Intestinal permeability of cyclic peptides: Common key backbone motifs identified

Journal of the American Chemical Society

Volumn 134, Issue 29, 2012, Pages 12125-12133

  Beck, Johannes G ^a   Chatterjee, Jayanta ^a   Laufer, Burkhardt ^a   Kiran, Marelli Udaya ^a   Frank, Andreas O ^a   Neubauer, Stefanie ^a   Ovadia, Oded ^b   Greenberg, Sarit ^b   Gilon, Chaim ^b   Hoffman, Amnon ^b   Kessler, Horst ^a,c  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^b HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^c KING ABDULAZIZ UNIVERSITY   (Saudi Arabia)

Author keywords

[No Author keywords available]

Indexed keywords

CACO-2 PERMEABILITY; CYCLIC PEPTIDES; CYCLOSPORINE A; DRUG CANDIDATES; HIGH PERMEABILITY; N-METHYLATION; PEPTIDE BONDS; SIMPLE RULES; STRUCTURAL SIMILARITY; TEMPLATE STRUCTURES; TYPE II;

ALKYLATION; BIOCHEMISTRY; FUNCTIONAL GROUPS;

PEPTIDES;

CYCLOPEPTIDE; CYCLOSPORIN A;

ARTICLE; BIOAVAILABILITY; CELL STRAIN CACO 2; INTESTINE MUCOSA PERMEABILITY; PROTEIN METHYLATION;

CACO-2 CELLS; DIPEPTIDES; HUMANS; INTESTINAL ABSORPTION; METHYLATION; MODELS, MOLECULAR; PEPTIDES, CYCLIC; PERMEABILITY; PROTEIN STRUCTURE, SECONDARY;

EID: 84864182405     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja303200d     Document Type: Article

References (48)

1. Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Adv. Drug Delivery Rev. 2001, 46, 3-26
2. Veber, D. F.; Johnson, S. R.; Cheng, H. Y.; Smith, B. R.; Ward, K. W.; Kopple, K. D. J. Med. Chem. 2002, 45, 2615-2623
3. Zhang, M. Q.; Wilkinson, B. Curr. Opin. Biotechnol. 2007, 18, 478-488
4. Wieland, T.; Faulstich, H. CRC Crit. Rev. Biochem. 1978, 5, 185-260
5. Tjia, J. F.; Webber, I. R.; Back, D. J. Br. J. Clin. Pharmacol. 1991, 31, 344-346
6. Kolars, J. C.; Awni, W. M.; Merion, R. M.; Watkins, P. B. Lancet 1991, 338, 1488-1490
7. Bauer, W.; Briner, U.; Doepfner, W.; Haller, R.; Huguenin, R.; Marbach, P.; Petcher, T. J.; Pless, J. Life Sci. 1982, 31, 1133-1140
8. Cathapermal, S. S.; Foegh, M. L.; Rau, C. S.; Ramwell, P. W. Drug Metab. Dispos. 1991, 19, 735-739
9. Biron, E.; Chatterjee, J.; Ovadia, O.; Langenegger, D.; Brueggen, J.; Hoyer, D.; Schmid, H. A.; Jelinek, R.; Gilon, C.; Hoffman, A.; Kessler, H. Angew. Chem., Int. Ed. 2008, 47, 2595-2599
10. Dahlem, A. M.; Hassan, A. S.; Swanson, S. P.; Carmichael, W. W.; Beasley, V. R. Pharmacol. Toxicol. 1989, 64, 177-181
11. Hess, S.; Linde, Y.; Ovadia, O.; Safrai, E.; Shalev, D. E.; Swed, A.; Halbfinger, E.; Lapidot, T.; Winkler, I.; Gabinet, Y.; Faier, A.; Yarden, D.; Xiang, Z.; Portitlo, F. P.; Haskell-Luevano, C.; Gilon, C.; Hoffman, A. J. Med. Chem. 2008, 51, 1026-1034
12. Fjellestad-Paulsen, A.; Höglund, P.; Lundin, S.; Paulsen, O. Clin. Endocrinol. 1993, 38, 177-182
13. Lundin, S.; Vilhardt, H. Acta Endocrinol. (Copenh.) 1986, 112, 457-460
14. Sivonen, K.; Kononen, K.; Carmichael, W. W.; Dahlem, A. M.; Rinehart, K. L.; Kiviranta, J.; Niemela, S. I. Appl. Environ. Microbiol. 1989, 55, 1990-1995
15. Francis, G. Nature 1878, 18, 11-12
16. Edler, L.; Ferno, S.; Lind, M. G.; Lundberg, R.; Nilsson, P. O. Ophelia 1985, 24, 103-109
17. Gussmann, H.; Molzahn, M. J.; Bicks, B. Monatsh. Veterinaermed. 1985, 40, 76-79
18. White, T. R.; Renzelman, C. M.; Rand, A. C.; Rezai, T.; McEwen, C. M.; Gelev, V. M.; Turner, R. A.; Linington, R. G.; Leung, S. S. F.; Kalgutkar, A. S.; Bauman, J. N.; Zhang, Y. Z.; Liras, S.; Price, D. A.; Mathiowetz, A. M.; Jacobson, M. P.; Lokey, R. S. Nat. Chem. Biol. 2011, 7, 810-817
19. Rezai, T.; Bock, J. E.; Zhou, M. V.; Kalyanaraman, C.; Lokey, R. S.; Jacobson, M. P. J. Am. Chem. Soc. 2006, 128, 14073-14080
20. Rezai, T.; Yu, B.; Millhauser, G. L.; Jacobson, M. P.; Lokey, R. S. J. Am. Chem. Soc. 2006, 128, 2510-2511
21. Pauletti, G. M.; Okumu, F. W.; Borchardt, R. T. Pharm. Res. 1997, 14, 164-168
22. Knipp, G. T.; Velde, D. G. V.; Siahaan, T. J.; Borchardt, R. T. Pharm. Res. 1997, 14, 1332-1340
23. Kim, D. C.; Burton, P. S.; Borchardt, R. T. Pharm. Res. 1993, 10, 1710-1714
24. Gray, R. A.; Vandervelde, D. G.; Burke, C. J.; Manning, M. C.; Middaugh, C. R.; Borchardt, R. T. Biochemistry 1994, 33, 1323-1331
25. Fricker, G.; Drewe, J. J. Pept. Sci. 1996, 2, 195-211
26. Wieland, T.; Nassal, M.; Kramer, W.; Fricker, G.; Bickel, U.; Kurz, G. Proc. Natl. Acad. Sci. U. S. A. 1984, 81, 5232-5236
27. Ziegler, K.; Frimmer, M.; Kessler, K.; Damm, I.; Eiermann, V.; Koll, S.; Zarbock, J. Biochim. Biophys. Acta 1985, 845, 86-93
28. Ovadia, O.; Greenberg, S.; Chatterjee, J.; Laufer, B.; Opperer, F.; Kessler, H.; Gilon, C.; Hoffman, A. Mol. Pharmaceutics 2011, 8, 479-487
29. Kessler, H.; Matter, H.; Gemmecker, G.; Kling, A.; Kottenhahn, M. J. Am. Chem. Soc. 1991, 113, 7550-7563
30. Venkatachalam, C. M. Biopolymers 1968, 6, 1425-1436
31. Loosli, H.-R.; Kessler, H.; Oschkinat, H.; Weber, H.-P.; Petcher, T. J.; Widmer, A. Helv. Chim. Acta 1985, 68, 682-704
32. Klages, J.; Neubauer, C.; Coles, M.; Kessler, H.; Luy, B. ChemBioChem 2005, 6, 1672-1678
33. Laufer, B.; Chatterjee, J.; Frank, A. O.; Kessler, H. J. Pept. Sci. 2009, 15, 141-146
34. Chatterjee, J.; Laufer, B.; Beck, J. G.; Helyes, Z.; Pinter, E.; Szolcsanyi, J.; Horvath, A.; Mandl, J.; Reubi, J. C.; Keri, G.; Kessler, H. ACS Med. Chem. Lett. 2011, 2, 509-514
35. Fricker, G.; Drewe, J.; Huwyler, J.; Gutmann, H.; Beglinger, C. Br. J. Pharmacol. 1996, 118, 1841-1847
36. Griesinger, C.; Ernst, R. R. J. Magn. Reson. 1987, 75, 261-271
37. Kumar, A.; Wagner, G.; Ernst, R. R.; Wüthrich, K. J. Am. Chem. Soc. 1981, 103, 3654-3658
38. Havel, T. F. Prog. Biophys. Mol. Biol. 1991, 56, 43-78
39. Mierke, D. F.; Geyer, A.; Kessler, H. Int. J. Pept. Protein Res. 1994, 44, 325-331
40. Lindahl, E.; Hess, B.; van der Spoel, D. J. Mol. Model. 2001, 7, 306-317
41. van der Spoel, D.; Lindahl, E.; Hess, B.; Groenhof, G.; Mark, A. E.; Berendsen, H. J. C. J. Comput. Chem. 2005, 26, 1701-1718
42. van der Spoel, D.; Lindahl, E.; Hess, B.; van Buuren, A. R.; Apol, P. J.; Meulenhoff, P. J.; Tieleman, D. P.; Sijbers, A. L. T. M.; Feenstra, K. A.; van Drunen, R.; Berendsen, H. J. C. GROMACS User Manual, version 4.0; 2005.
43. Humphrey, W.; Dalke, A.; Schulten, K. J. Mol. Graph. 1996, 14 (33-38) 27-38
44. SYBYL 8.0; Tripos International: 1699 South Hanley Rd., St. Louis, MI, 63144, USA.
45. MacKerell, A. D.; Banavali, N.; Foloppe, N. Biopolymers 2000, 56, 257-265
46. Brooks, B. R.; Bruccoleri, R. E.; Olafson, B. D.; States, D. J.; Swaminathan, S.; Karplus, M. J. Comput. Chem. 1983, 4, 187-217
47. Ryckaert, J. P.; Ciccotti, G.; Berendsen, H. J. C. J. Comput. Phys. 1977, 23, 327-341
48. Berendsen, H. J. C.; Postma, J. P. M.; van Gunsteren, W. F.; Dinola, A.; Haak, J. R. J. Chem. Phys. 1984, 81, 3684-3690