Fenretinide derivatives act as disrupters of interactions of serum retinol binding protein (sRBP) with transthyretin and the sRBP receptor

Journal of Medicinal Chemistry

Volumn 54, Issue 13, 2011, Pages 4378-4387

  Campos Sandoval, José Angel ^a   Redondo, Clara ^b   Kinsella, Gemma K ^a   Pal, Akos ^a   Jones, Geraint ^c   Eyre, Gwen S ^c   Hirst, Simon C ^c   Findlay, John B C ^a,b  

^a NATIONAL UNIVERSITY OF IRELAND   (Ireland)

^b UNIVERSITY OF LEEDS   (United Kingdom)

^c Sygnature Discovery Limited   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

3,7 DIMETHYL 1 MORPHOLINO 9 (2,6,6 TRIMETHYLCYCLOHEX 1 EN 1 YL)NONA 2,4,6,8 TETRAENAMIDE; ANTIDIABETIC AGENT; FENRETINIDE; FENRETINIDE DERIVATIVE; METHYL 2 [4 [3,7 DIMETHYL 9 (2,6,6 TRIMETHYLCYCLOHEX 1 EN 1 YL)NONA 2,4,6,8 TETRAENAMIDO]PHENOXY]ACETIC ACID; N (2,3 DIHYDROXYPROPYL) 3,7 DIMETHYL 9 (2,6,6 TRIMETHYLCYCLOHEX 1 EN 1 YL)NONA 2,4,6,8 TETRAENAMIDE; N (4 HYDROXYETHYL) 3,7 DIMETHYL 9 (2,6,6 TRIMETHYLCYCLOHEX 1 EN 1 YL)NONA 2,4,6,8 TETRAENAMIDE; N (4 HYDROXYPHENYL) 3,7 DIMETHYL 9 (2,6,6 TRIMETHYLCYCLOHEX 1 EN 1 YL)NONA 2,4,6,8 TETRAENAMIDE; N [4 (DIMETHYLAMINO)PHENYL] 3,7 DIMETHYL 9 (2,6,6 TRIMETHYLCYCLOHEX 1 EN 1 YL)NONA 2,4,6,8 TETRAENAMIDE; PLASMA RETINOL BINDING PROTEIN; PLASMA RETINOL BINDING PROTEIN RECEPTOR; PREALBUMIN; RECEPTOR; RETINOID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DISSOCIATION CONSTANT; DRUG MECHANISM; DRUG POTENCY; DRUG PROTEIN BINDING; HUMAN; HUMAN CELL; PROTEIN PROTEIN INTERACTION; STRUCTURE ACTIVITY RELATION;

FENRETINIDE; FLUORESCENCE; FLUORESCENCE RESONANCE ENERGY TRANSFER; HEK293 CELLS; HUMANS; MODELS, MOLECULAR; PREALBUMIN; PROTEIN BINDING; RECEPTORS, CELL SURFACE; RETINOL-BINDING PROTEINS; SERUM; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; SURFACE PLASMON RESONANCE;

EID: 79960176969     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm200256g     Document Type: Article

References (39)

1. Zanotti, G.; Folli, C.; Cendron, L.; Alfieri, B.; Nishida, S.; Gliubich, F.; Pasquato, N.; Negro, A.; Berni, R. Structural and mutational analyses of protein-protein interactions between transthyretin and retinol-binding protein FEBS J. 2008, 275, 5841-5854
2. Kanai, M.; Raz, A.; Goodman, D. Retinol-binding protein: The transport protein for vitamin A in human plasma J. Clin. Invest. 1968, 47, 2025-2044
3. Wolf, G. Multiple functions of vitamin A Physiol. Rev. 1984, 64, 873-937
4. Cowan, S.; Newcomer, M.; Jones, T. Crystallographic refinement of human serum retinol binding protein at 2 Å resolution Proteins 1990, 8, 44-61 (Pubitemid 20235331)
5. Monaco, H.; Rizzi, M.; Coda, A. Structure of a complex of two plasma proteins: Transthyretin and retinol-binding protein Science 1995, 268, 1039-1041
6. Goodman, D. Overview of current knowledge of metabolism of vitamin A and carotenoids J. Natl. Cancer Inst. 1984, 73, 1375-1379 (Pubitemid 15243580)
7. Kawaguchi, R.; Yu, J.; Honda, J.; Hu, J.; Whitelegge, J.; Ping, P.; Wiita, P.; Bok, D.; Sun, H. A membrane receptor for retinol binding protein mediates cellular uptake of vitamin A Science 2007, 315, 820-825
8. Kawaguchi, R.; Yu, J.; Wiita, P.; Honda, J.; Sun, H. An essential ligand-binding domain in the membrane receptor for retinol-binding protein revealed by large-scale mutagenesis and a human polymorphism J. Biol. Chem. 2008, 283, 15160-15168
9. Redondo, C.; Vouropoulou, M.; Evans, J.; Findlay, J. Identification of the retinol-binding protein (RBP) interaction site and functional state of RBPs for the membrane receptor FASEB J. 2008, 22, 1043-1054 (Pubitemid 351519959)
10. Sivaprasadarao, A.; Sundaram, M.; Findlay, J. Interactions of retinol-binding protein with transthyretin and its receptor Methods Mol. Biol. 1998, 89, 155-163
11. Yang, Q.; Graham, T.; Mody, N.; Preitner, F.; Peroni, O.; Zabolotny, J.; Kotani, K.; Quadro, L.; Kahn, B. Serum retinol binding protein 4 contributes to insulin resistance in obesity and type 2 diabetes Nature 2005, 436, 356-362 (Pubitemid 41065039)
12. Graham, T.; Yang, Q.; Blüher, M.; Hammarstedt, A.; Ciaraldi, T.; Henry, R.; Wason, C.; Oberbach, A.; Jansson, P.; Smith, U.; Kahn, B. Retinol-binding protein 4 and insulin resistance in lean, obese, and diabetic subjects N. Engl. J. Med. 2006, 354, 2552-2563 (Pubitemid 43882351)
13. Ost, A.; Danielsson, A.; Lidén, M.; Eriksson, U.; Nystrom, F.; Strålfors, P. Retinol-binding protein-4 attenuates insulin-induced phosphorylation of IRS1 and ERK1/2 in primary human adipocytes FASEB J. 2007, 21, 3696-3704 (Pubitemid 350075157)
14. Zanardi, S.; Serrano, D.; Argusti, A.; Barile, M.; Puntoni, M.; Decensi, A. Clinical trials with retinoids for breast cancer chemoprevention Endocr. Relat. Cancer 2006, 13, 51-68
15. Radu, R.; Han, Y.; Bui, T.; Nusinowitz, S.; Bok, D.; Lichter, J.; Widder, K.; Travis, G.; Mata, N. Reductions in serum vitamin A arrest accumulation of toxic retinal fluorophores: A potential therapy for treatment of lipofuscin-based retinal diseases Invest. Ophthalmol. Visual Sci. 2005, 46, 4393-4401 (Pubitemid 44264531)
16. Zanotti, G.; Marcello, M.; Malpeli, G.; Folli, C.; Sartori, G.; Berni, R. Crystallographic studies on complexes between retinoids and plasma retinol-binding protein J. Biol. Chem. 1994, 269, 29613-29620 (Pubitemid 24365116)
17. Berni, R.; Formelli, F. In vitro interaction of fenretinide with plasma retinol-binding protein and its functional consequences FEBS Lett. 1992, 308, 43-45
18. Preitner, F.; Mody, N.; Graham, T.; Peroni, O.; Kahn, B. Long-term Fenretinide treatment prevents high-fat diet-induced obesity, insulin resistance, and hepatic steatosis Am. J. Physiol. 2009, 297, E1420-E1429
19. Cogan, U.; Kopelman, M.; Mokady, S.; Shinitzky, M. Binding affinities of retinol and related compounds to retinol binding proteins Eur. J. Biochem. 1976, 65, 71-78
20. MOE (2008) Chemical Computing Group.
21. Malpeli, G.; Folli, C.; Berni, R. Retinoid binding to retinol-binding protein and the interference with the interaction with transthyretin Biochim. Biophys. Acta 1996, 1294, 48-54 (Pubitemid 26158189)
22. Coward, P.; Conn, M.; Tang, J.; Xiong, F.; Menjares, A.; Reagan, J. Application of an allosteric model to describe the interactions among retinol binding protein 4, transthyretin, and small molecule retinol binding protein 4 ligands Anal. Biochem. 2009, 384, 312-320
23. Wysocka-Kapcinska, M.; Campos-Sandoval, J.; Pal, A.; Findlay, J. Expression and characterization of recombinant human retinol-binding protein in Pichia pastoris Protein Expression Purif. 2010, 71, 28-32
24. Redondo, C.; Burke, B.; Findlay, J. The retinol-binding protein system: A potential paradigm for steroid-binding globulins? Horm. Metab. Res. 2006, 38, 269-278 (Pubitemid 43845220)
25. Sivaprasadarao, A.; Findlay, J. The interaction of retinol-binding protein with its plasma-membrane receptor Biochem. J. 1988, 255, 561-569
26. Cho, Y.; Youn, B.; Lee, H.; Lee, N.; Min, S.; Kwak, S.; Lee, H.; Park, K. Plasma retinol-binding protein-4 concentrations are elevated in human subjects with impaired glucose tolerance and type 2 diabetes Diabetes Care 2006, 29, 2457-2461 (Pubitemid 44912252)
27. Craig, R.; Chu, W.; Elbein, S. Retinol binding protein 4 as a candidate gene for type 2 diabetes and prediabetic intermediate traits Mol. Genet. Metab. 2007, 90, 338-344
28. Gavi, S.; Stuart, L.; Kelly, P.; Melendez, M.; Mynarcik, D.; Gelato, M.; McNurlan, M. Retinol-binding protein 4 is associated with insulin resistance and body fat distribution in nonobese subjects without type 2 diabetes J. Clin. Endocrinol. Metab. 2007, 92, 1886-1890 (Pubitemid 46997205)
29. Graham, T.; Wason, C.; Blüher, M.; Kahn, B. Shortcomings in methodology complicate measurements of serum retinol binding protein (RBP4) in insulin-resistant human subjects Diabetologia 2007, 50, 814-823 (Pubitemid 46355817)
30. Lee, D.; Lee, J.; Im, J. Association of serum retinol binding protein 4 and insulin resistance in apparently healthy adolescents Metabolism 2007, 56, 327-231
31. Janke, J.; Engeli, S.; Boschmann, M.; Adams, F.; Böhnke, J.; Luft, F.; Sharma, A.; Jordan, J. Retinol-binding protein 4 in human obesity Diabetes 2006, 55, 2805-2810 (Pubitemid 44923680)
32. Takashima, N.; Tomoike, H.; Iwai, N. Retinol-binding protein 4 and insulin resistance. N. Engl. J. Med. 2006, 355, 1392, author reply 1394-1395.
33. Manolescu, D.; Sima, A.; Bhat, P. All-trans retinoic acid lowers serum retinol-binding protein 4 concentrations and increases insulin sensitivity in diabetic mice J. Nutr. 2010, 140, 311-316
34. Noy, N.; Xu, Z. Interactions of retinol with binding proteins: Implications for the mechanism of uptake by cells Biochemistry 1990, 29, 3878-3883 (Pubitemid 20151299)
35. Berni, R.; Clerici, M.; Malpeli, G.; Cleris, L.; Formelli, F. Retinoids: In vitro interaction with retinol-binding protein and influence on plasma retinol FASEB J. 1993, 7, 1179-1184 (Pubitemid 23271038)
36. Johansson, H.; Gandini, S.; Guerrieri-Gonzaga, A.; Iodice, S.; Ruscica, M.; Bonanni, B.; Gulisano, M.; Magni, P.; Formelli, F.; Decensi, A. Effect of fenretinide and low-dose tamoxifen on insulin sensitivity in premenopausal women at high risk for breast cancer Cancer Res. 2008, 68, 9512-9518
37. Xie, Y.; Lashuel, H.; Miroy, G.; Dikler, S.; Kelly, J. Recombinant human retinol-binding protein refolding, native disulfide formation, and characterization Protein Expression Purif. 1998, 14, 31-37 (Pubitemid 28476577)
38. Lashuel, H.; Wurth, C.; Woo, L.; Kelly, J. The most pathogenic transthyretin variant, L55P, forms amyloid fibrils under acidic conditions and protofilaments under physiological conditions Biochemistry 1999, 38, 13560-13573
39. DeLano, W. L. (2002) The PyMOL Molecular Graphics System, DeLano Scientific, Palo Alto, CA.