C75 [4-methylene-2-octyl-5-oxo-tetrahydro-furan-3-carboxylic acid] activates carnitine palmitoyltransferase-1 in isolated mitochondria and intact cells without displacement of bound malonyl CoA

Journal of Pharmacology and Experimental Therapeutics

Volumn 312, Issue 1, 2005, Pages 127-133

  Yang, Nengyu ^a   Kays, Joanne S ^a   Skillman, Tiffanie R ^a   Burris, Lorri ^a   Seng, Thomas W ^a   Hammond, Craig ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 METHYLENE 2 OCTYL 5 OXO TETRAHYDROFURAN 3 CARBOXYLIC ACID; [5 [2 (NAPHTHALEN 2 YLOXY)ETHOXY]THIOPHEN 2 YL]OXO ACETIC ACID; ACETIC ACID DERIVATIVE; ACETYL COENZYME A CARBOXYLASE; C 75; CARBOXYLIC ACID DERIVATIVE; CARNITINE PALMITOYLTRANSFERASE; ENZYME ACTIVATOR; ENZYME INHIBITOR; MALONYL COENZYME A; RO 250187; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG BINDING SITE; DRUG MECHANISM; ENZYME ACTIVATION; ENZYME ACTIVITY; ENZYME BINDING; ENZYME INACTIVATION; HEART MITOCHONDRION; LIVER CELL; MOUSE; NONHUMAN; PICHIA PASTORIS; PRIORITY JOURNAL; PROTEIN EXPRESSION;

4-BUTYROLACTONE; ANIMALS; CARNITINE O-PALMITOYLTRANSFERASE; ENZYME ACTIVATION; HUMANS; MALONYL COENZYME A; MITOCHONDRIA, HEART; RATS; RECOMBINANT PROTEINS; TUMOR CELLS, CULTURED; YEASTS;

EID: 11844282154     PISSN: 00223565     EISSN: None     Source Type: Journal    
DOI: 10.1124/jpet.104.074104     Document Type: Article

References (36)

1. Abu-Elheiga L, Matzuk MM, Abo-Hashema KAH, and Wakil SJ (2001) Continuous fatty acid oxidation and reduced fat storage in mice lacking acetyl-CoA carboxylase 2. Science (Wash DC) 291:2613-2616.
2. Abu-Elheiga L, Oh W, Kordari P, and Wakil SJ (2003) Acetyl-CoA carboxylase 2 mutant mice are protected against obesity and diabetes induced by high-fat/high-carbohydrate diets. Proc Natl Acad Sci USA 100:10207-10212.
3. Anderson RC (1998) Carnitine palmitoyltransferase: a viable target for the treatment of NIDDM? Curr Pharm Des 4:1-15.
4. Bavenholm PN, Pigon J, Saha AK, Ruderman NB, and Efendic S (2000) Fatty acid oxidation and the regulation of malonyl-CoA in human muscle. Diabetes 49:1078-1083.
5. Bremer J, Woldegiorgis G, Schalinske K, and Shrago E (1985) Carnitine palmitoyltransferase. Activation by palmitoyl-CoA and inactivation by malonyl-CoA. Biochim Biophys Acta 833:9-16.
6. Chien D, Dean D, Saha AK, Flatt J, and Ruderman NB (2000) Malonyl-CoA content and fatty acid oxidation in rat muscle and liver in vivo. Am J Physiol 279:E259-E265.
7. Cohen I, Kohl C, McGarry JD, Girard J, and Prip-Buus C (1998) The N-terminal domain of rat liver carnitine palmitoyltransferase 1 mediates import into the outer mitochondrial membrane and is essential for activity and malonyl-CoA sensitivity. J Biol Chem 273:29896-29904.
8. Cook GA, Mynatt RL, and Kashfi K (1994) Yonetani-Theorell analysis of hepatic carnitine palmitoyltransferase-1 inhibition indicates two distinct inhibitory binding sites. J Biol Chem 269:8803-8807.
9. Dobbins RL, Szczepaniak LS, Bentley B, Esser V, Myhill J, and McGarry JD (2001) Prolonged inhibition of muscle carnitine palmitoyltransferase-1 promotes intramuscular lipid accumulation and insulin resistance in rats. Diabetes 50:123-130.
10. Eaton S, Fukumoto K, Paladio Duran N, Pierro A, Spitz L, Quant PA, and Bartlett K (2001) Carnitine palmitoyltransferase 1 and the control of mycardial β-oxidation flux. Biochem Soc Trans 29:245-250.
11. Fraser F, Corstorphine CG, and Zammit VA (1997) Topology of carnitine palmitoyltransferase 1 in the mitochondrial outer membrane. Biochem J 323:711-718.
12. Gerth K, Bedorf N, Irschik H, Hofle G, and Reichenbach H (1994) The soraphens: a family of novel antifungal compounds from Sorangium cellulosum (Myxobacteria). I. Soraphen A1 alpha: fermentation, isolation, biological properties. J Antibiot 47:23-31.
13. Glick BJ and Pon LA (1995) Isolation of highly purified mitochondria from Saccharomyces cerevisiae. Methods Enzymol 260:213-223.
14. Gubler M and Mizhrahi J (2003) inventors, Hoffmann La Roche, assignee. Use of soraphen derivatives. Int patent application WO03011867. 2003 Feb 13.
15. Harwood HJ, Petras SF, Shelly LD, Zaccaro LM, Perry DA, Makowski MR, Hargrove DM, Martin KA, Tracey WR, Chapman JG, et al. (2003) Isozyme-nonselective N-substituted bipiperidylcarboxamide acetyl-CoA carboxylase inhibitors reduce tissue malonyl-CoA concentrations, inhibit fatty acid synthesis and increase fatty acid oxidation in cultured cells and in experimental animals. J Biol Chem 278:37099-37111.
16. Jackson VN, Cameron JM, Zammit VA, and Price NT (1999) Sequencing and functional expression of the malonyl-CoA-sensitive carnitine palmitoyltransferase from Drosophila melanogaster. Biochem J 341:483-489.
17. Jackson VN, Zammit VA, and Price NT (2000) Identification of positive and negative determinants of malonyl-CoA sensitivity and carnitine affinity within the amino termini of rat liver- and muscle type carnitine palmitoyltransferase 1. J Biol Chem 275:38410-38416.
18. Kashfi K, Mynatt RL, and Cook GA (1994) Hepatic carnitine palmitoyltransferase-1 has two independent inhibitory binding sites for regulation of fatty acid oxidation. Biochim Biophys Acta 1212:245-252.
19. Kim J-Y, Hickner RC, Cortright RL, Dohm GL, and Houmard JA (2000) Lipid oxidation is reduced in obese human skeletal muscle. Am J Physiol 279:E1039-E1044.
20. Kolodziej MP and Zammit VA (1990) Sensitivity of inhibition of rat liver mitochondrial outer-membrane carnitine palmitoyltransferase by malonyl-CoA to chemical-and temperature-induced changes in membrane fluidity. Biochem J 272:421-425.
21. Kuhajda FP, Pizer ES, Li JN, Mani NS, Frehywot BL, and Towsend CA (2000) Synthesis and antitumor activity of an inhibitor of fatty acid synthase. Proc Natl Acad Sci USA 97:3450-3454.
22. Loftus TM, Jaworsky DE, Frehywot BL, Towsend CA, Ronnett GV, Lane MD, and Kuhajda FP (2000) Reduced food intake and body weight in mice treated with fatty acid synthase inhibitors. Science (Wash DC) 288:2379-2381.
23. McGarry JD and Brown NF (1997) The mitochondrial carnitine palmitoyltransferase system: from concept to molecular analysis. Eur J Biochem 244:1-14.
24. McGarry JD and Brown NF (2000) Reconstitution of purified, active and malonyl-CoA sensitive rat liver carnitine palmitoyltransferase 1: relationship between membrane environment and malonyl-CoA sensitivity. Biochem J 349:179-187.
25. McGarry JD, Leatherman GF, and Foster DW (1978) Carnitine palmitoyltransferase I: the site of inhibition of hepatic fatty acid oxidation by malonyl CoA. J Biol Chem 253:4128-4136.
26. Napal L, Dai J, Treber M, Haro D, Marrero PF, and Woldegiorgis G (2003) A single amino acid change (substitution of the conserved Glu-590 with alanine) in the C-terminal domain of rat liver carnitine palmitoyltransferase I increases its malonyl-CoA sensitivity close to that observed with the muscle isoform of the enzyme. J Biol Chem 278:34084-34089.
27. Pagliassotti MJ, Gayles EC, and Hill JO (1997) Fat and energy balance. Ann NY Acad Sci 827:431-448.
28. Shi J, Zhu H, Arvidson DN, Cregg JM, and Woldegiorgis G (1998) Deletion of the conserved first 18 N-terminal amino acid residues in rat liver carnitine palmitoyltransferase I abolishes malonyl CoA sensitivity and binding. Biochemistry 37:11033-11038.
29. Shi J, Zhu H, Arvidson DN, and Woldegiorgis G (1999) A single amino acid change (substitution of glutamate 3 with alanine) in the N-terminal region of rat liver carnitine palmitoyltransferase 1 abolishes malonyl-CoA inhibition and high affinity binding. J Biol Chem 274:9421-9426.
30. Shi J, Zhu H, Arvidson DN, and Woldegiorgis G (2000) The first 28 N-terminal amino acid residues of human heart muscle carnitine palmitoyltransferase 1 are essential for malonyl CoA sensitivity and high-affinity binding. Biochemistry 39:712-717.
31. Simoneau J-A, Veerkamp JH, Turcotte LP, and Kelley DE (1999) Markers of capacity to utilize fatty acids in human skeletal muscle: relation to insulin resistance and obesity and effects of weight loss. FASEB J 13:2051-2060.
32. Swanson ST, Foster DW, McGarry JD, and Brown NF (1998) Roles of the N-and C-terminal domains of carnitine palmitoyltransferase I isoforms in malonyl CoA sensitivity of the enzymes: insights from expression of chimaeric proteins and mutation of conserved histidine residues. Biochem J 335:513-519.
33. Thupari JN, Landree LE, Ronnett GV, and Kuhajda FP (2002) C75 increases peripheral energy utilization and fatty acid oxidation in diet-induced obesity. Proc Natl Acad Sci USA 99:9498-9502.
34. Zammit VA (1999) The malonyl-CoA-long-chain acyl-CoA axis in the maintenance of mammalian cell function. Biochem J 343:505-515.
35. Zhu H, Shi J, de Vries Y, Arvidson DN, Cregg JM, and Woldegiorgis G (1997) Functional Studies of yeast-expressed human heart muscle carnitine palmitoyltransferase1. Arch Biochem Biophys 347:53-61.
36. Zurlo F, Lillioja S, Esposito-Del Puente A, Nyomba BL, Raz I, Saad MF, Swinburn BA, Knowler WC, Bogardus C, and Ravussin E (1990) Low ratio of fat to carbohydrate oxidation as predictor of weight gain: study of 24-h RQ. Am J Physiol 259:E650-E657.