Crucial structural factors and mode of action of polyene amides as inhibitors for mitochondrial NADH - Ubiquinone oxidoreductase (complex i)

Biochemistry

Volumn 46, Issue 36, 2007, Pages 10365-10372

  Yoshida, Takehiko ^a   Murai, Masatoshi ^a   Abe, Masato ^a   Ichimaru, Naoya ^a   Harada, Toshiyuki ^a   Nishioka, Takaaki ^a   Miyoshi, Hideto ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL MEMBRANES; ENZYME INHIBITION; FUNCTIONAL GROUPS; HYDROGEN BONDS; LIPIDS; SYNTHESIS (CHEMICAL);

LIPID MEMBRANE PHASE; MEMBRANE SURFACE; POLYENE AMIDES;

AMIDES;

AMIDE; NATURAL PRODUCT; POLYENE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE DEHYDROGENASE (UBIQUINONE); DRUG DERIVATIVE; ENZYME INHIBITOR; METHANE; METHYL RADICAL; PIERICIDIN A; PYRIDINE DERIVATIVE; SUPEROXIDE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; COW; DRUG INHIBITION; DRUG SYNTHESIS; GEOMETRY; HEART; HYDROGEN BOND; HYDROPHOBICITY; LIPID MEMBRANE; MITOCHONDRION; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; ANIMAL; CATTLE; CHEMISTRY; CONFORMATION; DRUG ANTAGONISM; DRUG EFFECT; ELECTRON; ENZYMOLOGY; HEART MITOCHONDRION; METABOLISM;

BOVINAE;

AMIDES; ANIMALS; CATTLE; ELECTRON TRANSPORT COMPLEX I; ELECTRONS; ENZYME INHIBITORS; METHANE; MITOCHONDRIA, HEART; MOLECULAR CONFORMATION; POLYENES; PYRIDINES; STRUCTURE-ACTIVITY RELATIONSHIP; SUPEROXIDES;

EID: 35148848338     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi7010306     Document Type: Article

References (45)

1. Jansen, K. G. R., Reifenstahl, G., Höfle, G., irshik, H., Kunze, B., Reichenbach, H., and Thierbach, G. (1983) The myxalamides, new antibiotics from Myxococcus xanthus (myxobacterales), J. Antibiot. 36, 1150-1157.
2. Andrus, M. B., and Lepore, S. D. (1997) Synthesis of stipiamide and a new multidmg resistance reversal agent, 6,7-dehydrostipiamide, J. Am. Chem. Soc. 119, 2327-2328.
3. Kundim, B. A., Utou, Y., Sakagami, Y., Fudou, R., Yamanaka, S., and Ojika, M. (2004) Novel antifungal polyene amides from the myxobacterium Cystobacter fuscus: isolation, antifungal activity and absolute structure determination, Tetrahedron 60, 10217-10221.
4. Walker, J. E. (1992) The NADH-ubiquinone oxidoreductase (complex I) of respiratory chains, Q. Rev. Biophys. 25, 253-324.
5. Andrus, M. B., Lepore, S. D., and Turner, T. M. (1997) Total synthesis of stipiamide and designed polyenes as new agents for the reversal of multidrug resistance, J. Am. Chem. Soc. 119, 12159-12169.
6. Mapp, A. K., and Heathcock, C. H. (1999) Total synthesis of myxalamide A, J. Org. Chem. 64, 23-27.
7. 2, Org. Lett. 1, 1713-1715.
8. Coleman, R. S., Lu, X., and Modolo, I. (2007) Total synthesis of 2′-O-methylmyxalamide D and (6E)-2′-O- methylmyxalamide D, J. Am. Chem. Soc. 129, 3826-3827.
9. Friedrich, T., Van Heek, P., Leif, H., Ohnishi, T., Forche, E., Kunze, B., Jansen, R., Trowitzsch-Kienast, W., Höfle, G., Reichenbach, H., and Weiss, H. (1994) Two binding sites of inhibitors in NADH-ubiquinone oxidoreductase (complex I), Eur. J. Biochem. 219, 691-698.
10. Yagi, T., and Matsuno-Yagi, A. (2003) The proton-translocating NADH-quinone oxidoreductase in the respiratory chain: the secret unlocked, Biochemistry 42, 2266-2274.
11. Hirst, J. (2005) Energy transduction by respiratory complex I; an evaluation of current knowledge, Biochem. Soc. Trans., 525-529.
12. Brandt, U. (2006) Energy converting NADH-quinone oxidoreductase (complex I), Annu. Rev. Biochem. 75, 69-92.
13. Satoh, T., Miyoshi, H., Sakamoto, K., and Iwamura, H. (1996) Comparison of the inhibitory action of synthetic capsaicin analogues with various NADH-ubiquinone oxidoreductases, Biochim. Biophys. Acta 1273, 21-30.
14. Yabunaka, H., Kenmochi, A., Nakatogawa, A., Sakamoto, K., and Miyoshi, H. (2002) Hybrid ubiquinone; novel inhibitor of mitochondrial complex I, Biochim. Biophys. Acta 1556, 106-112.
15. Ueno, H., Miyoshi, H., Ebisui, K., and Iwamura, H. (1994) Comparison of the inhibitory action of natural rotenone and its stereoisomers with various NADH-ubiquinone reductases, Eur. J. Biochem. 225, 411-417.
16. Ueno, H., Miyoshi, H., Inoue, M., Niidome, Y., and Iwamura, H. (1996) Stmctural factors of rotenone required for inhibition of various NADH-ubiquinone oxidoreductases, Biochim. Biophys. Acta 1276, 195-202.
17. Kuwabara, K., Takada, M., Iwata, J., Tatsumoto, K., Sakamoto, K., Iwamura, H., and Miyoshi, H. (2000) Design syntheses and mitochondrial complex I inhibitory activity of novel acetogenin mimics, Eur. J. Biochem. 267, 2538-2546.
18. Takada, M., Kuwabara, K., Nakato, H., Tanaka, A., Iwamura, H., and Miyoshi, H. (2000) Definition of crucial stmctural factors of acetogenins, potent inhibitors of mitochondrial complex I, Biochim. Biophys. Acta 1460, 302-310.
19. Abe, M., Murai, M., Ichimaru, N., Kenmochi, A., Yoshida, T., Kubo, A., Kimura, Y., Moroda, A., Makabe, H., Nishioka, T., and Miyoshi, H. (2005) Dynamic function of the alkyl spacer of acetogenins in their inhibitory action with mitochondrial complex I (NADH-Ubiquinone Oxidoreductase), Biochemistry 44, 14898-14906.
20. Kim, Y. J., Furuhata, K., Yamanaka, S., Fudo, R., and Seto, H. (1991) Isolation and structural elucidation of stipiamide, a new antibiotic effective to multidrog-resistant cancer cells, J. Antibiot. 44, 553-556.
21. Andrus, M. B., Turner, T. M., Asgari, D., and Li, W. (1999) The synthesis and evaluation of a solution-phase indexed combinatorial library of non-natural polyenes for multidrug resistance reversal, J. Org. Chem. 64, 2978-2979.
22. Andrus, M. B., Turner, T. M., Sauna, Z. E., and Ambudkar, S. V. (2000) The synthesis and evaluation of a solution phase indexed combinatorial library of non-natural polyenes for reversal of P-glycoprotein mediated multidrug resistance, J. Org. Chem. 65, 4973-4983.
23. Sauna, Z. E., Andms, M. B., Turner, T. M., and Ambudkar, S. V. (2004) Biochemical basis of polyvalency as a strategy for enhancing the efficacy of P-glycoprotein (ABCB1) modulators: stipiamide homodimers separated with defined-length spacer reverse dmg efflux with greater efficacy, Biochemistry 43, 2262-2271.
24. Murai, M., Ishihara, A., Nishioka, T., Yagi, T., and Miyoshi, H. (2007) The ND1 subunit constmcts inhibitor binding domain in bovine heart mitochondrial complex I, Biochemistry 46, 6409-6416.
25. Matsuno-Yagi, A., and Hatefi, Y. (1985) Studies on the mechanism of oxidative phosphorylation, J. Biol. Chem. 260, 14424-14427.
26. Boveris, A. (1984) Determination of the production of superoxide radicals and hydrogen peroxide in mitochondria, Methods Enzymol 105, 429-435.
27. + by succinate, Methods Enzymol 10, 729-738.
28. Laemmli, U. K. (1970) Cleavage of stmctural proteins during the assembly of the head of bacteriophage T4, Nature 227, 680-685.
29. Miyoshi, H., Ohshima, M., Shimada, H., Akagi, T., Iwamura, H., and McLaughlin, J. L. (1998) Essential stmctural factors of annonaceous acetogenins as potent inhibitors of mitochondrial complex I, Biochim. Biophys. Acta 1365, 443-452.
30. 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.
31. Herrero, A., and Barja, G. (2000) Localization of the site of oxygen radical generation inside the complex I of heart and nonsynaptic brain mammalian mitochondria, J. Bioenerg. Biomembr. 32, 609-615.
32. Liu, Y., Fiskum, G., and Schubert, D. (2002) Generation of reactive oxygen species by the mitochondrial electron transport chain, J. Neurochem. 80, 780-787.
33. Lambert, A. J., and Brand, M. D. (2004) Superoxide production by NADH ubiquinone oxidoreductase (complex I) depends on the pH gradient across the mitochondrial inner membrane, Biochem. J. 382, 511-517.
34. Lambert, A. J., and Brand, M. D. (2004) Inhibitors of the quinone-shy; binding site allow rapid superoxide production from mitochondrial NADH-ubiquinone oxidoreductase (complex I), J. Biol. Chem. 279, 39414-39420.
35. Okun, J. G., Lümmen, P., and Brandt, U. (1999) Three classes of inhibitor share a common binding domain in mitochondrial complex I (NADH-ubiquinone oxidoreductase), J. Biol. Chem. 274, 2625-2630.
36. Sazanov, L. A., and Hinchliffe, P. (2006) Structure of the hydrophilic domain of respiratory complex I from Thermus thermophilus, Science 311, 1430-1436.
37. Hamada, T., Ichimaru, N., Abe, M., Fujita, D., Kenmochi, A., Nishioka, T., Zwicker, K., Brandt, U., and Miyoshi, H. (2004) Synthesis and inhibitory action of novel acetogenin mimics with bovine heart mitochondrial complex I, Biochemistry 43, 3651-3658.
38. Ichimam, N., Murai, M., Abe, M., Hamada, T., Yamada, Y., Makino, S., Nishioka, T., Makabe, H., Makino, A., Kobayashi, T., and Miyoshi, H. (2005) Synthesis and inhibition mechanism of Δlac-acetogenins: a novel type of inhibitor of bovine heart mitochondrial complex I, Biochemistry 44, 816-825.
39. 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.
40. Nakamaru-Ogiso, E., Sakamoto, K., Matsuno-Yagi, A., Miyoshi, H., and Yagi, T. (2003) The ND5 subunit was labeled by a photoaffinity analogue of fenpyroximate in bovine mitochondrial complex I, Biochemistry 42, 746-754.
41. Von, Jagow, G., and Link, T. A. (1986) Use of specific inhibitors on the mitochondrial bc complex, Methods Enzymol. 126, 253-271.
42. Esser, L., Quinn, B., Li, Y.-F., Zhang, M., Elberry, M., Yu, L., Yu, C.-A., and Xia, D. (2004) Crystallographic studies of quinol oxidation site inhibitors: a modified classification of inhibitors for the cytochrome bc complex, J. Mol. Biol. 341, 281-302.
43. H+ on the interaction of rotenone with complex I of submitochondrial particles, Biochim. Biophys. Acta 1140, 169-174.
44. Schuler, F., and Casida, J. E. (2001) Functional coupling of PSST and ND1 sununits in NADH-ubiquinone oxidoreductase established by photoaffinity labeling, Biochim. Biophys. Acta 1506, 79-87.
45. Ohnishi, S. T., Ohnishi, T., Muranaka, S., Fujita, H., Kimura, H., Uemura, K., Yoshida, K., and Utsumi, K. (2005) A possible site of superoxide generation in the complex I segment of rat heart mitochondria, J. Bioenerg. Biomembr. 37, 1-15.