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Chemical Compound Review

PubChem9420     benzene-1,3-dicarboxylic acid

Synonyms: SureCN22462, AGN-PC-00GTBL, ACMC-1BQVP, CCRIS 8899, I19209_ALDRICH, ...
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Disease relevance of isophthalic acid


High impact information on isophthalic acid

  • A fluorescent Na(+)-sensitive dye (Na(+)-binding benzofuran isophthalate, SBFI) was used to determine how these egg envelope components influence sperm Na(+) permeability [2].
  • Detection of intracellular free Na+ concentration of synaptosomes by a fluorescent indicator, Na(+)-binding benzofuran isophthalate: the effect of veratridine, ouabain, and alpha-latrotoxin [3].
  • METHODS: Cytosolic free Na+ concentration was measured in intact blood platelets of 20 essential hypertensive patients and 21 age- and sex-matched normotensive control subjects using the fluorescent dye Na(+)-binding benzofuran isophthalate [4].
  • After 3 hrs, supernatants were collected to measure nitrite/nitrate (nitric oxide), cytokines (tumor necrosis factor-alpha, interleukin-1beta, interleukin-6), and cGMP levels; cells were then loaded with a fluorescent indicator (Fura-2AM or sodium-binding benzofurzan isophthalate) to measure myocyte Ca2+ or Na+, respectively [5].
  • Twenty-four hrs postburn, left ventricular function (Langendorff), cardiomyocyte [Ca2+]i and [Na+]i measured by fura-2-AM or sodium-binding benzofurzan isophthalate loading of cardiomyocytes, and myocyte secretion of tumor necrosis factor-alpha (enzyme-linked immunosorbent assay) were assessed in shams and burns from each experimental group [6].

Biological context of isophthalic acid

  • The Cbl dimers were synthesized by cross-linking Cbl carboxylates, produced by acid hydrolysis of the b-, d-, and e-propionamide side chains of cyanocobalamin (CN-Cbl), through an isophthalate molecule [7].
  • Analysis of the nucleotide sequence for the isophthalate degradation operon located genes for a dioxygenase, a transport protein, a cis-dihydrodiol dehydrogenase, and a reductase [1].
  • The effect of oxidative stress, induced by ascorbate/Fe2+, on the intracellular free Na+ concentration ([Na+]i) of cultured chick retina cells was determined using the fluorescent indicator Na(+)-binding benzofuran isophthalate (SBFI) [8].
  • In the present study, we examined the effect of different functional groups at the P1 site of the parent inhibitor isophthalic acid bis-(L-prolylpyrrolidine) amide on the binding kinetics to POP [9].
  • STM imaging on graphite of the S-enantiomer of a chiral diacetylene isophthalic acid derivative reveals that molecular chirality is not expressed in the monolayer due to a specific molecular conformation preventing the stereogenic center to transfer its chiral information [10].

Anatomical context of isophthalic acid

  • A novel fluorescent Na+ indicator, Na(+)-binding benzofuran isophthalate (SBFI), was used to follow changes in the intracellular free Na+ concentration ([Na+]i) of synaptosomes [3].
  • We investigated the effects of Na(+) pump inhibition on [Na(+)](cyt) (with Na(+) binding benzofuran isophthalate) and Ca(2+) transients (with fura 2) in primary cultured arterial myocytes [11].
  • [Na+] gradients (Na+-binding benzofuran isophthalate fluorescence) between the patch pipette and the bulk cytosol were relatively small and could not account for the large differences between peak and steady-state Ip and reverse Na+/Ca2+ exchanger currents [12].

Associations of isophthalic acid with other chemical compounds


Gene context of isophthalic acid

  • Synthesis of cobalamin dimers using isophthalate cross-linking of corrin ring carboxylates and evaluation of their binding to transcobalamin II [7].
  • Sodium pump activity was measured as ouabain-sensitive (86)Rb uptake in freshly dispersed cells containing 20 mM sodium as measured with sodium-binding benzofluran isophthalate [18].

Analytical, diagnostic and therapeutic context of isophthalic acid

  • In co-culture of two bacteria, degradation was observed proceeding through monomethyl isophthalate (MMI) ester and isophthalic acid (IPA) before the aromatic ring opening [19].
  • Intracellular K+ concentration ([K+]i) of quiescent MCs, passages 3-8, grown to subconfluence on glass cover slips, was assessed by spectrofluorometry using the K(+)-sensitive dye, K(+)-binding benzofuran isophthalate (PBFI) [20].


  1. Molecular analysis of isophthalate and terephthalate degradation by Comamonas testosteroni YZW-D. Wang, Y.Z., Zhou, Y., Zylstra, G.J. Environ. Health Perspect. (1995) [Pubmed]
  2. Intracellular sodium changes during the speract response and the acrosome reaction in sea urchin sperm. Rodríguez, E., Darszon, A. J. Physiol. (Lond.) (2003) [Pubmed]
  3. Detection of intracellular free Na+ concentration of synaptosomes by a fluorescent indicator, Na(+)-binding benzofuran isophthalate: the effect of veratridine, ouabain, and alpha-latrotoxin. Deri, Z., Adam-Vizi, V. J. Neurochem. (1993) [Pubmed]
  4. Reduced cytosolic free Na+ concentration in intact platelets of essential hypertensives. Tepel, M., Bauer, S., Husseini, S., Zidek, W. J. Hypertens. (1992) [Pubmed]
  5. Nitric oxide donors alter cardiomyocyte cytokine secretion and cardiac function. Maass, D.L., White, J., Horton, J.W. Crit. Care Med. (2005) [Pubmed]
  6. Cardiomyocyte intracellular calcium and cardiac dysfunction after burn trauma. White, D.J., Maass, D.L., Sanders, B., Horton, J.W. Crit. Care Med. (2002) [Pubmed]
  7. Synthesis of cobalamin dimers using isophthalate cross-linking of corrin ring carboxylates and evaluation of their binding to transcobalamin II. Pathare, P.M., Wilbur, D.S., Hamlin, D.K., Heusser, S., Quadros, E.V., McLoughlin, P., Morgan, A.C. Bioconjug. Chem. (1997) [Pubmed]
  8. Intracellular free Na+ concentration increases in cultured retinal cells under oxidative stress conditions. Agostinho, P., Duarte, C.B., Oliveira, C.R. Neurosci. Res. (1996) [Pubmed]
  9. Slow-binding inhibitors of prolyl oligopeptidase with different functional groups at the P1 site. Venäläinen, J.I., Juvonen, R.O., Garcia-Horsman, J.A., Wallén, E.A., Christiaans, J.A., Jarho, E.M., Gynther, J., Männistö, P.T. Biochem. J. (2004) [Pubmed]
  10. Losing the expression of molecular chirality in self-assembled physisorbed monolayers. Zhang, J., Gesquière, A., Sieffert, M., Klapper, M., Müllen, K., De Schryver, F.C., De Feyter, S. Nano Lett. (2005) [Pubmed]
  11. Ouabain augments Ca(2+) transients in arterial smooth muscle without raising cytosolic Na(+). Arnon, A., Hamlyn, J.M., Blaustein, M.P. Am. J. Physiol. Heart Circ. Physiol. (2000) [Pubmed]
  12. Influence of prior Na+ pump activity on pump and Na+/Ca2+ exchange currents in mouse ventricular myocytes. Su, Z., Zou, A., Nonaka, A., Zubair, I., Sanguinetti, M.C., Barry, W.H. Am. J. Physiol. (1998) [Pubmed]
  13. Hydrolytic stability of terephthaloyl chloride and isophthaloyl chloride. Berti, W.R., Wolstenholme, B.W., Kozlowski, J.J., Sobocinski, R.L., Freerksen, R.W. Environ. Sci. Technol. (2006) [Pubmed]
  14. Self-assembly of dialkyltin(IV) moieties and aromatic dicarboxylates to complexes with a polymeric or a discrete trinuclear macrocyclic structure in the solid state and a mixture of fast interchanging cyclooligomeric structures in solution. García-Zarracino, R., Ramos-Quiñones, J., Höpfl, H. Inorganic chemistry. (2003) [Pubmed]
  15. Isophthalato-based 2D coordination polymers of Eu(III), Gd(III), and Tb(III): enhancement of the terbium-centered luminescence through thiophene derivatization. de Bettencourt-Dias, A. Inorganic chemistry. (2005) [Pubmed]
  16. Migration from can coatings: part 2. Identification and quantification of migrating cyclic oligoesters below 1000 Da. Schaefer, A., Ohm, V.A., Simat, T.J. Food additives and contaminants. (2004) [Pubmed]
  17. Pyrene-terminated phenylenethynylene rigid linkers anchored to metal oxide nanoparticles. Taratula, O., Rochford, J., Piotrowiak, P., Galoppini, E., Carlisle, R.A., Meyer, G.J. The journal of physical chemistry. B, Condensed matter, materials, surfaces, interfaces & biophysical. (2006) [Pubmed]
  18. Effects of extracellular calcium and potassium on the sodium pump of rat adrenal glomerulosa cells. Yingst, D.R., Davis, J., Schiebinger, R. Am. J. Physiol., Cell Physiol. (2001) [Pubmed]
  19. Biochemical pathway and degradation of phthalate ester isomers by bacteria. Gu, J.D., Li, J., Wang, Y. Water Sci. Technol. (2005) [Pubmed]
  20. Regulation of intracellular potassium in mesangial cells: a fluorescence analysis using the dye, PBFI. Kasner, S.E., Ganz, M.B. Am. J. Physiol. (1992) [Pubmed]
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