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Peptide and peptide mimetic inhibitors of antigen presentation by HLA-DR class II MHC molecules. Design, structure-activity relationships, and X-ray crystal structures.

Bolin DR, Swain AL, Sarabu R, Berthel SJ, Gillespie P, Huby NJ, Makofske R, Orzechowski L, Perrotta A, Toth K, Cooper JP, Jiang N, Falcioni F, Campbell R, Cox D, Gaizband D, Belunis CJ, Vidovic D, Ito K, Crowther R, Kammlott U, Zhang X, Palermo R, Weber D, Guenot J, Nagy Z, Olson GL
J Med Chem 43 2135-48 (2000)
Related entries: 1d5m, 1d5x, 1d5z

Cited: 50 times
EuropePMC logo PMID: 10841792

Abstract

Molecular features of ligand binding to MHC class II HLA-DR molecules have been elucidated through a combination of peptide structure-activity studies and structure-based drug design, resulting in analogues with nanomolar affinity in binding assays. Stabilization of lead compounds against cathepsin B cleavage by N-methylation of noncritical backbone NH groups or by dipeptide mimetic substitutions has generated analogues that compete effectively against protein antigens in cellular assays, resulting in inhibition of T-cell proliferation. Crystal structures of four ternary complexes of different peptide mimetics with the rheumatoid arthritis-linked MHC DRB10401 and the bacterial superantigen SEB have been obtained. Peptide-sugar hybrids have also been identified using a structure-based design approach in which the sugar residue replaces a dipeptide. These studies illustrate the complementary roles played by phage display library methods, peptide analogue SAR, peptide mimetics substitutions, and structure-based drug design in the discovery of inhibitors of antigen presentation by MHC class II HLA-DR molecules.

Reviews - 1d6e mentioned but not cited (1)

  1. Conformational variation in structures of classical and non-classical MHCII proteins and functional implications. Painter CA, Stern LJ. Immunol Rev 250 144-157 (2012)

Articles - 1d6e mentioned but not cited (4)

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Reviews citing this publication (6)

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  6. Current status of drugs in development for celiac disease. Kurppa K, Hietikko M, Sulic AM, Kaukinen K, Lindfors K. Expert Opin Investig Drugs 23 1079-1091 (2014)

Articles citing this publication (39)

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  10. Design of a conformationally defined and proteolytically stable circular mimetic of brain-derived neurotrophic factor. Fletcher JM, Morton CJ, Zwar RA, Murray SS, O'Leary PD, Hughes RA. J Biol Chem 283 33375-33383 (2008)
  11. Crystal structure of a SEA variant in complex with MHC class II reveals the ability of SEA to crosslink MHC molecules. Petersson K, Thunnissen M, Forsberg G, Walse B. Structure 10 1619-1626 (2002)
  12. Fuzzy neural network-based prediction of the motif for MHC class II binding peptides. Noguchi H, Hanai T, Honda H, Harrison LC, Kobayashi T. J Biosci Bioeng 92 227-231 (2001)
  13. Exploration of the P6/P7 region of the peptide-binding site of the human class II major histocompatability complex protein HLA-DR1. Zavala-Ruiz Z, Sundberg EJ, Stone JD, DeOliveira DB, Chan IC, Svendsen J, Mariuzza RA, Stern LJ. J Biol Chem 278 44904-44912 (2003)
  14. Predicting peptide binding to MHC pockets via molecular modeling, implicit solvation, and global optimization. Schafroth HD, Floudas CA. Proteins 54 534-556 (2004)
  15. Repertoire-scale determination of class II MHC peptide binding via yeast display improves antigen prediction. Rappazzo CG, Huisman BD, Birnbaum ME. Nat Commun 11 4414 (2020)
  16. Modified low molecular weight cyclic peptides as mimetics of BDNF with improved potency, proteolytic stability and transmembrane passage in vitro. Fletcher JM, Hughes RA. Bioorg Med Chem 17 2695-2702 (2009)
  17. Small molecule inhibitor of antigen binding and presentation by HLA-DR2b as a therapeutic strategy for the treatment of multiple sclerosis. Ji N, Somanaboeina A, Dixit A, Kawamura K, Hayward NJ, Self C, Olson GL, Forsthuber TG. J Immunol 191 5074-5084 (2013)
  18. Maternal MHC regulates generation of pathogenic antibodies and fetal MHC-encoded genes determine susceptibility in congenital heart block. Strandberg LS, Ambrosi A, Jagodic M, Dzikaite V, Janson P, Khademi M, Salomonsson S, Ottosson L, Klauninger R, Adén U, Sonesson SE, Sunnerhagen M, de Graaf KL, Kuchroo VK, Achour A, Winqvist O, Olsson T, Wahren-Herlenius M. J Immunol 185 3574-3582 (2010)
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  20. Protease-resistant human GAD-derived altered peptide ligands decrease TNF-alpha and IL-17 production in peripheral blood cells from patients with type 1 diabetes mellitus. Boehm BO, Rosinger S, Sauer G, Manfras BJ, Palesch D, Schiekofer S, Kalbacher H, Burster T. Mol Immunol 46 2576-2584 (2009)
  21. Structure-based design of altered MHC class II-restricted peptide ligands with heterogeneous immunogenicity. Chen S, Li Y, Depontieu FR, McMiller TL, English AM, Shabanowitz J, Kos F, Sidney J, Sette A, Rosenberg SA, Hunt DF, Mariuzza RA, Topalian SL. J Immunol 191 5097-5106 (2013)
  22. Design of glycopeptides used to investigate class II MHC binding and T-cell responses associated with autoimmune arthritis. Andersson IE, Andersson CD, Batsalova T, Dzhambazov B, Holmdahl R, Kihlberg J, Linusson A. PLoS One 6 e17881 (2011)
  23. A comparative study of MHC Class-II HLA-DRbeta1*0401-Col II and HLA-DRbeta1*0101-HA complexes: a theoretical point of view. Cárdenas C, Villaveces JL, Suárez C, Obregón M, Ortiz M, Patarroyo ME. J Struct Biol 149 38-52 (2005)
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  25. (E)-alkene and ethylene isosteres substantially alter the hydrogen-bonding network in class II MHC A(q)/glycopeptide complexes and affect T-cell recognition. Andersson IE, Batsalova T, Haag S, Dzhambazov B, Holmdahl R, Kihlberg J, Linusson A. J Am Chem Soc 133 14368-14378 (2011)
  26. Residue analysis of a CTL epitope of SARS-CoV spike protein by IFN-gamma production and bioinformatics prediction. Huang J, Cao Y, Bu X, Wu C. BMC Immunol 13 50 (2012)
  27. Recognition of Class II MHC Peptide Ligands That Contain β-Amino Acids. Cheloha RW, Woodham AW, Bousbaine D, Wang T, Liu S, Sidney J, Sette A, Gellman SH, Ploegh HL. J Immunol 203 1619-1628 (2019)
  28. In silico and in vivo studies of gp120-HIV-derived peptides in complex with G4-PAMAM dendrimers. Rolando Alberto RF, Martiniano B, Saúl RH, Jazmín GM, Mara GS, Alan Rubén EP, Manuel Jonathan FV, Juan Vicente MM, José CB. RSC Adv 10 20414-20426 (2020)
  29. An unstable Th epitope of P. falciparum fosters central memory T cells and anti-CS antibody responses. Parra-López CA, Bernal-Estévez D, Yin L, Vargas LE, Pulido-Calixto C, Salazar LM, Calvo-Calle JM, Stern LJ. PLoS One 9 e100639 (2014)
  30. Contribution of the flexible loop region to the function of staphylococcal enterotoxin B. Yanaka S, Kudou M, Tanaka Y, Sasaki T, Takemoto S, Sakata A, Hattori Y, Koshi T, Futaki S, Tsumoto K, Nakashima T. Protein Eng Des Sel 23 415-421 (2010)
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  32. Recombinant expression of the beta-subunit of HLA-DR10 for the selection of novel lymphoma targeting molecules. Albrecht H, Cosman M, Ngu-Schwemlein M, Corzett M, Curran KW, Dolan C, Fang X, DeNardo SJ, DeNardo GL, Balhorn R. Cancer Biother Radiopharm 22 531-542 (2007)
  33. Structural Insights Into HLA-DM Mediated MHC II Peptide Exchange. Painter CA, Stern LJ. Curr Top Biochem Res 13 39-55 (2011)
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  35. β-Phenylproline: the high β-turn forming propensity of proline combined with an aromatic side chain. Fatás P, Jiménez AI, Calaza MI, Cativiela C. Org Biomol Chem 10 640-651 (2012)
  36. Oxazole- and imidazole-based Ser-Leu dipeptide mimetics in potent inhibitors of antigen presentation by MHC class II DR molecules. Sarabu R, Bolin DR, Campbell R, Cooper JR, Cox D, Gaizband D, Makofske R, Nagy Z, Olson GL. Drug Des Discov 18 3-7 (2002)
  37. The N-terminal region of photocleavable peptides that bind HLA-DR1 determines the kinetics of fragment release. Negroni MP, Stern LJ. PLoS One 13 e0199704 (2018)
  38. Synthesis and Biological Evaluation of Hapten-Clicked Analogues of The Antigenic Peptide Melan-A/MART-126(27L)-35. Tarbe M, Miles JJ, Edwards ESJ, Miles KM, Sewell AK, Baker BM, Quideau S. ChemMedChem 15 799-807 (2020)
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