Amilorides bind to the quinone binding pocket of bovine mitochondrial complex i

Biochemistry

Volumn 54, Issue 17, 2015, Pages 2739-2746

  Murai, Masatoshi ^a   Murakami, Sonomi ^a   Ito, Takeshi ^a   Miyoshi, Hideto ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING SITES; HYDROCARBONS; MITOCHONDRIA; PHOTOREACTIVITY; SODIUM; SYNTHESIS (CHEMICAL);

ACCESSORY SUBUNITS; EXPERIMENTAL EVIDENCE; MITOCHONDRIAL COMPLEX; MITOCHONDRIAL NADH; PHOTOAFFINITY LABELING; PROTEOMIC ANALYSIS; STRUCTURAL FEATURE; SUBMITOCHONDRIAL PARTICLES;

MAMMALS;

ALKYNE; AMILORIDE; BULLATACIN; CUPROUS ION; FENPYROXIMATE; PROTEIN INHIBITOR; QUINAZOLINE; QUINONE DERIVATIVE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE DEHYDROGENASE (UBIQUINONE); UNCLASSIFIED DRUG; ACID SENSING ION CHANNEL BLOCKING AGENT; BENZOQUINONE; BENZOQUINONE DERIVATIVE; PHOTOAFFINITY LABELING;

AMINO TERMINAL SEQUENCE; ARTICLE; CATALYSIS; CLICK CHEMISTRY; COVALENT BOND; DRUG BINDING SITE; ENZYME ACTIVE SITE; ENZYME INHIBITION; ENZYME SUBSTRATE COMPLEX; HEART MITOCHONDRION; NONHUMAN; PHOTOAFFINITY LABELING; PRIORITY JOURNAL; PROTEOMICS; SUBMITOCHONDRIAL PARTICLE; AMINO ACID SEQUENCE; ANIMAL; BINDING SITE; BOVINE; CHEMISTRY; METABOLISM; MOLECULAR GENETICS;

BACTERIA (MICROORGANISMS); BOVINAE;

ACID SENSING ION CHANNEL BLOCKERS; AMILORIDE; AMINO ACID SEQUENCE; ANIMALS; BENZOQUINONES; BINDING SITES; CATTLE; ELECTRON TRANSPORT COMPLEX I; MOLECULAR SEQUENCE DATA; PHOTOAFFINITY LABELS; SUBMITOCHONDRIAL PARTICLES;

EID: 84928944969     PISSN: 00062960     EISSN: 15204995     Source Type: Journal    
DOI: 10.1021/acs.biochem.5b00187     Document Type: Article

References (37)

1. Brandt, U. (2006) Energy converting NADH:quinone oxidoreductase (complex I) Annu. Rev. Biochem. 75, 69-92
2. Hirst, J. (2013) Mitochondrial complex I Annu. Rev. Biochem. 82, 551-575
3. Carroll, J., Fearnley, I. M., Skehel, J. M., Shannon, R. J., Hirst, J., and Walker, J. E. (2006) Bovine complex I is a complex of 45 different subunits J. Biol. Chem. 43, 32724-32727
4. Baradaran, R., Berrisford, J. M., Minhas, G. S., and Sazanov, L. A. (2013) Crystal structure of the entire respiratory complex I Nature 494, 443-448
5. Zickermenn, V., Wirth, C., Nasiri, H., Siegmund, K., Schwalbe, H., Hunte, C., and Brandt, U. (2015) Mechanistic insight from the crystal structure of mitochondrial complex I Science 347, 44-49
6. Efremov, R. G. and Sazanov, L. A. (2011) Structure of the membrane domain of respiratory complex I Nature 476, 414-420
7. Mathiesen, C. and Hägerhäll, C. (2002) Transmembrane topology of the NuoL, M, and N subunits of NADH:quinone oxidoreductase and their homologues among membrane-bound hydrogenases and bona fide antiporters Biochim. Biophys. Acta 1556, 121-132
8. Roberts, P. G. and Hirst, J. (2012) The deactive from of respiratory complex I from mammalian mitochondria is a Na+/H+ antiporter J. Biol. Chem. 287, 34743-34751
9. Tocilescu, M. A., Zickermann, V., Zwicker, K., and Brandt, U. (2010) Quinone binding and reduction by respiratory complex I Biochim. Biophys. Acta 1797, 1883-1890
10. Murai, M., Ishihara, A., Nishioka, T., Yagi, T., and Miyoshi, H. (2007) The ND1 subunit constructs the inhibitor binding domain in bovine heart mitochondrial complex I Biochemistry 46, 6409-6416
11. Murai, M., Sekiguchi, K., Nishioka, T., and Miyoshi, H. (2009) Characterization of the inhibitor binding site in mitochondrial NADH-ubiquinone oxidoreductase by photoaffinity labeling using a quinazoline-type inhibitor Biochemistry 48, 688-698
12. Sekiguchi, K., Murai, M., and Miyoshi, H. (2009) Exploring the binding site of acetogenin in the ND1 subunit of bovine mitochondrial complex I Biochim. Biophys. Acta 1787, 1106-1111
13. Kakutani, N., Murai, M., Sakiyama, N., and Miyoshi, H. (2010) Exploring the binding site of Dlac-acetogenin in bovine heart mitochondrial NADH-ubiquinone oxidoreductase Biochemistry 49, 4794-4803
14. Murai, M., Mashimo, Y., Hirst, J., and Miyoshi, H. (2011) Exploring interactions between the 49 kDa and ND1 subunits in mitochondrial NADH-ubiquinone oxidoreductase (complex I) by photoaffinity labeling Biochemistry 50, 6901-6908
15. Shiraishi, Y., Murai, M., Sakiyama, N., Ifuku, K., and Miyoshi, H. (2012) Fenpyroximate binds to the interface between PSST and 49 kDa subunits in mitochondrial NADH-ubiquinone oxidoreductase Biochemistry 51, 1953-1963
16. Tocilescu, M. A., Fendel, U., Zwicker, K., Kerscher, S., and Brandt, U. (2007) Exploring the ubiquinone binding cavity of respiratory complex I J. Biol. Chem. 282, 29514-29520
17. Fendel, U., Tocilescu, M. A., Kerscher, S., and Brandt, U. (2008) Exploring the inhibitor binding pocket of respiratory complex I Biochim. Biophys. Acta 1777, 660-665
18. Kleyman, T. R. and Cragoe, E. J., Jr. (1988) Amiloride and its analogs as tools in the study of ion transport J. Membr. Biol. 105, 1-21
19. Putney, L. K., Denker, S. P., and Barber, D. L. (2002) The changing face of the Na+/H+ exchanger, NHE: Structure, regulation, and cellular actions Annu. Rev. Pharmacol. Toxicol. 42, 527-552
20. Nakamaru-Ogiso, E., Seo, B. B., Yagi, T., and Matsuno-Yagi, A. (2003) Amiloride inhibition of the proton-translocating NADH-quinone oxidoreductase of mammals and bacteria FEBS Lett. 549, 43-46
21. Stolpe, S. and Friedrich, T. (2004) The Escherichia coli NADH-ubiquinone oxidoreductase (complex I) is a primary proton pump but may be capable of secondary sodium antiport J. Biol. Chem. 279, 18377-18383
22. Murai, M., Habu, S., Murakami, S., Ito, T., and Miyoshi, H. (2015) Production of new amilories as potent inhibitors of mitochondrial respiratory complex I Biosci. Biotechnol. Biochem. 10.1080/09168451.2015.1010479
23. Ino, T., Nishioka, T., and Miyoshi, H. (2003) Characterization of inhibitor binding sites of mitochondrial complex I using fluorescent inhibitor Biochim. Biophys. Acta 1605, 15-20
24. Masuya, T., Murai, M., Ifuku, K., Morisaka, H., and Miyoshi, H. (2014) Site-specific chemical labeling of mitochondrial respiratory complex I through ligand-directed tosylate chemistry Biochemistry 53, 2307-2317
25. Matsuno-Yagi, A. and Hatefi, Y. (1985) Studies on the mechanism of oxidative phosphorylation J. Biol. Chem. 260, 14424-14427
26. Murai, M., Ichimaru, N., Abe, M., Nishioka, T., and Miyoshi, H. (2006) Mode of inhibitory action of δlac-acetogenins, a new class of inhibitors of bovine heart mitochondrial complex I Biochemistry 45, 9778-9787
27. Laemmli, U. K. (1970) Cleavage of structural proteins during the assembly of the head of bacteriophage T4 Nature 227, 680-685
28. Schägger, H. (2006) Tricine-SDS-PAGE Nat. Protoc. 1, 16-21
29. Rais, I., Kara, M., and Schägger, H. (2004) Two-dimensional electrophoresis for the isolation of integral membrane proteins and mass spectrometric identification Proteomics 4, 2567-2571
30. Cleveland, D. W., Fishcher, M. W., Kirschner, M. W., and Laemmli, U. K. (1977) Peptide mapping by limited proteolysis in sodium dodecyl sulfate and analysis by gel electrophoresis J. Biol. Chem. 252, 1102-1106
31. Kmita, K. and Zickermann, V. (2013) Accessory subunits of mitochondrial complex I Biochem. Soc. Trans. 41, 1272-1279
32. Vinothkumar, K. R., Zhu, P., and Hirst, J. (2014) Architecture of mammalian respiratory complex I Nature 515, 80-84
33. Earley, F. G. P., Patel, S. D., Ragan, C. I., and Attardi, G. (1987) Photolabeling of a mitochondrially encoded subunit of NADH dehydrogenase with [3H]dihydrorotenone FEBS Lett. 219, 108-113
34. Schuler, F., Yano, T., Bernardo, S. D., Yagi, T., Yankovskaya, V., Singer, T. P., and Casida, J. E. (1999) NADH-quinone oxidoreductase: PSST subunit couples electron transfer from iron-sulfur cluster N2 to quinone Proc. Natl. Acad. Sci. U.S.A. 96, 4149-4153
35. Masuya, T., Murai, M., Morisaka, H., and Miyoshi, H. (2014) Pinpoint chemical modification of Asp160 in the 49 kDa subunit of bovine mitochondrial complex I via a combination of ligand-directed tosyl chemistry and click chemistry Biochemistry 53, 7816-7823
36. Steuber, J. (2003) The C-terminally trunctuated NuoL subunit (ND5 homologue) of the Na+-dependent complex I from Escherichia coli transports Na+ J. Biol. Chem. 278, 26817-26822
37. Davies, K. and Solioz, M. (1992) Assessment of uncoupling by amiloride analogues Biochemistry 31, 8055-8058