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Chemical Compound Review

CHEBI:46755     2-[4-(2-hydroxyethyl)- 2,3,5,6...

Synonyms: bmse000202, bmse000792, bmse000877, bmse000890, LS-112020, ...
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Disease relevance of HEPES

  • Tris and phosphate ghosts lost the capacity to change shape after standing for 1-2 h at 0 degrees C. Hemolysis in HEPES or N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid yielded ghosts that were converted rapidly to disks in the absence of ATP and did not undergo further conversion to cup-forms [1].
  • Under these conditions, the NH4Cl-induced 22Na+ influx rate stimulated by intracellular acidosis was markedly attenuated in HEPES-buffered PSS but not in CO2/HCO3(-)-buffered PSS [2].
  • The H+ efflux rate during reperfusion, after 10 minutes of global ischemia, was 15.5 +/- 1.9 mmol.l-1 x min-1 (n = 10) in hearts perfused with HCO3(-)-buffered medium and 8.2 +/- 1.5 mmol.l-1 x min-1 (n = 9, p < 0.01) in hearts perfused with HEPES-buffered medium [3].
  • Tissue sections of livers preserved in Hanks' HEPES buffer but not in University of Wisconsin solution revealed the presence of extensive amounts of blebs in the sinusoidal lumen and loss of endothelial elements.(ABSTRACT TRUNCATED AT 250 WORDS)[4]
  • The sialidase is competitively inhibited by 2-deoxy-2, 3-dehydro-N-acetyl-neuraminic acid (Ki = 0.075 mM) and differently from many sialidases, with exception of Salmonella typhimurium sialidase, it is inhibited competitively by HEPES (Ki = 15 mM) [5].

Psychiatry related information on HEPES

  • The best sensitivity and response time were obtained using a sensor constructed with 2.5 mg of cells and operating in pH 8.5, 1 mM HEPES buffer [6].

High impact information on HEPES

  • We report here a simple method for preparing human erythrocyte membranes in 2.5 mM HEPES/1 mM EGTA at pH 7.0 (see Fig. 1 legend) in which the activation of the Ca2+-ATPase by Ca2+ and intracellular concentrations of calmodulin is highly cooperative and is complete by approximately 1 microM Ca2+ [7].
  • When nutrient solutions were buffered by HEPES (pH 7.3), ASA induced even greater depolarizations of the cell membranes [8].
  • Hepatocytes were isolated after collagenase disruption of the liver and incubated in a standard medium containing amino acids, bovine albumin, glucose, penicillin and streptomycin in HEPES buffer [9].
  • Loop formation depends on ATP hydrolysis and loop size increases linearly with time at a rate of 370 base pairs/min in phosphate buffer and about 10,000 base pairs/min in the HEPES buffer used for repair assay [10].
  • The lacking H+ efflux could be restored (1) by adding lysophosphatidylcholine (LPC), a product of PLA2 activity, to vacuoles in situ and (2) by exposing intact cells to isotonic, near-neutral HEPES buffers [11].

Chemical compound and disease context of HEPES

  • The recovery of pHi from an equivalent intracellular acidosis was more rapid when the cells were incubated in CO2/HCO3(-)-buffered PSS than in HEPES-buffered PSS [2].
  • We conclude that contractile reserve and recirculation fraction are impaired during hypertrophy, with a stronger effect under HEPES than HCO(3)(-) superfusion [12].
  • During perfusion with HCO/CO(2)- or HEPES-buffered media (pH 7.35) at 37 degrees C, 5- or 10-min anoxic insults were typified by an intracellular acidification on the induction of anoxia, a subsequent rise in pH(i) in the continued absence of O(2), and a further internal alkalinization on the return to normoxia [13].
  • Heat treatment of a wild-type Escherichia coli strain at 55 degrees C in 50 mM Tris-hydrochloride buffer with or without 10 mM magnesium sulfate or HEPES (N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid) buffer at pH 8.0 caused an increase in cell surface hydrophobicity [14].
  • Exposure of 12- to 14-day-old cultures to NMDA in Mg(2+)-free HEPES buffer (pH 7.4) for a 25-min period resulted in a concentration-dependent toxicity (EC50 = 54 microM) [15].

Biological context of HEPES

  • METHODS AND RESULTS: Rabbit cardiomyocytes were isolated by collagenase perfusion and incubated in HEPES-buffered Krebs-Henseleit solution at 37 degrees C, pH 7.4, in control conditions and in ATP depletion achieved by inhibiting glycolysis with 5 mmol/L iodoacetate [16].
  • Ferret hearts (n = 20) were Langendorff-perfused at constant flow with oxygenated HEPES-buffered Tyrode's solution at 37 degrees C. Isovolumic left ventricular pressure was measured along with the extracellular electrogram or with simultaneous phosphorus nuclear magnetic resonance spectra [17].
  • In HEPES-buffered PSS containing 20 mM Na+, the EIPA inhibition curve for the intracellular acidosis-induced 22Na+ influx was monophasic (IC50, 39 nM), whereas in an identical CO2/HCO3(-)-buffered PSS, the inhibition curve exhibited biphasic characteristics (IC50, 37.3 nM and 312 microM) [2].
  • In this study, we have conducted a systematic investigation of various aspects of cell viability and function of isolated hepatocytes stored at 4 degrees C for 24 and 48 hr in either University of Wisconsin solution or Hanks' HEPES buffer, a control solution clinically unsuitable for organ preservation [4].
  • Increasing the protonated HEPES concentration did not close the pore, indicating that a saturation of the binding sites occurs at 10 mm HEPES [18].

Anatomical context of HEPES

  • Experiments were performed at 37 degrees C in myocytes paced at 0.5 Hz in HEPES-buffered solution (extracellular pH = 7.40) [19].
  • Thrombi containing either 16 microg r-apo(a), 8 microg r-apo(a), or vehicle (HEPES-buffered saline, control) were formed in the jugular veins of a rabbit and showed significantly reduced endogenous thrombolysis after 60 minutes in a dose-dependent fashion, ID 2.7+/-0.9% and 4.6+/-1.8%, respectively, versus 7.4+/-1.6% of that of the control [20].
  • Our results clearly demonstrate that in both normal and SHR cardiac myocytes, bicarbonate-dependent pHi regulators can be significantly activated under resting or acidified pHi in HEPES-buffered medium, probably because of the cellular production of CO2 [21].
  • Spontaneously oscillating cells were common in culture medium, serum, or rat cerebrospinal fluid, but rare in HEPES buffer [22].
  • Tumor tissue (mainly tumor cells with a small number of stromal cells), tumor base tissue (more stromal cells than tumor cells), and control ovaries were preincubated in oxygenated 4-(2-hydroxyethyl)-1-piperazineethanesulfonic acid-minimum essential medium buffer at 37 degrees C for 30 min followed by a 3-h incubation in fresh, oxygenated medium [23].

Associations of HEPES with other chemical compounds


Gene context of HEPES


Analytical, diagnostic and therapeutic context of HEPES

  • When examined by light and electron microscopy, cells stored in both University of Wisconsin solution and Hanks' HEPES buffer for 24 hr appeared essentially normal except for the presence of numerous membrane blebs in the Hanks' HEPES buffer group [4].
  • High-resolution atomic force microscopy of force-dissected connexin26 gap junctions revealed that in HEPES buffer, the pore was closed at pH < 6.5 and opened reversibly by increasing the pH to 7 [18].
  • An apparent encapsulation constant for 2,4-DNP, log K(enc) (K(enc)=[6-2,4-DNP]/[6][2,4-DNP] (M(-1))), was 6.0+/-0.1 at pH 7.0 (50 mM HEPES with I=0.1 (NaNO(3))), as determined by UV titrations [33].
  • METHODS: In nominally HCO3(-)-free, HEPES-buffered Tyrode solution (35 degrees C), pHi and the intrinsic buffering power (beta i, measured in the presence of amiloride) was investigated using pH-sensitive microelectrodes [34].
  • RESULTS: We found a constant relationship between the amount of T(4) adsorbed to the dialysis or ultrafiltration membranes/materials and the initial T(4) concentration in HEPES buffer (protein-free medium) [35].


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  2. Intracellular pH in human arterial smooth muscle. Regulation by Na+/H+ exchange and a novel 5-(N-ethyl-N-isopropyl)amiloride-sensitive Na(+)- and HCO3(-)-dependent mechanism. Neylon, C.B., Little, P.J., Cragoe, E.J., Bobik, A. Circ. Res. (1990) [Pubmed]
  3. Mechanisms of pHi recovery after global ischemia in the perfused heart. Vandenberg, J.I., Metcalfe, J.C., Grace, A.A. Circ. Res. (1993) [Pubmed]
  4. Functional and morphological features of isolated hepatocytes preserved in University of Wisconsin solution. Sorrentino, D., Van Ness, K., Ribeiro, I., Miller, C.M. Hepatology (1991) [Pubmed]
  5. Identification and characterization of a sialidase released by the salivary gland of the hematophagous insect Triatoma infestans. Amino, R., Porto, R.M., Chammas, R., Egami, M.I., Schenkman, S. J. Biol. Chem. (1998) [Pubmed]
  6. Biosensor for direct determination of organophosphate nerve agents using recombinant Escherichia coli with surface-expressed organophosphorus hydrolase. 1. Potentiometric microbial electrode. Mulchandani, A., Mulchandani, P., Kaneva, I., Chen, W. Anal. Chem. (1998) [Pubmed]
  7. Human erythrocyte membranes exhibit a cooperative calmodulin-dependent Ca2+-ATPase of high calcium sensitivity. Downes, P., Michell, R.H. Nature (1981) [Pubmed]
  8. Effects of aspirin on pathways of ion permeation in Necturus antrum: role of nutrient HCO3. Soybel, D.I., Davis, M.B., West, A.B. Gastroenterology (1992) [Pubmed]
  9. Protein secretion in suspensions of isolated rat hepatocytes: no influence of acute ethanol administration. Mørland, J., Rothschild, M.A., Oratz, M., Mongelli, J., Donor, D., Schreiber, S.S. Gastroenterology (1981) [Pubmed]
  10. MutS mediates heteroduplex loop formation by a translocation mechanism. Allen, D.J., Makhov, A., Grilley, M., Taylor, J., Thresher, R., Modrich, P., Griffith, J.D. EMBO J. (1997) [Pubmed]
  11. The Galpha protein controls a pH-dependent signal path to the induction of phytoalexin biosynthesis in Eschscholzia californica. Viehweger, K., Schwartze, W., Schumann, B., Lein, W., Roos, W. Plant Cell (2006) [Pubmed]
  12. Contractile reserve but not tension is reduced in monocrotaline-induced right ventricular hypertrophy. Versluis, J.P., Heslinga, J.W., Sipkema, P., Westerhof, N. Am. J. Physiol. Heart Circ. Physiol. (2004) [Pubmed]
  13. Intracellular pH response to anoxia in acutely dissociated adult rat hippocampal CA1 neurons. Sheldon, C., Church, J. J. Neurophysiol. (2002) [Pubmed]
  14. Destruction of the outer membrane permeability barrier of Escherichia coli by heat treatment. Tsuchido, T., Katsui, N., Takeuchi, A., Takano, M., Shibasaki, I. Appl. Environ. Microbiol. (1985) [Pubmed]
  15. Ethanol inhibits NMDA receptor-mediated excitotoxicity in rat primary neuronal cultures. Chandler, L.J., Sumners, C., Crews, F.T. Alcohol. Clin. Exp. Res. (1993) [Pubmed]
  16. Existence and role of substrate cycling between AMP and adenosine in isolated rabbit cardiomyocytes under control conditions and in ATP depletion. Wagner, D.R., Bontemps, F., van den Berghe, G. Circulation (1994) [Pubmed]
  17. Calcium oscillations in digitalis-induced ventricular fibrillation: pathogenetic role and metabolic consequences in isolated ferret hearts. Kusuoka, H., Jacobus, W.E., Marban, E. Circ. Res. (1988) [Pubmed]
  18. Aminosulfonate Modulated pH-induced Conformational Changes in Connexin26 Hemichannels. Yu, J., Bippes, C.A., Hand, G.M., Muller, D.J., Sosinsky, G.E. J. Biol. Chem. (2007) [Pubmed]
  19. Effects of the nitric oxide donor sodium nitroprusside on intracellular pH and contraction in hypertrophied myocytes. Ito, N., Bartunek, J., Spitzer, K.W., Lorell, B.H. Circulation (1997) [Pubmed]
  20. Apolipoprotein(a) attenuates endogenous fibrinolysis in the rabbit jugular vein thrombosis model in vivo. Biemond, B.J., Friederich, P.W., Koschinsky, M.L., Levi, M., Sangrar, W., Xia, J., Büller, H.R., ten Cate, J.W. Circulation (1997) [Pubmed]
  21. DIDS-sensitive pHi regulation in single rat cardiac myocytes in nominally HCO3-free conditions. Wu, M.L., Tsai, M.L., Tseng, Y.Z. Circ. Res. (1994) [Pubmed]
  22. Calcium excitability and oscillations in suprachiasmatic nucleus neurons and glia in vitro. van den Pol, A.N., Finkbeiner, S.M., Cornell-Bell, A.H. J. Neurosci. (1992) [Pubmed]
  23. Steroid production in different parts of malignant and benign ovarian tumors in vitro. Ridderheim, M., Mählck, C.G., Selstam, G., Stendahl, U., Bäckström, T. Cancer Res. (1993) [Pubmed]
  24. Peripheral and integral subunits of the tonoplast H+-ATPase from oat roots. Lai, S.P., Randall, S.K., Sze, H. J. Biol. Chem. (1988) [Pubmed]
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  26. Hydrogen peroxide formation by reaction of peroxynitrite with HEPES and related tertiary amines. Implications for a general mechanism. Kirsch, M., Lomonosova, E.E., Korth, H.G., Sustmann, R., de Groot, H. J. Biol. Chem. (1998) [Pubmed]
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  30. Transforming growth factor beta 1 increases the number of apoptotic bodies and decreases intracellular pH in isolated periportal and perivenular rat hepatocytes. Benedetti, A., Di Sario, A., Svegliati Baroni, G., Jezequel, A.M. Hepatology (1995) [Pubmed]
  31. Acute pH-dependent regulation of AE2-mediated anion exchange involves discrete local surfaces of the NH2-terminal cytoplasmic domain. Stewart, A.K., Kerr, N., Chernova, M.N., Alper, S.L., Vaughan-Jones, R.D. J. Biol. Chem. (2004) [Pubmed]
  32. A new role for the transferrin receptor in the release of iron from transferrin. Bali, P.K., Zak, O., Aisen, P. Biochemistry (1991) [Pubmed]
  33. A cuboctahedral supramolecular capsule by 4:4 self-assembly of Tris(Zn(II)-cyclen) and trianionic trithiocyanurate in aqueous solution at neutral pH (cyclen=1,4,7,10-tetraazacyclododecane). Aoki, S., Shiro, M., Kimura, E. Chemistry (Weinheim an der Bergstrasse, Germany) (2002) [Pubmed]
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  35. Influence of adsorption and deproteination on potential free thyroxine reference methods. Holm, S.S., Andreasen, L., Hansen, S.H., Faber, J., Staun-Olsen, P. Clin. Chem. (2002) [Pubmed]
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