Biophysical and biochemical approach to locating an inhibitor binding site on cholesteryl ester transfer protein

Bioconjugate Chemistry

Volumn 19, Issue 8, 2008, Pages 1604-1613

  Cunningham, David ^a   Lin, Wen ^a   Hoth, Lise R ^a   Danley, Dennis E ^a   Ruggeri, Roger B ^a   Geoghegan, Kieran F ^a   Chrunyk, Boris A ^a   Boyd, James G ^a  

^a PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING SITES; BIOSENSORS; CRYSTAL STRUCTURE; DISEASES; DRUG DELIVERY; ESTERS; LIPOPROTEINS; MASS SPECTROMETRY; SURFACE PLASMON RESONANCE;

BINDING-SITES; CARDIOVASCULAR DISEASE; CHOLESTERYL ESTER TRANSFER PROTEINS; HIGH DENSITY LIPOPROTEIN; MOLECULAR BASIS; NEUTRAL LIPID; PLASMA CHOLESTEROL; PLASMA LIPOPROTEINS; PROTEIN A; PROTEIN TRANSFER;

SULFUR COMPOUNDS;

AGAROSE; BIOTIN; CHOLESTEROL ESTER TRANSFER PROTEIN; CHOLESTEROL ESTER TRANSFER PROTEIN INHIBITOR; CP 532623; DISULFIDE; MACROGOL; METHYL[1 (13 AZIDO 5,8,11 TRIOXA 2 AZATRIDECAN 1 OYL) 2 ETHYL 6 (TRIFLUOROMETHYL) 1,2,3,4 TETRAHYDROQUINOLIN 4 YL]CARBAMATE; METHYL[1 [15,22 DIOXO 26 [2 OXOHEXAHYDRO 1H THIENO(3,4 D)IMIDAZOL 4 YL] 5,8,11 TRIOXA 2,14,21 TRIAZAHEXACOSAN 1 OYL] 2 ETHYL 6 (TRIFLUOROMETHYL) 1,2,3,4 TETRAHYDROQUINOLIN 4 YL]CARBAMATE; PEPSIN A; STREPTAVIDIN; TORCETRAPIB; UNCLASSIFIED DRUG; [6 [(TERT BUTOXYCARBONYL)AMINO]HEXYL] 4 [ACETYL[3,5 BIS(TRIFLUOROMETHYL)BENZYL]AMINO 2 ETHYL 6 (TRIFLUOROMETHYL) 3,4 DIHYDROQUINOLINE 1 CARBOXYLATE; [6 [[6 [[5 [2 OXOHEXAHYDRO 1H THIENO(3,4 D)IMIDAZOL 4 YL]PENTANOYL]AMINO]HEXANOYL]AMINO]HEXYL] 4 [ACETYL[3,5 BIS(TRIFLUOROMETHYL)BENZYL]AMINO] 2 ETHYL 6 (TRIFLUOROMETHYL) 3,4 DIHYDROQUINOLINE 1 CARBOXYLATE; [8,11,27 TRIOXO 31 [2 OXOHEXAHYDRO 1H THIENO(3,4 D)IMIDAZOL 4 YL] 16,19,22 TRIOXA 7,12,26 TRIAZAHENTRIACONT 1 YL] 4 [ACETYL[3,5 BIS(TRIFLUOROMETHYL)BENZYL]AMINO] 2 ETHYL 6 (TRIFLUOROMETHYL) 3,4 DIHYDROQUINOLINE 1 CARBOXYLATE; [8,17,20,36 TETRAOXO 40 [2 OXOHEXAHYDRO 1H THIENO(3,4 D)IMIDAZOL 4 YL] 10,13,25,28,31 PENTAOXA 7,16,21,35 TETRAAZATETRACONT 1 YL] 4 [ACETYL[3,5 BIS(TRIFLUOROMETHYL)BENZYL]AMINO 2 ETHYL 6 (TRIFLUOROMETHYL) 3,4 DIHYDROQUINOLINE 1 CARBOXYLATE;

ARTICLE; BINDING SITE; BIOSENSOR; CRYSTAL STRUCTURE; MASS SPECTROMETRY; MUTAGENESIS; NUCLEOTIDE SEQUENCE; PEPTIDE MAPPING; PROTEIN BINDING; SURFACE PLASMON RESONANCE;

EID: 50249186350     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc800165n     Document Type: Article

References (27)

1. De Backer, G., Ambrosioni, E., Borch-Johnsen, K., Brotons, C., Cifkova, R., Dallongeville, J., Ebrahim, S., Faergeman, O., Graham, I., Mancia, G., Manger Cats, V., Orth-Gomer, K., Perk, J., Pyorala, K. L, Rodicio, J., Sans, S., Sansoy, V., Sechtem, U., Silber, S., Thomsen, T., and Wood, D. (2004) European guidelines on cardiovascular disease prevention in clinical practice. Atherosclerosis 173, 379-389.
2. Brousseau, M. E., Schaefer, E. J., Wolfe, M. L., Bloedon, L. T., Digenio, A. G., Clark, R. W., Mancuso, J. P., and Rader, D. J. (2004) Effects of an inhibitor of cholesteryl ester transfer protein on HDL cholesterol. N. Engl. J. Med. 350, 1505-1515.
3. Tall, A. R., Yvan-Charvet, L., and Wang, N. (2007) The failure of torcetrapib: Was it the molecule or the mechanism? Arterioscler., Thromb., Vasc. Biol. 27, 257-260.
4. Connolly, D. T., McIntyre, J., Heuvelman, D., Remsen, E. E., McKinnie, R. E., Vu, L., Melton, M., Monsell, R., Krul, E. S., and Glenn, K. (1996) Physical and kinetic characterization of recombinant human cholesteryl ester transfer protein. Biochem. J. 320, 39-47.
5. Qiu, X., Mistry, A., Ammirati, M. J., Chrunyk, B. A., Clark, R. W., Cong, Y., Culp, J. S., Danley, D. E., Freeman, T. B., Geoghegan, K. F., Griffor, M. C., Hawrylik, S. J., Hayward, C. M., Hensley, P., Hoth, L. R., Karam, G. A., Lira, M. E., Lloyd, D. B., McGrath, K. M., Stutzman-Engwall, K. J., Subashi, A. K., Subashi, T. A., Thompson, J. F., Wang, I.-K., Zhao, H., and Seddon, A. P. (2007) Crystal structure of cholesteryl ester transfer protein reveals a long tunnel and four bound lipid molecules. Nat. Struct. Mol. Biol. 14, 106-113.
6. Clark, R. W., Ruggeri, R. B., Cunningham, D., and Bamberger, M. J. (2006) Description of the torcetrapib series of cholesteryl ester transfer protein inhibitors, including mechanism of action. J. Lipid Res. 47, 537-552.
7. Okamoto, H., Yonemori, F., Wakitani, K., Minowa, T., Maeda, K., and Shinkai, H. (2000) A cholesteryl ester transfer protein inhibitor attenuates atherosclerosis in rabbits. Nature 406, 203-207.
8. Hope, H. R., Heuvelman, D., Duffin, K., Smith, C., Zablocki, J., Schilling, R., Hegde, S., Lee, L., Witherbee, B., Baganoff, M., Bruce, C., Tall, A. R., Krul, E., Glenn, K., and Connolly, D. T. (2000) Inhibition of cholesteryl ester transfer protein by substituted dithiobisnicotinic acid dimethyl ester: Involvement of a critical cysteine. J. Lipid Res. 41, 1604-1614.
9. Epps, D. E., and Vosters, A. F. (2002) The essential role of a free sulfhydryl group in blocking the cholesteryl site of cholesteryl ester transfer protein (CETP). Chem. Phys. Lipids 114, 113-122.
10. Mattingly, P. G. (1990) Mono-protected diamines. Nα-tert- Butoxycarbonyl α,ω-alkanediamine hydrochlorides from amino alcohols. Synthesis 366-368.
11. Damon, D. B., Dugger, R. W., Hubbs, S. E., Scott, J. M., and Scott, R. W. (2006) Asymmetric synthesis of the cholesteryl ester transfer protein inhibitor torcetrapib. Org. Process Res. Dev. 10, 472-480.
12. Perkins, D. N., Pappin, D. J. C., Creasy, D. M., and Cottrell, J. S. (1999) Probability-based protein identification by searching sequence databases using mass spectrometry data. Electrophoresis 20, 3551-3567.
13. Clark, R. W., Sutfin, T. A., Ruggeri, R. B., Willauer, A. T., Sugarman, E. D., Magnus-Aryitey, G., Cosgrove, P. G., Sand, T. M., Wester, R. T., Williams, J. A., Perlman, M. E., and Bamberger, M. J. (2004) Raising high-density lipoprotein in humans through inhibition of cholesteryl ester transfer protein: An initial multidose study of torcetrapib. Arterioscler., Thromb., Vasc. Biol. 24, 490-497.
14. Kelley, R. M., McCarthy, K. E., Miller, S. A., Nesler, M. J., Schildknegt, K., Wager, C. B., and Zandi, K. S. (2004) The Synthesis of Isotopically Labeled CETP Inhibitors. Synthesis and Applications of Isotopically Labelled Compounds, Proceedings of the 8th International Symposium, Boston, MA, June 15, 2003, pp11-14.
15. Rich, R. L., and Myszka, D. G. (2007) Higher-throughput, label-free, real-time molecular interaction analysis. Anal. Biochem. 361, 1-6.
16. Huber, W., and Mueller, F. (2006) Biomolecular interaction analysis in drug discovery using surface plasmon resonance technology. Curr. Pharm. Des. 12, 3999-4021.
17. Morrison, J. F., and Walsh, C. T. (1988) The behavior and significance of slow-binding enzyme inhibitors. Adv. Enzymol. Relat. Areas Mol. Biol. 61, 201-301.
18. Cannon, M. J., Myszka, D. G., Bagnato, J. D., Alpers, D. H., West, F. G., and Grissom, C. B. (2002) Equilibrium and kinetic analyses of the interactions between vitamin B12 binding proteins and cobalamins by surface plasmon resonance. Anal. Biochem. 305, 1-9.
19. Gobi, K. V., and Miura, N. (2004) Highly sensitive and interference-free simultaneous detection of two polycyclic aromatic hydrocarbons at parts-per-trillion levels using a surface plasmon resonance immunosensor. Sens. Actuators, B 103, 265-271.
20. Jenssen, K., Sewald, K., and Sewald, N. (2004) Synthesis of marimastat and a marimastat conjugate for affinity chromatography and surface plasmon resonance studies. Bioconjugate Chem. 15, 594-600.
21. Kaiser, T., Gudat, P., Stock, W., Pappert, G., Grol, M., Neumeier, D., and Luppa, P. B. (2000) Biotinylated steroid derivatives as ligands for biospecific interaction analysis with monoclonal antibodies using immunosensor devices. Anal. Biochem. 282, 173-185.
22. Kanon, N., Kyo, M., Inamori, K., Ando, A., Asami, A., Nakao, A., and Osada, H. (2006) SPR imaging of photo-cross-linked small-molecule arrays on gold. Anal. Chem. 78, 2226-2230.
23. Miyashita, M., Shimada, T., Miyagawa, H., and Akamatsu, M. (2005) Surface plasmon resonance-based immunoassay for 17β-estradiol and its application to the measurement of estrogen receptor-binding activity. Anal. Bioanal. Chem. 381, 667-673.
24. Schlecht, U., Nomura, Y., Bachmann, T., and Karube, I. (2002) Reversible surface thiol immobilization of carboxyl group containing haptens to a BIAcore biosensor chip enabling repeated usage of a single sensor surface. Bioconjugate Chem. 13, 188-193.
25. Svedhem, S., Enander, K., Karlsson, M., Sjoebom, H., Liedberg, B., Loefas, S., Martensson, L.-G., Sjoestrand, S. E., Svensson, S., Carlsson, U., and Lundstroem, I. (2001) Subtle differences in dissociation rates of interactions between destabilized human carbonic anhydrase ii mutants and immobilized benzenesulfonamide inhibitors probed by a surface plasmon resonance biosensor. Anal. Biochem. 296, 188-196.
26. Begum, R., Masatoki, S., and Matsuura, H. (1996) Conformational behavior of short poly(oxyethylene) compounds in formamide: a Raman spectroscopic study. J. Mol. Struct. 384, 115-120.
27. Green, N. S., Reisler, E., and Houk, K N. (2001) Quantitative evaluation of the lengths of homobifunctional protein cross-linking reagents used as molecular rulers. Protein Sci. 10, 1293-1304.