Backbone conformations and side chain flexibility of two somatostatin mimics investigated by molecular dynamics simulations

Proteins: Structure, Function and Bioinformatics

Volumn 75, Issue 3, 2009, Pages 659-670

  Interlandi, Gianluca ^a,b  

^a UNIVERSITY OF ZURICH   (Switzerland)

^b University of Washington   (United States)

Author keywords

Acromegaly; Cluster analysis; Conformational equilibrium; Drug design; Giantism; Native state analysis; NOE distance constraints; Small peptide design

Indexed keywords

OCTREOTIDE; PASIREOTIDE; SOMATOSTATIN DERIVATIVE; SOMATOSTATIN RECEPTOR;

ARTICLE; BINDING AFFINITY; CLUSTER ANALYSIS; CONFORMATIONAL TRANSITION; DISTANCE CONSTRAINT; DRUG CONFORMATION; DRUG DESIGN; DRUG RECEPTOR BINDING; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; PARAMETER; PRIORITY JOURNAL; SIMULATION; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

CLUSTER ANALYSIS; COMPUTER SIMULATION; CRYSTALLOGRAPHY, X-RAY; KINETICS; MODELS, MOLECULAR; OCTREOTIDE; PROTEIN CONFORMATION; SOMATOSTATIN; TEMPERATURE; THERMODYNAMICS; TIME FACTORS;

EID: 66149110418     PISSN: 08873585     EISSN: 10970134     Source Type: Journal    
DOI: 10.1002/prot.22277     Document Type: Article

References (33)

1. Weckbecker G, Lewis I, Albert R, Schmid HA, Hoyer D, Bruns C. Opportunities in somatostatin research: biological, chemical and therapeutic aspects. Nature Rev 2003;12:999-1017. (Pubitemid 37540581)
2. Reichlin S. Somatostatin. N Engl J Med 1983;309:1495-1501.
3. Reichlin S. Somatostatin. N Engl J Med 1983;309:1556-1563.
4. Yamada Y, Post SR, Wang K, Tager HS, Bell GI, Seino S. Cloning and functional-characterization of a family of human and mouse somatostatin receptors expressed in brain, gastrointestinal-tract, and kidney. Proc Natl Acad Sci USA 1992;89:251-255.
5. Patel YC. Somatostatin and its receptor family. Front Neuroendocrinol 1999;20:157-198.
6. Brazeau P, Vale W, Burgus R, Ling N, Butcher M, Rivier J, Guillemin R. Hypothalamic polypeptide that inhibits secretion of immunoreactive pituitary growth-hormone. Science 1973;179:77-79.
7. Patel YC, Wheatley T. Invivo and invitro plasma disappearance and metabolism of somatostatin-28 and somatostatin-14 in the rat. Endocrinology 1983;112:220-225.
8. Bauer W, Briner U, Doepfner W, Haller R, Huguenin R, Marbach P, Petcher TJ, Pless J. Sms 201-995 - a very potent and selective octapeptide analog of somatostatin with prolonged action. Life Sci 1982;31:1133-1140. (Pubitemid 13243115)
9. Bruns C, Raulf F, Hoyer D, Schloos J, Lubbert H, Weckbecker G. Binding properties of somatostatin receptor subtypes. Met Clin Exp 1996;45:17-20. (Pubitemid 26281932)
10. Maurer R, Gaehwiler BH, Buescher HH, Hill RC, Roemer D. Opiate antagonistic properties of an octapeptide somatostatin analog. Proc Natl Acad Sci USA 1982;79:4815-4817.
11. Wynants C, Vanbinst G, Loosli HR. SMS-201-995, a very potent analog of somatostatin assignment of the H-1 500 MHZ NMR-spectra and conformational- analysis in aqueous-solution. Int J Peptide Protein Res 1985;25:608-614. (Pubitemid 15041508)
12. Wynants C, Vanbinst G, Loosli HR. SMS-201-995, an octapeptide somatostatin analog assignment of the H-1-500 MHZ NMR-spectra and conformational-analysis of SMS 201-995 in dimethylsulfoxide. Int J Peptide Protein Res 1985;25:615-621. (Pubitemid 15041509)
13. Wynants C, Tourwe D, Kazmierski W, Hruby VJ, Vanbinst G. Conformation of 2 somatostatin analogs in aqueous-solution-study by NMR methods and circular-dichroism. Eur J Biochem 1989;185:371-381. (Pubitemid 19276641)
14. Widmer H, Widmer A, Braun W. Extensive distance geometry calculations with different noe calibrations-new criteria for structure selection applied to sandostatin and bpti. J Biomol NMR 1993;3:307-324.
15. Pohl E, Heine A, Sheldrick GM, Dauter Z, Wilson KS, Kallen J, Huber W, Pfaffli P. Structure of octreotide, a somatostatin analog. Acta Crystallogr 1995;51:48-59.
16. Melacini G, Zhu Q, Goodman M. Multiconformational nmr analysis of sandostatin (octreotide): equilibrium between beta-sheet and partially helical structures. Biochemistry 1997;36:1233-1241. (Pubitemid 27074947)
17. Bruns C, Lewis I, Briner U, Meno-Tetang G, Weckbecker G. Som230: a novel somatostatin peptidomimetic with broad somatotropin release inhibiting factor (srif) receptor binding and a unique antisecretory profile. Eur J Endocrinol 2002;146:707-716. (Pubitemid 34552506)
18. Lewis I, Bauer W, Albert R, Chandramouli N, Pless J, Weckbecker G, Bruns C. A novel somatostatin mimic with broad somatotropin release inhibitory factor receptor binding and superior therapeutic potential. J Med Chem 2003;46:2334-2344. (Pubitemid 36637918)
19. van der Hoek J, van der Lelij AJ, Feelders RA, de Herder WW, Uitterlinden P, Poon KW, Boerlin V, Lewis I, Krahnke T, Hofland LJ, Lamberts SW. The somatostatin analogue som230, compared with octreotide, induces differential effects in several metabolic pathways in acromegalic patients. Clin Endocrinol 2005;63:176-184. (Pubitemid 41097986)
20. Ma PM, Wang YF, van der Hoek J, Nedelman J, Schran H, Tran LL, Lamberts SWJ. Pharmacokinetic-pharmacodynamic comparison of a novel multiligand somatostatin analog, som230, with octreotide in patients with acromegaly. Clin Pharmacol Thers 2005;78:69-80. (Pubitemid 40956933)
21. Silva AP, Schoeffter P, Weckbecker G, Bruns C, Schmid HA. Regulation of crh-induced secretion of acth and corticosterone by som230 in rats. Eur J Endocrinol 2005;153:R7-R10. (Pubitemid 41410505)
22. Hofland LJ, van der Hoek J, Feelders R, van Aken MO, van Koetsveld PM, Waaijers M, Sprij-Mooij D, Bruns C, Weckbecker G, de Herder WW, Beckers A, Lamberts SWJ. The multi-ligand somatostatin analogue som230 inhibits acth secretion by cultured human corticotroph adenomas via somatostatin receptor type 5. Eur J Endocrinol 2005;152:645-654. (Pubitemid 40575811)
23. Ono K, Suzuki T, Miki Y, Taniyama Y, Nakamura Y, Noda Y, Watanabe M, Sasano H. Somatostatin receptor subtypes in human nonfunctioning neuroendocrine tumors and effects of somatostatin analogue som230 on cell proliferation in cell line nci-h727. Anticancer Res 2007;27:2231-2239. (Pubitemid 47228058)
24. Adams RL, Adams IP, Lindow SW, Atkin SL. Inhibition of endothelial proliferation by the somatostatin analogue som230. Clin Endocrinol 2004;61:431-436. (Pubitemid 39388480)
25. Brooks BR, Bruccoleri RE, Olafson BD, States DJ, Swaminathan S, Karplus M. CHARMM: A program for macromolecular energy, minimization, and dynamics calculations. J Comput Chem 1983;4:187-217.
26. Momany FA, Rone R. Validation of the general purpose QUANTA 3.2/CHARMm force field. J Comput Chem 1992;13:888-900.
27. MacKerell Jr., AD. e. a. All-atom empirical potential for molecular modeling and dynamics studies of proteins. J Phys Chem B 1998;102:3586-3616. (Pubitemid 128576688)
28. Hoover WG. Constant-pressure equations of motion. Phys Rev A 1986;34:2499-2500.
29. Hartigan JA. Clustering algorithms. NY: Wiley; 1975.
30. Tou JT, Gonzalez RC. Pattern recognition principles. Applied Mathematics and Computation, Reading, MA: Addison-Wesley, 1974.
31. Lewis IL, Albert R, Bauer W, Chandramouli N, Pless J, Oberer L, Bovermann G, van der Hoek J, Boerlin V, Lamberts SWJ, Schmid HA, Weckbecker G, Bruns C. The superior therapeutic properties of som230 originate from unique structural elements. Chimia 2004;58:222-227. (Pubitemid 38648530)
32. Yao J, Dyson HJ, Wright P. Threedimensional structure of a type vi turn in a linear peptide in water solution. Evidence for stacking of aromatic rings as a major stabilizing factor. J Mol Biol 1994;243:754-766. (Pubitemid 124002140)
33. Galzitskaya O, Caflisch A. Solution conformation of phakellistatin 8 investigated by molecular dynamics simulations. J Mol Graphics Modell 1999;17:19-27. (Pubitemid 30029314)