Improvement of drug-like properties of peptides: the somatostatin paradigm

Bibliography

• Beresford AP, Selick HE, Tarbit MH. The emerging importance of predictive ADME simulation in drug discovery. Drug Discov Today 2002;7(2):109-16
   PubMed Web of Science ®Google Scholar
• Wishart DS. Improving early drug discovery through ADME modelling: an overview. Drugs R D 2007;8(6):349-62
   PubMedGoogle Scholar
• Lombardino JG, Lowe JA III. The role of the medicinal chemist in drug discovery–then and now. Nat Rev 2004;3(10):853-62
   Google Scholar
• Yu H, Adedoyin A. ADME-Tox in drug discovery: integration of experimental and computational technologies. Drug Discov Today 2003;8(18):852-61
   PubMed Web of Science ®Google Scholar
• Kerns EH, Di L. Pharmaceutical profiling in drug discovery. Drug Discov Today 2003;8(7):316-23
   PubMed Web of Science ®Google Scholar
• Avdeef A. Physicochemical profiling (solubility, permeability and charge state). Curr Top Med Chem 2001;1(4):277-351
   PubMedGoogle Scholar
• Zamora I, Oprea T, Cruciani G, Surface descriptors for protein-ligand affinity prediction. J Med Chem 2003;46(1):25-33
   PubMed Web of Science ®Google Scholar
• Hamman JH, Enslin GM, Kotze AF. Oral delivery of peptide drugs–Barriers and developments. Biodrugs 2005;19(3):165-77
   PubMed Web of Science ®Google Scholar
• Samanen J, Ali F, Romoff T, Development of a small RGD peptide fibrinogen receptor antagonist with potent antiaggregatory activity in vitro. J Med Chem 1991;34(10):3114-25
   PubMed Web of Science ®Google Scholar
• Hess S, Linde Y, Ovadia O, Backbone cyclic peptidomimetic melanocortin-4 receptor agonist as a novel orally administrated drug lead for treating obesity. J Med Chem 2008;51(4):1026-34
   PubMed Web of Science ®Google Scholar
• Kessler H. Conformation and biological activity of cyclic peptides. Angew Chem Int Ed Engl 1982;21(7):512-23
   Web of Science ®Google Scholar
• Vale W, Brazeau P, Grant G, Preliminary observations on the mechanism of action of somatostatin, a hypothalamic factor inhibiting the secretion of growth hormone. C R Acad Sci Hebd Seances Acad Sci D 1972;275(25):2913-6
   PubMed Web of Science ®Google Scholar
• Weckbecker G, Lewis I, Albert R, Opportunities in somatostatin research: biological, chemical and therapeutic aspects. Nat Rev Drug Discov 2003;2(12):999-1017
   PubMed Web of Science ®Google Scholar
• Reisine T, Bell GI. Molecular biology of somatostatin receptors. Endocr Rev 1995;16(4):427-42
   PubMed Web of Science ®Google Scholar
• Corleto VD, Nasoni S, Panzuto E, Somatostatin receptor subtypes: basic pharmacology and tissue distribution. Dig Liver Dis 2004;36:S8-16
   PubMedGoogle Scholar
• Marbach PB, Bodmer W, Briner D, Discovery and development of somatostatin agonists. In: Borchardt RTRMF, Sawyer TK, Smith PL, editors, Integration of pharmaceutical discovery and development. Plenum Press, Case Histories NY; 1998. p. 183-209
   Google Scholar
• Raulf F, Perez J, Hoyer D, Differential expression of five somatostatin receptor subtypes, SSTR1-5, in the CNS and peripheral tissue. Digestion 1994;55(Suppl 3):46-53
   PubMedGoogle Scholar
• Hoyer D, Bell GI, Berelowitz M, Classification and nomenclature of somatostatin receptors. Trends Pharmacol Sci 1995;16(3):86-8
   PubMed Web of Science ®Google Scholar
• Lamberts SW, van der Lely AJ, de Herder WW, Octreotide. N Engl J Med 1996;334(4):246-54
   PubMed Web of Science ®Google Scholar
• Mezey E, Hunyady B, Mitra S, Cell specific expression of the sst2A and sst5 somatostatin receptors in the rat anterior pituitary. Endocrinology 1998;139(1):414-9
   PubMed Web of Science ®Google Scholar
• Kumar U, Sasi R, Suresh S, Subtype-selective expression of the five somatostatin receptors (hSSTR1-5) in human pancreatic islet cells: a quantitative double-label immunohistochemical analysis. Diabetes 1999;48(1):77-85
   PubMed Web of Science ®Google Scholar
• Mitra SW, Mezey E, Hunyady B, Colocalization of somatostatin receptor sst5 and insulin in rat pancreatic beta-cells. Endocrinology 1999;140(8):3790-6
   PubMed Web of Science ®Google Scholar
• Schally AV. Oncological applications of somatostatin analogues. Cancer Res 1988;48(24 Pt 1):6977-85
   PubMed Web of Science ®Google Scholar
• Scarpignato C, Pelosini I. Somatostatin analogs for cancer treatment and diagnosis: an overview. Chemotherapy 2001;47(Suppl 2):1-29
   PubMedGoogle Scholar
• Pollak MN, Schally AV. Mechanisms of antineoplastic action of somatostatin analogs. Proc Soc Exp Biol Med 1998;217(2):143-52
   PubMed Web of Science ®Google Scholar
• Bousquet C, Puente E, Buscail L, Antiproliferative effect of somatostatin and analogs. Chemotherapy 2001;47(Suppl 2):30-9
   PubMedGoogle Scholar
• Oberg K. Future aspects of somatostatin-receptor-mediated therapy. Neuroendocrinology 2004;80(Suppl 1):57-61
   PubMedGoogle Scholar
• Patel YC, Wheatley T. In vivo and in vitro plasma disappearance and metabolism of somatostatin-28 and somatostatin-14 in the rat. Endocrinology 1983;112(1):220-5
   PubMed Web of Science ®Google Scholar
• Toledano Y, Rot L, Greenman Y, Efficacy of long-term lanreotide treatment in patients with acromegaly. Pituitary 2009;12(4):285-93
   PubMed Web of Science ®Google Scholar
• Cai RZ, Szoke B, Lu R, Synthesis and biological-activity of highly potent octapeptide analogs of somatostatin. PNAS 1986;83(6):1896-900
   PubMed Web of Science ®Google Scholar
• Hannon JPBCW, Hoyer G, Somatostatin D. Receptor gene family -subtype selectivity for ligand binding. In: Srikant CB, editor, Somatostatin. Klower Academic Publishers, Boston; 2004. p. 87
   Google Scholar
• Hofland LJ, van Koetsveld PM, Waaijers M, Relative potencies of the somatostatin analogs octreotide, BIM-23014, and RC-160 on the inhibition of hormone release by cultured human endocrine tumor cells and normal rat anterior pituitary cells. Endocrinology 1994;134(1):301-6
   PubMed Web of Science ®Google Scholar
• Shimon I, Yan X, Taylor JE, Somatostatin receptor (SSTR) subtype-selective analogues differentially suppress in vitro growth hormone and prolactin in human pituitary adenomas. Novel potential therapy for functional pituitary tumors. J Clin Invest 1997;100(9):2386-92
   PubMed Web of Science ®Google Scholar
• Afargan M, Janson ET, Gelerman G, Novel long-acting somatostatin analog with endocrine selectivity: potent suppression of growth hormone but not of insulin. Endocrinology 2001;142(1):477-86
   PubMed Web of Science ®Google Scholar
• Chan JC, Cockram CS, Critchley JA. Drug-induced disorders of glucose metabolism. Mechanisms and management. Drug Saf 1996;15(2):135-57
   PubMed Web of Science ®Google Scholar
• Kahn SE, Klaff LJ, Schwartz MW, Treatment with a somatostatin analog decreases pancreatic B-cell and whole body sensitivity to glucose. J Clin Endocrinol Metab 1990;71(4):994-1002
   PubMed Web of Science ®Google Scholar
• Hassan Z, Wright J. Use of octreotide acetate to prevent rebound hypoglycaemia in sulfonylurea overdose. Emerg Med J 2007;24(8):580-1
   PubMed Web of Science ®Google Scholar
• Thanou M, Verhoef JC, Verheijden JHM, Intestinal absorption of octreotide using trimethyl chitosan chloride: studies in pigs. Pharm Res 2001;18(6):823-8
   PubMed Web of Science ®Google Scholar
• Miyasaka K, Masuda M, Kanai S, Inhibitory effects of octreotide on luminal cholecystokinin-releasing factor, plasma cholecystokinin, and pancreatic secretion in conscious rats. Pancreas 2002;24(3):269-75
   PubMed Web of Science ®Google Scholar
• Schonbrunn A. Selective agonism in somatostatin receptor signaling and regulation. Mol Cell Endocrinol 2008;286(1-2):35-9
   PubMed Web of Science ®Google Scholar
• Tulipano G, Schulz S. Novel insights in somatostatin receptor physiology. Eur J Endocrinol 2007;156(Suppl 1):S3-11
   PubMedGoogle Scholar
• Tigerstedt NM, Aavik E, Aavik S, Vasculoprotective effects of somatostatin receptor subtypes. Mol Cell Endocrinol 2007;279(1-2):34-8
   PubMed Web of Science ®Google Scholar
• Pawlikowski M, Melen-Mucha G. Somatostatin analogs– from new molecules to new applications. Curr Opin Pharmacol 2004;4(6):608-13
   PubMed Web of Science ®Google Scholar
• Susini C, Buscail L. Rationale for the use of somatostatin analogs as antitumor agents. Ann Oncol 2006;17(12):1733-42
   PubMed Web of Science ®Google Scholar
• Blaker M, Schmitz M, Gocht A, Differential expression of somatostatin receptor subtypes in hepatocellular carcinomas. J Hepatol 2004;41(1):112-8
   PubMed Web of Science ®Google Scholar
• Reubi JC, Maecke HR. Peptide-based probes for cancer imaging. J Nucl Med 2008;49(11):1735-8
   PubMed Web of Science ®Google Scholar
• Catnach SM, Anderson JV, Fairclough PD, Effect of octreotide on gall stone prevalence and gall-bladder motility in acromegaly. Gut 1993;34(2):270-3
   PubMed Web of Science ®Google Scholar
• Ziegler K, Frimmer M, Kessler H, Modified somatostatins as inhibitors of a multispecific transport system for bile acids and phallotoxins in isolated hepatocytes. Biochim Biophys Acta 1985;845(1):86-93
   PubMed Web of Science ®Google Scholar
• Ziegler K, Frimmer M, Kessler H, Azidobenzamido-008, a new photosensitive substrate for the ‘multispecific bile acid transporter’ of hepatocytes: evidence for a common transport system for bile acids and cyclosomatostatins in basolateral membranes. Biochim Biophys Acta 1988;945(2):263-72
   PubMed Web of Science ®Google Scholar
• Kessler H, Klein M, Muller A, Conformational prerequisites for the in vitro inhibition of cholate uptake in hepatocytes by cyclic analogs of antamanide and somatostatin. Angew Chem Int Ed Engl 1986;25(11):997-9
   Web of Science ®Google Scholar
• Liuzzi A, Oppizzi G. Evidence for octreotide subcutaneously in the treatment of acromegaly. J Endocrinol 1997;155(Suppl 1):S61-5
   PubMedGoogle Scholar
• Pasternak A, Pan YP, Marino D, Potent, orally bioavailable somatostatin agonists: Good absorption achieved by urea backbone cyclization. Bioorg Med Chem Lett 1999;9(3):491-6
   PubMed Web of Science ®Google Scholar
• Wolkenberg SE, Thut CJ. Recent progress in the discovery of selective, non-peptide ligands of somatostatin receptors. Curr Opin Drug Discov Dev 2008;11(4):446-57
   PubMed Web of Science ®Google Scholar
• Rohrer SP, Birzin ET, Mosley RT, Rapid identification of subtype-selective agonists of the somatostatin receptor through combinatorial chemistry. Science 1998;282(5389):737-40
   PubMed Web of Science ®Google Scholar
• Erchegyi J, Cescato R, Grace CR, Novel, potent, and radio-iodinatable somatostatin receptor 1 (sst(1)) selective analogues. J Med Chem 2009;52(9):2733-46
   PubMed Web of Science ®Google Scholar
• Grace CR, Durrer L, Koerber SC, Somatostatin receptor 1 selective analogues: 4. Three-dimensional consensus structure by NMR. J Med Chem 2005;48(2):523-33
   PubMed Web of Science ®Google Scholar
• Grace CR, Erchegyi J, Koerber SC, Novel sst2-selective somatostatin agonists. Three-dimensional consensus structure by NMR. J Med Chem 2006;49(15):4487-96
   PubMed Web of Science ®Google Scholar
• Grace CR, Erchegyi J, Reubi JC, Three-dimensional consensus structure of sst2-selective somatostatin (SRIF) antagonists by NMR. Biopolymers 2008;89(12):1077-87
   PubMed Web of Science ®Google Scholar
• Grace CRR, Koerber SC, Erchegyi J, Novel sst(4)-selective somatostatin (SRIF) agonists. 4. Three-dimensional consensus structure by NMR. J Med Chem 2003;46(26):5606-18
   PubMed Web of Science ®Google Scholar
• Kessler H. Peptoids–a new approach to the development of pharmaceuticals. Angew Chem Int Ed Engl 1993;32(4):543-4
   Web of Science ®Google Scholar
• Mattern RH, Moore SB, Tran TA, Synthesis, biological activities and conformational studies of somatostatin analogs. Tetrahedron 2000;56(50):9819-31
   Web of Science ®Google Scholar
• Miller SM, Simon RJ, Ng S, Proteolytic studies of homologous peptide and N-substituted glycine peptoid oligomers. Bioorg Med Chem Lett 1994;4(22):2657-62
   Web of Science ®Google Scholar
• Miller SM, Simon RJ, Ng S, Comparison of the proteolytic susceptibilities of homologous L-amino-acid, D-amino-acid, and N-substituted glycine peptide and peptoid oligomers. Drug Dev Res 1995;35(1):20-32
   Web of Science ®Google Scholar
• Lewis I, Bauer W, Albert R, A novel somatostatin mimic with broad somatotropin release inhibitory factor receptor binding and superior therapeutic potential. J Med Chem 2003;46(12):2334-44
   PubMed Web of Science ®Google Scholar
• Hruby VJ, Balse PM. Conformational and topographical considerations in designing agonist peptidomimetics from peptide leads. Curr Med Chem 2000;7(9):945-70
   PubMed Web of Science ®Google Scholar
• Weide T, Modlinger A, Kessler H. Spatial screening for the identification of the bioactive conformation of integrin ligands. In: Peters T, editor, Bioactive Conformation I. Springer, Berlin; 2007. p. 1-50
   Google Scholar
• Bauer W, Briner U, Doepfner W, SMS 201-995: a very potent and selective octapeptide analogue of somatostatin with prolonged action. Life Sci 1982;31(11):1133-40
   PubMed Web of Science ®Google Scholar
• Veber DF, Freidlinger RM, Perlow DS, A potent cyclic hexapeptide analogue of somatostatin. Nature 1981;292(5818):55-8
   PubMed Web of Science ®Google Scholar
• Grace CRR, Erchegyi J, Samant M, Ring size in octreotide amide modulates differently agonist versus antagonist binding affinity and selectivity. J Med Chem 2008;51(9):2676-81
   PubMed Web of Science ®Google Scholar
• Kessler H, Bernd M, Kogler H, Peptide conformations 28. Relayed heteronuclear correlation spectroscopy and conformational-analysis of cyclic hexapeptides containing the active sequence of somatostatin. JACS 1983;105(23):6944-52
   Web of Science ®Google Scholar
• Kessler H, Gratias R, Hessler G, Conformation of cyclic peptides. Principle concepts and the design of selectivity and superactivity in bioactive sequences by ‘spatial screening’. Pure Appl Chem 1996;68(6):1201-5
   Web of Science ®Google Scholar
• Aumailley M, Gurrath M, Muller G, Arg-Gly-Asp constrained within cyclic pentapeptides–strong and selective inhibitors of cell-adhesion to vitronectin and laminin fragment-P1. FEBS Lett 1991;291(1):50-4
   PubMed Web of Science ®Google Scholar
• Haubner R, Finsinger D, Kessler H. Stereoisomeric peptide libraries and peptidomimetics for designing selective inhibitors of the alpha(V)beta(3) integrin for a new cancer therapy. Angew Chem Int Ed Engl 1997;36(13-14):1375-89
   Web of Science ®Google Scholar
• Dechantsreiter MA, Planker E, Matha B, N-methylated cyclic RGD peptides as highly active and selective alpha(v)beta(3) integrin antagonists. J Med Chem 1999;42(16):3033-40
   PubMed Web of Science ®Google Scholar
• Gilon C, Halle D, Chorev M, Backbone cyclization: a new method for conferring conformational constraint on peptides. Biopolymers 1991;31(6):745-50
   PubMed Web of Science ®Google Scholar
• Gellerman G, Elgavi A, Salitra Y, Facile synthesis of orthogonally protected amino acid building blocks for combinatorial N-backbone cyclic peptide chemistry. J Pept Res 2001;57(4):277-91
   PubMedGoogle Scholar
• Muller D, Zeltser I, Bitan G, Building units for N-backbone cyclic peptides. 3. Synthesis of protected N(alpha)-(omega-Aminoalkyl)amino acids and N(alpha)-(omega-Carboxyalkyl)amino Acids. J Org Chem 1997;62(2):411-6
   PubMed Web of Science ®Google Scholar
• Gazal S, Gellerman G, Glukhov E, Synthesis of novel protected Nalpha(omega-thioalkyl) amino acid building units and their incorporation in backbone cyclic disulfide and thioetheric bridged peptides. J Pept Res 2001;58(6):527-39
   PubMedGoogle Scholar
• Falb E, Yechezkel T, Salitra Y, In situ generation of Fmoc-amino acid chlorides using bis-(trichloromethyl) carbonate and its utilization for difficult couplings in solid-phase peptide synthesis. J Pept Res 1999;53(5):507-17
   PubMedGoogle Scholar
• Kasher R, Oren DA, Barda Y, Miniaturized proteins: the backbone cyclic proteinomimetic approach. J Mol Biol 1999;292(2):421-9
   PubMed Web of Science ®Google Scholar
• Byk G, Halle D, Zeltser I, Synthesis and biological activity of NK-1 selective, N-backbone cyclic analogs of the C-terminal hexapeptide of substance P. J Med Chem 1996;39(16):3174-8
   PubMed Web of Science ®Google Scholar
• Hess S, Ovadia O, Shalev DE, Effect of structural and conformation modifications, including backbone cyclization, of hydrophilic hexapeptides on their intestinal permeability and enzymatic stability. J Med Chem 2007;50(24):6201-11
   PubMed Web of Science ®Google Scholar
• Gilon C, Huenges M, Matha B, A backbone-cyclic, receptor 5-selective somatostatin analogue: synthesis, bioactivity, and nuclear magnetic resonance conformational analysis. J Med Chem 1998;41(6):919-29
   PubMed Web of Science ®Google Scholar
• Falb E, Salitra Y, Yechezkel T, A bicyclic and hsst2 selective somatostatin analogue: design, synthesis, conformational analysis and binding. Bioorg Med Chem 2001;9(12):3255-64
   PubMed Web of Science ®Google Scholar
• Gazal S, Gelerman G, Ziv O, Human somatostatin receptor specificity of backbone-cyclic analogues containing novel sulfur building units. J Med Chem 2002;45(8):1665-71
   PubMed Web of Science ®Google Scholar
• Besser D, Muller B, Kleinwachter P, Synthesis and characterization of octapeptide somatostatin analogues with backbone cyclization: comparison of different strategies, biological activities and enzymatic stabilities. J Prakt Chem 2000;342(6):537-45
   Google Scholar
• Pierson ME, Comstock JM, Simmons RD, Synthesis and biological evaluation of potent, selective, hexapeptide CCK-A agonist anorectic agents. J Med Chem 1997;40(26):4302-7
   PubMed Web of Science ®Google Scholar
• Stewart BH, Reyner EL, Tse E, In vitro assessment of oral delivery for hexapeptide endothelin antagonists. Life sci 1996;58(12):971-82
   PubMed Web of Science ®Google Scholar
• Chatterjee J, Gilon C, Hoffman A, N-methylation of peptides: a new perspective in medicinal chemistry. Acc Chem Res 2008;41(10):1331-42
   PubMed Web of Science ®Google Scholar
• Rajeswaran WG, Hocart SJ, Murphy WA, N-Methyl scan of somatostatin octapeptide agonists produces interesting effects on receptor subtype specificity. J Med Chem 2001;44(9):1416-21
   PubMed Web of Science ®Google Scholar
• Miller SC, Scanlan TS. Site-selective N-methylation of peptides on solid support. JACS 1997;119(9):2301-2
   Web of Science ®Google Scholar
• Biron E, Chatterjee J, Kessler H. Optimized selective N-methylation of peptides on solid support. J Pept Sci 2006;12(3):213-9
   PubMed Web of Science ®Google Scholar
• Hartmann J, Szemplinski M, Chen SL, Blood-pressure reduction in hypertensive-diabetic rats by the somatostatin analog Mk-678. Life Sci 1989;45(3):267-74
   PubMed Web of Science ®Google Scholar
• Biron E, Chatterjee J, Ovadia O, Improving oral bioavailability of peptides by multiple N-methylation: somatostatin analogues. Angew Chem Int Ed Engl 2008;47(14):2595-9
   PubMed Web of Science ®Google Scholar
• Strowski MZ, Dashkevicz MP, Parmar RM, Somatostatin receptor subtypes 2 and 5 inhibit corticotropin-releasing hormone-stimulated adrenocorticotropin secretion from AtT-20 cells. Neuroendocrinology 2002;75(6):339-46
   PubMed Web of Science ®Google Scholar
• Tulipano G, Soldi D, Bagnasco M, Characterization of new selective somatostatin receptor subtype-2 (sst2) antagonists, BIM-23627 and BIM-23454. Effects of BIM-23627 on GH release in anesthetized male rats after short-term high-dose dexamethasone treatment. Endocrinology 2002;143(4):1218-24
   PubMed Web of Science ®Google Scholar
• Parmar RM, Chan WW, Dashkevicz M, Nonpeptidyl somatostatin agonists demonstrate that sst2 and sst5 inhibit stimulated growth hormone secretion from rat anterior pituitary cells. Biochem Biophys Res Commun 1999;263(2):276-80
   PubMed Web of Science ®Google Scholar
• Ludvigsen E, Stridsberg M, Taylor JE, Regulation of insulin and glucagon secretion from rat pancreatic islets in vitro by somatostatin analogues. Regul Pept 2007;138(1):1-9
   PubMed Web of Science ®Google Scholar
• Rosenbaum DM, Rasmussen SG, Kobilka BK. The structure and function of G-protein-coupled receptors. Nature 2009;459(7245):356-63
   PubMed Web of Science ®Google Scholar
• Milligan G. G protein-coupled receptor hetero-dimerization: contribution to pharmacology and function. Br J Pharmacol 2009;158(1):5-14
   PubMed Web of Science ®Google Scholar
• Duran-Prado M, Malagon MM, Gracia-Navarro F, Dimerization of G protein-coupled receptors: new avenues for somatostatin receptor signalling, control and functioning. Mol Cell Endocrinol 2008;286(1-2):63-8
   PubMed Web of Science ®Google Scholar
• George SR, O'Dowd BF, Lee SP. G-protein-coupled receptor oligomerization and its potential for drug discovery. Nat Rev 2002;1(10):808-20
   Google Scholar
• Pfeiffer M, Koch T, Schroder H, Homo- and heterodimerization of somatostatin receptor subtypes–Inactivation of sst(3) receptor function by heterodimerization with sst(2A). J Biol Chem 2001;276(17):14027-36
   PubMed Web of Science ®Google Scholar
• Verlander M. Industrial applications of solid-phase peptide synthesis–A status report. Int J Pept Res Ther 2007;13(1-2):75-82
   Web of Science ®Google Scholar
• Danho W, Swistok J, Khan W, Opportunities and challenges of developing peptide drugs in the pharmaceutical industry. Adv Exp Med Biol 2009;611:467-9
   PubMed Web of Science ®Google Scholar
• Demmer O, Frank AO, Kessler H. Design of cyclic peptides. In: Jensen K, editor, Peptide and protein design for biopharmaceutical applications. Wiley & Sons Ltd; 2009. p. 133-76
   Google Scholar
• Hasskarl J. Sorafenib. Rec Results Cancer Res 2010;184:61-70
   PubMedGoogle Scholar
• Lipinski CA, Lombardo F, Dominy BW, Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev 2001;46(1-3):3-26
   PubMed Web of Science ®Google Scholar
• Veber DF, Johnson SR, Cheng HY, Molecular properties that influence the oral bioavailability of drug candidates. J Med Chem 2002;45(12):2615-23
   PubMed Web of Science ®Google Scholar
• Lindholm A. Factors influencing the pharmacokinetics of cyclosporine in man. Ther Drug Monit 1991;13(6):465-77
   PubMed Web of Science ®Google Scholar
• Loosli HR, Kessler H, Oschkinat H, Peptide conformations 31. The conformation of cyclosporin-a in the crystal and in solution. Helvetica Chim Acta 1985;68(3):682-704
   Web of Science ®Google Scholar
• Biron E, Kessler H. Convenient synthesis of N-methylamino acids compatible with Fmoc solid-phase peptide synthesis. J Org Chem 2005;70(13):5183-9
   PubMed Web of Science ®Google Scholar
• Chatterjee J, Ovadia O, Zahn G, Highly selective cyclic hexapeptides antagonist of GPIIb-IIIa by multiple N-methylation. Adv Exp Med Biol 2009;611:209-10
   PubMed Web of Science ®Google Scholar
• Hurevich MT-G, Klein Y, Barda S, Novel method for the synthesis of urea backbone cyclic peptides using new Alloc protected glycine building units. J Pept Sci 2010;16(4):178-85
   PubMed Web of Science ®Google Scholar
• Hannon JP, Nunn C, Stolz B, Drug design at peptide receptors–Somatostatin receptor ligands. J Mol Neurosci 2002;18(1-2):15-27
   PubMed Web of Science ®Google Scholar
• Patel YC, Srikant CB. Subtype selectivity of peptide analogs for all five cloned human somatostatin receptors (hsstr 1-5). Endocrinology 1994;135(6):2814-7
   PubMed Web of Science ®Google Scholar