioate, Seracic acid, sebacic acid, ...
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Disease relevance of sebacic acid

  • We present case histories of two young children with episodes of hypoglycemia, elevation of SGOT, low insulin levels, increased urinary excretion of psi-hydroxy fatty acids (5-hydroxyhexanoic, 7-hydroxyoctanoic and 9-hydroxydecanoic), traces of the corresponding psi-ketoacids and elevations of urinary adipic, suberic, and sebacic acids [1].
  • The structure of Chlorobium vibrioforme 5-aminolaevulinic acid dehydratase (ALAD) complexed with the irreversible inhibitor 4,7-dioxosebacic acid has been solved [2].
  • Tetanus toxoid was found to be the most stable in the presence of anhydride monomers, while Ova was most stable in the presence of sebacic acid, and lysozyme was stable when incubated with all of the monomers studied [3].
  • The diacids (succinic acid, adipic acid, sebacic acid) were selected among compounds that were known to be of low systemic toxicity [4].
  • The biosynthesis of adipic, suberic and sebacic acids was studied using ketotic rats as the model, since ketosis in rats and humans is accompanied by excessive urinary excretion of adipic and suberic acids [5].

Psychiatry related information on sebacic acid

  • By means of gas chromatographic methods substantial amounts of the C6-C10-dicarboxylic acids, i.e. adipic, suberic and sebacic acids, have been found in the urine from children with unexplained attacks of lethargy and hypotonia, presumably related to episodes of fever and/or insufficient food intake [5].

High impact information on sebacic acid

  • 4-Oxosebacic acid (4-OSA) and 4,7-dioxosebacic acid (4,7-DOSA) are bisubstrate reaction intermediate analogs for PBGS [6].
  • We found for sebacic acid one binding site with affinity constant 3.69 x 10(4) M-1 and four to five sites with affinity constant 7.14 x 10(2) M-1 [7].
  • Poly(ester amide)s from dimethyl sebacate or sebacic acid and 2-aminoethanol or 4-amino-1-butanol were characterized by post-source decay matrix-assisted laser desorption/ionization time-of-flight (PSD-MALDI-TOF) and time-of-flight/time-of-flight tandem mass spectrometry (MALDI-TOF/TOF-MS/MS) [8].
  • The polymers are composed of various ratios of sebacic acid (SA) (to render the polymer insoluble in water) and poly(ethylene glycol) (PEG) (to reduce particle clearance by macrophages and improve aerosolization) [9].
  • Sebacic acid, a hydrophobic monomer, was copolymerized with PEG in order to produce water-insoluble polymers capable of providing continuous drug release kinetics following immersion in an aqueous environment [10].

Biological context of sebacic acid


Anatomical context of sebacic acid


Associations of sebacic acid with other chemical compounds

  • The microspheres degraded to form SA and FAD monomers [17].
  • Microspheres of a polyanhydride sebacic acid copolymer were impregnated with bethanechol, an acetylcholinesterase-resistant cholinomimetic [18].
  • This study evaluated the effect on the monkey brain of interstitial delivery of BCNU by the biodegradable polyanhydride copolymer poly[bis(p-carboxyphenoxy)propane]anhydride (PCPP) and sebacic acid (SA) in a 20:80 formulation (PCPP:SA) [19].
  • Studies of their urinary organic acids by gas chromatography-mass spectrometry (GC-MS) showed an excretion of dicarboxylic acids (adipic suberic and sebacic acids), unsaturated dicarboxylic acids (cis-octenedioic and decenedioic acids),5-hydroxyhexanoic acid, hexanoyl-glycine and suberylglycine [20].
  • With 0, 10, 30, or 50% D-glucose co-loading, the cumulative release of 125-IUdR from PCPP : SA polymers was 21, 70, 92, or 97% (p < 0.001), respectively, measured 26 days after incubation [21].

Gene context of sebacic acid

  • The imide component of the copolymers was based on trimellitylimidoglycine (TMA-gly), and the anhydride component was based on either sebacic acid (SA) or 1,6-bis(carboxyphenoxy)hexane (CPH) [22].
  • To measure radiosensitization, PCPP : SA polymer discs having 0% (empty) or 50% IUdR were placed in the tumor or contralateral flank [21].
  • Furthermore, the fungicidal activity of 10(-2) mol/l undecanedioic and sebacic acid was tested using a T. rubrum growth assay [23].
  • For example, p(RAM), p(HSAM), and their copolymers with sebacic acid decreased in Mw from about 10,000 to about 2000, and from about 30,000 to about 5000, respectively, while polymers based on RAS and HSAS remained stable [24].
  • Copolyanhydrides composed of dCPS and sebacic acid were further prepared by melt copolycondensation, and characterized by IR, NMR, UV-Vis, DSC and fluorometry [25].

Analytical, diagnostic and therapeutic context of sebacic acid

  • It was increased to 84-150% of that in the latter by prior treatment of the Mobr/Y mice at 7 days of age with a single subcutaneous injection of 50 micrograms of copper, retained as Cu+ in an alkyl polyether/sebacic acid solution [26].
  • The period of protein release was longer than that of SA and continued protein release was observed even after the microsphere matrix had completely degraded [17].
  • The effects of the site-directed alkylating inhibitor, 5-chlorolaevulinic acid, and 4,7-dioxosebacic acid, a putative intermediate analogue, were investigated by X-ray crystallography [27].
  • To measure release, PCPP : SA polymer discs having 200 microCi 125-IUdR were surgically placed in U251 xenografts (0.1-0.2 cc) growing in the flanks of nude mice [21].


  1. Episodic hypoglycemia with psi-hydroxy fatty acid excretion. Colle, E., Mamer, O.A., Montgomery, J.A., Miller, J.D. Pediatr. Res. (1983) [Pubmed]
  2. Structure of Chlorobium vibrioforme 5-aminolaevulinic acid dehydratase complexed with a diacid inhibitor. Coates, L., Beaven, G., Erskine, P.T., Beale, S.I., Wood, S.P., Shoolingin-Jordan, P.M., Cooper, J.B. Acta Crystallogr. D Biol. Crystallogr. (2005) [Pubmed]
  3. Protein stability in the presence of polymer degradation products: consequences for controlled release formulations. Determan, A.S., Wilson, J.H., Kipper, M.J., Wannemuehler, M.J., Narasimhan, B. Biomaterials (2006) [Pubmed]
  4. Design, synthesis, and preliminary characterization of tyrosine-containing polyarylates: new biomaterials for medical applications. Fiordeliso, J., Bron, S., Kohn, J. Journal of biomaterials science. Polymer edition. (1994) [Pubmed]
  5. C6-C10-dicarboxylic aciduria: biochemical considerations in relation to diagnosis of beta-oxidation defects. Gregersen, N., Kølvraa, S., Mortensen, P.B., Rasmussen, K. Scand. J. Clin. Lab. Invest. Suppl. (1982) [Pubmed]
  6. Species-specific inhibition of porphobilinogen synthase by 4-oxosebacic acid. Jaffe, E.K., Kervinen, J., Martins, J., Stauffer, F., Neier, R., Wlodawer, A., Zdanov, A. J. Biol. Chem. (2002) [Pubmed]
  7. Sebacic acid binding to human plasma albumin. Bertuzzi, A., Finotti, E., Mingrone, G., Greco, A.V. Biochem. Pharmacol. (1993) [Pubmed]
  8. Sequence determination in aliphatic poly(ester amide)s by matrix-assisted laser desorption/ionization time-of-flight and time-of-flight/time-of-flight tandem mass spectrometry. Rizzarelli, P., Puglisi, C., Montaudo, G. Rapid Commun. Mass Spectrom. (2005) [Pubmed]
  9. Poly(ether-anhydride) dry powder aerosols for sustained drug delivery in the lungs. Fiegel, J., Fu, J., Hanes, J. Journal of controlled release : official journal of the Controlled Release Society. (2004) [Pubmed]
  10. New polymeric carriers for controlled drug delivery following inhalation or injection. Fu, J., Fiegel, J., Krauland, E., Hanes, J. Biomaterials (2002) [Pubmed]
  11. Polyanhydride microspheres that display near-constant release of water-soluble model drug compounds. Tabata, Y., Langer, R. Pharm. Res. (1993) [Pubmed]
  12. Tracer study of metabolism and tissue distribution of sebacic acid in rats. Tataranni, P.A., Mingrone, G., De Gaetano, A., Raguso, C., Greco, A.V. Ann. Nutr. Metab. (1992) [Pubmed]
  13. Hydrolytic degradation of ricinoleic-sebacic-ester-anhydride copolymers. Krasko, M.Y., Domb, A.J. Biomacromolecules (2005) [Pubmed]
  14. Pharmacokinetics of sebacic acid in rats. Favuzzi, A.M., Mingrone, G., Bertuzzi, A., Salinari, S., Gandolfi, A., Greco, A.V. European review for medical and pharmacological sciences. (1999) [Pubmed]
  15. C6--C10-dicarboxylic aciduria in starved, fat-fed and diabetic rats receiving decanoic acid or medium-chain triacylglycerol. An in vivo measure of the rate of beta-oxidation of fatty acids. Mortensen, P.B. Biochim. Biophys. Acta (1981) [Pubmed]
  16. Toxicity of disodium sebacate. Greco, A.V., Mingrone, G., Arcieri Mastromattei, E., Finotti, E., Castagneto, M. Drugs under experimental and clinical research. (1990) [Pubmed]
  17. Controlled delivery systems for proteins using polyanhydride microspheres. Tabata, Y., Gutta, S., Langer, R. Pharm. Res. (1993) [Pubmed]
  18. Intracerebral drug delivery in rats with lesion-induced memory deficits. Howard, M.A., Gross, A., Grady, M.S., Langer, R.S., Mathiowitz, E., Winn, H.R., Mayberg, M.R. J. Neurosurg. (1989) [Pubmed]
  19. Biodegradable polymers for controlled delivery of chemotherapy with and without radiation therapy in the monkey brain. Brem, H., Tamargo, R.J., Olivi, A., Pinn, M., Weingart, J.D., Wharam, M., Epstein, J.I. J. Neurosurg. (1994) [Pubmed]
  20. Gas chromatography--mass spectrometry (GC--MS) diagnosis of two cases of medium chain acyl-CoA dehydrogenase deficiency. Divry, P., Vianey-Liaud, C., Cotte, J. J. Inherit. Metab. Dis. (1984) [Pubmed]
  21. Implantable biodegradable polymers for IUdR radiosensitization of experimental human malignant glioma. Williams, J.A., Dillehay, L.E., Tabassi, K., Sipos, E., Fahlman, C., Brem, H. J. Neurooncol. (1997) [Pubmed]
  22. Cytotoxicity testing of poly(anhydride-co-imides) for orthopedic applications. Attawia, M.A., Uhrich, K.E., Botchwey, E., Fan, M., Langer, R., Laurencin, C.T. J. Biomed. Mater. Res. (1995) [Pubmed]
  23. Dicarboxylic acids affect the growth of dermatophytes in vitro. Brasch, J., Friege, B. Acta Derm. Venereol. (1994) [Pubmed]
  24. Gamma-irradiation stability of saturated and unsaturated aliphatic polyanhydrides--ricinoleic acid based polymers. Teomim, D., Mäder, K., Bentolila, A., Magora, A., Domb, A.J. Biomacromolecules (2001) [Pubmed]
  25. Novel copolyanhydrides combining strong inherent fluorescence and a wide range of biodegradability: synthesis, characterization and in vitro degradation. Jiang, H., Chen, D., Zhao, P., Li, Y., Zhu, K. Macromolecular bioscience. (2005) [Pubmed]
  26. Copper metabolism in mottled mouse mutants. The effect of copper therapy on lysyl oxidase activity in brindled (Mobr) mice. Royce, P.M., Camakaris, J., Mann, J.R., Danks, D.M. Biochem. J. (1982) [Pubmed]
  27. 5-Aminolaevulinic acid dehydratase: metals, mutants and mechanism. Shoolingin-Jordan, P.M., Spencer, P., Sarwar, M., Erskine, P.E., Cheung, K.M., Cooper, J.B., Norton, E.B. Biochem. Soc. Trans. (2002) [Pubmed]
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