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Chemical Compound Review

valinomycin     6,18,30-trimethyl- 3,9,12,15,21,24,27,33,36...

Synonyms: Valinomicin, GNF-Pf-5297, CHEMBL602575, BSPBio_001226, KBioGR_000566, ...
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Disease relevance of valinomycin

  • The effect was not due to toxicity to the cells, nor appeared to be due to the effects of valinomycin as an uncoupler of oxidative phosphorylation [1].
  • Recent studies have identified older, low-density sickle red blood cells (SSRBCs) that were resistant to dehydration by valinomycin, a K(+) ionophore [2].
  • The effect of valinomycin on nontransformed 3T3 mouse and Rat-1 cells is nontoxic, whereas it acts with increasing toxicity on the transformed cells in the order 3T6 mouse, polyoma-3T3 mouse, temperature-sensitively Rous sarcoma virus-transformed Rat-1 at permissive temperature, and SV40-3T3 cells [3].
  • Experiments with E. coli phospholipid liposomes revealed that HLz dissipated the valinomycin-induced transmembrane electrochemical potential, but WLz did not [4].
  • We confirmed that in starved, valinomycin-treated cells of Streptococcus lactis 7962, Tl+ ions distributed themselves across the bacterial membrane in response to the potassium diffusion potential [5].

High impact information on valinomycin

  • Enhancement of the electrical excitability of neuroblastoma cells by valinomycin [6].
  • For comparison, intact liver cells were treated with valinomycin, a potassium ionophore, which gave rise to an atypical cell death, with chromatin condensation appearing without DNA fragmentation [7].
  • When the membrane potential is approximated by the Nernst potential for K+, as in the presence of the K+ ionophore valinomycin, equilibrium thermodynamics predicts that the Na+-HCO3- cotransport system should come to equilibrium and mediate no net flux when (Na)i/(Na)o = [(HCO3)o/(HCO3)i]n[(K)o/(K)i]n-1, where n is the HCO3-:Na+ stoichiometry [8].
  • No change in Na uptake pattern was observed with valinomycin, and initial Na uptake was not significantly different in normal versus uremic synaptosomes [9].
  • This bicarbonate- and pH gradient-stimulated butyrate uptake was not inhibited by either voltage clamping, with equimolar intravesicular and extravesicular K+ and valinomycin, or 4,4'-diisothiocyanatostilbene-2,2'-disulfonic acid (DIDS), an anion-exchange inhibitor [10].

Chemical compound and disease context of valinomycin


Biological context of valinomycin

  • PMN from patients with CGD had normal calculated resting membrane potentials and normal responses elicited by the potassium ionophore valinomycin [16].
  • Valinomycin (1 nM) did not stimulate the AR when added together with K+ (3-24 mM) to sperm incubated in 0.9 mM K+ for 3.5 h but markedly decreased sperm motility [17].
  • This pattern was not affected by valinomycin in potassium-based media, nor could variable stoichiometry be attributed to altered hydrolysis of the sugar phosphate substrate [18].
  • The phosphorylation was inhibited by DCCD any by tetraphenylboron and valinomycin [19].
  • The mechanistic stoichiometry of vectorial H+ ejection coupled to electron transport from added ferrocytochrome c to oxygen by the cytochrome oxidase (EC of rat liver mitoplasts was determined from measurements of the initial rates of electron flow and H+ ejection in the presence of K+ (with valinomycin) [20].

Anatomical context of valinomycin


Associations of valinomycin with other chemical compounds

  • The inhibition of secretion by valinomycin/K+ was ameliorated by imposition of a pH gradient, the second component of the delta P, and selective depletion of delta pH by nigericin also blocked secretion [26].
  • A combination of ionophores expected to dissipate the vesicular membrane potential (valinomycin plus monensin) also fully inhibited the translocation [27].
  • Light-induced changes in surface potential followed the changes observed in the M412 intermediate of the photocycle of bacteriorhodopsin as a function of pH, temperature, and response to antibiotics beauvericin and valinomycin [28].
  • Assays of the quenching of acridine orange fluorescence showed that addition of both ATP and valinomycin to K+-loaded proteoliposomes led to the formation of a pH gradient that was acidic inside [29].
  • Nevertheless, some, if not all, of the Mdr1 made in yeast was properly folded and functional because it could be photoaffinity labeled specifically with 8-azido-ATP and because cells overexpressing Mdr1 displayed increased resistance towards valinomycin, an ionophore known to interact with Mdr1 in animal cells [30].
  • 18F-FDG incorporation was significantly increased by 30 min of treatment with valinomycin and was still apparent after 3.5 h of incubation [31].

Gene context of valinomycin

  • However, IFN-gamma production induced by a combination of IL-15 and IL-18 was somewhat less sensitive to valinomycin, suggesting a protective effect of the cytokine combination against valinomycin [32].
  • Indeed, valinomycin inhibits P-gp with an IC(50) similar to cyclosporin A yet apparently does not affect CYP3A4 function, and emetine and nobiletin are also specific for interaction with P-gp [33].
  • In the case of cyclosporin A, vinblastine or valinomycin, this up-shift was found to be concomitant with the near-complete suppression of labeling with other mAbs specific for Pgp epitopes overlapping with UIC2, while pre-treatment with verapamil or Tween 80 brings about a modest suppression [34].
  • The stimulation of mitochondrial PPase activity by FCCP, but not by valinomycin and nigericin, was greatly enhanced by the presence of DTT [35].
  • Yeast cells expressing P-gp were valinomycin resistant [36].

Analytical, diagnostic and therapeutic context of valinomycin

  • Changes in nuclear K+ electrochemical activity and total nuclear K+ content in salivary glands of Chironomus tentans were measured with ion-selective microelectrodes based on valinomycin and with flameless atomic absorption spectrometry, respectively [37].
  • The nonshrinking, valinomycin-resistant (val-res) fractions, first detected by flow cytometry of density-fractionated SS RBCs, constituted up to 60% of the lightest, reticulocyte-rich (R1) cell fraction, and progressively smaller portions of the slightly denser R2 cells and discocytes [38].
  • The EC(50), based on ELISA, and SI for Reserpine, Aescim, and Valinomycin are 3.4 microM (SI = 7.3), 6.0 microM (SI = 2.5), and 0.85 microM (SI = 80), respectively [39].
  • In the presence of valinomycin and K+, the absorption spectrum of FCCP is significantly perturbed, and there is also a large induced circular dichroism signal [40].
  • Subsequent addition of valinomycin or the calcium ionophore A23187 leads to further fusion as shown by electron microscopy, light microscopy, and additional absorbance increase [41].


  1. A potassium ionophore (valinomycin) inhibits lymphocyte proliferation by its effects on the cell membrane. Daniele, R.P., Holian, S.K. Proc. Natl. Acad. Sci. U.S.A. (1976) [Pubmed]
  2. Rehydration of high-density sickle erythrocytes in vitro. Holtzclaw, J.D., Jiang, M., Yasin, Z., Joiner, C.H., Franco, R.S. Blood (2002) [Pubmed]
  3. Selective effects by valinomycin on cytotoxicity and cell cycle arrest of transformed versus nontransformed rodent fibroblasts in vitro. Kleuser, B., Rieter, H., Adam, G. Cancer Res. (1985) [Pubmed]
  4. Enhanced bactericidal action of lysozyme to Escherichia coli by inserting a hydrophobic pentapeptide into its C terminus. Ibrahim, H.R., Yamada, M., Matsushita, K., Kobayashi, K., Kato, A. J. Biol. Chem. (1994) [Pubmed]
  5. Active transport of thallous ions by Streptococcus lactis. Kashket, E.R. J. Biol. Chem. (1979) [Pubmed]
  6. Enhancement of the electrical excitability of neuroblastoma cells by valinomycin. Spector, I., Palfrey, C., Littauer, U.Z. Nature (1975) [Pubmed]
  7. Separate metabolic pathways leading to DNA fragmentation and apoptotic chromatin condensation. Sun, D.Y., Jiang, S., Zheng, L.M., Ojcius, D.M., Young, J.D. J. Exp. Med. (1994) [Pubmed]
  8. Stoichiometry of Na+-HCO-3 cotransport in basolateral membrane vesicles isolated from rabbit renal cortex. Soleimani, M., Grassi, S.M., Aronson, P.S. J. Clin. Invest. (1987) [Pubmed]
  9. Abnormal sodium transport in synaptosomes from brain of uremic rats. Fraser, C.L., Sarnacki, P., Arieff, A.I. J. Clin. Invest. (1985) [Pubmed]
  10. Mechanism of short-chain fatty acid uptake by apical membrane vesicles of rat distal colon. Mascolo, N., Rajendran, V.M., Binder, H.J. Gastroenterology (1991) [Pubmed]
  11. Reduced toxicity and enhanced antitumor effects in mice of the ionophoric drug valinomycin when incorporated in liposomes. Daoud, S.S., Juliano, R.L. Cancer Res. (1986) [Pubmed]
  12. The use of valinomycin, nigericin and trichlorocarbanilide in control of the protonmotive force in Escherichia coli cells. Ahmed, S., Booth, I.R. Biochem. J. (1983) [Pubmed]
  13. Effects of ionophores and dicyclohexylcarbodiimide on Mycoplasma gallisepticum adherence to erythrocytes. Banai, M., Razin, S., Schuldiner, S., Zilberstein, D., Kahane, I., Bredt, W. Infect. Immun. (1982) [Pubmed]
  14. Entry of poliovirus into cells is blocked by valinomycin and concanamycin A. Irurzun, A., Carrasco, L. Biochemistry (2001) [Pubmed]
  15. The use of HgCl2 to evaluate the cosubstrate: amino acid transport stoichiometry in Ehrlich ascites tumor cells. Dawson, W.D., Robinson, S.C., Smith, T.C. J. Cell. Physiol. (1983) [Pubmed]
  16. Use of lipophilic probes of membrane potential to assess human neutrophil activation. Abnormality in chronic granulomatous disease. Seligmann, B.E., Gallin, J.I. J. Clin. Invest. (1980) [Pubmed]
  17. Potassium ion influx and Na+,K+-ATPase activity are required for the hamster sperm acrosome reaction. Mrsny, R.J., Meizel, S. J. Cell Biol. (1981) [Pubmed]
  18. Variable stoichiometry of phosphate-linked anion exchange in Streptococcus lactis: implications for the mechanism of sugar phosphate transport by bacteria. Ambudkar, S.V., Sonna, L.A., Maloney, P.C. Proc. Natl. Acad. Sci. U.S.A. (1986) [Pubmed]
  19. Restoration of oxidative phosphorylation by purified N,N'-dicyclohexylcarbodiimide-sensitive latent adenosinetriphosphatase from Mycobacterium phlei. Lee, S.H., Cohen, N.S., Brodie, A.F. Proc. Natl. Acad. Sci. U.S.A. (1976) [Pubmed]
  20. Proton translocation stoichiometry of cytochrome oxidase: use of a fast-responding oxygen electrode. Reynafarje, B., Alexandre, A., Davies, P., Lehninger, A.L. Proc. Natl. Acad. Sci. U.S.A. (1982) [Pubmed]
  21. Membrane potentials and resistances of giant mitochondria. Metabolic dependence and the effects of valinomycin. Maloff, B.L., Scordilis, S.P., Reynolds, C., Tedeschi, H. J. Cell Biol. (1978) [Pubmed]
  22. Potassium-inhibited processing of IL-1 beta in human monocytes. Walev, I., Reske, K., Palmer, M., Valeva, A., Bhakdi, S. EMBO J. (1995) [Pubmed]
  23. In vitro import of cytochrome c peroxidase into the intermembrane space: release of the processed form by intact mitochondria. Kaput, J., Brandriss, M.C., Prussak-Wieckowska, T. J. Cell Biol. (1989) [Pubmed]
  24. Estimation of membrane potentials of individual lymphocytes by flow cytometry. Shapiro, H.M., Natale, P.J., Kamentsky, L.A. Proc. Natl. Acad. Sci. U.S.A. (1979) [Pubmed]
  25. Ionic requirements for induction of maturation (meiosis) in full-grown and medium-sized Xenopus laevis oocytes. Baltus, E., Hanocq-Quertier, J., Pays, A., Brachet, J. Proc. Natl. Acad. Sci. U.S.A. (1977) [Pubmed]
  26. Energetically distinct early and late stages of HlyB/HlyD-dependent secretion across both Escherichia coli membranes. Koronakis, V., Hughes, C., Koronakis, E. EMBO J. (1991) [Pubmed]
  27. Vesicle transmembrane potential is required for translocation to the cytosol of externally added FGF-1. Małecki, J., Wiedłocha, A., Wesche, J., Olsnes, S. EMBO J. (2002) [Pubmed]
  28. Surface charge changes in purple membranes and the photoreaction cycle of bacteriorhodopsin. Carmeli, C., Quintanilha, A.T., Packer, L. Proc. Natl. Acad. Sci. U.S.A. (1980) [Pubmed]
  29. Reconstitution of the lysosomal proton pump. D'Souza, M.P., Ambudkar, S.V., August, J.T., Maloney, P.C. Proc. Natl. Acad. Sci. U.S.A. (1987) [Pubmed]
  30. Functional expression of human mdr1 in the yeast Saccharomyces cerevisiae. Kuchler, K., Thorner, J. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  31. Treatment of breast tumor cells in vitro with the mitochondrial membrane potential dissipater valinomycin increases 18F-FDG incorporation. Smith, T.A., Blaylock, M.G. J. Nucl. Med. (2007) [Pubmed]
  32. Inhibition of human NK cell function by valinomycin, a toxin from Streptomyces griseus in indoor air. Paananen, A., Mikkola, R., Sareneva, T., Matikainen, S., Andersson, M., Julkunen, I., Salkinoja-Salonen, M.S., Timonen, T. Infect. Immun. (2000) [Pubmed]
  33. Quantitative distinctions of active site molecular recognition by P-glycoprotein and cytochrome P450 3A4. Wang, E., Lew, K., Barecki, M., Casciano, C.N., Clement, R.P., Johnson, W.W. Chem. Res. Toxicol. (2001) [Pubmed]
  34. Distinct groups of multidrug resistance modulating agents are distinguished by competition of P-glycoprotein-specific antibodies. Nagy, H., Goda, K., Fenyvesi, F., Bacsó, Z., Szilasi, M., Kappelmayer, J., Lustyik, G., Cianfriglia, M., Szabó, G. Biochem. Biophys. Res. Commun. (2004) [Pubmed]
  35. Characterization of a mitochondrial inorganic pyrophosphatase in Saccharomyces cerevisiae. Lundin, M., Deopujari, S.W., Lichko, L., da Silva, L.P., Baltscheffsky, H. Biochim. Biophys. Acta (1992) [Pubmed]
  36. Use of chemical chaperones in the yeast Saccharomyces cerevisiae to enhance heterologous membrane protein expression: high-yield expression and purification of human P-glycoprotein. Figler, R.A., Omote, H., Nakamoto, R.K., Al-Shawi, M.K. Arch. Biochem. Biophys. (2000) [Pubmed]
  37. Change in nuclear potassium electrochemical activity and puffing of potassium-sensitive salivary chromosome regions during Chironomus development. Wuhrmann, P., Ineichen, H., Riesen-Willi, U., Lezzi, M. Proc. Natl. Acad. Sci. U.S.A. (1979) [Pubmed]
  38. Identification and characterization of a newly recognized population of high-Na+, low-K+, low-density sickle and normal red cells. Bookchin, R.M., Etzion, Z., Sorette, M., Mohandas, N., Skepper, J.N., Lew, V.L. Proc. Natl. Acad. Sci. U.S.A. (2000) [Pubmed]
  39. Small molecules targeting severe acute respiratory syndrome human coronavirus. Wu, C.Y., Jan, J.T., Ma, S.H., Kuo, C.J., Juan, H.F., Cheng, Y.S., Hsu, H.H., Huang, H.C., Wu, D., Brik, A., Liang, F.S., Liu, R.S., Fang, J.M., Chen, S.T., Liang, P.H., Wong, C.H. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
  40. Complex formation between the uncoupler carbonyl cyanide p-trifluoromethoxyphenylhydrazone (FCCP) and valinomycin in the presence of potassium. O'Brien, T.A., Nieva-Gomez, D., Gennis, R.B. J. Biol. Chem. (1978) [Pubmed]
  41. The role of calcium in fusion of artificial vesicles. Ingolia, T.D., Koshland, D.E. J. Biol. Chem. (1978) [Pubmed]
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