Skip to main content
SpringerLink
Log in
Book cover

Insecticides Design Using Advanced Technologies pp 197–215Cite as

Mitochondrial Electron Transport Complexes as Biochemical Target Sites for Insecticides and Acaricids

  • Chapter

This is a preview of subscription content, log in via an institution.

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   129.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   169.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD   169.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • Ahlers PM, Zwicker K, Kerscher S, Brandt U (2000) Function of conserved acidic residues in the PSST homologue of complex I (NADH:ubiquinone oxidoreductase) from Yarrowia lipolytica. J Biol Chem 275:23577–23582.

    Article  PubMed  CAS  Google Scholar 

  • Albracht SP, Hedderich R (2000) Learning from hydrogenases: location of a proton pump and of a second FMN in bovine NADH-ubiquinone oxidoreductase (Complex I). FEBS Lett 485:1–6.

    Article  PubMed  CAS  Google Scholar 

  • Ball EG, Anfinsen CB, Cooper O (1947) The inhibitory action of naphthoquinones on respiratory processes. J Biol Chem 168:257–270.

    CAS  Google Scholar 

  • Bartlett DW, Clough JM, Godwin JR, Hall AA, Hamer M, Parr-Dobrzanski B (2002) The strobilurine fungicides. Pest Manag Sci 58:649–662.

    Article  PubMed  CAS  Google Scholar 

  • Berry EA, Guergova-Kuras M, Huang LS, Crofts AR (2000) Structure and function of cytochrome bc complexes. Annu Rev Biochem 69:1005–1075.

    Article  PubMed  CAS  Google Scholar 

  • Bianchi C, Genova ML, Parenti Castelli G, Lenaz G (2004). The mitochondrial respiratory chain is partially organized in a supercomplex assembly: kinetic evidence using flux control analysis. J Biol Chem 279:36562–36569.

    Article  PubMed  CAS  Google Scholar 

  • Brandt U (1999) Proton translocation in the respiratory chain involving ubiquinone – a hypothetical semiquinone switch mechanism for complex I. Biofactors 9:95–101.

    Article  PubMed  CAS  Google Scholar 

  • Brandt U, Haase U, Schägger H, von Jagow G (1991) Significance of the “Rieske” iron–sulfur protein for formation and function of the ubiquinol-oxidation pocket of mitochondrial cytochrome c reductase (bc1 complex). J Biol Chem 266:19958–19964.

    PubMed  CAS  Google Scholar 

  • Brandt U, Schägger H, von Jagow G (1988) Characterisation of binding of the methoxyacrylate inhibitors to mitochondrial cytochrome c reductase. Eur J Biochem 173:499–506.

    Article  PubMed  CAS  Google Scholar 

  • Crofts AR (2004) The cytochrome bc1 complex: function in the context of structure. Annu Rev Physiol 66:689–733.

    Article  PubMed  CAS  Google Scholar 

  • Crofts AR, Berry EA (1998) Structure and function of the cytochrome bc1 complex of mitochondria and photosynthetic bacteria. Curr Opin Struct Biol 8:501–509.

    Article  PubMed  CAS  Google Scholar 

  • Darrouzet E, Dupuis A (1997) Genetic evidence for the existence of two quinone related inhibitor binding sites in NADH-CoQ reductase. Biochim Biophys Acta 1319:1–4.

    Article  PubMed  CAS  Google Scholar 

  • Darrouzet E, Issartel JP, Lunardi J, Dupuis A (1998) The 49-kDa subunit of NADH-ubiquinone oxidoreductase (Complex I) is involved in the binding of piericidin and rotenone, two quinone-related inhibitors. FEBS Lett 431:34–38.

    Article  PubMed  CAS  Google Scholar 

  • Degli Esposti M (1998) Inhibitors of NADH-ubiquinone reductase: an overview. Biochim Biophys Acta 1364:222–235.

    Article  PubMed  CAS  Google Scholar 

  • Degli Esposti M, Ghelli A, Crimi M, Estornell E, Fato R, Lenaz G (1993) Complex I and complex III of mitochondria have common inhibitors acting as ubiquinone antagonists. Biochem Biophys Res Commun 190:1090–1096.

    Article  PubMed  CAS  Google Scholar 

  • Dekeyser MA (2005) Acaricide mode of action. Pest Manag Sci 61:103–110.

    Article  PubMed  CAS  Google Scholar 

  • Duarte M, Populo H, Videira A, Friedrich T, Schulte U (2002) Disruption of iron-sulphur cluster N2 from NADH: ubiquinone oxidoreductase by site-directed mutagenesis. Biochem J 364:833–839.

    Article  PubMed  CAS  Google Scholar 

  • Earley FG, Patel SD, Ragan I, Attardi G (1987) Photolabelling of a mitochondrially encoded subunit of NADH dehydrogenase with [3H]dihydrorotenone. FEBS Lett 219:108–112.

    Article  PubMed  CAS  Google Scholar 

  • Esser L, Quinn B, Li YF, Zhang M, Elberry M, Yu L, Yu CA, Xia D (2004) Crystallographic studies of quinol oxidation site inhibitors: a modified classification of inhibitors for the cytochrome bc1 complex. J Mol Biol 341:281–302.

    Article  PubMed  CAS  Google Scholar 

  • Friedrich T (1998) The NADH:ubiquinone oxidoreductase (complex I) from Escherichia coli. Biochim Biophys Acta 1364:134–146.

    Article  PubMed  CAS  Google Scholar 

  • Friedrich T, Böttcher B (2004) The gross structure of the respiratory complex I: a Lego System. Biochim Biophys Acta 1608:1–9.

    Article  PubMed  CAS  Google Scholar 

  • Friedrich T, Ohnishi T, Forche E, Kunze B, Jansen R, Trowitzsch W, Höfle G, Reichenbach H, Weiss H (1994a) Two binding sites for naturally occurring inhibitors in mitochondrial and bacterial NADH:ubiquinone oxidoreductase (complex I). Biochem Soc Trans 22:226–230.

    PubMed  CAS  Google Scholar 

  • Friedrich T, van Heek P, Leif H, Ohnishi T, Forche E, Kunze B, Jansen R, Trowitzsch-Kienast W, Höfle G, Reichenbach H, Weiss H (1994b) Two binding sites of inhibitors in NADH: ubiquinone oxidoreductase (complex I). Relationship of one site with the ubiquinone-binding site of bacterial glucose:ubiquinone oxidoreductase. Eur J Biochem 219:691–698.

    Article  PubMed  CAS  Google Scholar 

  • Fry M, Pudney M (1992) Site of action of the antimalarial hydroxynaphthoquinone, 2-[trans-4-(4′-chlorophenyl) cyclohexyl]-3-hydroxy-1, 4-naphthoquinone (566C80). Biochem Pharmacol 43:1545–1553.

    Article  PubMed  CAS  Google Scholar 

  • Gong X, Xie T, Yu L, Hesterberg M, Scheide D, Friedrich T, Yu CA (2003) The ubiquinone-binding site in NADH:ubiquinone oxidoreductase from Escherichia coli. J Biol Chem 278:25731–25737.

    Article  PubMed  CAS  Google Scholar 

  • Grigorieff N (1999) Structure of the respiratory NADH:ubiquinone oxidoreductase (complex I). Curr Opin Struct Biol 9:476–483.

    Article  PubMed  CAS  Google Scholar 

  • Guenebaut V, Schlitt A, Weiss H, Leonard K, Friedrich T (1998) Consistent structure between bacterial and mitochondrial NADH:ubiquinone oxidoreductase (complex I). J Mol Biol 276:105–112.

    Article  PubMed  CAS  Google Scholar 

  • Hedderich R (2004) Energy-converting [NiFe] hydrogenases from Archaea and extremophiles: ancestors of complex I. J Bioenerg Biomembr 36:65–75.

    Article  PubMed  CAS  Google Scholar 

  • Hirst J, Carroll J, Fearnley IM, Shannon RJ, Walker JE (2003) The nuclear encoded subunits of complex I from bovine heart mitochondria. Biochim Biophys Acta 1604:135–150.

    Article  PubMed  CAS  Google Scholar 

  • Hollingshaus JG (1987) Inhibition of mitochondrial electron transport by hydramethylnon: a new amidinohydrazone insecticide. Pestic Biochem Physiol 27:61–70.

    Article  CAS  Google Scholar 

  • Hollingworth RM, Ahammadsahib KI (1995) Inhibitors of respiratory complex I: mechanisms, pesticidal actions and toxicology. Rev Pestic Toxicol 3:277–302.

    CAS  Google Scholar 

  • Holt PJ, Morgan DJ, Sazanov LA (2003) The location of NuoL and NuoM subunits in the membrane domain of the Escherichia coli complex I: implications for the mechanism of proton pumping. J Biol Chem 278:43114–43120.

    Article  PubMed  CAS  Google Scholar 

  • Hunte C (2001) Insights from the structure of the yeast cytochrome bc1 complex: crystallization of membrane proteins with antibody fragments. FEBS Lett 504:126–132.

    Article  PubMed  CAS  Google Scholar 

  • Hunte C, Palsdottir H, Trumpower BL (2003) Protonmotive pathways and mechanisms in the cytochrome bc1 complex. FEBS Lett 545:39–46.

    Article  PubMed  CAS  Google Scholar 

  • Jewess PJ (1994) Insecticides and acaricides which act at the rotenone-binding site of mitochondrial NADH:ubiquinone oxidoreductase; competitive displacement studies using a 3H-labelled rotenone analogue. Biochem Soc Trans 22:247–251.

    PubMed  CAS  Google Scholar 

  • Jewess PJ, Chamberlain K, Boogaard AB, Devonshire AL, Khambay BP (2002) Insecticidal 2-hydroxy-3-alkyl-1, 4-naphthoquinones: correlation of inhibition of ubiquinol cytochrome c oxidoreductase (complex III) with insecticidal activity. Pest Manag Sci 58:243–247.

    Article  PubMed  CAS  Google Scholar 

  • Kashani-Poor N, Zwicker K, Kerscher S, Brandt U (2001) A central functional role for the 49-kDa subunit within the catalytic core of mitochondrial complex I. J Biol Chem 276: 24082–24087.

    Article  PubMed  CAS  Google Scholar 

  • Kessl JJ, Lange BB, Merbitz-Zahradnik T, Zwicker K, Hill P, Meunier B, Palsdottir H, Hunte C, Meshnik S, Trumpower BL (2003) Molecular basis for atovaquone binding to the cytochrome bc1 complex. J Biol Chem 278:31312–31318.

    Article  PubMed  CAS  Google Scholar 

  • Khambay BP, Batty D, Jewess PJ, Bateman GL, Hollomon DW (2003) Mode of action and pesticidal activity of the natural product dunnione and of some analogues. Pest Manag Sci 59:174–182.

    Article  PubMed  CAS  Google Scholar 

  • Khambay BPS, Batty D, Beddie DG, Denholm I, Cahill MR (1997) A new group of plant-derived naphthoquinone pesticides. Pestic Sci 50:291–296.

    Article  CAS  Google Scholar 

  • Kinoshita S, Koura Y, Kariya H, Ohsaki N, Watanabe T (1999) AKD-2023: a novel miticide. Biological activity and mode of action. Pestic Sci 55:659–660.

    Article  CAS  Google Scholar 

  • Koura Y, Kinoshita S, Takasuka K, Koura S, Osaki N, Matsumoto S, Miyoshi H (1998) Respiratory inhibition of acaricide AKD-2023 and its deacetyl metabolite. Nippon Noyaku Gakkaishi 23:18–21.

    CAS  Google Scholar 

  • Lancaster CR (2002) Succinate:quinone oxidoreductases: an overview. Biochim Biophys Acta 1553:1–6.

    Article  PubMed  CAS  Google Scholar 

  • Lindell SD, Ort O, Lümmen P, Klein R (2004) The design and synthesis of novel inhibitors of NADH:ubiquinone oxidoreductase. Bioorg Med Chem Lett 14:511–514.

    Article  PubMed  CAS  Google Scholar 

  • Lümmen P (1998) Complex I inhibitors as insecticides and acaricides. Biochim Biophys Acta 1364:287–296.

    Article  PubMed  Google Scholar 

  • Lümmen P (1999) Biochemical aspects of N-heterocyclic complex-I inhibitors with insecticidal activity. Biochem Soc Trans 27:602–606.

    PubMed  Google Scholar 

  • Michel H, Behr J, Harrenga A, Kannt A (1998) Cytochrome c oxidase: structure and spectroscopy. Annu Rev Biophys Biomol Struct 27:329–356.

    Article  PubMed  CAS  Google Scholar 

  • Miyoshi H (2001) Probing the ubiquinone reduction site in bovine mitochondrial complex I using a series of synthetic ubiquinones and inhibitors. J Bioenerg Biomembr 33:223–231.

    Article  PubMed  CAS  Google Scholar 

  • Nakamaru-Ogiso E, Sakamoto K, Matsuno-Yagi A, Miyoshi H, Yagi T (2003) The ND5 subunit was labeled by a photoaffinity analogue of fenpyroximate in bovine mitochondrial complex I. Biochemistry 42:746–754.

    Article  PubMed  CAS  Google Scholar 

  • Okun JG, Lümmen P, Brandt U (1999) Three classes of inhibitors share a common binding domain in mitochondrial complex I (NADH:ubiquinone oxidoreductase). J Biol Chem 274:2625–2630.

    Article  PubMed  CAS  Google Scholar 

  • Palsdottir H, Lojero CG, Trumpower BL, Hunte C (2003) Structure of the yeast cytochrome bc1 complex with a hydroxyquinone anion Qo site inhibitor bound. J Biol Chem 278:31303–31311.

    Article  PubMed  CAS  Google Scholar 

  • Phillips WG, Rejda-Heath JM (1993) Thiazole carboxanilide fungicides: a new structure-activity relationship for succinate dehydrogenase inhibitors. Pestic Sci 38:1–7.

    Article  CAS  Google Scholar 

  • Pilkington SJ, Arizmendi JM, Fearnley IM, Runswick MJ, Skehel JM, Walker JE (1993) Structural organization of complex I from bovine mitochondria. Biochem Soc Trans 21:26–31.

    PubMed  CAS  Google Scholar 

  • Rich PR, Fisher N (1999) Generic features of quinone-binding sites. Biochem Soc Trans 27:561–565.

    PubMed  CAS  Google Scholar 

  • Rich PR (1996) Quinone binding sites of membrane proteins as targets for inhibitors. Pestic Sci 47:287–296.

    Article  CAS  Google Scholar 

  • Rich PR (2003) The molecular machinery of Keilin's respiratory chain. Biochem Soc Trans 31:1095–1105.

    Article  PubMed  CAS  Google Scholar 

  • Rich PR (2004) The quinone chemistry of bc complexes. Biochim Biophys Acta 1658:165–171.

    Article  PubMed  CAS  Google Scholar 

  • Roehl F, Sauter H (1994) Species dependence of mitochondrial respiration inhibition by strobilurin analogues. Biochem Soc Trans 22:63S.

    PubMed  CAS  Google Scholar 

  • Sauter H, Steglich W, Anke T (1999) Strobilurins: evolution of a new class of active substances. Angew Chem Int Ed 38:1329–1349.

    Article  CAS  Google Scholar 

  • Schägger H (2002) Respiratory chain supercomplexes of mitochondria and bacteria. Biochim Biophys Acta 1555:154–159.

    Article  PubMed  Google Scholar 

  • Schägger H, de Coo R, Bauer MF, Hofmann S, Godinot C, Brandt U (2004) Significance of respirasomes for the assembly/stability of human respiratory chain complex I. J Biol Chem 279:36349–36353.

    Article  PubMed  Google Scholar 

  • Schuler F, Casida JE (2001a) Functional coupling of PSST and ND1 subunits in NADH:ubiquinone oxidoreductase established by photoaffinity labeling. Biochim Biophys Acta 1506:79–87.

    Article  PubMed  CAS  Google Scholar 

  • Schuler F, Casida JE (2001b) The insecticide target in the PSST subunit of complex I. Pest Manag Sci 57:932–940.

    Article  PubMed  CAS  Google Scholar 

  • Singer TP, Ramsay RR (1994) The reaction sites of rotenone and ubiquinone with mitochondrial NADH dehydrogenase. Biochim Biophys Acta 1187:198–202.

    Article  PubMed  CAS  Google Scholar 

  • Slater EC (2003) Keilin, cytochrome, and the respiratory chain. J Biol Chem 278:16455–16461.

    Article  PubMed  CAS  Google Scholar 

  • Steuber J (2003) The C-terminally truncated NuoL subunit (ND5 homologue) of the Na+-dependent complex I from Escherichia coli transports Na+. J Biol Chem 278:26817–26822.

    Article  PubMed  CAS  Google Scholar 

  • Steuber J, Schmid C, Rufibach M, Dimroth P (2000) Na+ translocation by complex I (NADH:quinone oxidoreductase) of Escherichia coli. Mol Microbiol 35:428–434.

    Article  PubMed  CAS  Google Scholar 

  • Sun F, Huo X, Zhai Y, Wang A, Xu J, Su D, Bartlam M, Rao Z (2005) Crystal structure of mitochondrial respiratory membrane protein complex II. Cell 121:1043–1057.

    Article  PubMed  CAS  Google Scholar 

  • Tsukihara T, Aoyama H, Yamashita E, Tomizaki T, Yamaguchi H, Shinzawa-Itoh K, Nakashima R, Yaono R, Yoshikawa S (1996) The whole structure of the 13-subunit oxidized cytochrome c oxidase at 2.8 A. Science 272:1136–1144.

    Article  PubMed  CAS  Google Scholar 

  • Walker JE, Arizmendi JM, Dupuis A, Fearnley IM, Finel M, Medd SM, Pilkington SJ, Runswick MJ, Skehel JM (1992) Sequences of 20 subunits of NADH:ubiquinone oxidoreductase from bovine heart mitochondria. Application of a novel strategy for sequencing proteins using the polymerase chain reaction. J Mol Biol 226:1051–1072.

    Article  PubMed  CAS  Google Scholar 

  • Xia D, Yu CA, Kim H, Xia JZ, Kachurin AM, Zhang L, Yu L, Deisenhofer J (1997) Crystal structure of the cytochrome bc1 complex from bovine heart mitochondria. Science 277:60–66.

    Article  PubMed  CAS  Google Scholar 

  • Yagi T, Matsuno-Yagi A (2003) The proton-translocating NADH-quinone oxidoreductase in the respiratory chain: the secret unlocked. Biochemistry 42:2266–2274.

    Article  PubMed  CAS  Google Scholar 

  • Yano T (2002) The energy-transducing NADH: quinone oxidoreductase, complex I. Mol Aspects Med 23:345–368.

    Article  PubMed  CAS  Google Scholar 

  • Yano T, Dunham WR, Ohnishi T (2005) Characterization of the ΔμH+-sensitive ubisemiquinone species (SQNf) and the interaction with cluster N2: new insight into the energy-coupled electron transfer in complex I. Biochemistry 44:1744–1754.

    Article  PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Bayer CropScience AG, Alfred Nobel Str. 50, 40789, Monheim, Germany

    Peter Lümmen

Authors
  1. Peter Lümmen
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Department of Entomology, Agricultural Research Organization, The Volcani Center, 50250, Bet Dagan, Israel

    Isaac Ishaaya

  2. Department of Entomology, Agricultural Research Organization, Gilat Research Center, 85280, M.P. Negev, Israel

    A. Rami Horowitz

  3. Bayer CropScience AG, Research Insecticides Biology, Alfred-Nobel Str. 50, 40789, Monheim, Germany

    Ralf Nauen

Rights and permissions

Reprints and permissions

Copyright information

© 2007 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Lümmen, P. (2007). Mitochondrial Electron Transport Complexes as Biochemical Target Sites for Insecticides and Acaricids. In: Ishaaya, I., Horowitz, A.R., Nauen, R. (eds) Insecticides Design Using Advanced Technologies. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-46907-0_8

Download citation

Publish with us

Policies and ethics

Search

Navigation