Comparative study of chemical approaches to the solid-phase synthesis of a tumor-seeking α-MSH analogue

International Journal of Peptide Research and Therapeutics

Volumn 14, Issue 3, 2008, Pages 273-281

  Valldosera, Magdalena ^a   Monsò, Marta ^a   Xavier, Catarina ^b   Raposinho, Paula ^b   Correia, João D G ^b   Santos, Isabel ^b   Gomes, Paula ^a  

^a UNIVERSITY OF PORTO   (Portugal)

^b INSTITUTO TECNOLÓGICO E NUCLEAR   (Portugal)

Author keywords

Cyclic peptides; Melanocortin; MTII; On resin lactamization; Orthogonal; SPPS; MSH

Indexed keywords

EID: 65949086743     PISSN: 15733149     EISSN: 15733904     Source Type: Journal    
DOI: 10.1007/s10989-008-9143-2     Document Type: Article

References (41)

1. Aletras A, Barlos K, Gatos D, Koutsogianni S, Mamos P (1995) Preparation of the very acid-sensitive Fmoc-Lys(Mtt)-OH. Int J Peptide Protein Res 45:488-496
2. Al-Obeidi F, Castrucci AML, Hadley ME, Hruby VJ (1989) Potent and prolonged acting cyclic lactam analogues of α-melanotropin: design based on molecular dynamics. J Med Chem 32:2555-2561
3. Arnott G, Clayden J, Hamilton SD (2006) Azabicyclic amino acids by stereoselective dearomatizing cyclization of the enolates of N-nicotinoyl glycine derivatives. Org Lett 8:5325-5328 (Pubitemid 44861559)
4. Bednarek MA, MacNeil T, Kalyani RN, Tang R, Van der Ploeg LHT, Weinberg DH (2001) Selective, high affinity peptide antagonists of α-melanotropin action at human melanocortin receptor 4: their synthesis and biological evaluation in vitro. J Med Chem 44:3665-3672 (Pubitemid 33026674)
5. Besser D, Müller B, Agricola I, Reissmann S (2000a) Synthesis of differentially protected N-acylated reduced pseudodipeptides as building units for backbone cyclic peptides. J Peptide Sci 6:130-138 (Pubitemid 30179496)
6. Besser D,Müller B, Kleinwächter P, Greiner G, Seyfarth L, Steinmetzer T, Arad O, Reissmann S (2000b) Synthesis and characterization of octapeptide somatostatin analogues with backbone cyclization: comparison of different strategies, biological activities and enzymatic stabilities. J Prakt Chem 342:537-545
7. Chan WC, Bycroft BW, Evans DJ, White PD (1995) A novel 4-aminobenzyl ester-based carboxy-protecting group for synthesis of atypical peptides by Fmoc-But solid-phase chemistry. J Chem Soc Chem Comm 1995:2209-2210
8. Charpentier B, Dor A, Roy P, England P, Pham H, Durieux C, Roques BP (1989) Synthesis and binding affinities of cyclic and related linear analogues of CCK8 selective for central receptors. J Med Chem 32:1184-1190 (Pubitemid 19149968)
9. Che Y, Marshall GR (2006) Engineering cyclic tetrapeptides containing chimeric amino acids as preferred reverse-turn scaffolds. J Med Chem 49:111-124 (Pubitemid 43077326)
10. Chhabra SR, Hothi B, Evans DJ, White PD, Bycroft BW, Chan WC (1998) An appraisal of new variants of Dde amine protecting group for solid phase peptide synthesis. Tetrahedron Lett 39: 1603-1606 (Pubitemid 28101583)
11. Díaz-Mochón J, Bialy L, Bradley M (2006) Full orthogonality between Dde, Fmoc: the direct synthesis of PNA-peptide conjugates. Org Lett 6:1127-1129 (Pubitemid 38591839)
12. Dorr RT, Lines R, Levine N, Brooks C, Xiang L, Hruby VJ, Hadley ME (1996) Evaluation of melanotan-II, a superpotent cyclic melanotropic peptide in a pilot phase-I clinical study. Life Sci 58:1777-1784 (Pubitemid 26148611)
13. Felix AM, Wang CT, Heimer EP, Fournier A (1988) Applications of BOP reagent in solid phase synthesis. Int J Peptide Protein Res 31:231-238
14. Flora D, Mo H, Mayer JP, Khan MA, Yan LZ (2005) Detection and control of aspartimide formation in the synthesis of cyclic peptides. Bioorg Med Chem Lett 15:1065-1068 (Pubitemid 40458649)
15. García-Martín F, Quintanar-Audelo M, García-Ramos Y, Cruz LC, Gravel C, Furic R, Côté S, Tulla-Puche J, Albericio F (2006) ChemMatrix, a poly(ethylene glycol)-based support for the solid-phase synthesis of complex peptides. J Comb Chem 8: 213-220 (Pubitemid 43503929)
16. Gilon C, Halle D, Chorev M, Selinger Z, Byk G (1991) Backbone cyclization: a new conformational constraint on peptides. Biopolymers 31:745-750
17. Gomes P, Giralt E, Andreu D (2001) Antigenicity modulation upon peptide cyclization: application of the GH loop of foot-and-mouth disease virus strain C1-Barcelona. Vaccine 19:3459-3466 (Pubitemid 32710296)
18. Grieco P, Cai M, Mayorov AV, Trivedi D, Hruby VJ (2006) Structure-activity studies of new melanocortin peptides containing an aromatic amino acid at the N-terminal position. Peptides 27:472-481 (Pubitemid 43162919)
19. Gude M, Ryf J, White PD (2003) An accurate method for the quantitation of Fmoc-derivatized solid phase supports. Lett Peptide Sci 9:203-206
20. Hadley ME, Hruby VJ, Sharma SD (1997) Cyclic bridged analogs of α-MSH and methods thereof. United States Patent 5,683,981. November 4
21. Holder JR, Haskell-Luevano C (2004) Melanocortin ligands: 30 years of structure-activity relationship (SAR) studies. Med Res Rev 24:325-356 (Pubitemid 38490035)
22. Hruby VJ, Lu D, Sharma SD, Castrucci AL, Kesterson RA, Al-Obeidi FA, Hadley ME, Cone RD (1995) Cyclic lactam α-melanotropin analogues of Ac-Nle4-cyclo{Asp5, DPhe7, Lys10}-α-melano-cyte- stimulating hormone-(4-10)-NH2 with bulky aromatic amino acids at position 7 show high antagonist potency and selectivity at specific melanocortin receptors. J Med Chem 38:3454-3561
23. Johnson T, Liley M, Cheeseright TJ, Begum F (2000) Problems in the synthesis of cyclic peptides through use of the Dmab protecting group (2000). J Chem Soc, Perkin Trans 1:2811-2820 (Pubitemid 35290714)
24. Kaiser E, Colescott RL, Bossinger CD, Cook PI (1970) Color test for detection of free terminal amino groups in solid-phase synthesis of peptides. Anal Biochem 34:595-598
25. Kaul R, Surprenant S, Lubell WD (2005) Systematic study of the synthesis of macrocyclic dipeptide β-turn mimics possessing 8-, 9-, and 10-membered rings by ring-closing metathesis. J Org Chem 70:3838-3844 (Pubitemid 40675310)
26. Keramida M, Tselios T, Mantzourani E, Papazisis K, Mavromoustakos T, Klaussen C, Agelis G, Deraos S, Friligou I, Habibi H, Matsoukas J (2006) Design, synthesis, and molecular modeling of a novel amide-linked cyclic GnRH analogue cyclo(4-9)[Lys4, D-Trp6, Glu9]GnRH: stimulation of gonadotropin gene expression. J Med Chem 49:105-110 (Pubitemid 43078591)
27. Liederer BM, Fuchs T, Velde DV, Siahaan TJ, Borchardt RT (2006) Effects of amino acid chirality and the chemical linker on the cell permeation characteristics of cyclic prodrugs of opioid peptides. J Med Chem 49:1261-1270 (Pubitemid 43271882)
28. Lyttle MH, Hudson D (1992) Allyl based side-chain protection for SPPS. In: Smith JA, Rivier JE (eds) Peptides: chemistry, structure and biology. ESCOM, Leiden, pp 583-584
29. Mayorov AV, Cai M, Chandler KB, Petrov RR, Van Scoy AR, Yu Z, Tanaka DK, Trivedi D, Hruby VJ (2006) Development of cyclic γ-MSH analogues with selective hMC3R agonist and hMC3R/hMC5R antagonist activities. J Med Chem 49:1946-1952
30. Nielsen TE, Quement SL, Meldal M (2005) Solid-phase synthesis of bicyclic dipeptide mimetics by intramolecular cyclization of alcohols, thiols, amines, and amides with N-acyliminium intermediates. Org Lett 7:3601-3604 (Pubitemid 41224531)
31. Norgren AS, Büttner F, Prabpai S, Kongsaeree P, Arvidsson PI (2006) 2-aminoacids in the design of conformationally homogeneous cyclo-peptide scaffolds. J Org Chem 71:6814-6821 (Pubitemid 44645656)
32. Poteau R, Trinquier G (2005) All-cis cyclic peptides. J Am Chem Soc 127:13875-13889 (Pubitemid 41437038)
33. 3]&α: effect of cyclization on tumor-seeking properties. J Biol Inorg Chem 13:449-459
34. 3-labeled pyrazolyl-α-melanocyte stimulating hormone analog conjugate for melanoma targeting. Nucl Med Biol 35:91-99
35. Reissmann S, Imhof D (2004) Development of conformationally restricted analogues of bradykinin and somatostatin using constrained amino acids and different types of cyclization. Curr Med Chem 11:2823-2844 (Pubitemid 39377885)
36. Rovero P (2000) Homodetic cyclic peptides. In: Kates SA, Albericio F (eds) Solid-phase synthesis. Marcel Dekker, Inc., New York, pp 331-364
37. Schaaper WMM, Adan RAH, Posthum TA, Oosterom J, Gispen W-H, Meloen RH (1998) Synthesis of cyclic α-MSH peptides. Lett Peptide Sci 5:205-208
38. Schiller PW, Nguyen TMD, Miller J (1985) Synthesis of side-chain to side-chain cyclized peptide analogs on solid supports. Int J Peptide Protein Res 25:171-177
39. Schiller PW, Nguyen TMD, Lemiueux C (1988) Synthesis and opioid activity profiles of cyclic dynorphin analogs. Tetrahedron 44:733-743 (Pubitemid 18051780)
40. 4]-α-MSH(4-11)-NH2. Biochemistry 27:8181-8188
41. Yue C, Thierry J, Potier P (1993) 2-Phenyl isopropyl esters as carboxyl terminus protecting groups in the fast synthesis of peptide fragments. Tetrahedron Lett 34:323-326