(-)-CHANA, a Fluorogenic probe for detecting amyloid binding alcohol dehydrogenase HSD10 activity in living cells

ACS Chemical Biology

Volumn 5, Issue 12, 2010, Pages 1105-1114

  Muirhead, Kirsty E A ^a   Froemming, Mary ^b   Li, Xiaoguang ^b   Musilek, Kamil ^c   Conway, Stuart J ^d   Sames, Dalibor ^b   Gunn Moore, Frank J ^a  

^a UNIVERSITY OF ST ANDREWS   (United Kingdom)

^b Och Spine at New York Presbyterian Hospitals   (United States)

^c UNIVERSITY OF DEFENCE   (Czech Republic)

^d UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

17 BETA HYDROXYSTEROID DEHYDROGENASE 10; 3 (6 DIMETHYLAMINO 2 NAPHTHYL) 2 CYCLOHEXANOL; ALCOHOL DEHYDROGENASE; AMYLOID BETA PROTEIN; FLUORESCENT DYE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CELL ACTIVITY; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME METABOLISM; FLUORESCENCE MICROSCOPY; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROTEIN BINDING;

17-HYDROXYSTEROID DEHYDROGENASES; 2-NAPHTHYLAMINE; AMYLOID; CELL SURVIVAL; CYCLOHEXANOLS; FLUORESCENT DYES; HEK293 CELLS; HUMANS; ISOMERISM; KINETICS; MOLECULAR STRUCTURE;

EID: 78650528416     PISSN: 15548929     EISSN: 15548937     Source Type: Journal    
DOI: 10.1021/cb100199m     Document Type: Article

References (22)

1. Yan, S. D., Fu, J., Soto, C., Chen, X., Zhu, H., Al-Mohanna, F., Collison, K., Zhu, A., Stern, E., Saido, T., Tohyama, M., Ogawa, S., Roher, A., and Stern, D. (1997) An intracellular protein that binds amyloid-β peptide and mediates neurotoxicity in Alzheimer's disease Nature 389, 689-695
2. Powell, A. J., Read, J. A., Banfield, M. J., Gunn-Moore, F., Yan, S. D., Lustbader, J., Stern, A. R., Stern, D. M., and Brady, R. L. (2000) Recognition of structurally diverse substrates by type II 3 hydroxyacyl-CoA dehydrogenase (HADH II)/amyloid-β binding alcohol dehydrogenase (ABAD) J. Mol. Biol. 303, 311-327
3. Lustbader, J. W., Cirilli, M., Lin, C., Xu, H. W., Takuma, K., Wang, N., Caspersen, C., Chen, X., Pollak, S., Chaney, M., Trinchese, F., Liu, S., Gunn-Moore, F., Lue, L.-F., Walker, D. G., Kuppusamy, P., Zewier, Z. L., Arancio, O., Stern, D., Yan, S. S., and Wu, H. (2004) ABAD directly links A 102 to mitochondrial toxicity in Alzheimer's disease Science 304, 448-452
4. Kissinger, C. R., Rejto, P. A., Pelletier, L. A., Thomson, J. A., Showalter, R. E., Abreo, M. A., Agree, C. S., Margosiak, S., Meng, J. J., Aust, R. M., Vanderpool, D., Li, B., Tempczyk-Russell, A., and Villafranca, J. E. (2004) Crystal structure of human ABAD/HSD10 with a bound inhibitor: implications for design of Alzheimer's disease therapeutics J. Mol. Biol. 342, 943-952
5. He, X.-Y., Merz, G., Mehta, P., Schulz, H., and Yang, S.-Y. (1999) Human brain short chain L-3-hydroxyacyl coenzyme A dehydrogenase is a single-domain multifunctional enzyme. Characterization of a novel 17-β-hydroxysteroid dehydrogenase J. Biol. Chem. 274, 15014-15019
6. Oppermann, U. C. T., Salim, S., Tjernberg, L. O., Terenius, L., and Jornvall, H. (1999) Binding of amyloid β-peptide to mitochondrial hydroxyacyl-CoA dehydrogenase (ERAB): regulation of an SDR enzyme activity with implications for apoptosis in Alzheimer's disease FEBS Lett. 451, 238-242
7. Yan, S. D., Shi, Y., Zhu, A., Fu, J., Zhu, H., Zhu, Y., Gibson, L., Stern, E., Collison, K., Al-Mohanna, F., Ogawa, S., Roher, A., Clarke, S. G., and Stern, D. M. (1999) Role of ERAB/L-3-hydroxyacyl-coenzyme A dehydrogenase type II activity in Aβ-induced cytotoxicity J. Biol. Chem. 274, 2145-2156
8. He, X. Y., Yang, Y. Z., Schulz, H., and Yang, S. Y. (2000) Intrinsic alcohol dehydrogenase and hydroxysteroid dehydrogenase activities of human mitochondrial short-chain L-3-hydroxyacyl-CoA dehydrogenase Biochem. J. 345, 139-143
9. Yang, S.-Y., He, X.-Y., and Schulz, H. (2005) 3-Hydroxyacyl-CoA dehydrogenase and short chain-3-hydroxyacyl-CoA dehydrogenase in human health and disease FEBS J. 272, 4874-4883
10. Muirhead, K. E., Borger, E., Aitken, L., Conway, S. J., and Gunn-Moore, F. J. (2010) The consequences of mitochondrial amyloid β-peptide in Alzheimer's disease Biochem. J. 426, 255-70
11. He, X.-Y., Schulz, H., and Yang, S.-Y. (1998) A human brain L-3-hydroxyacyl-coenzyme A dehydrogenase is identical to an amyloid β-peptide-binding protein involved in Alzheimer's disease J. Biol. Chem. 273, 10741-10746 (Pubitemid 28227690)
12. Ofman, R., Jos Ruiter, P. N., Feenstra, M., Duran, M., Bwee Poll-The, T., Zschocke, J., Ensenauer, R., Lehnert, W., Sass, J. O., Sperl, W., and Ronald Wanders, J. A. (2003) 2-Methyl-3-hydroxybutyryl-CoA dehydrogenase deficiency is caused by mutations in the HADH2 gene Am. J. Hum. Genet. 72, 1300-1307
13. He, X.-Y., Wegiel, J., Yang, Y.-Z., Pullarkat, R., Schulz, H., and Yang, S.-Y. (2005) Type 10 17β-hydroxysteroid dehydrogenase catalyzing the oxidation of steroid modulators of γ-aminobutyric acid type A receptors Mol. Cell. Endocrinol. 229, 111-117
14. Takuma, K., Yao, J., Huang, J., Xu, H., Chen, X., Luddy, J., Trillat, A.-C., Stern, D. M., Arancio, O., and Yan, S. S. (2005) ABAD enhances Aβ-induced cell stress via mitochondrial dysfunction FASEB J. 19, 597-598
15. Yan, Y., Liu, Y., Sorci, M., Belfort, G., Lustbader, J. W., Yan, S. S., and Wang, C. (2007) Surface plasmon resonance and nuclear magnetic resonance studies of ABAD-Aβ interaction Biochemistry 46, 1724-1731
16. Yao, J., Taylor, M., Davey, F., Ren, Y., Aiton, J., Coote, P., Fang, F., Chen, J. X., Yan, S. D., and Gunn-Moore, F. J. (2007) Interaction of amyloid binding alcohol dehydrogenase/Aβ mediates up-regulation of peroxiredoxin II in the brains of Alzheimer's disease patients and a transgenic Alzheimer's disease mouse model Mol. Cell. Neurosci. 35, 377-382
17. Ren, Y., Xu, H. W., Davey, F., Taylor, M., Aiton, J., Coote, P., Fang, F., Yao, J., Chen, D., Chen, J. X., Yan, S. D., and Gunn-Moore, F. J. (2008) Endophilin I expression is increased in the brains of Alzheimer disease patients J. Biol. Chem. 283, 5685-91
18. Froemming, M. K. and Sames, D. (2007) Harnessing functional plasticity of enzymes: a fluorogenic probe for imaging 17β-HSD10 dehydrogenase, an enzyme involved in Alzheimer's and Parkinson's diseases J. Am. Chem. Soc. 129, 14518-22
19. II-catalyzed hydrogen transfer Angew. Chem., Int. Ed. Engl. 36, 288-290
20. Luche, J.-L., Rodriguez-Hahn, L., and Crabbe, P. (1978) Reduction of natural enones in the presence of cerium trichloride J. Chem. Soc., Chem. Commun. 601-602
21. Frackowiak, J., Mazur-Kolecka, B., Kaczmarski, W., and Dickson, D. (2001) Deposition of Alzheimer's vascular amyloid-β is associated with decreased expression of brain L-3-hydroxyacyl-coenzyme A dehydrogenase (ERAB) Brain Res. 907, 44-53
22. Klein, W. L. (2002) Aβ toxicity in Alzheimer's disease: globular oligomers (ADDLs) as new vaccine and drug targets Neurochem. Int. 41, 345-352