Mechanisms of molecular recognition: Structural characteristics of transthyretin ligand interactions

Recent Advances in Transthyretin Evolution, Structure and Biological Functions

Volumn , Issue , 2009, Pages 1-21

  Cody, Vivian ^a   Wojtczak, Andrzej ^b  

^a HAUPTMAN WOODWARD MEDICAL RESEARCH INSTITUTE   (United States)

^b NICOLAUS COPERNICUS UNIVERSITY   (Poland)

Author keywords

Active site topology; Conformational flexibility; Protein protein interactions; Transthyretin

Indexed keywords

EID: 82455201581     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1007/978-3-642-00646-3_1     Document Type: Chapter

References (79)

1. Adamski-Werner SL, Palaninathan SK, Sacchettini JC, Kelly JW (2004) Diflunisal analogues stabilize the native state of transthyretin. Potent inhibition of amyloidogenesis. J. Med. Chem. 47:355-374
2. Armen RS, DeMarco ML, Alonso DOV, Daggett V (2004) Pauling and Cory's alpha-pleated sheet structure may define the prefibrillar amyloidogenic intermediate in amyloid disease. Proc. Natl. Acad. Sci. USA 101:11622-11627
3. Benson MD, Kincaid JC (2007) The molecular biology and clinical features of amylobid neuropathy. Muscle Nerve 36:411-423
4. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE (2000) The protein data bank. Nucleic Acids Res. 28:235-242
5. Blake CCF, Geisow MJ, Oatley SJ, Rerat C, Rerat B (1978) Structure of prealbumin: secondary, tertiary and quaternary interactions determined by fourier refinement at 1.8A. J. Mol. Biol. 121:339-356
6. Blake CCF, Oately SJ (1977) Protein-DNA and protein-hormone interactions in prealbumin: a model of the thyroid hormone nuclear receptor? Nature 268:115-129
7. Blake CCF, Serpell L (1996) Synchrotron X-ray studies suggest that the core of the transthyretin fibril is a continuous b-sheet helix. Structure 4:989-998
8. Cheng S-Y, Pages RA, Saroff HA, Edelhock H, Robbins J (1977) Analysis of thyroid hormone binding to human serum prealbumin by 8-anilinonapthalene-1- sulfonate fluorescence. Biochemistry 16:3707-3713
9. Ciszak E, Luft J, Cody V (1992) Crystal structure determination at 2.3-Å resolution of human transthyretin-30, 50-dibromo-20, 4, 40, 6-tetrahydroxyaurone complex. Proc. Natl. Acad. Sci. USA. 89:6644-6648
10. Cody V (1980) Thyroid-hormone interactions: molecular conformation, protein binding, and hormone action. Endocr. Rev. 1:140-166
11. Cody V (2002) Mechanisms of molecular recognition: crystal structure analysis of human and rat transthyretin inhibitor complexes. Clin. Chem. Lab. Med. 40:1237-1243
12. Cody V (2005) Thyroid hormone structure-function relationships. In: Braverman LE and Utiger RD (eds) Werner & Ingbar's The Thyroid: a fundamental and clinical text, 9th edn. Lippincott Williams & Wilkins, Philadelphia, pp 151-157
13. Cody V, Murray-Rust P (1984) Iodine... X (O, N, S) intermolecular contacts: models of thyroid hormone-protein binding interactions using information from the Cambridge Crystallographic Data Files. J. Mol. Struct. 112:189-199
14. Cody V, Wojtczak A, Ciszak E, Luft JR (1991) Differences in inhibitor and stubstrate binding in transthyretin crystal complexes. In: Gordon A, Gross J, Hennemann G (eds) Progress in thyroid research, Balema, Rotterdam, pp. 793-796
15. Davis PJ, Cody V, Davis FB, Warnick PR, Schoenl M, Edwards L (1987) Milrinone, a noniodinated bipyridine, competes with thyroid hormone for binding sites on human serum prealbumin (TBPA). Biochem. Pharmacol. 36:3635-3640
16. Eneqvist T, Andersson K, Olofsson A, Lundgren E, Sauer-Eriksson AE (2000) The b-slip: a novel concept in transthyretin amyloidosis. Mol. Cell 6:1207-1218
17. Eneqvist T, Lundberg E, Karlsson A, Huang S, Santos CRA, Power DM, Sauer-Eriksson AE (2004) High resolution crystal structures of piscine transthyretin reveal different binding modes for triiodothyronine and thyroxine. J. Biol. Chem. 279:26411-26416
18. Eneqvist T, Olofsson A, Ando Y, Miyakawa T, Katsuragi S, Jass J, Lundgren E, Sauer-Eriksson AE (2002) Disulfide-bond formation in the transthyretin mutant Y114C prevents amyloid fibril formation in vivo and in vitro. Biochemistry 41:13143-13151
19. Ferguson RN, Edeldoch H, Saroff HA, Robbins J (1975) Negative cooperativity in the binding of thyroxine to human serum transthyretin. Biochemistry 14:282-289
20. Ferrao-Gonzales AD, Souto SO, Silva JL, Foguel D (2000) The preaggregated state of an amyloidogenic protein: hydrostatic pressure converts native transthyretin into the amyloidogenic state. Proc. Natl. Acad. Sci. USA. 97:6445-6450
21. Folli C, Pasquato N, Ramazzina I, Battistutta R, Zanotti G, Berni R (2003) Distinctive binding and structural properties of piscine transthyretin. FEBS Lett. 555:279-284
22. Gales L, Saraiva MJ, Damas AM (2007) Structural basis for the protective effect of sulfite against transthyretin amyloid formation. Biochim. Biophys. Acta 1774:59-61
23. Ghosh M, Meerts IATM, Cook A, Bergman A, Brouwer A, Johnson LN (2000) Structure of human transthyretin complexed with bromophenols: a new modeofbinding. Acta Cryst. D 56:1085-1095
24. Gonzalez G (1989) Fluorescent derivative of cysteine-10 reveals thyroxine-dependent conformational modifications in human serum prealbumin. Arch. Biochem. Biophys. 271:200-205
25. Gonzalez G, Tapia G (1992) Fluorescence study of the thyroxine-dependent conformational changes in human serum transthyretin. FEBS Lett. 297:253-256
26. Green NS, Palaninathan SK, Sacchettini JC, Kelly JW (2003) Synthesis and characterization of potent bivalent amyloidosis inhibitors that bind prior to transthyretin tetramerization. J. Am. Chem. Soc. 125:13404-13414
27. Hamilton JA, Steinrauf LK, Braden BC, Liepniks J, Benson MD, Holmgren G, Sandgren O, Steen L (1993) The X-ray crystal structure refinements of normal human transthyretin and the amyloidogenic Val30Met variant to 1.7 Å resolution. J. Biol. Chem. 268:2416-2424
28. Hammarström P, Wiseman RL, Powers ET, Kelly JW (2003) Prevention of transthyretin amyloid disease by changing protein misfolding energetics. Science 299:713-716
29. Hörnberg A, Hultdin UW, Olofsson A, Sauer-Eriksson AE (2005) The effect of iodide and chloride on transthyretin structure and stability. Biochemistry 44:9290-9299
30. Hurshman-Babbes AR, Powers ET, Kelly JW (2008) Quantification of the thermodynamically linked quaternary and tertiary structural stabilities of transthyretin and its disease-associated variants: the relationship between stability and amyloidosis. Biochemistry 47:6969-6984.
31. Irace G, Edelhoch H (1978) Thyroxine-induced conformational changes in prealbumin. Biochemistry 17:5729-5733
32. Jiang X, Smith CS, Petrassi HM, Hammarstrom P, White JT, Sacchettini JC, Kelly JW (2001) An engineered transthyretin monomer that is nonamyloidogenic, unless it is partially denatured. Biochemistry 40:11442-11452
33. Johnson SM, Connelly S, Wilson IA, Kelly JW (2008) Toward optimization of the linker substructure common to transthyretin amyloidogenesis inhibitors using biochemical and structural studies. J. Med. Chem. 51:6348-6358
34. Johnson SM, Wiseman RL, Sekijima Y, Green NS, Adamski-Werner SL, Kelly JW (2005) Native state kinetic stabilization as a strategy to ameliorate protein misfolding diseases: a focus on the transthyretin amyloidoses. Acc. Chem. Res. 38:911-921
35. Karlsson A, Oloffson A, Eneqvist T, Sauer-Eriksson AE (2005) Cys-114-linked dimers of transthyretin are compatible with amyloid formation. Biochemistry 44:13063-13070
36. Kelly JW (1998) The alternative conformations of amyloidogenic proteins and their multi-step assembly pathways. Curr. Opin. Struc. Biol. 8:101-106
37. Kelly JW, Lansbury PTJ (1994) A chemical approach to elucidate the mechanism of transthyretin and beta-protein amyloid fibril formation. Amyloid 1:186-205
38. Klabunde T, Petrassi HM, Oza VB, Raman P, Kelly JW, Sacchettini JC (2000) Rational design of potent human transthyretin amyloid disease inhibitors. Nat. Struct. Biol. 7:312-321
39. Lai Z, Colon W, Kelly JW (1996) The acid-mediated denaturation pathway of transthyretin yields a conformational intermediate that can self-assemble into amyloid. Biochemistry 35:6470-6482
40. Laidman J, Forse GJ, Todd O, Yeates TO (2006) Conformational change and assembly through edge beta strands in transthyretin and other amyloid proteins. Acc. Chem. Res. 39:576-583
41. Lashuel HA, Lai Z, Kelly JW (1998) Characterization of the transthyretin acid denaturation pathways by analytical ultracentrifugation: implications for wild-type, V30M, and L55P amyloid fibril formation. Biochemistry 37:17851-17864
42. Liu K, Cho HS, Lashuel HA, Kelly JW, Wemmer DE (2000) A glimpse of a possible amyloidogenic intermediate of transthyretin. Nat. Struct. Biol. 7:754-757
43. Miroy GJ, Lai Z, Lashuel HA, Peterson SA, Strang C, Kelly JW (1996) Inhibiting transthyretin amyloid fibril formation via protein stabilization. Proc. Natl. Acad. Sci. USA. 93:15051-15056
44. Morais-de-Sa E, Neto-Silva RM, Bereira PJB, Saraiva MJ, Damas AM (2006) The binding of 2, 4-dinitrophenol to wild-type and amyloidogenic transthyretin. Acta Cryst. D 62:512-519
45. Morais-de-Sa E, Pereira PJB, Saraiva MJ, Damas AM (2004) The crystal structure of transthyretin in complex with diethylstilbestrol. J. Biol. Chem. 279:53483-53490
46. Muziol T, Cody V, Luft JR, Pangborn W, Wojtczak A (2001a) Complex of rat transthyretin with tetraiodothyroacetic acid refined at 2.1 and 1.8A resolution. Acta Biochim. Polonica 48:877-884
47. Muziol T, Cody V, Wojtczak A (2001b) Comparison of binding interactions of dibromoflavonoids with transthyretin. Acta Biochim. Polonica 48:885-892
48. Neumann P, Cody V, Wojtczak A (2001) Structural basis of negative cooperativity in transthyretin. Acta Biochim. Polonica 48:867-875
49. Neumann P, Cody V, Wojtczak A (2005) Ligand binding at the transthyretin dimer-dimer interface: crystal structure of the transthyretin-T4Ac complex at 2.2 Å resolution. Acta Cryst. D 61:1313-1319
50. Olofsson A, Ippel HJ, Baranov V, Horstedt P, Wijmenga S, Lundgren E (2001) Capture of a dimeric intermediate during transthyretin amyloid formation. J. Biol. Chem. 276:39592-39599
51. Olofsson A, Ippel JH, Wijmenga SS, Lundgren E, Ohman A (2004) Probing solvent accessibility of transthyretin amyloid by solution NMR spectroscopy. J. Biol. Chem. 279:5699-5707
52. Oza VB, Smith C, Raman P, Koepf EK, Lashuel HA, Petrassi HM, Chiang KP, Powers ET, Sachettinni J, Kelly JW (2002) Synthesis, structure, and activity of diclofenac analogues as transthyretin amyloid fibril formation inhibitors. J. Med. Chem. 45:321-332
53. Palaninathan SK, Mohamedmohaideen NN, Snee QC, Kelly JW, Sacchettini JC (2008) Structural insight into pH-induced conformational changes within the native human transthyretin tetramer. J. Mol. Biol. 382:1157-1167
54. Palhano FL, Leme LP, Gusnardo RG, Foguel D (2009) Trapping the monomer of a non-amyloidogenic variant of transthyretin: exploring its possible use as a therapeutic strategy against transthyretin amyloidogenic diseases. J. Biol. Chem. 284:1443-1453
55. Pasquato N, Berni R, Folli C, Alfieri B, Cendron L, Zanotti G (2007) Acidic pH-induced conformational changes in amyloidogenic mutant transthyretin. J. Mol. Biol. 366:711-719
56. Peterson SA, Klabunde T, Lashuel HA, Purkey H, Sacchettini JC, Kelly JW (1998) Inhibiting transthyretin conformational changes that lead to amyloid fibril formation. Proc. Natl. Acad. Sci. USA. 95:12956-12960
57. Petrassi HM, Johnson SM, Purkey H, Chiang KP, Walkup T, Jiang X, Powers ET, Kelly JW (2005) Potent and selective structure-based dibenzofuran inhibitors of transthyretin amyloidogenesis: kinetic stabilization of the native state. J. Am. Chem. Soc. 127:6662-6671
58. Petrassi HM, Klabunde T, Sacchettini JC, Kelly JW (2000) Structure-based design of N-phenyl phenoxazine transthyretin amyloid fibril inhibitors. J. Am. Chem. Soc. 122:2178-2192
59. Quintas A, Saraiva MJM, Brito RMM (1997) The amyloidogenic potential of transthyretin variants correlates with their tendency to aggregate in solution. FEBS Lett. 418:297-300
60. Reixach N, Foss TR, Santelli E, Pascual J, Kelly JW, Buxbaum JN (2008) Human-murine transthyretin heterotetramers are kinetically stable and non-amyloidogenic. J. Biol. Chem. 283:2098-2107
61. Robbins J (1996) Thyroid hormone transport proteins and the physiology of hormone binding. In: Braverman LE, Utidger RD (eds) Werner & Ingbar's The Thyroid: a fundamental and clinical text, 7th edn. Lippincott Williams & Wilkins, Philadelphia, pp. 96-110
62. Schormann N, Murrell JR, Benson MD (1996) Tertiary structures of amyloidogenic and non-amyloidogenic transthyretin variants: new model for amyloid fibril formation. Amyloid 5:175-187
63. Sebastiao MP, Lamzin V, Saraiva MJ, Damas AM (2001) Transthyretin stability as a key factor in amyloidogenesis: X-ray analysis at atomic resolution. J. Mol. Biol. 306:733-744
64. Sebastiao MP, Saraiva MJ, Damas AM (1998) The crystal structure of amyloidogenic Leu55Pro transthyretin variant reveals a possible pathway for transthyretin polymerization into amyloid fibrils. J. Biol. Chem. 273:24715-24722
65. Serag AA, Altenbach C, Gingery M, Hubbell WL, Yeates TO (2001) Identification of a subunit interface in transthyretin amyloid fibrils: evidence for self-assembly from oligomeric building blocks. Biochemistry 40:9089-9096
66. Serag AA, Altenbach C, Gingery M, Hubbell WL, Yeates TO (2002) Arrangement of subunits and ordering of beta-strands in an amyloid sheet. Nat. Struct. Biol. 9:734-739
67. Steinrauf LK, Hamilton JA, Braden BC, Murrell JR, Bensen MD (1993) X-ray crystal structure of the Ala-109-Thr variant of human transthyretin which produces euthyroid hyperthyroxinemia. J. Biol. Chem. 268:2425-2430
68. Steward RE, Armen RS, Daggett V (2008) Different disease-causing mutations in transthyretin trigger the same conformational conversion. Prot. Eng. Design Selec. 21:187-195
69. Sorensen J, Hamelberg D, Schiott B, McCammon JA (2007) Comparative MD analysis of the stability of transthyretin providing insight into the fibrillation mechanism. Biopolymers 86:73-82
70. Sunde M, Richardson SJ, Chang L, Pettersson TM, Schreiber G, Blake CCF (1996) The Crystal structure of transthyretin from chicken. Eur. J. Biochem. 236:491-499
71. Wang H, Tang Y, Ming Lei M (2007) Models for binding cooperativities of inhibitors with transthyretin. Arch. Biochem. Biophys. 466:85-97
72. Westermark P, Benson MD, Buxbaum JN, Cohen AS, Brangione B, Ikeda S-I, Masters CL, Merlini G, Saraiva MJ, Sipe JD (2007) A primer of amyloid nonmenclature. Amyloid 14:179-1834
73. White JT, Kelly JW (2001) Support for the multigenic hypothesis of amyloidosis: the binding stoichiometry of retinol-binding protein, vitamin A, and thyroid hormone influences transthyretin amyloidogenicity in vitro. Proc. Natl. Acad. Sci. USA 98:13019-13024
74. Wojtczak A (1997) Crystal structure of rat transthyretin at 2.5 Å resolution: First report on a unique tetrameric structure. Acta Biochim. Polon. 44:505-518
75. Wojtczak A, Luft JR, Cody V (1992) Mechanism of molecular recognition: Structural aspects of 3, 3'-diiodo-L-thyronine binding to human serum transthyretin. J. Biol. Chem. 267:353-357
76. Wojtczak A, Luft JR, Cody V (1993) Structural aspects of inotropic bipyridine binding: crystal structure determination to 1.9 Å of the human serum transthyretin-milrinone complex. J. Biol. Chem. 268:6202-6206
77. Wojtczak A, Cody V, Luft JR, Pangborn W (1996) Structures of human transthyretin complexed with thyroxine at 2.0Å resolution and 3', 5'-dinitro-N-acetyl-L-thyronine at 2.2Å resolution. Acta Cryst. D 52:758-765
78. Wojtczak A, Cody V, Luft J, Pangborn W (2001a) Structure of rat transthyretin (rTTR) complex with thyroxine at 2.5Å resolution: first non-biased insight into thyroxine binding reveals different hormone orientation in two binding sites. Acta Cryst. D 57:1061-1070
79. Wojtczak A, Neumann P, Cody V (2001b) Structure of a new polymorphic monoclinic form of human transthyretin at 3Å resolution reveals a mixed complex between unliganded and T4-bound tetramers of TTR. Acta Crsyt. B 57:957-967