A chemical genetic screen for modulators of asymmetrical 2,2'-dimeric naphthoquinones cytotoxicity in yeast

PLoS ONE

Volumn 5, Issue 5, 2010, Pages

  Emadi, Ashkan ^a   Ross, Ashley E ^a   Cowan, Kathleen M ^a   Fortenberry, Yolanda M ^a   Vuica Ross, Milena ^a  

^a JOHNS HOPKINS UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,2' NAPHTHOQUINONE DERIVATIVE; 3 HYDROXY 3' IODO 7 METHOXY 2,2' BINAPHTHALENYL 1,4,1',4' TETRAONE; 3,3' DICHLORO 8 HYDROXY 2,2' BINAPHTHALENYL 1,4,1',4' TETRAONE; 8 (3 CHLORO 1,4 DIOXO 1,4, DIHYDRONAPHTHALEN 2 YL) 9 HYDROXY 3,3 DIMETHYL 3H BENZO[F]CHROMENE 7,10 DIONE; DIMER; NAPHTHALENE DERIVATIVE; QUINONE DERIVATIVE; REACTIVE OXYGEN METABOLITE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE (PHOSPHATE) DEHYDROGENASE (QUINONE); UNCLASSIFIED DRUG; NAPHTHOQUINONE; SACCHAROMYCES CEREVISIAE PROTEIN;

ANTIFUNGAL RESISTANCE; ANTIFUNGAL SUSCEPTIBILITY; ARTICLE; CELL FUNCTION; CELL MEMBRANE DEPOLARIZATION; CELL RESPIRATION; CHEMICAL GENETICS; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOTOXICITY; DELETION MUTANT; DRUG STRUCTURE; FUNGAL STRAIN; GENE OVEREXPRESSION; GENETIC ANALYSIS; GENETIC MODEL; GROWTH INHIBITION; HIGH THROUGHPUT SCREENING; IC 50; MITOCHONDRIAL MEMBRANE POTENTIAL; NONHUMAN; PROTEIN FUNCTION; WILD TYPE; YEAST; AEROBIC METABOLISM; CHEMISTRY; CULTURE MEDIUM; CYTOLOGY; DRUG EFFECT; ENZYMOLOGY; FERMENTATION; FUNGAL GENOME; GENETIC SCREENING; GENETICS; ISOMERISM; METABOLISM; MICROBIAL VIABILITY; MITOCHONDRION; REPRODUCIBILITY; SACCHAROMYCES CEREVISIAE;

MAMMALIA;

AEROBIOSIS; CULTURE MEDIA; FERMENTATION; GENETIC TESTING; GENOME, FUNGAL; ISOMERISM; MEMBRANE POTENTIAL, MITOCHONDRIAL; MICROBIAL VIABILITY; MITOCHONDRIA; NAPHTHOQUINONES; REACTIVE OXYGEN SPECIES; REPRODUCIBILITY OF RESULTS; SACCHAROMYCES CEREVISIAE; SACCHAROMYCES CEREVISIAE PROTEINS;

EID: 77956280188     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0010846     Document Type: Article

References (42)

1. O'Brien PJ (1991) Molecular mechanisms of quinone cytotoxicity. Chem Biol Interact 80: 1-41.
2. Laatsch H (1994) Conocurvone-Prototype of a New Class of Anti-HIV Active Compounds? AngewChem Int Ed Engl 33: 422-424.
3. Decosterd LA, Parsons IC, Gustafson KR, Cardellina JH, II, McMahon JB, et al. (1993) HIV inhibitory natural products. 11. Structure, absolute stereochemistry, and synthesis of conocurvone, a potent, novel HIV-inhibitory naphtho-quinone trimer from a Conospermum sp. J Am Chem Soc 115: 6673-6679.
4. Emadi A, Harwood JS, Kohanim S, Stagliano KW (2002) Regiocontrolled synthesis of the trimeric quinone framework of conocurvone. Org Lett 4: 521-524.
5. Stagliano KW, Emadi A (2004) Anti-Retroviral Multi-Quinone Compounds and Regiospecific Synthesis Thereof. Patent Number 6,828,347, issused by United States Patent Trademark Office.
6. Stagliano KW, Emadi A, Lu Z, Malinakova HC, Twenter B, et al. (2006) Regiocontrolled synthesis and HIV inhibitory activity of unsymmetrical binaphthoquinone and trimeric naphthoquinone derivatives of conocurvone. Bioorg Med Chem 14: 5651-5665.
7. Rockwell S, Sartorelli AC, Tomasz M, Kennedy KA (1993) Cellular pharmacology of quinone bioreductive alkylating agents. Cancer Metastasis Rev 12: 165-176.
8. Westmoreland TJ, Wickramasekara SM, Guo AY, Selim AL, Winsor TS, et al. (2009) Comparative genome-wide screening identifies a conserved doxorubicin repair network that is diploid specific in Saccharomyces cerevisiae. PLoS One 4: e5830.
9. Miskimins R, Schneider S, Johns V, Bernstein H (1982) Topoisomerase involvement in multiplicity reactivation of phage T4. Genetics 101: 157-177.
10. Kanaan YM, Das JR, Bakare O, Enwerem NM, Berhe S, et al. (2009) Biological evaluation of 2,3-dichloro-5,8-dimethoxy-1,4-naphthoquinone as an anti-breast cancer agent. Anticancer Res 29: 191-199.
11. Hallak M, Win T, Shpilberg O, Bittner S, Granot Y, et al. (2009) The anti-leukaemic activity of novel synthetic naphthoquinones against acute myeloid leukaemia: induction of cell death via the triggering of multiple signalling pathways. Br J Haematol 147: 459-470.
12. Clayson DB, Mehta R, Iverson F (1994) International Commission for Protection Against Environmental Mutagens and Carcinogens. Oxidative DNA damage-the effects of certain genotoxic and operationally non-genotoxic carcinogens. Mutat Res 317: 25-42.
13. Wang X, Thomas B, Sachdeva R, Arterburn L, Frye L, et al. (2006) Mechanism of arylating quinone toxicity involving Michael adduct formation and induction of endoplasmic reticulum stress. Proc Natl Acad Sci U S A 103: 3604-3609.
14. Baetz K, McHardy L, Gable K, Tarling T, Reberioux D, et al. (2004) Yeast genome-wide drug-induced haploinsufficiency screen to determine drug mode of action. Proc Natl Acad Sci USA 101: 4525-4530.
15. Giaever G, Chu AM, Ni L, Connelly C, Riles L, et al. (2002) Functional profiling of the Saccharomyces cerevisiae genome. Nature 418: 387-391.
16. Lopez A, Parsons AB, Nislow C, Giaever G, Boone C (2008) Chemical-genetic approaches for exploring the mode of action of natural products. Prog Drug Res 66: 237, 239-271.
17. Zewail A, Xie MW, Xing Y, Lin L, Zhang PF, et al. (2003) Novel functions of the phosphatidylinositol metabolic pathway discovered by a chemical genomics screen with wortmannin. Proc Natl Acad Sci USA 100: 3345-3350.
18. Stagliano KW, Lu Z, Emadi A, Harwood JS, Harwood CA (2004) Effect of methoxyl group position on the regioselectivity of ammonia substitution reactions involving 3,39-dichloro-2,29-binaphthoquinones. J Org Chem 69: 5128-5131.
19. Riles L, Shaw RJ, Johnston M, Reines D (2004) Large-scale screening of yeast mutants for sensitivity to the IMP dehydrogenase inhibitor 6-azauracil. Yeast 21: 241-248.
20. Ashburner M, Ball CA, Blake JA, Botstein D, Butler H, et al. (2000) Gene ontology: tool for the unification of biology. The Gene Ontology Consortium. Nat Genet 25: 25-29.
21. Steinmetz LM, Scharfe C, Deutschbauer AM, Mokranjac D, Herman ZS, et al. (2002) Systematic screen for human disease genes in yeast. Nat Genet 31: 400-404.
22. Ohnishi T, Sottocasa G, Ernster L (1966) Current approaches to the mechanism of energy-coupling in the respiratory chain. Studies with yeast mitochondria. Bull Soc Chim Biol (Paris) 48: 1189-1203.
23. Davermann D, Martinez M, McKoy J, Patel N, Averbeck D, et al. (2002) Impaired mitochondrial function protects against free radical-mediated cell death. Free Radic Biol Med 33: 1209-1220.
24. Chandel NS, Schumacker PT (1999) Cells depleted of mitochondrial DNA (rho0) yield insight into physiological mechanisms. FEBS Lett 454: 173-176.
25. Bittner S (2006) When quinones meet amino acids: chemical, physical and biological consequences. Amino Acids 30: 205-224.
26. Luttik MA, Overkamp KM, Kotter P, de Vries S, van Dijken JP, et al. (1998) The Saccharomyces cerevisiae NDE1 and NDE2 genes encode separate mitochondrial NADH dehydrogenases catalyzing the oxidation of cytosolic NADH. J Biol Chem 273: 24529-24534.
27. Small WC, McAlister-Henn L (1998) Identification of a cytosolically directed NADH dehydrogenase in mitochondria of Saccharomyces cerevisiae. J Bacteriol 180: 4051-4055.
28. Li W, Mo W, Shen D, Sun L, Wang J, et al. (2005) Yeast model uncovers dual roles of mitochondria in action of artemisinin. PLoS Genet 1: e36.
29. Funk M, Niedenthal R, Mumberg D, Brinkmann K, Ronicke V, et al. (2002) Vector systems for heterologous expression of proteins in Saccharomyces cerevisiae. Methods Enzymol 350: 248-257.
30. Tran UC, Clarke CF (2007) Endogenous synthesis of coenzyme Q in eukaryotes. Mitochondrion 7 Suppl: S62-71.
31. Davidson JF, Schiestl RH (2001) Mitochondrial respiratory electron carriers are involved in oxidative stress during heat stress in Saccharomyces cerevisiae. Mol Cell Biol 21: 8483-8489.
32. Sollner S, Nebauer R, Ehammer H, Prem A, Deller S, et al. (2007) Lot6p from Saccharomyces cerevisiae is a FMN-dependent reductase with a potential role in quinone detoxification. FEBS J 274: 1328-1339.
33. Vasiliou V, Ross D, Nebert DW (2006) Update of the NAD(P)H:quinone oxidoreductase (NQO) gene family. Hum Genomics 2: 329-335.
34. Bey EA, Wuerzberger-Davis SM, Pink JJ, Yang CR, Araki S, et al. (2006) Mornings with Art, lessons learned: feedback regulation, restriction threshold biology, and redundancy govern molecular stress responses. J Cell Physiol 209: 604-610.
35. Pardee AB, Li YZ, Li CJ (2002) Cancer therapy with beta-lapachone. Curr Cancer Drug Targets 2: 227-242.
36. Pink JJ, Planchon SM, Tagliarino C, Varnes ME, Siegel D, et al. (2000) NAD(P)H:Quinone oxidoreductase activity is the principal determinant of beta-lapachone cytotoxicity. J Biol Chem 275: 5416-5424.
37. Siegel D, Ross D (2000) Immunodetection of NAD(P)H:quinone oxidoreductase 1 (NQO1) in human tissues. Free Radic Biol Med 29: 246-253.
38. Ollinger K, Brunmark A (1991) Effect of hydroxy substituent position on 1,4-naphthoquinone toxicity to rat hepatocytes. J Biol Chem 266: 21496-21503.
39. Fox TD, Folley LS, Mulero JJ, McMullin TW, Thorsness PE, et al. (1991) Analysis and manipulation of yeast mitochondrial genes. Methods Enzymol 194: 149-165.
40. Boyle EI, Weng S, Gollub J, Jin H, Botstein D, et al. (2004) GO::TermFinder- open source software for accessing Gene Ontology information and finding significantly enriched Gene Ontology terms associated with a list of genes. Bioinformatics 20: 3710-3715.
41. Lorenz MC, Muir RS, Lim E, McElver J, Weber SC, et al. (1995) Gene disruption with PCR products in Saccharomyces cerevisiae. Gene 158: 113-117.
42. Kuzyk MA, Ohlund LB, Elliott MH, Smith D, Qian H, et al. (2009) A comparison of MS/MS-based, stable-isotope-labeled, quantitation performance on ESI-quadrupole TOF and MALDI-TOF/TOF mass spectrometers. Proteomics 9: 3328-3340.