2ipk Citations

Fluorogenic probes for monitoring peptide binding to class II MHC proteins in living cells.

Nat. Chem. Biol. 3 222-8 (2007)
Cited: 44 times
EuropePMC logo PMID: 17351628

Abstract

A crucial step in the immune response is the binding of antigenic peptides to major histocompatibility complex (MHC) proteins. Class II MHC proteins present their bound peptides to CD4(+) T cells, thereby helping to activate both the humoral and the cellular arms of the adaptive immune response. Peptide loading onto class II MHC proteins is regulated temporally, spatially and developmentally in antigen-presenting cells. To help visualize these processes, we have developed a series of novel fluorogenic probes that incorporate the environment-sensitive amino acid analogs 6-N,N-dimethylamino-2-3-naphthalimidoalanine and 4-N,N-dimethylaminophthalimidoalanine. Upon binding to class II MHC proteins these fluorophores show large changes in emission spectra, quantum yield and fluorescence lifetime. Peptides incorporating these fluorophores bind specifically to class II MHC proteins on antigen-presenting cells and can be used to follow peptide binding in vivo. Using these probes we have tracked a developmentally regulated cell-surface peptide-binding activity in primary human monocyte-derived dendritic cells.

Articles - 2ipk mentioned but not cited (4)

  1. High-density mapping of the MHC identifies a shared role for HLA-DRB1*01:03 in inflammatory bowel diseases and heterozygous advantage in ulcerative colitis. Goyette P, Boucher G, Mallon D, Ellinghaus E, Jostins L, Huang H, Ripke S, Gusareva ES, Annese V, Hauser SL, Oksenberg JR, Thomsen I, Leslie S, International Inflammatory Bowel Disease Genetics Consortium, Australia and New Zealand IBDGC, Belgium IBD Genetics Consortium, Italian Group for IBD Genetic Consortium, NIDDK Inflammatory Bowel Disease Genetics Consortium, United Kingdom IBDGC, Wellcome Trust Case Control Consortium, Quebec IBD Genetics Consortium, Daly MJ, Van Steen K, Duerr RH, Barrett JC, McGovern DP, Schumm LP, Traherne JA, Carrington MN, Kosmoliaptsis V, Karlsen TH, Franke A, Rioux JD. Nat. Genet. 47 172-179 (2015)
  2. Electrostatic modifications of the human leukocyte antigen-DR P9 peptide-binding pocket and susceptibility to primary sclerosing cholangitis. Hov JR, Kosmoliaptsis V, Traherne JA, Olsson M, Boberg KM, Bergquist A, Schrumpf E, Bradley JA, Taylor CJ, Lie BA, Trowsdale J, Karlsen TH. Hepatology 53 1967-1976 (2011)
  3. An effective and effecient peptide binding prediction approach for a broad set of HLA-DR molecules based on ordered weighted averaging of binding pocket profiles. Shen WJ, Zhang S, Wong HS. Proteome Sci 11 S15 (2013)
  4. An automated framework for understanding structural variations in the binding grooves of MHC class II molecules. Yeturu K, Utriainen T, Kemp GJ, Chandra N. BMC Bioinformatics 11 Suppl 1 S55 (2010)


Reviews citing this publication (9)

  1. Macro-/micro-environment-sensitive chemosensing and biological imaging. Yang Z, Cao J, He Y, Yang JH, Kim T, Peng X, Kim JS. Chem Soc Rev 43 4563-4601 (2014)
  2. Fluorescent amino acids: modular building blocks for the assembly of new tools for chemical biology. Krueger AT, Imperiali B. Chembiochem 14 788-799 (2013)
  3. Toward a Network Model of MHC Class II-Restricted Antigen Processing. Miller MA, Ganesan AP, Eisenlohr LC. Front Immunol 4 464 (2013)
  4. The lymph self-antigen repertoire. Clement CC, Santambrogio L. Front Immunol 4 424 (2013)
  5. Peptide-based ligand screening and functional analysis of protein kinase C. Ohashi N, Nomura W, Narumi T, Tamamura H. Biopolymers 100 613-620 (2013)
  6. Monitoring protein interactions and dynamics with solvatochromic fluorophores. Loving GS, Sainlos M, Imperiali B. Trends Biotechnol. 28 73-83 (2010)
  7. Environmentally sensitive fluorescent sensors based on synthetic peptides. Choulier L, Enander K. Sensors (Basel) 10 3126-3144 (2010)
  8. Photochemical approaches to T-cell activation. Huse M. Immunology 130 151-157 (2010)
  9. Imaging in the era of molecular oncology. Weissleder R, Pittet MJ. Nature 452 580-589 (2008)

Articles citing this publication (31)

  1. Development of SNAP-tag fluorogenic probes for wash-free fluorescence imaging. Sun X, Zhang A, Baker B, Sun L, Howard A, Buswell J, Maurel D, Masharina A, Johnsson K, Noren CJ, Xu MQ, Corrêa IR. Chembiochem 12 2217-2226 (2011)
  2. A versatile amino acid analogue of the solvatochromic fluorophore 4-N,N-dimethylamino-1,8-naphthalimide: a powerful tool for the study of dynamic protein interactions. Loving G, Imperiali B. J. Am. Chem. Soc. 130 13630-13638 (2008)
  3. The lymph as a pool of self-antigens. Clement CC, Rotzschke O, Santambrogio L. Trends Immunol. 32 6-11 (2011)
  4. Design, synthesis and evaluation of high-affinity binders for the celiac disease associated HLA-DQ2 molecule. Kapoerchan VV, Wiesner M, Hillaert U, Drijfhout JW, Overhand M, Alard P, van der Marel GA, Overkleeft HS, Koning F. Mol. Immunol. 47 1091-1097 (2010)
  5. A general screening strategy for peptide-based fluorogenic ligands: probes for dynamic studies of PDZ domain-mediated interactions. Sainlos M, Iskenderian WS, Imperiali B. J. Am. Chem. Soc. 131 6680-6682 (2009)
  6. Environment-sensitive fluorescent turn-on probes targeting hydrophobic ligand-binding domains for selective protein detection. Zhuang YD, Chiang PY, Wang CW, Tan KT. Angew. Chem. Int. Ed. Engl. 52 8124-8128 (2013)
  7. Sensing peptide-oligonucleotide interactions by a two-color fluorescence label: application to the HIV-1 nucleocapsid protein. Shvadchak VV, Klymchenko AS, de Rocquigny H, Mély Y. Nucleic Acids Res. 37 e25 (2009)
  8. Thiol-reactive derivatives of the solvatochromic 4-N,N-dimethylamino-1,8-naphthalimide fluorophore: a highly sensitive toolset for the detection of biomolecular interactions. Loving G, Imperiali B. Bioconjug. Chem. 20 2133-2141 (2009)
  9. Concurrent quantification of multiple nanoparticle bound states. Rauwerdink AM, Weaver JB. Med Phys 38 1136-1140 (2011)
  10. Tools for investigating peptide-protein interactions: peptide incorporation of environment-sensitive fluorophores through SPPS-based 'building block' approach. Sainlos M, Imperiali B. Nat Protoc 2 3210-3218 (2007)
  11. Tools for investigating peptide-protein interactions: peptide incorporation of environment-sensitive fluorophores via on-resin derivatization. Sainlos M, Imperiali B. Nat Protoc 2 3201-3209 (2007)
  12. Clarifying the mechanism of superantigen toxicity. Fraser JD. PLoS Biol. 9 e1001145 (2011)
  13. Uber-responsive peptide-based sensors of signaling proteins. Sharma V, Lawrence DS. Angew. Chem. Int. Ed. Engl. 48 7290-7292 (2009)
  14. Increased structural flexibility at the active site of a fluorophore-conjugated beta-lactamase distinctively impacts its binding toward diverse cephalosporin antibiotics. Wong WT, Chan KC, So PK, Yap HK, Chung WH, Leung YC, Wong KY, Zhao Y. J. Biol. Chem. 286 31771-31780 (2011)
  15. AU4S: a novel synthetic peptide to measure the activity of ATG4 in living cells. Ni Z, Gong Y, Dai X, Ding W, Wang B, Gong H, Qin L, Cheng P, Li S, Lian J, He F. Autophagy 11 403-415 (2015)
  16. Environment-sensitive fluorophores with benzothiadiazole and benzoselenadiazole structures as candidate components of a fluorescent polymeric thermometer. Uchiyama S, Kimura K, Gota C, Okabe K, Kawamoto K, Inada N, Yoshihara T, Tobita S. Chemistry 18 9552-9563 (2012)
  17. Synthesis of fluorescent enone derived alpha-amino acids. Fowler LS, Ellis D, Sutherland A. Org. Biomol. Chem. 7 4309-4316 (2009)
  18. Spacer-free BODIPY fluorogens in antimicrobial peptides for direct imaging of fungal infection in human tissue. Mendive-Tapia L, Zhao C, Akram AR, Preciado S, Albericio F, Lee M, Serrels A, Kielland N, Read ND, Lavilla R, Vendrell M. Nat Commun 7 10940 (2016)
  19. Carrying yourself: self antigen composition of the lymphatic fluid. Santambrogio L, Stern LJ. Lymphat Res Biol 11 149-154 (2013)
  20. Short and scalable synthesis of an anhydride precursor of the environment-sensitive fluorophore 6-dimethylaminonaphthalimide. Baathulaa K, Xu Y, Qian X. Nat Protoc 6 1990-1997 (2011)
  21. Comment Self-reporting peptides illuminate the MHC groove. Yewdell JW, Lev A. Nat. Chem. Biol. 3 201-202 (2007)
  22. Probing microenvironment of micelle and albumin using diethyl 6-(dimethylamino)naphthalene-2,3-dicarboxylate: An electroneutral solvatochromic fluorescent probe. Mallick S, Pal K, Koner AL. J Colloid Interface Sci 467 81-89 (2016)
  23. Monitoring penetratin interactions with lipid membranes and cell internalization using a new hydration-sensitive fluorescent probe. Zamotaiev OM, Postupalenko VY, Shvadchak VV, Pivovarenko VG, Klymchenko AS, Mély Y. Org. Biomol. Chem. 12 7036-7044 (2014)
  24. Red fluorescent turn-on ligands for imaging and quantifying G protein-coupled receptors in living cells. Karpenko IA, Kreder R, Valencia C, Villa P, Mendre C, Mouillac B, Mély Y, Hibert M, Bonnet D, Klymchenko AS. Chembiochem 15 359-363 (2014)
  25. Acid cleavable surface enhanced raman tagging for protein detection. Zhang D, Vangala K, Li S, Yanney M, Xia H, Zou S, Sygula A. Analyst 136 520-526 (2011)
  26. Design Principles for SuCESsFul Biosensors: Specific Fluorophore/Analyte Binding and Minimization of Fluorophore/Scaffold Interactions. de Picciotto S, Dickson PM, Traxlmayr MW, Marques BS, Socher E, Zhao S, Cheung S, Kiefer JD, Wand AJ, Griffith LG, Imperiali B, Wittrup KD. J. Mol. Biol. 428 4228-4241 (2016)
  27. Solvent-induced multicolour fluorescence of amino-substituted 2,3-naphthalimides studied by fluorescence and transient absorption measurements. Fujii M, Namba M, Yamaji M, Okamoto H. Photochem. Photobiol. Sci. 15 842-850 (2016)
  28. Far-red/near-infrared fluorescence light-up probes for specific in vitro and in vivo imaging of a tumour-related protein. Chen C, Hua Y, Hu Y, Fang Y, Ji S, Yang Z, Ou C, Kong D, Ding D. Sci Rep 6 23190 (2016)
  29. Expression of a single-chain human leukocyte antigen-DRA/DRB3*01:01 molecule and differential binding of a monoclonal antibody in the presence of specifically bound human platelet antigen-1a peptide. Bouwmans EE, Smethurst PA, Garner SF, Ouwehand WH, Morley SL. Transfusion 54 1478-1485 (2014)
  30. d-PET-controlled "off-on" Polarity-sensitive Probes for Reporting Local Hydrophilicity within Lysosomes. Zhu H, Fan J, Mu H, Zhu T, Zhang Z, Du J, Peng X. Sci Rep 6 35627 (2016)
  31. Preparation of a Trp-BODIPY fluorogenic amino acid to label peptides for enhanced live-cell fluorescence imaging. Mendive-Tapia L, Subiros-Funosas R, Zhao C, Albericio F, Read ND, Lavilla R, Vendrell M. Nat Protoc 12 1588-1619 (2017)