ALDH2 mediates 5-nitrofuran activity in multiple species

Chemistry and Biology

Volumn 19, Issue 7, 2012, Pages 883-892

  Zhou, Linna ^a   Ishizaki, Hironori ^b,c   Spitzer, Michaela ^d   Taylor, Kerrie L ^b,c   Temperley, Nicholas D ^b   Johnson, Stephen L ^e   Brear, Paul ^b   Gautier, Philippe ^b,c   Zeng, Zhiqiang ^b,c   Mitchell, Amy ^b   Narayan, Vikram ^b   McNeil, Ewan M ^b   Melton, David W ^b   Smith, Terry K ^a   Tyers, Mike ^d   Westwood, Nicholas J ^a   Patton, E Elizabeth ^b,c  

^a UNIVERSITY OF ST ANDREWS   (United Kingdom)

^b UNIVERSITY OF EDINBURGH   (United Kingdom)

^c UNIVERSITY OF EDINBURGH   (United Kingdom)

^d UNIVERSITY OF EDINBURGH   (United Kingdom)

^e WASHINGTON UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5 NITROFURAN; ALDEHYDE DEHYDROGENASE ISOENZYME 2; ANTITRYPANOSOMAL AGENT; BR 00087; BTB 05727; BTB 13657; DAIDZIN; DISULFIRAM; GLYCERYL TRINITRATE; NIFURTIMOX; NITROFURAN DERIVATIVE; SEW 00138; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIMICROBIAL ACTIVITY; ANTIPROTOZOAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG PROTEIN BINDING; ENZYME METABOLISM; ENZYME SUBSTRATE; HUMAN; HUMAN CELL; IN VITRO STUDY; NONHUMAN; PROTEIN EXPRESSION; SPECIES DIVERSITY; YEAST; ZEBRA FISH;

ALDEHYDE DEHYDROGENASE; ANIMALS; DOSE-RESPONSE RELATIONSHIP, DRUG; HUMANS; MELANOCYTES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NITROFURANS; RECOMBINANT PROTEINS; SACCHAROMYCES CEREVISIAE; SPECIES SPECIFICITY; STRUCTURE-ACTIVITY RELATIONSHIP; ZEBRAFISH;

BACTERIA (MICROORGANISMS); DANIO RERIO;

EID: 84864408346     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2012.05.017     Document Type: Article

References (43)

1. M.P. Arolfo, D.H. Overstreet, L. Yao, P. Fan, A.J. Lawrence, G. Tao, W.M. Keung, B.L. Vallee, M.F. Olive, and J.T. Gass Suppression of heavy drinking and alcohol seeking by a selective ALDH-2 inhibitor Alcohol. Clin. Exp. Res. 33 2009 1935 1944
2. M. Aslett, C. Aurrecoechea, M. Berriman, J. Brestelli, B.P. Brunk, M. Carrington, D.P. Depledge, S. Fischer, B. Gajria, and X. Gao TriTrypDB: a functional genomic resource for the Trypanosomatidae Nucleic Acids Res. 38 Database issue 2010 D457 D462
3. J.A. Castro, M.M. de Mecca, and L.C. Bartel Toxic side effects of drugs used to treat Chagas' disease (American trypanosomiasis) Hum. Exp. Toxicol. 25 2006 471 479
4. C.H. Chen, G.R. Budas, E.N. Churchill, M.H. Disatnik, T.D. Hurley, and D. Mochly-Rosen Activation of aldehyde dehydrogenase-2 reduces ischemic damage to the heart Science 321 2008 1493 1495
5. C.H. Chen, L. Sun, and D. Mochly-Rosen Mitochondrial aldehyde dehydrogenase and cardiac diseases Cardiovasc. Res. 88 2010 51 57
6. Z. Chen, J. Zhang, and J.S. Stamler Identification of the enzymatic mechanism of nitroglycerin bioactivation Proc. Natl. Acad. Sci. USA 99 2002 8306 8311
7. J.R. Coura, and P.A. Viñas Chagas disease: a new worldwide challenge Nature 465 2010 S6 S7
8. G.A. Cross Trypanosomes at the gates Science 309 2005 355
9. I.M. de Oliveira, J.A. Henriques, and D. Bonatto In silico identification of a new group of specific bacterial and fungal nitroreductases-like proteins Biochem. Biophys. Res. Commun. 355 2007 919 925
10. N. Druesne-Pecollo, B. Tehard, Y. Mallet, M. Gerber, T. Norat, S. Hercberg, and P. Latino-Martel Alcohol and genetic polymorphisms: effect on risk of alcohol-related cancer Lancet Oncol. 10 2009 173 180
11. M.L. Dubuisson, B. De Wergifosse, P. Kremers, J. Marchand-Brynaert, A. Trouet, and J.F. Rees Protection against nitrofurantoin-induced oxidative stress by coelenterazine analogues and their oxidation products in rat hepatocytes Free Radic. Res. 34 2001 285 296
12. J.A. Frearson, S. Brand, S.P. McElroy, L.A. Cleghorn, O. Smid, L. Stojanovski, H.P. Price, M.L. Guther, L.S. Torrie, and D.A. Robinson N-myristoyltransferase inhibitors as new leads to treat sleeping sickness Nature 464 2010 728 732
13. H. Ishizaki, M. Spitzer, J. Wildenhain, C. Anastasaki, Z. Zeng, S. Dolma, M. Shaw, E. Madsen, J. Gitlin, and R. Marais Combined zebrafish-yeast chemical-genetic screens reveal gene-copper-nutrition interactions that modulate melanocyte pigmentation Dis. Model Mech. 3 2010 639 651
14. T. Ito, H. Ando, T. Suzuki, T. Ogura, K. Hotta, Y. Imamura, Y. Yamaguchi, and H. Handa Identification of a primary target of thalidomide teratogenicity Science 327 2010 1345 1350
15. S. Jawaid, T.H. Khan, H.M. Osborn, and N.A. Williams Tyrosinase activated melanoma prodrugs Anticancer. Agents Med. Chem. 9 2009 717 727
16. W.M. Keung, and B.L. Vallee Daidzin and daidzein suppress free-choice ethanol intake by Syrian golden hamsters Proc. Natl. Acad. Sci. USA 90 1993 10008 10012
17. W.M. Keung, and B.L. Vallee Daidzin: a potent, selective inhibitor of human mitochondrial aldehyde dehydrogenase Proc. Natl. Acad. Sci. USA 90 1993 1247 1251
18. C. Laggner, D. Kokel, V. Setola, A. Tolia, H. Lin, J.J. Irwin, M.J. Keiser, C.Y. Cheung, D.L. Minor Jr., and B.L. Roth Chemical informatics and target identification in a zebrafish phenotypic screen Nat. Chem. Biol. 8 2012 144 146
19. N. Lassen, T. Estey, R.L. Tanguay, A. Pappa, M.J. Reimers, and V. Vasiliou Molecular cloning, baculovirus expression, and tissue distribution of the zebrafish aldehyde dehydrogenase 2 Drug Metab. Dispos. 33 2005 649 656
20. D.W. Logan, S.F. Burn, and I.J. Jackson Regulation of pigmentation in zebrafish melanophores Pigment Cell Res. 19 2006 206 213
21. E.D. Lowe, G.Y. Gao, L.N. Johnson, and W.M. Keung Structure of daidzin, a naturally occurring anti-alcohol-addiction agent, in complex with human mitochondrial aldehyde dehydrogenase J. Med. Chem. 51 2008 4482 4487
22. S.A. Marchitti, C. Brocker, D. Stagos, and V. Vasiliou Non-P450 aldehyde oxidizing enzymes: the aldehyde dehydrogenase superfamily Expert Opin. Drug Metab. Toxicol. 4 2008 697 720
23. J.D. Maya, B.K. Cassels, P. Iturriaga-Vásquez, J. Ferreira, M. Faúndez, N. Galanti, A. Ferreira, and A. Morello Mode of action of natural and synthetic drugs against Trypanosoma cruzi and their interaction with the mammalian host Comp. Biochem. Physiol. A Mol. Integr. Physiol. 146 2007 601 620
24. F. Medda, R.J. Russell, M. Higgins, A.R. McCarthy, J. Campbell, A.M. Slawin, D.P. Lane, S. Lain, and N.J. Westwood Novel cambinol analogs as sirtuin inhibitors: synthesis, biological evaluation, and rationalization of activity J. Med. Chem. 52 2009 2673 2682
25. J. Mikus, and D. Steverding A simple colorimetric method to screen drug cytotoxicity against Leishmania using the dye Alamar Blue Parasitol. Int. 48 2000 265 269
26. K. Nussbaum, J. Honek, C.M. Cadmus, and T. Efferth Trypanosomatid parasites causing neglected diseases Curr. Med. Chem. 17 2010 1594 1617
27. T. O'Reilly-Pol, and S.L. Johnson Neocuproine ablates melanocytes in adult zebrafish Zebrafish 5 2008 257 264
28. C. Paulos, J. Paredes, I. Vasquez, S. Thambo, A. Arancibia, and G. Gonzalez-Martin Pharmacokinetics of a nitrofuran compound, nifurtimox, in healthy volunteers Int. J. Clin. Pharmacol. Ther. Toxicol. 27 1989 454 457
29. G. Priotto, S. Kasparian, W. Mutombo, D. Ngouama, S. Ghorashian, U. Arnold, S. Ghabri, E. Baudin, V. Buard, and S. Kazadi-Kyanza Nifurtimox-eflornithine combination therapy for second-stage African Trypanosoma brucei gambiense trypanosomiasis: a multicentre, randomised, phase III, non-inferiority trial Lancet 374 2009 56 64
30. D.N. Rao, and R.P. Mason Generation of nitro radical anions of some 5-nitrofurans, 2- and 5-nitroimidazoles by norepinephrine, dopamine, and serotonin. A possible mechanism for neurotoxicity caused by nitroheterocyclic drugs J. Biol. Chem. 262 1987 11731 11736
31. D.N. Rao, L. Harman, A. Motten, J. Schreiber, and R.P. Mason Generation of radical anions of nitrofurantoin, misonidazole, and metronidazole by ascorbate Arch. Biochem. Biophys. 255 1987 419 427
32. J. Rihel, D.A. Prober, A. Arvanites, K. Lam, S. Zimmerman, S. Jang, S.J. Haggarty, D. Kokel, L.L. Rubin, R.T. Peterson, and A.F. Schier Zebrafish behavioral profiling links drugs to biological targets and rest/wake regulation Science 327 2010 348 351
33. G.L. Saulnier Sholler, G.M. Bergendahl, L. Brard, A.P. Singh, B.W. Heath, P.M. Bingham, T. Ashikaga, B.A. Kamen, A.C. Homans, and M.A. Slavik A phase 1 study of nifurtimox in patients with relapsed/refractory neuroblastoma J. Pediatr. Hematol. Oncol. 33 2011 25 30
34. T.J. Sobreira, F. Marlétaz, M. Simões-Costa, D. Schechtman, A.C. Pereira, F. Brunet, S. Sweeney, A. Pani, J. Aronowicz, and C.J. Lowe Structural shifts of aldehyde dehydrogenase enzymes were instrumental for the early evolution of retinoid-dependent axial patterning in metazoans Proc. Natl. Acad. Sci. USA 108 2011 226 231
35. A.Y. Sokolova, S. Wyllie, S. Patterson, S.L. Oza, K.D. Read, and A.H. Fairlamb Cross-resistance to nitro drugs and implications for treatment of human African trypanosomiasis Antimicrob. Agents Chemother. 54 2010 2893 2900
36. W. Song, Z. Zou, F. Xu, X. Gu, X. Xu, and Q. Zhao Molecular cloning and expression of a second zebrafish aldehyde dehydrogenase 2 gene (aldh2b) DNA Seq. 17 2006 262 269
37. K.L. Taylor, N.J. Grant, N.D. Temperley, and E.E. Patton Small molecule screening in zebrafish: an in vivo approach to identifying new chemical tools and drug leads Cell Commun. Signal. 8 2010 11
38. B. Thisse, S. Pflumio, M. Fürthauer, B. Loppin, V. Heyer, A. Degrave, R. Woehl, A. Lux, T. Steffan, X.Q. Charbonnier, and C. Thisse Expression of the Zebrafish Genome during Embryogenesis 2001 ZFIN, University of Oregon Eugene, OR
39. P. Wenzel, U. Hink, M. Oelze, S. Schuppan, K. Schaeuble, S. Schildknecht, K.K. Ho, H. Weiner, M. Bachschmid, T. Münzel, and A. Daiber Role of reduced lipoic acid in the redox regulation of mitochondrial aldehyde dehydrogenase (ALDH-2) activity. Implications for mitochondrial oxidative stress and nitrate tolerance J. Biol. Chem. 282 2007 792 799
40. C.T. Yang, and S.L. Johnson Small molecule-induced ablation and subsequent regeneration of larval zebrafish melanocytes Development 133 2006 3563 3573
41. L. Yao, P. Fan, Z. Jiang, A. Gordon, D. Mochly-Rosen, and I. Diamond Dopamine and ethanol cause translocation of epsilonPKC associated with εRACK: cross-talk between cAMP-dependent protein kinase A and protein kinase C signaling pathways Mol. Pharmacol. 73 2008 1105 1112
42. L. Yao, P. Fan, M. Arolfo, Z. Jiang, M.F. Olive, J. Zablocki, H.L. Sun, N. Chu, J. Lee, and H.Y. Kim Inhibition of aldehyde dehydrogenase-2 suppresses cocaine seeking by generating THP, a cocaine use-dependent inhibitor of dopamine synthesis Nat. Med. 16 2010 1024 1028
43. L.I. Zon, and R.T. Peterson In vivo drug discovery in the zebrafish Nat. Rev. Drug Discov. 4 2005 35 44