Structure-activity relationship of for-l-Met l-Leu-l-Phe-OMe analogues in human neutrophils

Bioorganic Chemistry

Volumn 34, Issue 5, 2006, Pages 298-318

  Cavicchioni, Giorgio ^a   Fraulini, Anna ^a   Falzarano, Sofia ^a   Spisani, Susanna ^a  

^a UNIVERSITY OF FERRARA   (Italy)

Author keywords

Chemotaxis; fMLP binding; Human neutrophils; N Formylpeptides; Structure activity relationship; Superoxide anion production

Indexed keywords

ALKYL GROUP; AMIDE; CARBOXYL GROUP; DEPSIPEPTIDE; FORMYLMETHIONYLLEUCYLPHENYLALANINE; FORMYLMETHIONYLLEUCYLPHENYLALANINE DERIVATIVE; FORMYLPEPTIDE; HYDRAZONE DERIVATIVE; LEUCINE; METHIONINE; OXIME; PHENYLALANINE; SUPEROXIDE; THIOAMIDE; UNCLASSIFIED DRUG;

AMINO ACID SUBSTITUTION; CHEMOTAXIS; CROSS LINKING; HUMAN; HUMAN CELL; LIGAND BINDING; PRIORITY JOURNAL; REVIEW; STRUCTURE ACTIVITY RELATION;

CHEMOTACTIC FACTORS; CHEMOTAXIS, LEUKOCYTE; HUMANS; MOLECULAR STRUCTURE; N-FORMYLMETHIONINE LEUCYL-PHENYLALANINE; NEUTROPHILS; PROTEIN BINDING; RECEPTORS, FORMYL PEPTIDE; STRUCTURE-ACTIVITY RELATIONSHIP;

BACTERIA (MICROORGANISMS);

EID: 33748614308     PISSN: 00452068     EISSN: 10902120     Source Type: Journal    
DOI: 10.1016/j.bioorg.2006.07.001     Document Type: Review

References (84)

1. Showell H.J., Freer R.J., Zigmond S.H., Schiffmann E., Aswanikumar S., Corcoran B.A., and Becker E.L. J. Exp. Med. 143 (1976) 1154-1169
2. Freer R.J., Day A.R., Radding J.A., Schiffmann E., Aswanikumar S., Showell H.J., and Becker E.L. Biochemistry 19 (1980) 2404-2410
3. Freer R.J., Day A.R., Muthukumaraswamy N., Pinon D., Wu A., Showell H.J., and Becker E.L. Biochemistry 21 (1982) 257-263
4. Iqbal M., Balaram P., Showell H.J., Freer R.J., and Becker E.L. FEBS Lett. 165 (1984) 171-174
5. Sukumar M., Raj P.A., Balaram P., and Becker E.L. Biochem. Biophys. Res. Commun 128 (1985) 339-344
6. Rot A., Henderson L.E., Copeland T.D., and Leonard E.J. Proc. Natl. Acad. Sci. USA 84 (1987) 7967-7971
7. Toniolo C., Crisma M., Valle G., Bonora G.M., Polinelli S., Becker E.L., Freer R.J., Sudhanand R., Balaji Rao P., Balaram P., and Sukumar M. Peptide Res. 2 (1989) 275-281
8. Michel A.G., Lajoie G., and Hassani C.A. Int. J. Pept. Protein Res. 36 (1990) 489-498
9. Caterina M.J., and Devreotes P.N. FASEB J. 5 (1991) 3078-3085
10. Radel S., Genco R.J., and De Nardin E. Biochem. Int. 25 (1991) 745-753
11. Murphy P.M., Özçelik T., Kenney R.T., Tiffany H.L., McDermott D., and Francke U. J. Biol. Chem. 267 (1992) 7637-7643
12. Quehenberger O., Prossnitz E.R., Cavanagh S.L., Cochrane C.G., and Ye R.D. J. Biol. Chem. 268 (1993) 18167-18175
13. Lala A., Sharma A., Sojar H.T., Radel S., Genco R.J., and De Nardin E. Biochim. Biophys. Acta 1178 (1993) 302-306
14. Klotz K.N., Krotec K.L., Gripentrog J., and Jesaitis A.J. J. Immunol. 152 (1994) 801-810
15. Prasad S., Balaji Rao R., Bergstrand H., Lundquist B., Becker E.L., and Balaram P. Int. J. Pept. Protein Res. 48 (1996) 312-318
16. Spisani S., Traniello S., Cavicchioni G., Formaggio F., Crisma M., and Toniolo C. J. Pept. Sci. 7 (2002) 56-65
17. Dentino A.R., Raj P.A., and De Nardin E. Arch. Biochem. Biophys. 337 (1997) 267-274
18. Prossnitz E.R. Pharmacol. Ther. 74 (1997) 73-102
19. Toniolo C., Bonora G.M., Showell H., Freer R.J., and Becker E.L. Biochemistry 23 (1984) 698-704
20. Spisani S., Cavalletti T., Gavioli R., Scatturin A., Vertuani G., and Traniello S. Inflammation 10 (1986) 363-369
21. Edmundson A.B., and Ely K.R. Mol. Immunol. 22 (1985) 463-475
22. Spisani S., and Cavicchioni G. Bioorg. Chem. 28 (2000) 252-259
23. Pagani Zecchini G., Paglialunga Paradisi M., Torrini I., Lucente G., Traniello S., and Spisani S. Arch. Pharm. (Weinheim) 326 (1993) 461-465
24. Cavicchioni G., Vertuani G., Scatturin A., and Spisani S. Bioorg. Med. Chem. Lett. 4 (1994) 1551-1554
25. Cavicchioni G., Breveglieri A., Boggian M., Vertuani G., Reali E., and Spisani S. J. Pept. Sci. 2 (1996) 135-140
26. Dugas H., Laroche M., Ptak M., and Labbé H. Int. J. Pept. Protein Res. 41 (1993) 595-605
27. Pagani Zecchini G., Paglialunga Paradisi M., Torrini I., Lucente G., Mastropietro G., Paci M., and Spisani S. Arch. Pharm. Pharm. Med. Chem. 329 (1996) 517-523
28. Spisani S., Breveglieri A., Fabbri E., Vertuani G., Rizzuti O., and Cavicchioni G. Pept. Res. 9 (1996) 279-282
29. Cavicchioni G., and Spisani S. Curr. Top. Pept. Protein Res. 2 (1997) 33-39
30. Wu A., Muthukumaraswamy N., Glasel J.a., Mackin W.M., Becker E.L., and Freer R.J. FEBS Lett. 159 (1983) 150-152
31. Pettersen E.O., Larsen R.O., Borretzen B., Dornish J.M., and Oftebro R. Anticancer Res. 11 (1991) 369-373
32. Sauvè G., Rao V.S., Lajoie B., and Belleau B. Can. J. Chem. 63 (1985) 3089-3101
33. Belleau B., Lajoie G., Sauvè G., Rao V.S., and Di Paola A. Int. J. Immunopharmacol. 11 (1989) 467-471
34. Toniolo C., Crisma M., and Becker E.L. Il Farmaco 45 (1990) 921-925
35. Torrini I., Paglialunga Paradisi M., Pagani Zecchini G., Lucente G., Mastropietro G., and Spisani S. J. Pept. Res. 55 (2000) 102-109
36. Torrini I., Nalli M., Paglialunga Paradisi M., Pagani Zecchini G., Lucente G., and Spisani S. J. Pept. Res. 58 (2001) 56-66
37. Gao J.L., Becker E.L., Freer R.J., Muthukumaraswamy N., and Murphy P.M. J. Exp. Med. 180 (1994) 2191-2197
38. Derian C.K., Solomon H.F., Higgins III J.D., Beblavy M.J., Santulli R.J., Bridger G.J., Pike M.C., Kroon D.J., and Fischman A.J. Biochemistry 35 (1996) 1265-1269
39. Higgins III J.D., Bridger G.J., Derian C.K., Beblavy M.J., Hernandez P.E., Gaul F.E., Abrams M.J., Pike M.C., and Solomon H.F. J. Med. Chem. 39 (1996) 1013-1015
40. Prossnitz E.R., and Ye R.D. Pharmacol. Ther. 74 (1997) 73-102
41. Torrini I., Pagani Zecchini G., Paglialunga Paradisi M., Lucente G., Gavuzzo E., Mazza F., Pochetti G., Spisani S., and Giuliani A.L. Int. J. Pept. Protein Res. 38 (1991) 495-504
42. Harvath L., and Aksamit R.R. J. Immunol. 133 (1984) 1471-1476
43. Toniolo C., Bonora G.M., Freer R.J., Kennedy S.P., Pittenger K.L., and Becker E.L. Peptides 9 (1989) 1195-1205
44. Houston M.E., Harvath L., and Honek J.F. Bioorg. Med. Chem. Lett. 7 (1997) 3007-3012
45. Torrini I., Pagani Zecchini G., Paglialunga Paradisi M., Lucente G., Gavuzzo E., Mazza F., Pochetti G., Traniello S., and Spisani S. Biopolymers 34 (1994) 1-9
46. Spisani S., Breveglieri A., Reali E., Scatturin A., Vertuani G., and Cavicchioni G. Protein Pept. Lett. 2 (1995) 415-418
47. Cavicchioni G., Monesi L.G., Ferretti M.E., Fabbri E., Rizzuti O., and Spisani S. Arch. Pharm. Pharm. Med. Chem. 11 (1998) 368-370
48. Spisani S., Ferretti M.E., Fabbri E., Alvoni S., and Cavicchioni G. Protein Pept. Lett. 5 (1998) 155-158
49. Witkowska R., Zabrocki J., Spisani S., Falzarano M.S., Toniolo C., and Formaggio F. J. Pept. Sci. 9 (2003) 354-360
50. Torrini I., Paglialunga Paradisi M., Pagani Zecchini G., Lucente G., Gavuzzo E., Mazza F., Pochetti G., Traniello S., and Spisani S. Biopolymers 42 (1997) 415-426
51. Giordano C., Lucente G., Mollica A., Nalli M., Pagani Zecchini G., Paglialunga Paradisi M., Gavuzzo E., Mazza F., and Spisani S. J. Pept. Sci. 10 (2004) 510-523
52. Mollica A., Paglialunga Paradisi M., Varani K., Spisani S., and Lucente G. Bioorg. Med. Chem. 14 (2006) 2253-2265
53. Spisani S., and Cavicchioni G. Bioorg. Chem. 8 (2000) 39-44
54. Boulay F., Tardif M., Brouchon L., and Vignais P. Biochem. Biophys. Res. Comm. 168 (1990) 1103-1109
55. Radel S., Genco R.J., and De Nardin E. Infect. Immun. 62 (1994) 1726-1732
56. Antony Raj P., and Balaram P. Biopolymers 24 (1985) 1131-1146
57. Bardi R., Piazzesi A.M., Toniolo C., Raj P.A., Ragothama S., and Balaram P. Int. J. Pept. Protein Res. 27 (1986) 229-238
58. Semus S.F., Becker E.L., Toniolo C., and Freer R.J. Biochem. Biophys. Res. Commun. 157 (1988) 569-574
59. Formaggio F., Pantano M., Crisma M., Toniolo C., Boesten W.H.J., Schoemaker H.E., Kamphuis J., and Becker E.L. Bioorg. Med. Chem. Lett. 3 (1993) 953-956
60. Sudhanand R., Balaji Rao R., Bergstrand H., Lundquist B., Becker E.L., and Balaram P. Int. J. Pept. Protein Res. 48 (1996) 312-318
61. Y. Wzady, C.A. Hassiani, M. Lakhdar, A. Ezzamarty, Peptides, in: J. Martinez, J.A. Fehrentz (Eds.), EDK, Paris, 2001, pp. 689-690.
62. Giordano C., Lucente G., Nalli M., Pagani Zecchini G., Paglialunga Paradisi M., Varani K., and Spisani S. Il Farmaco 58 (2003) 1121-1130
63. Pagani Zecchini G., Morera E., Nalli M., Paglialunga Paradisi M., Lucente G., and Spisani S. Il Farmaco 56 (2001) 851-858
64. Morera E., Lucente G., Ortar G., Nalli M., Mazza F., Gavuzzo E., and Spisani S. Bioorg. Med. Chem. 10 (2002) 147-157
65. Pagani Zecchini G., Paglialunga Paradisi M., Torrini I., Lucente G., Mastropietro G., Paci M., and Spisani S. Arch. Pharm. Med. Chem. 329 (1996) 517-523
66. Cavicchioni G., and Spisani S. J. Pept. Res. 58 (2001) 257-262
67. Cavicchioni G., Turchetti M., and Spisani S. J. Pept. Res. 60 (2002) 223-231
68. Toniolo C., Formaggio F., Crisma M., Valle G., Boesten W.H.J., Schoemaker H.E., Kamphuis J., Temussi P.A., Becker E.L., and Précigoux G. Tetrahedron 49 (1993) 3641-3653
69. Spisani S., Turchetti M., Varani K., Falzarano S., and Cavicchioni G. Eur. J. Pharmacol. 469 (2003) 13-19
70. Gavuzzo E., Lucente G., Mazza F., Pagani Zecchini G., Paglialunga Paradisi M., Pochetti G., and Torrini I. Int. J. Pept. Protein Res. 37 (1991) 268-276
71. Toniolo C., Formaggio F., Crisma M., Valle G., Boesten W.H.J., Schoemaker H.E., Kamphuis J., Temussi P.A., Becker E.L., and Precigoux G. Tetrahedron 49 (1993) 3641-3653
72. Pagani Zecchini G., Paglialunga Paradisi M., Torrini I., and Spisani S. Arch. Pharm. Pharm. Med. Chem. 328 (1995) 673-676
73. Torrini I., Pagani Zecchini G., Paglialunga Paradisi M., and Spisani S. Arch. Pharm. Pharm. Med. Chem. 329 (1996) 143-148
74. Dentino A.R., Antony Raj P., and De Nardin E. Arch. Biochem. Biophys. 337 (1997) 267-274
75. Pagani Zecchini G., Paglialunga Paradisi M., Torrini I., and Spisani S. Archiv. Pharm. 328 (1995) 673-676
76. Torrini I., Pagani Zecchini G., Paglialunga Paradisi M., Lucente G., Gavuzzo E., Mazza F., Pochetti G., Traniello S., and Spisani S. Biopolymers 35 (1995) 347-358
77. Pagani Zecchini G., Paglialunga Paradisi M., Torrini I., Lucente G., Traniello S., and Spisani S. Archiv. Pharm. 326 (1993) 955-958
78. Pagani Zecchini G., Paglialunga Paradisi M., Torrini I., Lucente G., Gavuzzo E., Mazza F., Pochetti G., and Spisani S. Tetrahedron Lett. 32 (1991) 4375-4376
79. Pagani Zecchini G., Paglialunga Paradisi M., Torrini I., Lucente G., Gavuzzo E., Mazza F., Pochetti G., Paci M., Sette M., Di Nola A., Veglia G., Traniello S., and Spisani S. Biopolymers 33 (1993) 437-451
80. Ferretti M.E., Spisani S., Pareschi M.C., Buzzi M., Cavallaro R., Traniello S., Reali E., Torrini I., Paglialunga Paradisi M., Pagani Zecchini G., and Biondi C. Cell. Signal. 6 (1994) 91-101
81. Spisani S., Traniello S., Torrini I., Pagani Zecchini G., and Paglialunga Paradisi M. Minerva Biotechnol. 7 (1995) 54-60
82. Pagani Zecchini G., Torrini I., Paglialunga Paradisi M., Lucente G., and Spisani S. Il Farmaco 49 (1994) 739-742
83. Torrini I., Pagani Zecchini G., Paglialunga Paradisi M., Lucente G., Gavuzzo E., Mazza F., Pochetti S., and Spisani S. Tetrahedron 49 (1993) 489-496
84. Cavicchioni G., Fraulini A., Turchetti M., Varani K., Falzarano S., Pavan B., and Spisani S. Eur. J. Pharmacol. 512 (2005) 1-8