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Chemical Compound Review

alpha-CHCA     2-cyano-3-(4- hydroxyphenyl)prop-2-enoic acid

Synonyms: SureCN26826, ACMC-1CB5R, AG-C-36028, AG-J-10996, KBioGR_000707, ...
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Disease relevance of NSC 173138


High impact information on NSC 173138

  • MCT1-independent intracellular pH control mechanisms did not contribute to the forskolin or H89 effects on MCT1 kinetic function as determined with amiloride, monocarboxylate-independent acid loading, or the transport inhibitor alpha-cyano-4-hydroxycinnamate [4].
  • Recovery was not affected by 1 mM SITS or by 40 mM alpha-cyano-4-hydroxycinnamate (CHC), which inhibits anion exchange in neutrophils [5].
  • 2. Labelling of these 35-50 kDa polypeptides was decreased markedly in the presence of the specific inhibitors of lactate transport alpha-cyano-4-hydroxycinnamate and 4,4'-dibenzamidostilbene-2,2'-disulphonate (DBDS), which compete with DIDS for binding to the transporter [6].
  • 8. 8. The initial rate of change of pHi in the presence of L-lactate was significantly inhibited 39.1 +/- 6.2% by 2-5 mmol l-1 alpha-cyano-4-hydroxycinnamate (n = 9; P less than 0.05, paired t test) [7].
  • This carrier catalyses the exchange of small carboxylate anions with intracellular lactate, is competitively inhibited by alpha-cyano-4-hydroxycinnamate and non-competitively inhibited by picrate [8].

Biological context of NSC 173138


Anatomical context of NSC 173138


Associations of NSC 173138 with other chemical compounds


Gene context of NSC 173138


  1. Brain lactate is an obligatory aerobic energy substrate for functional recovery after hypoxia: further in vitro validation. Schurr, A., Payne, R.S., Miller, J.J., Rigor, B.M. J. Neurochem. (1997) [Pubmed]
  2. Niacin protects the isolated heart from ischemia-reperfusion injury. Trueblood, N.A., Ramasamy, R., Wang, L.F., Schaefer, S. Am. J. Physiol. Heart Circ. Physiol. (2000) [Pubmed]
  3. The monocarboxylate transport inhibitor, alpha-cyano-4-hydroxycinnamate, has no effect on retinal ischemia. Melena, J., Safa, R., Graham, M., Casson, R.J., Osborne, N.N. Brain Res. (2003) [Pubmed]
  4. Modulation of monocarboxylic acid transporter-1 kinetic function by the cAMP signaling pathway in rat brain endothelial cells. Smith, J.P., Drewes, L.R. J. Biol. Chem. (2006) [Pubmed]
  5. Regulation of intracellular pH in human neutrophils. Simchowitz, L., Roos, A. J. Gen. Physiol. (1985) [Pubmed]
  6. Identification and partial purification of the erythrocyte L-lactate transporter. Poole, R.C., Halestrap, A.P. Biochem. J. (1992) [Pubmed]
  7. A microelectrode study of the mechanisms of L-lactate entry into and release from frog sartorius muscle. Mason, M.J., Thomas, R.C. J. Physiol. (Lond.) (1988) [Pubmed]
  8. Transport of pyruvate nad lactate into human erythrocytes. Evidence for the involvement of the chloride carrier and a chloride-independent carrier. Halestrap, A.P. Biochem. J. (1976) [Pubmed]
  9. Inhibition of pyruvate oxidation in rat islets by alpha-cyano-4-hydroxycinnamate. Differential effects on insulin secretion and inositol lipid metabolism. Best, L., Tomlinson, S. Biochem. Pharmacol. (1988) [Pubmed]
  10. Characteristics of L-lactic acid transport in basal membrane vesicles of human placental syncytiotrophoblast. Inuyama, M., Ushigome, F., Emoto, A., Koyabu, N., Satoh, S., Tsukimori, K., Nakano, H., Ohtani, H., Sawada, Y. Am. J. Physiol., Cell Physiol. (2002) [Pubmed]
  11. Stimulatory effect of ethanol on weak organic acid uptake in rat renal tubules. Nikiforov, A.A., Ostretsova, I.B. Biochem. Pharmacol. (1994) [Pubmed]
  12. Comparison of glucose and lactate as substrates during NMDA-induced activation of hippocampal slices. Chih, C.P., He, J., Sly, T.S., Roberts, E.L. Brain Res. (2001) [Pubmed]
  13. Oxidative phosphorylation in myocardial mitochondria 'in situ': a calorimetric study on permeabilized cardiac muscle preparations. Köhnke, D., Schramm, M., Daut, J. Mol. Cell. Biochem. (1997) [Pubmed]
  14. The mitochondrial pyruvate carrier. Kinetics and specificity for substrates and inhibitors. Halestrap, A.P. Biochem. J. (1975) [Pubmed]
  15. The specificity and metabolic implications of the inhibition of pyruvate transport in isolated mitochondria and intact tissue preparations by alpha-Cyano-4-hydroxycinnamate and related compounds. Halestrap, A.P., Denton, R.M. Biochem. J. (1975) [Pubmed]
  16. Alpha-cyano-4-hydroxycinnamate decreases both glucose and lactate metabolism in neurons and astrocytes: implications for lactate as an energy substrate for neurons. McKenna, M.C., Hopkins, I.B., Carey, A. J. Neurosci. Res. (2001) [Pubmed]
  17. Lactate transport in rat adipocytes: identification of monocarboxylate transporter 1 (MCT1) and its modulation during streptozotocin-induced diabetes. Hajduch, E., Heyes, R.R., Watt, P.W., Hundal, H.S. FEBS Lett. (2000) [Pubmed]
  18. Retinal glucose metabolism in mice lacking the L-glutamate/aspartate transporter. Sarthy, V.P., Dudley, V.J., Tanaka, K. Vis. Neurosci. (2004) [Pubmed]
  19. Short-chain fatty acid (SCFA) uptake into Caco-2 cells by a pH-dependent and carrier mediated transport mechanism. Stein, J., Zores, M., Schröder, O. European journal of nutrition. (2000) [Pubmed]
  20. Effect of alpha-cyano-4-hydroxycinnamate on the protomer-polymer transition of acetyl-CoA carboxylase. Beynen, A.C., Geelen, M.J., Buechler, K.F. Indian J. Biochem. Biophys. (1982) [Pubmed]
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