emetine

Summary

Summary: The principal alkaloid of ipecac, from the ground roots of Uragoga (or Cephaelis) ipecacuanha or U. acuminata, of the Rubiaceae. It is used as an amebicide in many different preparations and may cause serious cardiac, hepatic, or renal damage and violent diarrhea and vomiting. Emetine inhibits protein synthesis in EUKARYOTIC CELLS but not PROKARYOTIC CELLS.

Top Publications

  1. Itoh T, Miyazaki M, Fukuoka H, Nagata K, Ohsawa A. Formal total synthesis of (-)-emetine using catalytic asymmetric allylation of cyclic imines as a key step. Org Lett. 2006;8:1295-7 pubmed
    ..The allyl adduct thus obtained was transformed to a chiral synthetic intermediate for (-)-emetine in good yield. The procedure was applied to the total synthesis of ent-emetine.
  2. Möller M, Wink M. Characteristics of apoptosis induction by the alkaloid emetine in human tumour cell lines. Planta Med. 2007;73:1389-96 pubmed
    Cytotoxic and apoptosis-inducing effects of the alkaloid emetine from Psychotria ipecacuanha (Rubiaceae) were studied in human cell lines...
  3. Nieto A, Guillermo Pérez D, Orozco E, Paz F, Gomez C. Entamoeba histolytica EhPgp5 transcriptional activation depends on putative emetine response elements. Exp Parasitol. 2005;110:233-7 pubmed
    ..drug resistant clone C2 trophozoites and its activity increases when trophozoites are cultured in the presence of emetine, suggesting that the EhPgp5 gene shows an inducible drug dependent mechanism...
  4. Mehrotra P, Kitchlu S, Dwivedi A, Agnihotri P, Srivastava S, Roy R, et al. Emetine ditartrate: a possible lead for emergency contraception. Contraception. 2004;69:379-87 pubmed
    ..We are reporting for the first time the detailed profile of emetine ditartrate, a compound whose pregnancy interceptive efficacy has been studied in mouse, rat, hamster, guinea pig ..
  5. Burchard G, Mirelman D. Entamoeba histolytica: virulence potential and sensitivity to metronidazole and emetine of four isolates possessing nonpathogenic zymodemes. Exp Parasitol. 1988;66:231-42 pubmed
    ..All the E. histolytica isolates tested were similarly sensitive to metronidazole and emetine (IC50 1-10 micrograms/ml). The results indicate that the pathogenic potential of E...
  6. Zhou Y, Kim Y, Mohammed K, Jones D, Muhammad I, Dunbar D, et al. Terpenoid tetrahydroisoquinoline alkaloids emetine, klugine, and isocephaeline inhibit the activation of hypoxia-inducible factor-1 in breast tumor cells. J Nat Prod. 2005;68:947-50 pubmed
    Klugine (1), isocephaeline (2), and emetine (4) inhibited hypoxia-inducible factor-1 (HIF-1) activation by hypoxia in T47D breast tumor cells (IC(50) values 0.2, 1.1, and 0.11 muM, respectively)...
  7. Abbas A, Huang F, Li R, Ekström J, Wigström H. Emetine treatment masks initial LTP without affecting long-term stability. Brain Res. 2011;1426:18-29 pubmed publisher
    Applying emetine, a protein synthesis inhibitor, at 20-40?M for 90-120 min prior to LTP induction in hippocampal slices from young rats (2-3 weeks) and washing it out afterwards revealed a slowly developing potentiation that reached ..
  8. Carbajal Rivera M, Ordaz Téllez M, Castañeda Sortibrán A, Rodriguez Arnaiz R. Emetine and/or its metabolites are genotoxic in somatic cells of Drosophila melanogaster. J Toxicol Environ Health A. 2007;70:1713-6 pubmed
    b>Emetine is one of the two active ingredients of syrup of ipecac which is used medicinally as antiparasitic and emetic, however little is known about its genotoxic activity...
  9. Kong H, Lee S, Beebe K, Scroggins B, Gupta G, Lee M, et al. Emetine promotes von Hippel-Lindau-independent degradation of hypoxia-inducible factor-2? in clear cell renal carcinoma. Mol Pharmacol. 2010;78:1072-8 pubmed publisher
    ..Using this cell line, we have identified emetine as a specific inhibitor of HIF-2? protein stability and transcriptional activity...

More Information

Publications62

  1. Boon Unge K, Yu Q, Zou T, Zhou A, Govitrapong P, Zhou J. Emetine regulates the alternative splicing of Bcl-x through a protein phosphatase 1-dependent mechanism. Chem Biol. 2007;14:1386-92 pubmed
    ..In this study, the regulation of the alternative splicing of pre-mRNA of Bcl-x was examined in response to emetine. Treatment of different types of cancer cells with emetine dihydrochloride downregulated the level of Bcl-xL mRNA ..
  2. Asano T, Kushida H, Sadakane C, Ishihara K, Wakui Y, Yanagisawa T, et al. Metabolism of ipecac alkaloids cephaeline and emetine by human hepatic microsomal cytochrome P450s, and their inhibitory effects on P450 enzyme activities. Biol Pharm Bull. 2001;24:678-82 pubmed
    In this study, we identified the metabolites and the CYP forms that are specifically involved in emetine O-demethylation in human liver microsomes, and cleared the inhibitory potential of cephaeline and emetine on the activity of the ..
  3. Silber T. Ipecac syrup abuse, morbidity, and mortality: isn't it time to repeal its over-the-counter status?. J Adolesc Health. 2005;37:256-60 pubmed
    ..Classic findings are abnormal EKG and echocardiography and/or elevation of muscle enzymes (CPK, adolase). Emetine, the alkaloid in ipecac, can be confirmed in serum, urine, and tissue by high performance liquid chromatography...
  4. de Oliveira L, Rossi A, Martins E, Batista F, Silva R. Molecular phylogeography of Carapichea ipecacuanha, an amphitropical shrub that occurs in the understory of both semideciduous and evergreen forests. Mol Ecol. 2010;19:1410-22 pubmed publisher
    ..existing data on root alkaloid profiles, we used high-performance liquid chromatography to assess the levels of emetine and cephaeline in 33 specimens from the two Brazilian ranges...
  5. Vignier N, Schlossarek S, Fraysse B, Mearini G, Kramer E, Pointu H, et al. Nonsense-mediated mRNA decay and ubiquitin-proteasome system regulate cardiac myosin-binding protein C mutant levels in cardiomyopathic mice. Circ Res. 2009;105:239-48 pubmed publisher
    ..Inhibition of nonsense-mediated mRNA decay in cultured cardiac myocytes or in vivo with emetine or cycloheximide increased the level of nonsense mRNAs severalfold but not of the other mRNAs...
  6. Gelinas J, Banko J, Peters M, Klann E, Weeber E, Nguyen P. Activation of exchange protein activated by cyclic-AMP enhances long-lasting synaptic potentiation in the hippocampus. Learn Mem. 2008;15:403-11 pubmed publisher
    ..Activation of Epac represents a novel signaling pathway for rapid regulation of the stability of enduring forms of LTP and, perhaps, of hippocampus- dependent long-term memories. ..
  7. Baker Herman T, Mitchell G. Phrenic long-term facilitation requires spinal serotonin receptor activation and protein synthesis. J Neurosci. 2002;22:6239-46 pubmed
    ..A broad-spectrum serotonin receptor antagonist (methysergide) or protein synthesis inhibitors (emetine or cycloheximide) were injected intrathecally in the cervical spinal cord of anesthetized rats...
  8. Kim W, Kim J, Jang S. Anti-inflammatory lipid mediator 15d-PGJ2 inhibits translation through inactivation of eIF4A. EMBO J. 2007;26:5020-32 pubmed
    ..These findings reveal a novel cross-talk between translation and inflammatory response, and offer new approaches to develop anticancer and anti-inflammatory drugs that target translation factors including eIF4A. ..
  9. Xu J, Kang N, Jiang L, Nedergaard M, Kang J. Activity-dependent long-term potentiation of intrinsic excitability in hippocampal CA1 pyramidal neurons. J Neurosci. 2005;25:1750-60 pubmed
    ..CaM kinase inhibitors KN-62 and autocamtide-2-related inhibitory peptide, and the protein synthesis inhibitors emetine and anisomycin...
  10. Puskarjov M, Ahmad F, Kaila K, Blaesse P. Activity-dependent cleavage of the K-Cl cotransporter KCC2 mediated by calcium-activated protease calpain. J Neurosci. 2012;32:11356-64 pubmed publisher
    ..Here, we show that the application of protein synthesis inhibitors cycloheximide and emetine to acute rat hippocampal slices have no effect on total KCC2 protein level and K-Cl cotransporter function...
  11. Philippe L, Tosca L, Zhang W, Piquemal M, Ciapa B. Different routes lead to apoptosis in unfertilized sea urchin eggs. Apoptosis. 2014;19:436-50 pubmed publisher
    ..We also compare the effects induced by Emetine, an inhibitor of protein synthesis, with those triggered by Staurosporine, a non specific inhibitor of protein ..
  12. Wagner C, Lükewille U, Kaltenbach S, Moschen I, Bröer A, Risler T, et al. Functional and pharmacological characterization of human Na(+)-carnitine cotransporter hOCTN2. Am J Physiol Renal Physiol. 2000;279:F584-91 pubmed
    ..Most potent blockers were the antibiotic emetine and the ion channel blockers quinidine and verapamil. The apparent IC(50) for emetine was 4.2 +/- 1.2 microM...
  13. Nakajima Y. [Antiprotozoal drugs]. Nihon Rinsho. 2003;61 Suppl 2:774-9 pubmed
  14. Majeed M, Krause K, Clark R, Kihlstrom E, Stendahl O. Localization of intracellular Ca2+ stores in HeLa cells during infection with Chlamydia trachomatis. J Cell Sci. 1999;112 ( Pt 1):35-44 pubmed
    ..These changes may trigger the association of certain proteins such as annexins with chlamydia-containing vesicles, and thereby regulation of membrane-membrane interaction during endosome aggregation and inclusion formation. ..
  15. Kantamreddia V, Wright C. Complete NMR assignments of tubulosine. Nat Prod Commun. 2012;7:19-20 pubmed
    ..The data obtained allowed the unambiguous assignment of all proton and carbon signals in 1 for the first time. ..
  16. Zahedi K, Whitehead A. Regulation of mouse serum amyloid P gene expression by cytokines in vitro. Biochim Biophys Acta. 1993;1176:162-8 pubmed
    ..This increase in the cellular content of SAP mRNA did not require new protein synthesis and was at least partially due to an increase in the transcription rate of the SAP gene. ..
  17. Matthews H, Usman Idris M, Khan F, Read M, Nirmalan N. Drug repositioning as a route to anti-malarial drug discovery: preliminary investigation of the in vitro anti-malarial efficacy of emetine dihydrochloride hydrate. Malar J. 2013;12:359 pubmed publisher
    ..Previously described fixed-ratio methods were adopted to investigate drug interactions. Emetine dihydrochloride hydrate, an anti-protozoal drug previously used for intestinal and tissue amoebiasis was shown to ..
  18. Navakkode S, Sajikumar S, Frey J. The type IV-specific phosphodiesterase inhibitor rolipram and its effect on hippocampal long-term potentiation and synaptic tagging. J Neurosci. 2004;24:7740-4 pubmed
    ..This supports our hypothesis that cAMP-dependent processes are directly involved in the synthesis of plasticity-related proteins...
  19. Toye P, Sinden R, Canning E. The action of metabolic inhibitors on microgametogenesis in Plasmodium yoelii nigeriensis. Z Parasitenkd. 1977;53:133-41 pubmed
    ..DNA synthesis is not required during the three successive mitotic division of the parasite genome during microgametogenesis. The mature microgametocyte therefore contains the 8c DNA required for microgamete production...
  20. Alkadhi K, Al Hijailan R, Alzoubi K. Long-term depression in the superior cervical ganglion of the rat. Brain Res. 2008;1234:25-31 pubmed publisher
    ..Additionally, pretreatment with the protein synthesis inhibitor emetine (1 microM) totally prevented the expression of gLTD...
  21. Tan G, Kinghorn A, Hughes S, Pezzuto J. Psychotrine and its O-methyl ether are selective inhibitors of human immunodeficiency virus-1 reverse transcriptase. J Biol Chem. 1991;266:23529-36 pubmed
    ..Other members of the ipecac class of alkaloids, e.g. emetine hydrochloride, were inactive against all of these enzymes, including HIV-1 RT...
  22. Amer M, Li J, O Regan D, Steele D, Porter K, Sivaprasadarao A, et al. Translocon closure to Ca2+ leak in proliferating vascular smooth muscle cells. Am J Physiol Heart Circ Physiol. 2009;296:H910-6 pubmed publisher
    ..Puromycin, emetine, and anisomycin are chemicals that inhibit protein synthesis, acting via the translocon; all three agents ..
  23. Mera y Sierra R, Agramunt V, Cuervo P, Mas Coma S. Human fascioliasis in Argentina: retrospective overview, critical analysis and baseline for future research. Parasit Vectors. 2011;4:104 pubmed publisher
    ..The number of fascioliasis-hydatidosis co-infected patients (14) is outstanding. Emetine appears as the drug most used (186), replaced by triclabendazole in recent years (21)...
  24. Möller M, Weiss J, Wink M. Reduction of cytotoxicity of the alkaloid emetine through P-glycoprotein (MDR1/ABCB1) in human Caco-2 cells and leukemia cell lines. Planta Med. 2006;72:1121-6 pubmed
    The cytotoxicity of the alkaloid emetine was determined in six human cell lines that differ in the expression of ABC transporters, such as multiple drug resistance protein 1 (MDR1/ABCB1) and multidrug resistance associated protein 1 (..
  25. Dömling A, Richter W. Myxobacterial epothilones and tubulysins as promising anticancer agents. Mol Divers. 2005;9:141-7 pubmed
    ..In this article a known class, epothilones, as well as a novel class, tubulysins, are presented...
  26. Carrada Bravo T. [Fascioliasis: diagnosis, epidemiology and treatment]. Rev Gastroenterol Mex. 2003;68:135-42 pubmed
    ..Treatment is with emetine hydrochloride given intramusculary...
  27. Dohra H, Fujishima M. Effects of antibiotics on the early infection process of a macronuclear endosymbiotic bacterium Holospora obtusa of Paramecium caudatum. FEMS Microbiol Lett. 1999;179:473-7 pubmed
    ..vacuoles and escape of the bacterium from the vacuoles to the host cytoplasm were significantly arrested with emetine. The results suggest that newly synthesized host proteins play an important role in the early infection process.
  28. Williams A, Murrell M, Brammah S, Minchenko J, Christodoulou J. A novel system for assigning the mode of inheritance in mitochondrial disorders using cybrids and rhodamine 6G. Hum Mol Genet. 1999;8:1691-7 pubmed
  29. Orozco E, López C, Gomez C, Pérez D, Marchat L, Bañuelos C, et al. [Multiple drug resistance in Entamoeba histolytica]. Rev Invest Clin. 2002;54:349-56 pubmed
  30. Huusko P, Ponciano Jackson D, Wolf M, Kiefer J, Azorsa D, Tuzmen S, et al. Nonsense-mediated decay microarray analysis identifies mutations of EPHB2 in human prostate cancer. Nat Genet. 2004;36:979-83 pubmed
  31. Pan S, Combs A. Emetine inhibits glycolysis in isolated, perfused rat hearts. Cardiovasc Toxicol. 2003;3:311-8 pubmed
    This work was designed to test whether phosphofructokinase is a target for emetine action on the heart...
  32. Kambayashi T, Kraft Leavy J, Dauner J, Sullivan B, Laur O, Jensen P. The nonclassical MHC class I molecule Qa-1 forms unstable peptide complexes. J Immunol. 2004;172:1661-9 pubmed
    ..We propose that the CD94/NKG2A-Qa-1/Qdm recognition system has evolved as a rapid sensor of the integrity of the MHC class I biosynthesis and Ag presentation pathway. ..
  33. Yang Z, Lau R, Marcadier J, Chitayat D, Pearson C. Replication inhibitors modulate instability of an expanded trinucleotide repeat at the myotonic dystrophy type 1 disease locus in human cells. Am J Hum Genet. 2003;73:1092-105 pubmed
    ..both leading- and lagging-strand synthesis with aphidicolin or blocking only lagging strand synthesis with emetine significantly enhanced CTG expansions...
  34. Foreman K, Jesse J, Kuo P, Gupta G. Emetine dihydrochloride: a novel therapy for bladder cancer. J Urol. 2014;191:502-9 pubmed publisher
    ..In the 1970s the natural alkaloid emetine dihydrochloride demonstrated modest anticancer efficacy as a single agent in clinical trials but this was not ..
  35. Gonzalez C, Kramar C, Garagoli F, Rossato J, Weisstaub N, Cammarota M, et al. Medial prefrontal cortex is a crucial node of a rapid learning system that retrieves recent and remote memories. Neurobiol Learn Mem. 2013;103:19-25 pubmed publisher
  36. Shultz J, Chalfant C. Emetine and the alternative splicing of Bcl-X: where to next?. Chem Biol. 2007;14:1313-4 pubmed
    ..report on the regulation of the alternative splicing of Bcl-x pre-mRNA in response to emetine, a potent protein synthesis inhibitor, as well as define a major player in the signaling mechanism.
  37. Wolf M, Edgren H, Muggerud A, Kilpinen S, Huusko P, Sørlie T, et al. NMD microarray analysis for rapid genome-wide screen of mutated genes in cancer. Cell Oncol. 2005;27:169-73 pubmed
  38. Shimizu Y, Todo S, Imashuku S. Selective synthesis and retention of 66k protein in a human neuroblastoma cell line (NCG) treated with a cytotoxic dosage of delta 12-prostaglandin J2. Prostaglandins. 1987;34:769-81 pubmed
    ..5% and 78.2% of the control values, respectively. Two protein synthesis inhibitors, cycloheximide (CHM) and emetine, exhibited a dose-dependent protective effect for neuroblastoma cells against delta 12-PGJ2 cytotoxicity...
  39. Rao K, Bhattacharya R, Venkatachalam S. Thymidylate synthase activity and the cell growth are inhibited by the beta-carboline-benzoquinolizidine alkaloid deoxytubulosine. J Biochem Mol Toxicol. 1998;12:167-73 pubmed
    ..Inhibition kinetics showed that TS has a Ki value of 7 x 10(-6) M for DTB and that the inhibition is a simple linear "noncompetitive" type. ..
  40. Asano T, Ishihara K, Wakui Y, Yanagisawa T, Kimura M, Kamei H, et al. Absorption, distribution and excretion of 3H-labeled cephaeline- and emetine-spiked ipecac syrup in rats. Eur J Drug Metab Pharmacokinet. 2002;27:17-27 pubmed
    ..00-3.33 hours following oral dosing of ipecac syrup. The maximum plasma radioactivity levels of 3H-emetine (2.71, 6.47 and 9.62 ng eq./mL) were reached at 1.08-2.33 hours following ipecac syrup administration...
  41. Dana S, Wasmuth J. Linkage of the leuS, emtB, and chr genes on chromosome 5 in humans and expression of human genes encoding protein synthetic components in human--Chinese hamster hybrids. Somatic Cell Genet. 1982;8:245-64 pubmed
    ..alters ribosomal protein S14 and results in the cell line being resistant to the protein synthesis inhibitor, emetine, while the mutation in the chr locus renders the cells resistant to sodium chromate...
  42. Nishimoto Y, Ito D, Yagi T, Nihei Y, Tsunoda Y, Suzuki N. Characterization of alternative isoforms and inclusion body of the TAR DNA-binding protein-43. J Biol Chem. 2010;285:608-19 pubmed publisher
    ..Our findings provide new biological and pathological insight into the development of TDP-43 proteinopathies. ..
  43. Smirnova O, Mishina V, Zatsepina O. [Cytopathological effects of protein synthesis inhibitor emetine on HeLa cells and their nucleoli]. Tsitologiia. 2003;45:1179-87 pubmed
    ..b>Emetine is one of such inhibitors...
  44. Ratner D, Pentz W, Pelletier D. Prespore gene expression in Dictyostelium requires concomitant protein synthesis. Biochim Biophys Acta. 1989;1008:71-8 pubmed
    ..Other inhibitors of in vivo protein synthesis have been examined, with emetine shown to be a particularly effective but reversible agent...
  45. Frawley P, Smith J. Chemical aversion therapy in the treatment of cocaine dependence as part of a multimodal treatment program: treatment outcome. J Subst Abuse Treat. 1990;7:21-9 pubmed
    ..Fifty (50) percent of the cocaine/alcohol group had been totally abstinent (80% were currently abstinent). Validation of results was obtained from "significant others" for 90% of patients. ..
  46. Fayadat L, Siffroi Fernandez S, Lanet J, Franc J. Degradation of human thyroperoxidase in the endoplasmic reticulum involves two different pathways depending on the folding state of the protein. J Biol Chem. 2000;275:15948-54 pubmed
    ..Moreover, this is the first study describing a protein degradation process involving two distinct degradation pathways (proteasome and ER cysteine/serine proteases) at the ER level, depending on the folding state of the protein. ..
  47. Rao K, Bhattacharya R, Veankatachalam S. Inhibition of thymidylate synthase by pergularinine, tylophorinidine and deoxytubulosine. Indian J Biochem Biophys. 1999;36:442-8 pubmed
  48. Tsukagoshi K, Okuzono N, Nakajima R. Separation and determination of emetine dithiocarbamate metal complexes by capillary electrophoresis with chemiluminescence detection of the tris(2,2'-bipyridine)-ruthenium(II) complex. J Chromatogr A. 2002;958:283-9 pubmed
    b>Emetine dithiocarbamate metal complexes, which were prepared from emetine, carbon disulfide, and metal(II), indicated large chemiluminescence intensities on tris(2,2'-bipyridine)-ruthenium(II) chemiluminescence...
  49. Yamashita M, Yamashita M, Azuma J. Urinary excretion of ipecac alkaloids in human volunteers. Vet Hum Toxicol. 2002;44:257-9 pubmed
    ..po to 12 healthy human volunteers at a dose of either 20 mL or 30 mL, and urinary excretions of cephaeline and emetine as well as blood and vomit concentrations were detected by HPLC...
  50. Trépardoux F. [Emétine and quinine, a therapy to rescue Bellini in 1835]. Rev Hist Pharm (Paris). 2002;50:401-26 pubmed
    ..As emetine and quinine since 1822 were both available as pure alcaloids, produced by the pharmacist Joseph Pelletier, it is ..
  51. Portillo López A, Gould M, Stephano J. MAPK is involved in metaphase I arrest in oyster and mussel oocytes. Biol Cell. 2003;95:275-82 pubmed
    ..Treatment of oyster oocytes with the protein synthesis inhibitor, emetine (500 microM), also caused them to resume meiosis, although substantial MAPK activity remained...
  52. Cruz López O, Adán Pimentel A, Tamariz Cruz O, Muñoz López A, Cruz López M, Cruz López M, et al. [Hepatic fasciolasis diagnosed in state phase]. Rev Gastroenterol Mex. 2006;71:59-62 pubmed
    ..5 mg/kg) was administered during 10 days. Symptoms disappeared within 48 hours. The lack of knowledge about fasciolosis makes it hard to diagnose it. The publication of case reports must help to facilitate its diagnosis. ..
  53. Söderlund G, Haarhaus M, Chisalita S, Arnqvist H. Inhibition of puromycin-induced apoptosis in breast cancer cells by IGF-I occurs simultaneously with increased protein synthesis. Neoplasma. 2004;51:1-11 pubmed
    ..inducing effect of puromycin in MCF-7 breast cancer cells and compare this effect with cycloheximide and emetine, 2 other inhibitors of protein synthesis...