Structure-activity relationship study of a CXC chemokine receptor type 4 antagonist, FC131, using a series of alkene dipeptide isosteres

Journal of Medicinal Chemistry

Volumn 55, Issue 6, 2012, Pages 2746-2757

  Kobayashi, Kazuya ^a   Oishi, Shinya ^a   Hayashi, Ryoko ^a   Tomita, Kenji ^a   Kubo, Tatsuhiko ^a   Tanahara, Noriko ^a   Ohno, Hiroaki ^a   Yoshikawa, Yasushi ^b   Furuya, Toshio ^b   Hoshino, Masaru ^a   Fujii, Nobutaka ^a  

^a KYOTO UNIVERSITY   (Japan)

^b PharmaDesign Inc   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ALPHA CHEMOKINE; CHEMOKINE RECEPTOR CXCR4 ANTAGONIST; DIPEPTIDE DERIVATIVE; FC 122; FC 131; METHYL GROUP; PEPTIDOMIMETIC AGENT; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG CONFORMATION; DRUG POTENCY; DRUG RECEPTOR BINDING; HUMAN; HUMAN CELL; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION;

ALKENES; DIPEPTIDES; HEK293 CELLS; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PEPTIDES, CYCLIC; PEPTIDOMIMETICS; RADIOLIGAND ASSAY; RECEPTORS, CXCR4; STATIC ELECTRICITY; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84858722535     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm2016914     Document Type: Article

References (43)

1. Fung, S.; Hruby, V. J. Design of cyclic and other templates for potent and selective peptide α-MSH analogues Curr. Opin. Chem. Biol. 2005, 9, 352-358 (Pubitemid 41019680)
2. Mosberg, H. I.; Hurst, R.; Hruby, V. J.; Gee, K.; Yamaura, H. I.; Galligan., J. J.; Burks, T. F. Bis-penicillamine enkephalins possess highly improved specificity toward δ opioid receptors Proc. Natl. Acad. Sci. U.S.A. 1983, 80, 5871-5874 (Pubitemid 14227575)
3. March, D. R.; Abbenante, G.; Bergman, D. A.; Brinkworth, R. I.; Wickramasinghe, W.; Begun, J.; Martin, J. L.; Fairlie, D. P. Substrate-based cyclic peptidomimetics of Phe-Ile-Val that inhibit HIV-1 protease using a novel enzyme-binding mode J. Am. Chem. Soc. 1996, 118, 3375-3379 (Pubitemid 26145091)
4. Burton, P. S.; Conradi, R. A.; Ho, N. F. H.; Hilgers, A. R.; Borchardt, R. T. How structural features influence the biomembrane permeability of peptides J. Pharm. Sci. 1996, 85, 1336-1340 (Pubitemid 27014190)
5. Rezai, T.; Yu, B.; Millhauser, G. L.; Jacobson, M. P.; Lokey, R. S. Testing the conformational hypothesis of passive membrane permeability using synthetic cyclic peptide diastereomers J. Am. Chem. Soc. 2006, 128, 2510-2511 (Pubitemid 43327908)
6. Kessler, H. Conformation and biological activity of cyclic peptides Angew. Chem., Int. Ed. Engl. 1982, 21, 512-523
7. Aumailley, M.; Gurrath, M.; Müller, G.; Calvete, J.; Timpl, R.; Kessler, H. Arg-Gly-Asp constrained within cyclic pentapeptides. Strong and selective inhibitors of cell adhesion to vitronectin and laminin fragment P1 FEBS Lett. 1991, 291, 50-54
8. 3 integrin antagonists J. Med. Chem. 1999, 42, 3033-3040 (Pubitemid 29384038)
9. 3 antagonists J. Am. Chem. Soc. 1996, 118, 7461-7472 (Pubitemid 26279800)
10. 3) antagonists J. Med. Chem. 1997, 40, 2289-2292 (Pubitemid 27342562)
11. Nicolaou, K. C.; Trujillo, J. I.; Jandeleit, B.; Chibale, K.; Rosenfeld, M.; Diefenbach, B.; Cheresh, D. A.; Goodman, S. L. Design, synthesis and biological evaluation of nonpeptide integrin antagonists Bioorg. Med. Chem. 1998, 6, 1185-1208 (Pubitemid 28398955)
12. 3 antagonists lead compounds Bioorg. Med. Chem. Lett. 1999, 9, 937-942 (Pubitemid 29179884)
13. A receptor Life Sci. 1992, 50, 247-255
14. B Biochem. Biophys. Res. Commun. 1994, 200, 1708-1712
15. Iqbal, J.; Sanghi, R.; Das, S. K. Endothelin receptor antagonists: an overview of their synthesis and structure-activity relationship Mini-Rev. Med. Chem. 2005, 5, 381-408 (Pubitemid 40467694)
16. Cardillo, G.; Gentilucci, L.; Tolomelli, A.; Spinosa, R.; Calienni, M.; Qasem, A. R.; Spampinato, S. Synthesis and evaluation of the affinity toward μ-opioid receptors of atypical, lipophilic ligands based on the sequence c [-Tyr-Pro-Trp-Phe-Gly-] J. Med. Chem. 2004, 47, 5198-5203 (Pubitemid 39314916)
17. Gentilucci, L.; Squassabia, F.; Demarco, R.; Artali, R.; Cardillo, G.; Tolomelli, A.; Spampinato, S.; Bedini, A. Investigation of the interaction between the atypical agonist c[YpwFG] and MOR FEBS J. 2008, 275, 2315-2337 (Pubitemid 351569568)
18. Veber, D. F.; Freidinger, R. M.; Perlow, D. S.; Paleveda, W. J., Jr.; Holly, F. W.; Strachan, R. G.; Nutt, R. F.; Arison, B. H.; Homnick, C.; Randall, W. C.; Glitzer, M. S.; Saperstein, R.; Hirschmann, R. A potent cyclic hexapeptide analogue of somatostatin Nature 1981, 292, 55-58 (Pubitemid 11048543)
19. Veber, D. F.; Saperstein, R.; Nutt, R. F.; Freidinger, R. M.; Brady, S. F.; Curley, P.; Perlow, D. S.; Paleveda, W. J.; Colton, C. D.; Zacchei, A. G.; Tocco, D. J.; Hoff, D. R.; Vandlen, R. L.; Gerich, J. E.; Hall, L.; Mandarino, L.; Cordes, E. H.; Anderson, P. S.; Hirschmann, R. A super active cyclic hexapeptide analog of somatostatin Life Sci. 1984, 34, 1371-1378 (Pubitemid 14165251)
20. Fujii, N.; Oishi, S.; Hiramatsu, K.; Araki, T.; Ueda, S.; Tamamura, H.; Otaka, A.; Kusano, S.; Terakubo, S.; Nakashima, H.; Broach, J. A.; Trent, J. O.; Wang, Z.; Peiper, S. C. Molecular-size reduction of a potent CXCR4-chemokine antagonist using orthogonal combination of conformation- and sequence-based libraries Angew. Chem., Int. Ed. 2003, 42, 3251-3253 (Pubitemid 36917168)
21. Inokuchi, E.; Oishi, S.; Kubo, T.; Ohno, H.; Shimura, K.; Matsuoka, M.; Fujii, N. Potent CXCR4 antagonists containing amidine type peptide bond isosteres ACS Med. Chem. Lett. 2011, 2, 477-480 and references therein
22. Ueda, S.; Oishi, S.; Wang, Z.; Araki, T.; Tamamura, H.; Cluzeau, J.; Ohno, H.; Kusano, S.; Nakashima, H.; Trent, J. O.; Peiper, S. C.; Fujii, N. Structure-activity relationships of cyclic peptide-based chemokine receptor CXCR4 antagonists: disclosing the importance of side-chain and backbone functionalities J. Med. Chem. 2007, 50, 192-198 (Pubitemid 46147700)
23. Hann, M. M.; Sammes, P. G.; Kennewell, P. D.; Taylor, J. B. On double bond isosteres of the peptide bond; an enkephalin analogue J. Chem. Soc., Chem. Commun. 1980, 234-235
24. Hann, M. M.; Sammes, P. G.; Kennewell, P. D.; Taylor, J. B. On the double bond isostere of the peptide bond: preparation of an enkephalin analogue J. Chem. Soc., Perkin. Trans. 1 1982, 307-314
25. Christos, T. E.; Arvanitis, A.; Cain, G. A.; Johnson, A. L.; Pottorf, R. S.; Tam, S. W.; Schmidt, W. K. Stable isosteres of neurotensin C-terminal pentapeptides derived by modification of the amide function Bioorg. Med. Chem. Lett. 1993, 3, 1035-1040 (Pubitemid 23185559)
26. Wipf, P.; Henninger, T. C.; Geib, S. J. Methyl- and (trifloromethyl) alkene peptide isosteres: synthesis and evaluation of their potential as β-turn promoters and peptide mimetics J. Org. Chem. 1998, 63, 6088-6089
27. Xiao, J.; Weisblum, B.; Wipf, P. Trisubstituted (E)-alkene dipeptide isosteres as β-turn promoters in the gramicidin S cyclodecapeptide scaffold Org. Lett. 2006, 8, 4731-4734 (Pubitemid 44629446)
28. Oishi, S.; Miyamoto, K.; Niida, A.; Yamamoto, M.; Ajito, K.; Tamamura, H.; Otaka, A.; Kuroda, Y.; Asai, A.; Fujii, N. Application of tri- and tetrasubstituted alkene dipeptide mimetics to conformational studies of cyclic RGD peptides Tetrahedron 2006, 62, 1416-1424 (Pubitemid 43099809)
29. Narumi, T.; Tomita, K.; Inokuchi, E.; Kobayashi, K.; Oishi, S.; Ohno, H.; Fujii, N. Diastereoselective synthesis of highly functionalized fluoroalkene dipeptide isosteres and its application to Fmoc-based solid-phase synthesis of a cyclic pentapeptide mimetic Tetrahedron 2008, 64, 4332-4346
30. Narumi, T.; Hayashi, R.; Tomita, K.; Kobayashi, K.; Tanahara, N.; Ohno, H.; Naito, T.; Kodama, E.; Matsuoka, M.; Oishi, S.; Fujii, N. Synthesis and biological evaluation of selective CXCR4 antagonists containing alkene dipeptide isosteres Org. Biomol. Chem. 2010, 8, 616-621
31. 3 mediated reaction Angew. Chem., Int. Ed. Engl. 1990, 29, 801-803
32. N2′ reaction Org. Lett. 2002, 4, 1055-1058
33. Oishi, S.; Niida, A.; Kamano, T.; Miwa, Y.; Taga, T.; Odagaki, Y.; Hamanaka, N.; Yamamoto, M.; Ajito, K.; Tamamura, H.; Otaka, A.; Fujii, N. Regio- and stereoselective ring-opening of chiral 1,3-oxazolidin-2-one derivatives by organocopper reagents provides novel access to di-, tri- and tetra-substituted alkene dipeptide isosteres J. Chem. Soc., Perkin Trans. 1 2002, 1786-1793 (Pubitemid 34916985)
34. Ando, K. Highly selective synthesis of Z -unsaturated esters by using new Horner-Emmons reagents, ethyl (diarylphosphono)acetates J. Org. Chem. 1997, 62, 1934-1939 (Pubitemid 127493467)
35. Yu, J. S.; Kleckley, T. S.; Wiemer, D. F. Synthesis of farnesol isomers via a modified Wittig procedure Org. Lett. 2005, 7, 4803-4806 (Pubitemid 41579867)
36. Peterson, D. J. A carbonyl olefination reaction using silyl-substituted organometallic compounds J. Org. Chem. 1968, 33, 780-784
37. Hartzell, S. L.; Sullivan, D. F.; Rathke, M. W. Reaction of lithio tert -butyl trimethylsilylacetate with aldehydes and ketones. A synthesis of α,β-unsaturated esters Tetrahedron Lett. 1974, 15, 1403-1406
38. Våbenø, J.; Nikiforovich, G. V.; Marshall, G. R. Insight into the binding mode for cyclopentapeptide antagonists of the CXCR4 receptor Chem. Biol. Drug Des. 2006, 67, 346-354
39. Våbenø, J.; Nikiforovich, G. V.; Marshall, G. R. A minimalistic 3D pharmacophore model for cyclopentapeptide CXCR4 antagonists Biopolymers 2006, 84, 459-471 (Pubitemid 44523320)
40. Demmer, O.; Dijkgraaf, I.; Schumacher, U.; Marinelli, L.; Cosconati, S.; Gourni, E.; Wester, H. J.; Kessler, H. Design, synthesis, and functionalization of dimeric peptides targeting chemokine receptor CXCR4 J. Med. Chem. 2011, 54, 7648-7662
41. Yoshikawa, Y.; Kobayashi, K.; Oishi, S.; Fujii, N.; Furuya, T. Molecular modeling study of cyclic pentapeptide CXCR4 antagonists: new insight into CXCR4-FC131 interactions Bioorg. Med. Chem. Lett. 2012, 22, 2146-2150
42. Wu, B.; Chien, E. Y. T.; Mol, C. D.; Fenalti, G.; Liu, W.; Katritch, V.; Abagyan, R.; Brooun, A.; Wells, P.; Bi, F. C.; Hamel, D. J.; Kuhn, P.; Handel, T. M.; Cherezov, V.; Stevens, R. C. Structure of the CXCR4 chemokine GPCR with small-molecule and cyclic peptide antagonists Science 2010, 330, 1066-1071
43. Molecular Operating Environment (MOE), Chemical Computing Group Inc., Montreal, QC, Canada.