Potent cyclic monomeric and dimeric peptide inhibitors of VLA-4 (α4β1 integrin)-mediated cell adhesion based on the Ile-Leu-Asp-Val tetrapeptide

Journal of Peptide Science

Volumn 6, Issue 7, 2000, Pages 321-341

  Dutta, Anand S ^a   Crowther, Mandy ^a   Gormley, James J ^a   Hassall, Lorraine ^a   Hayward, Christopher F ^a   Gellert, Paul R ^a   Kittlety, Rod S ^a   Alcock, Peter J ^a   Jamieson, Alec ^a   Moores, Julie M ^a   Rees, Amanda ^a   Wood, Linda J ^a   Reilly, Christopher F ^a   Haworth, Duncan ^a  

^a ASTRAZENECA   (United Kingdom)

Author keywords

4 1 integrin; Cyclic peptides; Fibronectin; VCAM 1; VLA 4

Indexed keywords

ADENOSINE DIPHOSPHATE; AMIDE; ASPARTIC ACID; BETA1 INTEGRIN; CARBOXYL GROUP; CYCLOPEPTIDE; DIMER; FIBRONECTIN; INTEGRIN; ISOLEUCINE; LEUCINE; LYMPHOCYTE FUNCTION ASSOCIATED ANTIGEN 1; LYSINE; MONOMER; OVALBUMIN; PIPERAZINE; TETRAPEPTIDE; VALINE; VERY LATE ACTIVATION ANTIGEN;

AMINO ACID SEQUENCE; AMINO TERMINAL SEQUENCE; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CARBOXY TERMINAL SEQUENCE; CELL ADHESION; CELL STRAIN U937; CHEMICAL BOND; CHO CELL; DELAYED HYPERSENSITIVITY; HUMAN; HUMAN CELL; MOUSE; NONHUMAN; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; THROMBOCYTE AGGREGATION;

AMINO ACID SEQUENCE; ANIMALS; CELL ADHESION; CELL LINE; CHO CELLS; CRICETINAE; DELAYED-ACTION PREPARATIONS; DIMERIZATION; DRUG STABILITY; HUMANS; HYPERSENSITIVITY, DELAYED; INTEGRIN ALPHA4BETA1; INTEGRINS; LACTIC ACID; MICE; MICE, INBRED BALB C; OVALBUMIN; PEPTIDES, CYCLIC; POLYGLYCOLIC ACID; POLYMERS; RECEPTORS, LYMPHOCYTE HOMING; U937 CELLS;

CRICETINAE; CRICETULUS GRISEUS;

EID: 0033943476     PISSN: 10752617     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-1387(200007)6:7<321::AID-PSC259>3.0.CO;2-A     Document Type: Article

References (41)

1. Hemler ME, Elices MJ, Parker C, Takada Y. VLA-4: structure of the integrin VLA-4 and its cell-cell and cell-matrix adhesion functions. Immunol. Rev. 1990; 114: 45-65.
2. Cox D, Aoki T, Seki J, Motoyama Y, Yoshida K. The pharmacology of the integrins. Med. Res. Rev. 1994; 14: 195-228.
3. Smyth SS, Joneckis CC, Parise LV. Regulation of vascular integrins. Blood 1993; 81: 2827-2843.
4. Wahl SM, Allen JB, Hines KL. Imamichi T, Wahl AM, Furcht LT, McCarthy JB. Synthetic fibronectin peptides suppress arthritis in rats by interrupting leukocyte adhesion and recruitment. J. Clin. Invest. 1994; 94: 655-662.
5. Chisholm PL, Williams CA, Lobb RR. Monoclonal antibodies to the integrin α-4 subunit inhibit the murine contact hypersensitivity response. Eur. J. Immunol. 1993; 23: 682-688.
6. Barbadillo C, G-Arroyo A, Salas C, Mulero J, Sanchez-Madrid F, Andreu JL. Anti-integrin immunotherapy in rheumatoid arthritis: protective effect of anti-α4 antibody in adjuvant arthritis. Springer Semin. Immunopathol. 1995; 16: 427-436.
7. Zeidler A, Brauer R, Thoss K, Bahnsen J, Heinrichs V, Jablonski-Westrich D, Wroblewski M, Rebstock S. Hamann A. Therapeutic effects of antibodies against adhesion molecules in murine collagen Type II-induced arthritis. Autoimmunity 1995; 21: 245-252.
8. Yednock TA, Cannon C, Fritz LC, Sanchez-Madrid F, Steinman L, Karin N. Prevention of experimental autoimmune encephalomyelitis by antibodies against α4β1 integrin. Nature 1992; 356: 63-66.
9. Baron JL, Madri JA, Ruddle NH, Hashim J, Janeway CA Jr. Surface expression of α4 integrin by CD4 T cells is required for their entry into brain parenchyma: J. Exp. Med. 1993; 177: 57-68.
10. Kent SJ, Karlik SJ, Cannon C, Hines DK, Yednock TA, Fritz LC, Horner HC. A monoclonal antibody to α4 integrin suppresses and reverses active experimental allergic encephalomyelitis. J. Neuroimmunol. 1995; 58: 1-10.
11. Pretolani M, Ruffle C, Lapa e Silva J-R, Joseph D, Lobb RR, Vargaftig BB. Antibody to very late antigen 4 prevents antigen-induced bronchial hyperreactivity and cellular infiltration in the guinea pig airways. J. Exp. Med. 1994; 180: 795-805.
12. 4-integrins mediate antigen-induced late bronchial responses and prolonged airway hyper-responsiveness in sheep. J. Clin. Invest. 1994; 93: 776-787.
13. Yang X-D, Karin N, Tisch R, Steinman L, McDevitt HO. Inhibition of insulitis and prevention of diabetes in nonobese diabetic mice by blocking L-selectin and very late antigen 4 adhesion receptors. Proc. Natl. Acad. Sci. USA 1993; 90: 10494-10498.
14. Burkly LC, Jakubowski A, Hattori M. Protection against adoptive transfer of autoimmune diabetes mediated through very late antigen-4 integrin. Diabetes 1994; 43: 529-534.
15. Baron JL, Reich E-P, Visintin I, Janeway CA Jr. The pathogenesis of adoptive murine autoimmune diabetes requires an interaction between α4-integrins and vascular cell adhesion molecule-1. J. Clin. Invest. 1994; 93:1700-1708.
16. Podolsky DK, Lobb R, King N, Benjamin CD, Pepinsky B, Sehgal P, deBeaumont M. Attenuation of colitis in the cotton-top tamarin by anti-α4 Integrin monoclonal antibody. J. Clin. Invest. 1993; 92: 372-380.
17. Isobe M, Suzuki J, Yagita H, Okumura K, Yamazaki S, Nagai R, Yazaki Y, Sekiguchi M. Immunosuppression to cardiac allografts and soluble antigens by anti-vascular cellular adhesion molecule-1 and anti-very late antigen-4 monoclonal antibodies. J. Immunol. 1994; 153: 5810-5818.
18. Humphries MJ, Komoriya A, Akiyama SK, Olden K, Yamada KM. Identification of two distinct regions of the type III connecting segment of human plasma fibronectin that promote cell-specific adhesion. J. Biol. Chem. 1987; 262: 6886-6892.
19. Humphries MJ. The molecular basis and specificity of integrin-ligand interactions. J. Cell Sciences 1990; 97: 585-592.
20. Komoriya A, Green LJ, Mervic M, Yamada SS, Yamada KM, Humphries MJ. The minimal essential sequence for a major cell type-specific adhesion site (CS-1) within the alternatively spliced type III connecting segment domain of fibronectin is leucine-aspartic acid-valine. J. Biol. Chem. 1991; 266: 15075-15079.
21. Viles JH, Mitchell JBO, Gough SL, Doyle PM, Harris JC, Sadler PJ, Thornton JM. Multiple solution conformations of the integrin binding cyclic pentapeptide cyclo(Ser-D-Leu-Asp-Val-Pro). Analysis of the (φ, ψ) space available to cyclic pentapeptides. Eur. J. Biochem. 1996; 242: 352-362.
22. Doyle PM, Harris JC, Moody CM, Sadler PJ, Sims M, Thornton JM, Uppenbrink J, Viles JH. Solution structure of a biologically active cyclic LDV peptide analogue containing a type II' β-turn mimetic. Int. J. Pept. Protein Res. 1996; 47: 427-436.
23. Vanderslice P, Ren K, Revelle JK, Kim DC, Scott D, Bjercke RJ, Yeh ETH, Beck PJ, Kogan TP. A cyclic hexapeptide is a potent antagonist of α4 integrins. J. Immunol 1997; 158: 1710-1718.
24. Lin K, Ateeq HS, Hsiung SH, Chong LT, Zimmerman CN, Castro A, Lee W, Hammond CE, Kalkunte S, Chen L-L, Pepinsky RB, Leone DR, Sprague AG, Abraham WM, Gill A, Lobb RR, Adams SP. Selective, tight-binding inhibitors of integrin α4β1 that inhibit allergic airway responses. J. Med. Chem. 1999; 42: 920-934.
25. Cardarelli PM, Cobb RR, Nowlin DM, Scholz W, Gorcsan F, Moscinski M, Yasuhara M, Chiang S-L, Lobl TJ. Cyclic RGD peptide inhibits α4β1 interaction with connecting fragment 1 and vascular cell adhesion molecule. J. Biol. Chem. 1994; 269: 18668-18673.
26. Nowlin DM, Gorcsan F, Moscinski M, Chiang S-L, Lobl TJ, Cardarelli PM. A novel cyclic pentapeptide inhibits α4β1 and α5β1 integrin-mediated cell adhesion. J. Biol. Chem. 1993; 268: 20352-20359.
27. Jackson DY, Quan C, Artis DR, Rawson T, Blackburn B, Struble M, Fitzgerald G, Chan K, Mullins S. Burnier JP, Fairbrother WJ, Clark K, Berisini M, Chui H, Renz M, Jones S, Fong S. Potent α4β1 peptide antagonists as potential anti-inflammatory agents. J. Med. Chem. 1997; 40: 3359-3368.
28. Quan C, Skelton NJ. Clark K, Jackson DY, Renz ME, Chiu HH, Keating SM, Beresini MH, Fong S, Artis DR. Transfer of a protein binding epitope to a minimal designed peptide. Biopolymers 1998; 47: 265-275.
29. Peri F, Grell D, Dumy P, Yokokawa Y, Welzenbach K, Weitz-Schmidt G, Mutter M. Assembly of binding loops on aromatic templates as VCAM-1 mimetics. J. Pept. Sci. 1999; 5: 313-322.
30. Souers AJ, Virgilio AA, Schurer SS, Ellman JA. Novel inhibitors of α4β1 integrin receptor interactions through library synthesis and screening. Bioorg. Med. Chem. Lett. 1998; 8: 2297-2302.
31. 5CO), a novel, selective, cyclic peptide inhibitor of VLA-4-mediated cell adhesion. Br. J. Pharmacol. 1999; 126: 1751-1760.
32. Brown T, Jones JH. Protection of histidine side-chains with π-benzyloxymethyl-or π-bromobenzyloxymethyl-groups. J. Chem. Soc. Chem. Commun. 1981; 648-649.
33. Colombo R, Colombo F, Jones JH. Acid-labile histidine side-chain protection: N(π)-t-butoxymethyl group. J. Chem. Soc. Chem. Commun. 1984; 292-293.
34. Thaisrivongs S, Blinn JR, Pals DT, Turner SR. Conformationally constrained renin inhibitory peptides: cyclic(3-1)-1-(carboxymethyl)-L-prolyl-L-phenylalanyl-L-histidinamide as a conformational restriction at the P2-P4 tripeptide portion of the angiotensinogen template. J. Med. Chem. 1991; 34: 1276-1282.
35. 2 synthase inhibitor and receptor antagonist in vitro. Br. J. Pharmacol. 1993; 110: 1600-1606.
36. Dutta AS, Furr BJA, Hutchinson FG. Zoladex: discovery, pharmacodynamics and formulation. Drug News & Perspect. 1993; 6: 325-332.
37. Dutta AS, Furr BJA, Hutchinson FG. The discovery and development of goserelin (Zoladex). Pharm. Med. 1993; 7: 9-28.
38. Pitt CG. The controlled parenteral delivery of polypeptides and proteins. Int. J. Pharm 1990; 59: 173-196.
39. Lee KC, Soltis EE, Newman PS, Burton KW, Mehta RC, DeLuca PP. In vivo assessment of salmon calcitonin sustained release from biodegradable microspheres. J. Control. Rel. 1991; 17: 199-206.
40. Kwong AK, Chou S, Sun AM, Sefton MV, Goosen MFA. In vitro and in vivo release of insulin from poly(lactic acid) microbeads and pellets. J. Control. Rel. 1986; 4: 47-62.
41. 2 integrin)-mediated cell adhesion. Discovery of compounds like cyclo (MePhe-Leu-Asp-Val-D-Arg-D-Arg) (ZD 7349) compatible with depot formulation. J. Peptide Sci. (Accepted for publication).