Detection of transglutaminase activity using click chemistry

Amino Acids

Volumn 43, Issue 3, 2012, Pages 1251-1263

  Van Geel, Remon ^a   Debets, Marjoke F ^a   Löwik, Dennis W P M ^a   Pruijn, Ger J M ^a   Boelens, Wilbert C ^a  

^a RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

Author keywords

Alkyne; Azide; Click chemistry; Cycloaddition; Protein modification; Transglutaminase

Indexed keywords

ALIPHATIC AMINE; ALKYNE; AMIDE; AZIDE; CUPROUS ION; GLUTAMINE; PROTEIN GLUTAMINE GAMMA GLUTAMYLTRANSFERASE;

ARTICLE; CATALYSIS; CELL LABELING; CELL MEMBRANE PERMEABILITY; CELL SPECIFICITY; CLICK CHEMISTRY; CONTROLLED STUDY; CYCLOADDITION; DERIVATIZATION; ENZYME ACTIVITY; ENZYME ANALYSIS; ENZYME SUBSTRATE; PRIORITY JOURNAL; PROCEDURES; PROTEIN CROSS LINKING; PROTEIN PROTEIN INTERACTION;

ACYLATION; ALKYNES; AMINES; AMINO ACID SEQUENCE; ANIMALS; AZIDES; BIOCATALYSIS; BIOTIN; CADAVERINE; CELL MEMBRANE; CLICK CHEMISTRY; CROSS-LINKING REAGENTS; CYCLOADDITION REACTION; ENZYME INHIBITORS; FLUORESCEIN-5-ISOTHIOCYANATE; FLUORESCENT DYES; GTP-BINDING PROTEINS; HELA CELLS; HSP20 HEAT-SHOCK PROTEINS; HUMANS; MICE; PEPTIDE FRAGMENTS; PERMEABILITY; STAINING AND LABELING; TRANSGLUTAMINASES;

EID: 84867079035     PISSN: 09394451     EISSN: 14382199     Source Type: Journal    
DOI: 10.1007/s00726-011-1198-2     Document Type: Article

References (46)

1. Achyuthan KE, Greenberg CS (1987) Identification of a guanosine triphosphate-binding site on guinea-pig liver transglutaminase. Role of GTP and calcium-ions in modulating activity. J Biol Chem 262(4):1901-1906
2. Agard NJ, Prescher JA, Bertozzi CR (2004) A strain-promoted [3+2] azide-alkyne cycloaddition for covalent modification of biomolecules in living systems. J Am Chem Soc 126(46):15046-15047 (Pubitemid 39557262)
3. Alea MP, Kitamura M, Martin G, Thomas V, Hitomi K, El Alaoui S (2009) Development of an isoenzyme-specific colorimetric assay for tissue transglutaminase 2 cross-linking activity. Anal Biochem 389(2):150-156
4. Baskin JM, Bertozzi CR (2007) Bioorthogonal click chemistry: covalent labeling in living systems. QSAR Comb Sci 26(11-12): 1211-1219
5. Baumgartner W, Golenhofen N, Weth A, Hiiragi T, Saint R, Griffin M, Drenckhahn D (2004) Role of transglutaminase 1 in stabilisation of intercellular junctions of the vascular endothelium. Histochem Cell Biol 122(1):17-25 (Pubitemid 39070589)
6. Boros S, Ahrman E, Wunderink L, Kamps B, de Jong WW, Boelens WC, Emanuelsson CS (2006) Site-specific transamidation and deamidation of the small heat-shock protein Hsp20 by tissue transglutaminase. Proteins Struct Funct Bioinf 62(4):1044-1052 (Pubitemid 43364167)
7. Boros S, Kamps B, Wunderink L, de Bruijn W, de Jong WW, Boelens WC (2004) Transglutaminase catalyzes differential crosslinking of small heat shock proteins and amyloid-beta. FEBS Lett 576(1-2):57-62 (Pubitemid 39330457)
8. Chang PV, Prescher JA, Sletten EM, Baskin JM, Miller IA, Agard NJ, Lo A, Bertozzi CR (2010) Copper-free click chemistry in living animals. Proc Natl Acad Sci USA 107(5):1821-1826
9. Dafik L, Khosla C (2011) Dihydroisoxazole analogs for labeling and visualization of catalytically active transglutaminase 2. Chem Biol 18(1):58-66
10. Debets MF, van Berkel SS, Schoffelen S, Rutjes F, van Hest JCM, van Delft FL (2010a) Aza-dibenzocyclooctynes for fast and efficient enzyme PEGylation via copper-free (3+2) cycloaddition. Chem Commun 46(1):97-99
11. Debets MF, van der Doelen CW, Rutjes FP, van Delft FL (2010b) Azide: a unique dipole for metal-free bioorthogonal ligations. Chem Biochem 11(9):1168-1184
12. DeGraw AJ, Palsuledesai C, Ochocki JD, Dozier JK, Lenevich S, Rashidian M, Distefano MD (2010) Evaluation of alkynemodified isoprenoids as chemical reporters of protein prenylation. Chem Biol Drug Des 76(6):460-471
13. Dommerholt J, Schmidt S, Temming R, Hendriks LJA, Rutjes F, van Hest JCM, Lefeber DJ, Friedl P, van Delft FL (2010) Readily accessible bicyclononynes for bioorthogonal labeling and threedimensional imaging of living cells. Angew Chem Int Ed 49(49):9422-9425
14. Esposito C, Caputo I (2005) Mammalian transglutaminases, identification of substrates as a key to physiological function and physiopathological relevance. FEBS J 272(3):615-631 (Pubitemid 40208867)
15. Fesus L, PiacentiniM(2002) Transglutaminase 2: an enigmatic enzyme with diverse functions. Trends Biochem Sci 27(10):534-539 (Pubitemid 35279599)
16. Folk JE (1983) Mechanism and basis for specificity of transglutaminase- catalyzed-epsilon-(gamma-glutamyl) lysine bond formation. Adv Enzymol Relat Areas Mol Biol 54:1-56
17. Goddard-Borger ED, Stick RV (2007) An efficient, inexpensive, and shelf-stable diazotransfer reagent: imidazole-1-sulfonyl azide hydrochloride. Org Lett 9(19):3797-3800
18. Griffin M, Casadio R, Bergamini CM (2002) Transglutaminases: nature's biological glues. Biochem J 368:377-396 (Pubitemid 35454517)
19. Hasegawa G, Suwa M, Ichikawa Y, Ohtsuka T, Kumagai S, Kikuchi M, Sato Y, Saito Y (2003) A novel function of tissue-type transglutaminase: protein disulphide isomerase. Biochem J 373:793-803 (Pubitemid 36981089)
20. Hong V, Presolski SI, Ma C, Finn MG (2009) Analysis and optimization of copper-catalyzed azide-alkyne cycloaddition for bioconjugation. Angew Chem Int Ed 48(52):9879-9883
21. Hsu TL, Hanson SR, Kishikawa K, Wang SK, Sawa M, Wong CH (2007) Alkynyl sugar analogs for the labeling and visualization of glycoconjugates in cells. Proc Natl Acad Sci USA 104(8): 2614-2619 (Pubitemid 46327928)
22. Im MJ, Riek RP, Graham RM (1990) A novel guanine nucleotidebinding protein coupled to the alpha 1-adrenergic receptor, II. Purification, characterization, and reconstitution. J Biol Chem 265(31):18952-18960
23. Jeon JH, Kim CW, Shin DM, Kim KI, Cho SY, Kwon JC, Choi KH, Kang HS, Kim IG (2003) Differential incorporation of biotinylated polyamines by transglutaminase 2. FEBS Lett 534(1-3): 180-184
24. Kolb HC, Finn MG, Sharpless KB (2001) Click chemistry: diverse chemical function from a few good reactions. Angew Chem Int Ed 40(11):2004-2021
25. Krapcho AP, Kuell CS (1990) Mono-protected diamines. N- tertbutoxycarbonyl- alpha, omega-alkanediamines from alpha, omega- alkanediamines. Synth Commun 20(16):2559-2564
26. Lai TS, Slaughter TF, Peoples KA, Hettasch JM, Greenberg CS (1998) Regulation of human tissue transglutaminase function by magnesium-nucleotide complexes, Identification of distinct binding sites for Mg-GTP and Mg-ATP. J Biol Chem 273(3): 1776-1781 (Pubitemid 28133710)
27. Lajemi M, Demignot S, Borge L, ThenetGauci S, Adolphe M (1997) The use of fluoresceincadaverine for detecting amine acceptor protein substrates accessible to active transglutaminase in living cells. Histochem J 29(8):593-606 (Pubitemid 27431488)
28. Laughlin ST, Baskin JM, Amacher SL, Bertozzi CR (2008) In vivo imaging of membrane-associated glycans in developing zebrafish. Science 320(5876):664-667 (Pubitemid 351928348)
29. Lesort M, Tucholski J, Miller ML, Johnson GVW (2000) Tissue transglutaminase: a possible role in neurodegenerative diseases. Prog Neurobiol 61(5):439-463 (Pubitemid 30169054)
30. Lutz JF (2008) Copper-free azide-alkyne cycloadditions: new insights and perspectives. Angew Chem Int Ed 47(12):2182-2184
31. McNeil PL, Kirchhausen T (2005) An emergency response team for membrane repair. Natl Rev Mol Cell Biol 6(6):499-505 (Pubitemid 40780561)
32. Neef AB, Schultz C (2009) Selective fluorescence labeling of lipids in living cells. Angew Chem Int Ed 48(8):1498-1500
33. Nemes Z, Petrovski G, Fesus L (2005) Tools for the detection and quantitation of protein transglutamination. Anal Biochem 342(1):1-10 (Pubitemid 40805622)
34. Ning XH, Guo J, Wolfert MA, Boons GJ (2008) Visualizing metabolically labeled glycoconjugates of living cells by copper- free and fast huisgen cycloadditions. Angew Chem Int Ed 47(12):2253-2255
35. Parameswaran KN, Cheng XF, Chen EC, Velasco PT, Wilson JH, Lorand L (1997) Hydrolysis of gamma:epsilon isopeptides by cytosolic transglutaminases and by coagulation factor XIII(a). J Biol Chem 272(15):10311-10317 (Pubitemid 27171714)
36. Park D, Choi SS, Ha KS (2010) Transglutaminase 2: a multifunctional protein in multiple subcellular compartments. Amino Acids 39(3):619-631
37. Reif S, Lerner A (2004) Tissue transglutaminase-the key player in celiac disease: a review. Autoimmun Rev 3(1):40-45 (Pubitemid 38197969)
38. Rostovtsev VV, Green LG, Fokin VV, Sharpless KB (2002) A stepwise Huisgen cycloaddition process: copper(I)-catalyzed regioselective ''ligation'' of azides and terminal alkynes. Angew Chem Int Ed 41(14):2596-2599 (Pubitemid 34803480)
39. Samelak A, Sobieszczuk-Nowicka E, Legocka J (2010) Transglutaminases and their biological role. Postepy Biol Komorki 37(3):599-612
40. Schaertl S, Prime M, Wityak J, Dominguez C, Munoz-Sanjuan I, Pacifici RE, Courtney S, Scheel A, Macdonald D (2010) A profiling platform for the characterization of transglutaminase 2 (TG2) inhibitors. J Biomol Screening 15(5):478-487
41. Sletten EM, Bertozzi CR (2009) Bioorthogonal chemistry: fishing for selectivity in a sea of functionality. Angew Chem Int Ed 48(38):6974-6998
42. Speers AE, Cravatt BF (2004) Profiling enzyme activities in vivo using click chemistry methods. Chem Biol 11(4):535-546 (Pubitemid 38511759)
43. Tornoe CW, Christensen C, Meldal M (2002) Peptidotriazoles on solid phase: [1, 2, 3]-triazoles by regiospecific copper(I)- catalyzed 1, 3-dipolar cycloadditions of terminal alkynes to azides. J Org Chem 67(9):3057-3064 (Pubitemid 34457265)
44. Verhaar R, Jongenelen CAM, Gerard M, Baekelandt V, Van Dam AM, Wilhelmus MMM, Drukarch B (2011) Blockade of enzyme activity inhibits tissue transglutaminase-mediated transamidation of alpha-synuclein in a cellular model of Parkinson's disease. Neurochem Int 58(7):785-793
45. Wilhelm B, Meinhardt A, Seitz J (1996) Transglutaminases: purification and activity assays. J Chromatogr B 684(1-2):163-177 (Pubitemid 26340389)
46. Zhang JW, Lesort M, Guttmann RP, Johnson GVW (1998) Modulation of the in situ activity of tissue transglutaminase by calcium and GTP. J Biol Chem 273(4):2288-2295 (Pubitemid 28069282)