Tackling lipophilicity of peptide drugs: Replacement of the backbone n -methyl group of Cilengitide by N -oligoethylene glycol (N -OEG) chains

Bioconjugate Chemistry

Volumn 25, Issue 1, 2014, Pages 11-17

  Fernández Llamazares, Ana I ^a,b   Adan, Jaume ^c   Mitjans, Francesc ^c   Spengler, Jan ^a,b   Albericio, Fernando ^a,b,d,e  

^a INSTITUTE FOR RESEARCH IN BIOMEDICINE   (Spain)

^b BIOMATERIALES Y NANOMEDICINA CIBER BBN   (Spain)

^c LEITAT TECHNOLOGICAL CENTER   (Spain)

^d UNIVERSITY OF BARCELONA   (Spain)

^e UNIVERSITY OF KWAZULU NATAL   (South Africa)

Author keywords

[No Author keywords available]

Indexed keywords

BIOACTIVITY; CELL ADHESION; CHELATION; ENDOTHELIAL CELLS; ETHYLENE; GLYCOLS; HYDROPHOBICITY; LIGANDS; SYNTHESIS (CHEMICAL);

CYCLOPEPTIDES; ETHYLENE OXIDES; GLYCOL CHAINS; INTEGRIN RECEPTORS; LIPOPHILICITY; METHYL GROUP; OLIGOETHYLENE GLYCOLS; PEPTIDE DRUGS; RGD PEPTIDE; SELECTIVE LIGANDS;

PEPTIDES;

CILENGITIDE; ETHYLENE OXIDE; FIBRINOGEN; INTEGRIN; MACROGOL; METHYL GROUP; VITRONECTIN; ETHYLENE GLYCOL DERIVATIVE; LIGAND; SNAKE VENOM;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BIOLOGICAL ACTIVITY; CELL ADHESION; CELL STRAIN HT29; DRUG PURIFICATION; DRUG SYNTHESIS; EPIMERIZATION; GLIOMA CELL; HUMAN; HUMAN CELL; HYDROPHOBICITY; IC 50; LIPOPHILICITY; SOLID; STEREOSPECIFICITY; STRUCTURE ACTIVITY RELATION; UMBILICAL VEIN ENDOTHELIAL CELL; ANTAGONISTS AND INHIBITORS; CHEMICAL PHENOMENA; CHEMISTRY; CONFORMATION; DOSE RESPONSE; DRUG EFFECTS; HT 29 CELL LINE; METABOLISM; SYNTHESIS; TUMOR CELL LINE;

CELL ADHESION; CELL LINE, TUMOR; DOSE-RESPONSE RELATIONSHIP, DRUG; ETHYLENE GLYCOLS; FIBRINOGEN; HT29 CELLS; HUMAN UMBILICAL VEIN ENDOTHELIAL CELLS; HUMANS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; INTEGRINS; LIGANDS; MOLECULAR CONFORMATION; SNAKE VENOMS; STRUCTURE-ACTIVITY RELATIONSHIP; VITRONECTIN;

EID: 84892776045     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc4003844     Document Type: Article

References (48)

1. Chatterjee, J., Gilon, C., Hoffman, A., and Kessler, H. (2008) N -methylation of peptides: a new perspective in medicinal chemistry Acc. Chem. Res. 10, 1331-1342
2. Chatterjee, J., Rechenmacher, F., and Kessler, H. (2013) N -Methylation of peptides and proteins: an important element for modulating biological functions Angew. Chem., Int. Ed. 52, 254-269
3. Olsen, C. A. (2010) Peptoid-peptide hybrid backbone architectures ChemBioChem 11, 152-160
4. Gilon, C., Halle, D., Chorev, M., Selinger, Z., and Byk, G. (1991) Backbone cyclization: a new method for conferring conformational constraint on peptides Biopolymers 31, 745-750
5. Reichwein, J. F. and Liskamp, R. M. J. (1998) Site-specific N -alkylation of peptides on the solid phase Tetrahedron Lett. 39, 1243-1246
6. 4-cyclosporin A derivatives as potential anti-HIV I drugs Tetrahedron Lett. 41, 7193-7196
7. Reichwein, J. F., Versluis, C., and Liskamp, R. M. J. (2000) Synthesis of cyclic peptides by ring-closing metathesis J. Org. Chem. 65, 6187-6195
8. Patgiri, A., Witten, M. R., and Arora, P. S. (2010) Solid phase synthesis of hydrogen bond surrogate derived α-helices: resolving the case of a difficult amide coupling Org. Biomol. Chem. 8, 1773-1776
9. Rijkers, D. T. S., Höppener, J. W. M., Posthuma, G., Lips, C. J. M., and Liskamp, R. M. J. (2002) Inhibition of amyloid fibril formation of human amylin by N -alkylated amino acid and α-hydroxy acid residue containing peptides Chem.-Eur. J. 8, 4285-4291
10. Ying, J., Gu, X., Cai, M., Dedek, M., Vagner, J., Trivedi, D. B., and Hruby, V. J. (2006) Design, synthesis, and biological evaluation of new cyclic melanotropin peptide analogues selective for the human melanocortin-4 receptor J. Med. Chem. 49, 6888-6896
11. Byk, G. and Gilon, C. (1992) Building units for N -backbone cyclic peptides. 1. Synthesis of protected N -(ω-aminoalkylene) amino acids and their incorporation into dipeptide units J. Org. Chem. 57, 5687-5692
12. Bitan, G. and Gilon, C. (1995) Building units for N -backbone cyclic peptides. 2. Synthesis of protected N -(ω-thioalkylene) amino acids and their incorporation into dipeptide units Tetrahedron 51, 10513-10522
13. Muller, D., Zeltser, I., Bitan, G., and Gilon, C. (1997) Building units for N -backbone cyclic peptides. 3. Synthesis of protected N -(ω-aminoalkyl) amino acids and N -(ω-carboxyalkyl) amino acids J. Org. Chem. 62, 411-416
14. α-functionalized alkyl amino acids by reductive alkylation of natural amino acids J. Chem. Soc., Perkin Trans. 1, 1501-1510
15. Falb, F., Yechezkel, T., and Gilon, C. (1999) 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. 53, 507-517
16. Müller, B., Besser, D., Kleinwächter, P., Arad, O., and Reissmann, S. (1999) Synthesis of N -carboxyalkyl and N -aminoalkyl functionalized dipeptide building units for the assembly of backbone cyclic peptides J. Pept. Res. 54, 383-393
17. Schumann, C., Seyfarth, L., Greiner, G., and Reissmann, S. (2000) Synthesis of different types of dipeptide building units containing N-or C -terminal arginine for the assembly of backbone cyclic peptides J. Pept. Res. 55, 428-435
18. Besser, D., Müller, B., Agricola, I., and Reissmann, S. (2000) Synthesis of differentially protected N -acylated reduced pseudodipeptides as building units for backbone cyclic peptides J. Pept. Sci. 6, 130-138
19. Schumann, C., Seyfarth, L., Greiner, G., Paegelow, I., and Reissmann, S. (2002) Synthesis and biological activities of new side chain and backbone cyclic bradykinin analogues J. Pept. Res. 60, 128-140
20. Imhof, D., Nothmann, D., Zoda, M. S., Hampel, K., Wegert, J., Böhmer, F. D., and Reissmann, S. (2005) Synthesis of linear and cyclic phosphopeptides as ligands for the N-terminal SH2-domain of protein tyrosine phosphatase SHP-1 J. Pept. Sci. 11, 390-400
21. Zoda, M. S., Zacharias, M., and Reissmann, S. (2010) Syntheses and activities of backbone-side chain cyclic octapeptide ligands with N-functionalized phosphotyrosine for the N-terminal SH2-domain of the protein tyrosine phosphatase SHP-1 J. Pept. Sci. 16, 403-413
22. Fernández-Llamazares, A. I., García, J., Soto-Cerrato, V., Pérez-Tomás, R., Spengler, J., and Albericio, F. (2013) N -triethylene glycol (N -TEG) as a surrogate for the N -methyl group: application to Sansalvamide A peptide analogs Chem. Commun. 49, 6430-6432
23. Arnott, J. A. and Planey, S. L. (2012) The influence of lipophilicity in drug discovery and design Expert Opin. Drug Discovery 7, 863-875
24. Mas-Moruno, C., Rechenmacher, F., and Kessler, H. (2010) Cilengitide: the first anti-angiogenic small molecule drug candidate. Design, synthesis and clinical evaluation Anti-cancer Agents Med. Chem. 10, 753-768
25. Tam, J. P. and Lu, Y.-A. (1995) Coupling difficulty associated with interchain clustering and phase transition in solid phase peptide synthesis J. Am. Chem. Soc. 117, 1058-12063
26. Thern, B., Rudolph, J., and Jung, G. (2002) Total synthesis of the nematicidal cyclododecapeptide Omphalotin A by using racemization-free triphosgene-mediated couplings in the solid phase Angew. Chem., Int. Ed. 41, 2307-2309
27. Thern, B., Rudolph, J., and Jung, G. (2002) Triphosgene as highly efficient reagent for the solid-phase coupling of N -alkylated amino acids-total synthesis of cyclosporin O Tetrahedron Lett. 43, 5013-5016
28. Lloyd-Williams, P., Albericio, F., and Giralt, E. (1997) Chemical approaches to the synthesis of peptides and proteins, CRC Press, Boca Raton.
29. El-Faham, A. and Albericio, F. (2011) Peptide coupling reagents, more than a letter soup Chem. Rev. 111, 6557-6602
30. Gund, P. and Veber, D. F. (1979) On the ease of base-catalyzed epimerization of N -methylated peptides and diketopiperazines J. Am. Chem. Soc. 101, 1885-1887
31. Valkó, K. (2004) Application of high-performance liquid chromatography based measurements of lipophilicity to model biological distribution J. Chromatogr., A 1037, 299-310
32. Gaberc-Porekar, V., Zore, I., Podobnik, B., and Menart, V. (2008) Obstacles and pitfalls in the PEGylation of therapeutic proteins Curr. Opin. Drug Discovery 11, 242-250
33. Parrott, M. C. and DeSimone., J. M. (2012) Relieving PEGylation Nat. Chem. 4, 13-14
34. Mueller, C., Capelle, M. A. H., Arvinte, T., Seyrek, E., and Borchard, G. (2011) Tryptophan-mPEGs: Novel excipients that stabilize salmon calcitonin against aggregation by non-covalent PEGylation Eur. J. Biopharm. 79, 646-657
35. Veronese, F. M. (2001) Peptide and protein PEGylation: a review of problems and solutions Biomaterials 22, 405-417
36. Wirth, P., Souppe, J., Tritsch, D., and Biellmann, J.-F. (1991) Chemical modification of horseradish peroxidase with ethanal-methoxypolyethylene glycol: solubility in organic solvents, activity and properties Bioorg. Chem. 19, 133-142
37. Grun, J., Revell, J. D., Conza, M., and Wennemers, H. (2006) Peptide-polyethylene glycol conjugates: synthesis and properties of peptides bearing a C-terminal polyethylene glycol chain Bioorg. Med. Chem. 14, 6197-6201
38. Camenisch, G., Alsenz, J., van de Waterbeemd, H., and Folkers, G. (1998) Estimation of permeability by passive diffusion through Caco-2 cell monolayers using the drugs' lipophilicity and molecular weight Eur. J. Pharm. Sci. 6, 313-319
39. Goldberg, M. and Gómez-Orellana, I. (2003) Challenges for the oral delivery of macromolecules Nat. Rev. Drug Discovery 2, 289-295
40. Yamada, K., Murakami, M., Yamamoto, A., Takada, K., and Muranishi, S. (1992) Improvement of intestinal absorption of thyrotropin-releasing hormone by chemical modification with lauric acid J. Pharm. Pharmacol. 44, 717-721
41. Hashizume, M., Douen, T., Murakami, M., Yamamoto, A., Takada, K., and Muranishi, S. (1992) Improvement of large intestinal absorption of insulin by chemical modification with palmitic acid in rats J. Pharm. Pharmacol. 44, 555-559
42. Yodoya, E., Uemura, K., Tenma, T., Fujita, T., Murakami, M., Yamamoto, A., and Muranishi, S. (1994) Enhanced permeability of tetragastrin across the rat intestinal membrane and its reduced degradation by acylation with various fatty acids J. Pharmacol. Exp. Ther. 271, 1509-1513
43. Asada, H., Douen, T., Waki, M., Adachi, S., Fujita, T., Yamamoto, A., and Muranishi, S. (1995) Absorption characteristics of chemically modified-insulin derivatives with various fatty acids in the small and large intestine J. Pharm. Sci. 84, 682-687
44. Uchiyama, T., Kotani, A., Tatsumi, H., Kishida, T., Okamoto, A., Okada, N., Murakami, M., Fujita, T., Fujiwara, Y., Kiso, Y., Muranishi, S., and Yamamoto, A. (2000) Development of novel lipophilic derivatives of DADLE (leucine enkephalin analogue): intestinal permeability characateristics of DADLE derivatives in rats Pharm. Res. 17, 1461-1467
45. Lee, Y., Nam, J. H., Shin, H. C., and Byun, Y. (2001) Conjugation of low-molecular-weight heparin and deoxycholic acid for the development of a new oral anticoagulant agent Circulation 104, 3116-3120
46. Clement, S., Still, J. G., and Kosutic, G. (2002) Oral insulin product hexyl-insulin monoconjugate 2 (HIM2) in type 1 diabetes mellitus: the glucose stabilization effects of HIM2 Diabetes Technol. Ther. 4, 459-466
47. Royo, S., Gaus, K., and Sewald., N. (2009) Synthesis of chemically modified bioactive peptides: recent advances, challenges and developments for medicinal chemistry Future Med. Chem. 1, 1289-1310
48. Veronese, F. M. and Mero, A. (2008) The impact of PEGylation on biological therapies Biodrugs 22, 315-329