Peptides targeting chemokine receptor CXCR4: Structural behavior and biological binding studies

Journal of Peptide Science

Volumn 20, Issue 4, 2014, Pages 270-278

  Costantini, Susan ^a   Raucci, Raffaele ^b   Colonna, Giovanni ^b   Mercurio, Flavia Anna ^c,d,e   Trotta, Anna Maria ^a   Paola, Ringhieri ^c,d   Leone, Marilisa ^e   Rossi, Filomena ^c,d,e   Pellegrino, Carmela ^a   Castello, Giuseppe ^a   Scala, Stefania ^a  

^a NATIONAL CANCER INSTITUTE   (Italy)

^b SECOND UNIVERSITY OF NAPLES   (Italy)

^c UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^d CIRPeB   (Italy)

^e CNR   (Italy)

Author keywords

antagonists; cancer; CXC chemokines; CXCR4; inflammation; molecular docking; molecular dynamics; molecular recognition; NMR

Indexed keywords

CHEMOKINE RECEPTOR CXCR4; PEPTIDE TRANSPORTER 1; PEPTIDE TRANSPORTER 2;

AMINO ACID SEQUENCE; ARTICLE; BINDING AFFINITY; HUMAN; HUMAN CELL; IN VITRO STUDY; MOLECULAR DOCKING; MOLECULAR DYNAMICS; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN BINDING; PROTEIN CONFORMATION; PROTEIN SECONDARY STRUCTURE; PROTEIN STRUCTURE; PROTEIN TARGETING; T CELL LEUKEMIA;

ANTAGONISTS; CANCER; CXC CHEMOKINES; CXCR4; INFLAMMATION; MOLECULAR DOCKING; MOLECULAR DYNAMICS; MOLECULAR RECOGNITION; NMR;

AMINO ACID SEQUENCE; HUMANS; MOLECULAR SEQUENCE DATA; PEPTIDES; RECEPTORS, CXCR4; SEQUENCE HOMOLOGY, AMINO ACID;

EID: 84896111950     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.2614     Document Type: Article

References (56)

1. Lasagni L, Francalanci M, Annunziato F, Lazzeri E, Giannini S, Cosmi L, Sagrinati C, Mazzinghi B, Orlando C, Maggi E, Marra F, Romagnani S, Serio M, Romagnani P,. An alternatively spliced variant of CXCR3 mediates the inhibition of endothelial cell growth induced by IP-10, Mig, and I-TAC, and acts as functional receptor for platelet factor 4. J. Exp. Med. 2003; 197: 1537-1549.
2. Sun X, Cheng G, Hao M, Zheng J, Zhou X, Zhang J, Taichman RS, Pienta KJ, Wang J,. CXCL12/CXCR4/CXCR7 chemokine axis and cancer progression. Cancer Metastasis Rev. 2010; 29: 709-722.
3. Feng Y, Broder CC, Kennedy PE, Berger EA, HIV-1 entry cofactor: functional cDNA cloning of a seven-transmembrane, G protein-coupled receptor. Science 1996; 272: 872-877.
4. Aiuti A, Tavian M, Cipponi A, Ficara F, Zappone E, Hoxie J, Peault B, Bordignon C,. Expression of CXCR4, the receptor for stromal cell-derived factor-1 on fetal and adult human lympho-hematopoietic progenitors. Eur. J. Immunol. 1999; 29: 1823-1831.
5. Aiuti A, Webb IJ, Bleul C, Springer T, Gutierrez-Ramos JC,. The chemokine SDF-1 is a chemoattractant for human CD34+ hematopoietic progenitor cells and provides a new mechanism to explain the mobilization of CD34+ progenitors to peripheral blood. J. Exp. Med. 1997; 185: 111-120.
6. Rubin JB, Chemokine signaling in cancer: one hump or two? Semin. Cancer Biol. 2009; 19: 116-22.
7. Teicher BA, Fricker SP,. CXCL12 SDF-1;/CXCR4 pathway in cancer. Clin. Cancer Res. 2010; 16: 2927-31.
8. Levoye A, Balabanian K, Baleux F, Bachelerie F, Lagane B, CXCR7 heterodimerizes with CXCR4 and regulates CXCL12-mediated G protein signaling. Blood 2009; 113: 6085-93.
9. Balabanian K, Lagane B, Infantino S, Chow KY, Harriague J, Moepps B, Arenzana-Seisdedos F, Thelen M, Bachelerie F,. The chemokine SDF-1/CXCL12 binds to and signals through the orphan receptor RDC1 in T lymphocytes. J. Biol. Chem. 2005; 280: 35760-6.
10. Boldajipour B, Mahabaleshwar H, Kardash E, Reichman-Fried M, Blaser H, Minina S, Wilson D, Xu Q, Raz E,. Control of chemokine-guided cell migration by ligand sequestration. Cell 2008; 132: 463-73.
11. Zabel BA, Wang Y, Lewen S, Berahovich RD, Penfold ME, Zhang P, Powers J, Summers BC, Miao Z, Zhao B, Jalili A, Janowska-Wieczorek A, Jaen JC, Schall TJ,. Elucidation of CXCR7-mediated signaling events and inhibition of CXCR4-mediated tumor cell transendothelial migration by CXCR7 ligands. J. Immunol. 2009; 183: 3204-11.
12. Ma Q, Jones D, Borghesani PR, Segal RA, Nagasawa T, Kishimoto T, Bronson RT, Springer TA,. Impaired B-lymphopoiesis, myelopoiesis, and derailed cerebellar neuron migration in CXCR4- and SDF-1-deficient mice. Proc. Natl. Acad. Sci. U. S. A. 1998; 95: 9448-9453.
13. Tachibana K, Hirota S, Iizasa H, Yoshida H, Kawabata K, Kataoka Y, Kitamura Y, Matsushima K, Yoshida N, Nishikawa S, Kishimoto T, Nagasawa T,. The chemokine receptor CXCR4 is essential for vascularization of the gastrointestinal tract. Nature 1998; 393: 591-594.
14. Ben-Baruch A, Organ selectivity in metastasis: regulation by chemokines and their receptors. Clin. Exp. Metastasis 2008; 25: 345-356.
15. Müller A, Homey B, Soto H, Ge N, Catron D, Buchanan ME, McClanahan T, Murphy E, Yuan W, Wagner SN, Barrera JL, Mohar A, Verástegui E, Zlotnik A,. Involvement of chemokine receptors in breast cancer metastasis. Nature 2001; 410: 50-56.
16. Scala S, Giuliano P, Ascierto PA, Ieranò C, Franco R, Napolitano M, Ottaiano A, Lombardi ML, Luongo M, Simeone E, Castiglia D, Mauro F, De Michele I, Calemma R, Botti G, Caracò C, Nicoletti G, Satriano RA, Castello G,. Human melanoma metastases express functional CXCR4. Clin. Cancer Res. 2006; 12: 2427-33.
17. Scala S, Ottaiano A, Ascierto PA, Cavalli M, Simeone E, Giuliano P, Napolitano M, Franco R, Botti G, Castello G,. Expression of CXCR4 predicts poor prognosis in patients with malignant melanoma. Clin. Cancer Res. 2005; 11: 1835-41.
18. Ottaiano A, Di Palma A, Napolitano M, Pisano C, Pignata S, Tatangelo F, Botti G, Acquaviva AM, Castello G, Ascierto PA, Iaffaioli RV, Scala S,. Inhibitory effects of anti-CXCR4 antibodies on human colon cancer cells. Cancer Immunol. Immunother. 2005; 54: 781-91.
19. Furusato B, Mohamed A, Uhlén M, Rhim JS,. CXCR4 and cancer. Pathol. Int. 2010; 60: 497-505.
20. Zagzag D, Lukyanov Y, Lan L, Ali MA, Esencay M, Mendez O, Yee H, Voura EB, Newcomb EW,. Hypoxia-inducible factor 1 and VEGF upregulate CXCR4 in glioblastoma: implications for angiogenesis and glioma cell invasion. Lab. Invest. 2006; 86: 1221-1232.
21. Choi WT, Duggineni S, Xu Y, Huang Z, An J,. Drug discovery research targeting the CXC chemokine receptor 4 CXCR4. J. Med. Chem. 2012; 55: 977-994.
22. De Clercq E,. The bicyclam AMD3100 story. Nat. Rev. Drug Discov. 2003; 2: 581-587.
23. Crump MP, Gong JH, Loetscher P, Rajarathnam K, Amara A, Arenzana-Seisdedos F, Virelizier JL, Baggiolini M, Sykes BD, Clark-Lewis I,. Solution structure and basis for functional activity of stromal cell-derived factor-1; dissociation of CXCR4 activation from binding and inhibition of HIV-1. EMBO J. 1997; 16: 6996-7007.
24. Wu B, Chien EY, Mol CD, Fenalti G, Liu W, Katritch V, Abagyan R, Brooun A, Wells P, Bi FC, Hamel DJ, Kuhn P, Handel TM, Cherezov V, Stevens RC,. Structures of the CXCR4 chemokine GPCR with small-molecule and cyclic peptide antagonists. Science 2010; 330: 1066-1071.
25. Palczewski K, Kumasaka T, Hori T, Behnke CA, Motoshima H, Fox BA, Le Trong I, Teller DC, Okada T, Stenkamp RE, Yamamoto M, Miyano M,. Crystal structure of rhodopsin: a G protein-coupled receptor. Science 2000; 289: 739-745.
26. Autiero I, Costantini S, Colonna G,. Human sirt-1: molecular modeling and structure-function relationships of an unordered protein. PLoS One 2009; 4: e7350.
27. Palladino P, Portella L, Colonna G, Raucci R, Saviano G, Rossi F, Napolitano M, Scala S, Castello G, Costantini S,. The N-terminal peptide of CXCL11 as structural template for CXCR3 antagonist: synthesis, conformational analysis and binding studies. Chem. Biol. Drug Des. 2012; 80: 254-265.
28. Thompson JD, Higgins DG, Gibson T,. CLUSTAL W: improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position-specific gap penalties and weight matrix choice. Nucleic Acids Res. 1994; 2: 4673-4680.
29. Sali A, Blundell TL,. Comparative protein modelling by satisfaction of spatial restraints. J. Mol. Biol. 1993; 234: 779-815.
30. Sippl MJ,. Recognition of errors in three-dimensional structures of proteins. Proteins 1993; 17: 355-362.
31. Laskowski RA, MacArthur MW, Moss DS, Thornton JM,. PROCHECK: a program to check the stereochemical quality of protein structures. J. Appl. Crystallogr. 1993; 26: 283-291.
32. Kabsch W, Sander C,. Dictionary of protein secondary structure: pattern recognition of hydrogen-bonded and geometrical features. Biopolymers 1983; 2: 2577-2637.
33. Schneidman-Duhovny D, Inbar Y, Nussinov R, Wolfson HJ,. PatchDock and SymmDock: servers for rigid and symmetric docking. Nucleic Acids Res. 2005; 33: W363-W367.
34. Murphy JW, Yuan H, Kong Y, Xiong Y, Lolis EJ,. Heterologous quaternary structure of CXCL12 and its relationship to the CC chemokine family. Proteins 2010; 78: 1331-7.
35. Vangone A, Spinelli R, Scarano V, Cavallo L, Oliva R,. COCOMAPS: a web application to analyze and visualize contacts at the interface of biomolecular complexes. Bioinformatics 2011; 27: 2915-6.
36. Costantini S, Colonna G, Facchiano AM,. ESBRI: a web server for evaluating salt bridges in proteins. Bioinformation 2008; 3: 137-8.
37. Chang WC, White PD,. Fmoc Solid Phase Peptide Synthesis. Oxford University Press: New York, 2000.
38. Wüthrich K,. NMR of Proteins and Nucleic Acids. John Wiley & Sons: New York, 1986.
39. Griesinger C, Otting G, Wüthrich K, Ernst RR, Clean M,. TOCSY for proton spin system identification in macromolecules. J. Am. Chem. Soc. 1988; 110: 7870-7872.
40. Piantini U, Sorensen OW, Ernst RR,. Multiple quantum filters for elucidating NMR coupling networks. J. Am. Chem. Soc. 1982; 104: 6800-6801.
41. Dalvit C,. Efficient multiple-solvent suppression for the study of the interaction of organic solvents with biomolecules. J. Biomol. NMR 1998; 11: 437-444.
42. Bartels C, Xia T, Billeter M, Gunthert P, Wüthrich K,. The program XEASY for computer-supported NMR spectral analysis of biological macromolecules. J. Biomol. NMR 1995; 6: 1-10.
43. Van Der Spoel D, Lindahl E, Hess B, Groenhof G, Mark AE, Berendsen HJ,. GROMACS: fast, flexible, and free. J. Comput. Chem. 2005; 26: 1701-1718.
44. Paladino A, Costantini S, Colonna G, Facchiano AM,. Molecular modelling of miraculin: structural analyses and functional hypotheses. BBRC 2008; 367: 26-32.
45. Paladino A, Colonna G, Facchiano AM, Costantini S,. Functional hypothesis on Miraculin' sweetness by a molecular dynamics approach. BBRC 2010; 396: 726-730.
46. Bax A, Davis DG,. Practical aspects of two-dimensional transverse NOE spectroscopy. J. Magn. Reson. 1985; 63: 207-213.
47. Plaxco KW, Morton CJ, Grimshaw SB, Jones JA, Pitkeathly M, Campbell ID, Dobson CM,. The effects of guanidine hydrochloride on the 'random coil' conformations and NMR chemical shifts of the peptide series GGXGG. J. Biomol. NMR 1997; 10: 221-230.
48. 1H chemical shifts in proteins, J. Biomol. NMR 1997; 9: 359-369.
49. Demmer O, Frank AO, Hagn F, Schottelius M, Marinelli L, Cosconati S, Brack-Werner R, Kremb S, Wester HJ, Kessler H,. A conformationally frozen peptoid boosts CXCR4 affinity and anti-HIV activity. Angewandte Chemie Int. Ed. Engl. 2012; 51: 8110-3.
50. Tamamura H, Fujii N,. The therapeutic potential of CXCR4 antagonists in the treatment of HIV infection, cancer metastasis and rheumatoid arthritis. Expert Opin. Ther. Targets 2005; 9: 1267-82.
51. Horuk R,. Chemokine receptor antagonists: overcoming developmental hurdles. Nat. Rev. Drug Discov. 2009; 8: 23-33.
52. Costantini S, Raucci R, De Vero T, Castello G, Colonna G,. Common structural interactions between the receptors CXCR3, CXCR4 and CXCR7 complexed with their natural ligands, CXCL11 and CXCL12, by a modeling approach. Cytokine 2013; 64: 316-21.
53. Accardo A, Mansi R, Salzano G, Morisco A, Aurilio M, Parisi A, Maione F, Cicala C, Ziaco B, Tesauro D, Aloj L, De Rosa G, Morelli G,. Bombesin peptide antagonist for target-selective delivery of liposomal doxorubicin on cancer cells. J. Drug Target. 2013; 21: 240-249.
54. Accardo A, Tesauro D, Aloj L, Tarallo L, Arra C, Mangiapia G, Vaccaro M, Pedone C, Paduano L, Morelli G,. Peptide containing aggregates as selective nanocarriers for therapeutics. ChemMedChem 2008; 3: 594-602.
55. Accardo A, Mansi R, Morisco A, Mangiapia G, Paduano L, Tesauro D, Radulescu A, Aurilio M, Aloj L, Arra C, Morelli G,. Peptide modified nanocarriers for selective targeting of bombesin receptors. Mol Biosys. 2010; 6: 878-887.
56. Morisco A, Accardo A, Gianolio E, Tesauro D, Benedetti E, Morelli G,. Micelles derivatized with octreotide as potential target-selective contrast agents in MRI. J. Pept. Sci. 2009; 15: 242-250.