Potent CXCR4 antagonists containing amidine type peptide bond isosteres

ACS Medicinal Chemistry Letters

Volumn 2, Issue 6, 2011, Pages 477-480

  Inokuchi, Eriko ^a   Oishi, Shinya ^a   Kubo, Tatsuhiko ^a   Ohno, Hiroaki ^a   Shimura, Kazuya ^a   Matsuoka, Masao ^a   Fujii, Nobutaka ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Amidine; chemokine; CXCR4 antagonist; FC131; nitrile oxide; peptidomimetics

Indexed keywords

AMIDINE; CHEMOKINE RECEPTOR CXCR4; CHEMOKINE RECEPTOR CXCR4 ANTAGONIST; FC 122; FC 131; GLYCINE DERIVATIVE; NITRILE OXIDE; PENTAPEPTIDE; STROMAL CELL DERIVED FACTOR 1; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CHEMICAL BOND; CYCLIZATION; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG SYNTHESIS; HUMAN IMMUNODEFICIENCY VIRUS 1; PRIORITY JOURNAL; VIRUS STRAIN;

HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 79959282841     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml200047e     Document Type: Article

References (26)

1. Loetscher, M.; Geiser, T.; O'Reilly, T.; Zwahlen, R.; Baggiolini, M.; Moser, B. Cloning of a human seven-transmenbrane domain receptor, LESTR, that is highly expressed in leukocytes J. Biol. Chem. 1994, 269, 232-237 (Pubitemid 24026649)
2. Nagasawa, T.; Kikutani, H.; Kishimoto, T. Molecular cloning and structure of a pre-B-cell growth-stimulating factor Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 2305-2309 (Pubitemid 24092092)
3. Müller, A.; Homey, B.; Soto, H.; Ge, N.; Catron, D.; Buchanan, M. E.; McClanahan, T.; Murphy, E.; Yuan, W.; Wagner, S. N.; Barrera, J. L.; Mohar, A.; Veraistegui, E.; Zlotnik, A. Involvement of chemokine receptors in breast cancer metastasis Nature 2001, 410, 50-56 (Pubitemid 32225831)
4. Feng, Y.; Broder, C. C.; Kennedy, P. E.; Berger, E. A. HIV-1 entry cofactor: functional cDNA cloning of a seven-transmembrane, G protein-coupled receptor Science 1996, 272, 872-877 (Pubitemid 26154590)
5. O'Hayre, M.; Salanga, C. L.; Handel, T. M.; Hamel, D. Emerging concepts and approaches for chemokine-receptor drug discovery Expert Opin. Drug Discovery 2010, 5, 1109-1122
6. Tamamura, H.; Xu, Y.; Hattori, T.; Zhang, X.; Arakaki, R.; Kanbara, K.; Omagari, A.; Otaka, A.; Ibuka, T.; Yamamoto, N.; Nakashima, H.; Fujii, N. A low-molecular-weight inhibitor against the chemokine receptor CXCR4: A strong anti-HIV peptide T140 Biochem. Biophys. Res. Commun. 1998, 253, 877-882 (Pubitemid 29039238)
7. Bridger, G. J.; Skerlj, R. T.; Thornton, D.; Padmanabhan, S.; Martellucci, S. A.; Henson, G. W.; Abrams, M. J.; Yamamoto, N.; De Vreese, K.; Pauwels, R.; De Clercq, E. Synthesis and structure-activity relationships of phenylenebis(methylene)-linked bis-tetraazamacrocycles that inhibit HIV replication. Effects of macrocyclic ring size and substituents on the aromatic linker J. Med. Chem. 1995, 38, 366-378
8. Doranz, B. J.; Grovit-Ferbas, K.; Sharron, M. P.; Mao, S.-H.; Bidwell Goetz, M.; Daar, E. S.; Doms, R. W.; O'Brien, W. A. A small-molecule inhibitor directed against the chemokine receptor CXCR4 prevents its use as an HIV-1 coreceptor J. Exp. Med. 1997, 186, 1395-1400 (Pubitemid 27469036)
9. Bridger, G. J.; Skerlj, R. T.; Hernandez-Abad, P. E.; Bogucki, D. E.; Wang, Z.; Zhou, Y.; Nan, S.; Boehringer, E. M.; Wilson, T.; Crawford, J.; Metz, M.; Hatse, S.; Princen, K.; De Clercq, E.; Schols, D. Synthesis and structure-activity relationships of azamacrocyclic C-X-C chemokine receptor 4 antagonists: Analogues containing a single azamacrocyclic ring are potent inhibitors of T-cell tropic (X4) HIV-1 replication J. Med. Chem. 2010, 53, 1250-1260
10. Skerlj, R. T.; Bridger, G. J.; Kaller, A.; McEachern, E. J.; Crawford, J. B.; Zhou, Y.; Atsma, B.; Langille, J.; Nan, S.; Veale, D.; Wilson, T.; Harwig, C.; Hatse, S.; Princen, K.; De Clercq, E.; Schols, D. Discovery of novel small molecule orally bioavailable C-X-C chemokine receptor 4 antagonists that are potent inhibitors of T-tropic (X4) HIV-1 replication J. Med. Chem. 2010, 53, 3376-3388
11. Zhan, W.; Liang, Z.; Zhu, A.; Kurtkaya, S.; Shim, H.; Snyder, J. P.; Liotta, D. C. Discovery of small molecule CXCR4 antagonists J. Med. Chem. 2007, 50, 5655-5664 (Pubitemid 350106020)
12. Rosenkilde, M. M.; Gerlach, L.-O.; Jakobsen, J. S.; Skerlj, R. T.; Bridger, G. J.; Schwartz, T. W. Molecular mechanism of AMD3100 antagonism in the CXCR4 receptor J. Biol. Chem. 2004, 279, 3033-3041
13. Zhang, W.; Navenot, J.-M.; Haribabu, B.; Tamamura, H.; Hiramatsu, K.; Omagari, A.; Pei, G.; Manfredi, J. P.; Fujii, N.; Broach, J. R.; Peiper, S. C. A point mutation that confers constitutive activity to CXCR4 reveals that T140 is an inverse agonist and that AMD3100 and ALX40-4C are weak partial agonists J. Biol. Chem. 2002, 277, 24515-24521 (Pubitemid 34951977)
14. 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. Structures of the CXCR4 chemokine GPCR with small-molecule and cyclic peptide antagonists Science 2010, 330, 1066-1071
15. 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)
16. 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)
17. Tamamura, H.; Araki, T.; Ueda, S.; Wang, Z.; Oishi, S.; Esaka, A.; Trent, J. O.; Nakashima, H.; Yamamoto, N.; Peiper, S. C.; Otaka, A.; Fujii, N. Identification of novel low molecular weight CXCR4 antagonists by structural tuning of cyclic tetrapeptide scaffolds J. Med. Chem. 2005, 48, 3280-3289 (Pubitemid 40628048)
18. Tamamura, H.; Hiramatsu, K.; Ueda, S.; Wang, Z.; Kusano, S.; Terakubo, S.; Trent, J. O.; Peiper, S. C.; Yamamoto, N.; Nakashima, H.; Otaka, A.; Fujii, N. Stereoselective synthesis of [ l -Arg- l / d -3-(2-naphthyl)alanine]-type (E)-alkene dipeptide isosteres and its application to the synthesis and biological evaluation of pseudopeptide analogues of the CXCR4 antagonist FC131 J. Med. Chem. 2005, 48, 380-391
19. 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
20. Inokuchi, E.; Yamada, A.; Hozumi, K.; Tomita, K.; Oishi, S.; Ohno, H.; Nomizu, M.; Fujii, N. Org. Biomol. Chem. 2011, DOI: 10.1039/c0ob01193b.
21. Moser, H.; Fliri, A.; Steiger, A.; Costello, G.; Schreiber, J.; Eschenmoser, A. Poly(dipeptamidinium) salts: Definition and methods of preparation Helv. Chim. Acta 1986, 69, 1224-1262
22. Jones, R. C. F.; Ward, G. J. Amide bond isosteres: imidazolines in pseudopeptide chemistry Tetrahedron Lett. 1988, 29, 3853-3856
23. Epimerizations in the preparation of protected cyclic peptides 13b and 13f were verified by the comparative HPLC analysis of the amidine isomers 14b / 14c and the amidoxime isomers 13f /13g, respectively (14b, 90% de; 13f, 95% de; see the Supporting Information for details).
24. Vaibena, J.; Nikiforovich, G. V.; Marshall, G. R. A minimalistic 3D pharmacophore model for cyclopentapeptide CXCR4 antagonists Biopolymers 2006, 84, 459-471 (Pubitemid 44523320)
25. Vaibena, 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
26. Oishi, S.; Masuda, R.; Evans, B.; Ueda, S.; Goto, Y.; Ohno, H.; Hirasawa, A.; Tsujimoto, G.; Wang, Z.; Peiper, S. C.; Naito, T.; Kodama, E.; Matsuoka, M.; Fujii, N. Synthesis and application of fluorescein- and biotin-labeled molecular probes for the chemokine receptor CXCR4 ChemBioChem 2008, 9, 1154-1158