Transglutaminase-mediated macromolecular assembly: Production of conjugates for food and pharmaceutical applications

Amino Acids

Volumn 46, Issue 3, 2014, Pages 767-776

  Mariniello, L ^a   Porta, R ^a   Sorrentino, A ^a   Giosafatto, C V L ^a   Rossi Marquez, G ^a   Esposito, M ^a   Di Pierro, P ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

Crosslinking; Polymers; Protein conjugates; Transglutaminase

Indexed keywords

BIOPOLYMER; CASEIN; DRUG; MACROGOL; MANNAN; MICROBIAL ENZYME; NATURAL PRODUCT; POLYMER; POLYPEPTIDE; POLYSACCHARIDE; PROTEIN DERIVATIVE; PROTEIN GLUTAMINE GAMMA GLUTAMYLTRANSFERASE; MACROMOLECULE;

CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; COMPLEX FORMATION; CONJUGATE; CONJUGATION; COVALENT BOND; CROSS LINKING; DERIVATIZATION; DRUG DELIVERY SYSTEM; DRUG MANUFACTURE; ENZYMATIC ASSAY; ENZYME ACTIVITY; ENZYME SUBSTRATE; ENZYME SYNTHESIS; FOOD PROCESSING; MACROMOLECULAR ASSEMBLY; MACROMOLECULE; PRIORITY JOURNAL; PROTEIN FUNCTION; PROTEIN GLYCOSYLATION; PROTEIN MODIFICATION; PROTEIN PROCESSING; SHORT SURVEY; SURFACE PROPERTY; FOOD; METABOLISM;

FOOD; MACROMOLECULAR SUBSTANCES; PHARMACEUTICAL PREPARATIONS; TRANSGLUTAMINASES;

EID: 84896316042     PISSN: 09394451     EISSN: 14382199     Source Type: Journal    
DOI: 10.1007/s00726-013-1561-6     Document Type: Short Survey

References (80)

1. Aberg CM, Chen TH, Olumide A, Raghavan SR, Payne GF (2004) Enzymatic grafting of peptides from casein hydrolysate to chitosan. Potential for value-added byproducts from food-processing wastes. J Agric Food Chem 52:788-793
2. Ando H, Adachi M, Umeda K, Matsuura A, Nonaka M, Uchio R, Tanaka H, Motoki M (1989) Purification and characterization of a novel transglutaminase derived from microorganisms. Agric Biol Chem 53:2613-2617 (Pubitemid 20077525)
3. Anghileri A, Lantto R, Kruus K, Arosio C, Freddi G (2007) Tyrosinase-catalyzed grafting of sericin peptides onto chitosan and production of protein-polysaccharide bioconjugates. J Biotechnol 127:508-519 (Pubitemid 44827392)
4. Besheer A, Hertel TC, Kressler J, Mader K, Pietzsch M (2009) Enzymatically catalyzed HES conjugation using microbial transglutaminase: proof of feasibility. J Pharm Sci 98:4420-4428
5. Bourtoom T (2008) Edible films and coatings: characteristics and properties. Int Food Res J 15:1-12
6. Brands CMJ, Alink GM, Van Boekel MAJS, Jongen WMF (2000) Mutagenicity of heated sugar-casein systems: effect of the Maillard reaction. J Agric Food Chem 48:2271-2275 (Pubitemid 30431225)
7. Cheng HN, Gross RA (2005) Polymer Biocatalysis and Biomaterials. ACS, Washington, DC
8. Coussons PJ, Price NC, Kelly SM, Smith B, Sawyer L (1992) Factors that govern the specificity of transglutaminase-catalysed modification of proteins and peptides. Biochem J 282:929-930
9. Di Pierro P, Chico B, Villalonga R, Mariniello L, Damiao AE, Masi P, Porta R (2006) Chitosan-whey protein edible films produced in the absence or presence of transglutaminase: analysis of their mechanical and barrier properties. Biomacromolecules 7:744-749
10. Di Pierro P, Chico B, Villalonga R, Mariniello L, Masi P, Porta R (2007) Transglutaminase-catalyzed preparation of chitosan-ovalbumin films. Enzyme Microb Tech 40:437-441 (Pubitemid 46098908)
11. Di Pierro P, Mariniello L, Sorrentino A, Villalonga R, Chico B, Porta R (2010) Putrescine-polysaccharide conjugates as transglutaminase substrates and their possible use in producing crosslinked films. Amino Acids 38:669-675
12. Di Pierro P, Rossi Marquez G, Mariniello L, Sorrentino A, Villalonga R, Porta R (2013) Effect of transglutaminase on the mechanical and barrier properties of whey protein/pectin films prepared at complexation pH. J Agric Food Chem, in press
13. Dickinson E (2003) Hydrocolloids at interfaces and the influence on the properties of dispersed systems. Food Hydrocoll 17:25-39
14. Dickinson E (2008) Interfacial structure and stability of food emulsions as affected by protein-polysaccharide interactions. Soft Matter 4:932-942
15. Doumeche B, Picard J, Larreta-Garde W (2007) Biomacromolecules 8:3613-3618
16. Duncan R, Vicent MJ (2013) Polymer therapeutics-prospects for 21st century: the end of the beginning. Adv Drug Deliv Rev 65:60-70
17. 5)spermine derivative of substance P. J Neurochem 65:420-426
18. Faergemand M, Otte J, Qvist KB (1998) Cross-linking of whey proteins by enzymatic oxidation. J Agric Food Chem 46:1326-1333 (Pubitemid 128498765)
19. Fesus L, Piacentini M (2002) Transglutaminase 2: an enigmatic enzyme with diverse functions. Trends Biochem Sci 27:534-539 (Pubitemid 35279599)
20. Fontana A, Spolaore B, Mero A, Veronese FM (2008) Site-specific modification and PEGylation of pharmaceutical proteins mediated by transglutaminase. Adv Drug Delivery Rev 60:13-28 (Pubitemid 350181164)
21. Freddi G, Anghileri A, Sampaio S, Buchert J, Monti P, Taddei P (2006) Tyrosinase-catalyzed modification of Bombyx mori silk fibroin: grafting of chitosan under heterogeneous reaction conditions. J Biotechnol 125:281-294 (Pubitemid 44192552)
22. Giosafatto CVL, Rigby NM, Wellner N, Ridout M, Husband F, Mackie AR (2012) Microbial transglutaminase-mediated modification of ovalbumin. Food Hydrocoll 26:261-267
23. Girard M, Turgeon SL, Gauthier SF (2002) Inter biopolymer complexing between beta-lactoglobulin and low- and high-methylated pectin measured by potentiometric titration and ultrafiltration. Food Hydrocoll 16:585-591 (Pubitemid 35177847)
24. Greenwald R, Choe Y, McGuire J, Conover C (2003) Effective drug delivery by PEGylated drug conjugates. Adv Drug Delivery Rev 55:217-250 (Pubitemid 36135917)
25. Guerra-Hernandez E, Gomez CL, Garcia-Villanova B, Sanchez NC, Gomez JMR (2002) Effect of storage on non-enzymatic browning of liquid infant milk formulae. J Sci Food Agric 82:587-592 (Pubitemid 34281224)
26. Hallberg RK, Dubin PL (1998) Effect of pH on the binding of beta-lactoglobulin to sodium polystyrene sulfonate. J Phys Chem 102:8629-8633 (Pubitemid 128611813)
27. Harris JM, Chess R (2003) Effect of PEGylation on pharmaceuticals. Nature Rev Drug Discov 2:214-221
28. Hattori T, Kimura K, Seyrek E, Dubin PL (2001) Binding of bovine serum albumin to heparin determined by turbidimetric titration and frontal analysis continuous capillary electrophoresis. Anal Biochem 295:158-167 (Pubitemid 32756969)
29. Jain A, Jain SK (2008) PEGylation: an approach for drug delivery. A review. Crit Rev Ther Drug Carrier Syst 25:403-447
30. Kang GD, Lee KH, Ki CS, Nahm JH, Park JH (2004) Silk fibroin/chitosan conjugate crosslinked by tyrosinase. Macromol Res 12(534):539
31. Kashiwagi T, Yokoyama K, Ishikawa K, Ono K, Ejima D, Matui H, Suzuki E (2002) Crystal structure of microbial transglutaminase from Streptoverticillium mobaraense. J Biol Chem 277:44252-44260 (Pubitemid 36157858)
32. Kinstler O, Molineux G, Treuheit M, Ladd D, Gegg C (2002) Mono-N-terminal poly(ethylene glycol)-protein conjugates. Adv Drug Deliv Rev 54:477-485 (Pubitemid 34615544)
33. Lewandowski AT, Yi HM, Luo XL, Payne GF, Ghodssi R, Rubloff GW, Bentley WE (2008) Protein assembly onto patterned microfabricated devices through enzymatic activation of fusion pro-tag. Biotechnol Bioeng 99:499-507 (Pubitemid 351158247)
34. Lorand L, Graham RM (2003) Transglutaminases: crosslinking enzymes with pleiotropic functions. Nat Rev Mol Cell Biol 4:140-156 (Pubitemid 36172696)
35. MacDougall AJ, Brett GM, Morris VJ, Rigby NM, Ridout MJ, Ring SG (2001) The effect of peptide behaviour-pectin interactions on the gelation of a plant cell wall pectin. Carbohydr Res 335:115-126 (Pubitemid 32905346)
36. Malik DK, Baboota S, Ahuja A, Hasan S, Ali J (2007) Recent advances in protein and peptide drug delivery systems. Curr Drug Deliv 4:141-151 (Pubitemid 46557490)
37. Mariniello L, Giosafatto CVL, Di Pierro P, Sorrentino A, Porta R (2007a) Synthesis and resistance to proteolysis of transglutaminase-crosslinked phaseolin, the major storage protein from Phaseolus vulgaris. J. Agr Food Chem 55:4717-4721 (Pubitemid 46960898)
38. Mariniello L, Giosafatto CVL, Moschetti G, Aponte M, Masi P, Sorrentino A, Porta R (2007b) Fennel waste-based films suitable for protecting cultivations. Biomacromolecules 8:3008-3014 (Pubitemid 350011619)
39. Mariniello L, Giosafatto CVL, Di Pierro P, Sorrentino A, Porta R (2010) Swelling, mechanical and barrier properties of albedo-based films prepared in the presence of phaseolin crosslinked or not by transglutaminase. Biomacromolecules 11:2394-2398
40. Marx CK, Hertel TC, Pietzsch M (2008) Purification and activation of a recombinant histidine-tagged protransglutaminase after soluble expression in E. coli and partial characterization of the active enzyme. Enzyme Microb Technol 42:568-575
41. Maullu C, Raimondo D, Caboi F, Giorgetti A, Sergi M, Valentini M, Tonon G, Tramontano A (2009) Site-directed enzymatic PEGylation of the human granulocyte colony-stimulating factor. FEBS J 276:6741-6750
42. Mayer AM (2006) Polyphenol oxidases in plants and fungi: going places? A review. Phytochemistry 67:2318-2331
43. Mero A, Spolaore B, Veronese FM, Fontana A (2009) Transglutaminase- mediated PEGylation of proteins: direct identification of the sites of protein modification by mass spectrometry using a novel monodisperse PEG. Bioconjugate Chem 20:384-389
44. Miller AG, Gerrard JA (2005) The Maillard reaction and food protein crosslinking. Prog Food Biopolymer Res 1:69-86
45. Ohtsuka T, Sawa A, Kawabata R, Nio N, Motoki M (2000) Substrate specificities of microbial transglutaminase for primary amines. J Agric Food Chem 48:6230-6233 (Pubitemid 32056869)
46. Pasut G, Guiotto A, Veronese F (2004) Protein, peptide and non-peptide drug PEGylation for therapeutic applications. Expert Opin Ther Pat 14:1-36
47. Pavlou A, Reichert J (2004) Recombinant protein therapeutics: success rates, market trends and values to 2010. Nat Biotechnol 22:1513-1519 (Pubitemid 40039448)
48. Picard J, Giraudier S, Larreta-Garde V (2009) Soft Matter 5:4198
49. Porta R, Di Pierro P, Sorrentino A, Mariniello L (2011a) Promising perspectives for transglutaminase in "bioplastics" production. J Biotechnol Biomat 1:3. http://dx.doi.org/10.4172/2155-952X.1000102e
50. Porta R, Mariniello L, Di Pierro P, Sorrentino A, Giosafatto CVL (2011b) Transglutaminase crosslinked pectin and chitosan-based edible films: a review. Crit Rev Food Sci Nutr 51:1-16
51. Porta R, Giosafatto CVL, Di Pierro P, Sorrentino A, Mariniello L (2013) Transglutaminase-mediated modification of ovomucoid. Effect on its trypsin inhibitory activity and antigenic properties. Amino Acids 44:285-292
52. Ramezani R, Esmailpour M, Aminlari M (2008) Effect of conjugation with glucosamine on the functional properties of lysozyme and casein. J Sci Food Agric 88:2730-2737
53. Roberts MJ, Bentley MD, Harris JM (2002) Chemistry for peptide and protein PEGylation. Adv Drug Deliv Rev 54:459-476 (Pubitemid 34615543)
54. Rossi Marquez G, Di Pierro P, Esposito M, Mariniello L, Porta R (2013) Application of transglutaminase-crosslinked whey protein/pectin films as water barrier coatings in fried and baked foods. Food Bioproc Technol. doi:10.1007/s11947-012-1045-9
55. Sato H, Ikeda M, Suzuki K, Hirayama K (1996) Site-specific modification of interleukin-2 by the combined use of genetic engineering techniques and transglutaminase. Biochemistry 35:13072-13080 (Pubitemid 26349457)
56. Sato H, Yamamoto K, Hayashi E, Takahara Y (2000) Transglutaminase- mediated dual and site-specific incorporation of poly(ethylene glycol) derivatives into a chimeric interleukin-2. Bioconjugate Chem 11:502-509 (Pubitemid 30597719)
57. Sato H, Hayashi E, Yamada N, Yatagai M, Takahara Y (2001) Further studies on the site-specific protein modification by microbial transglutaminase. Bioconjugate Chem 12:701-710 (Pubitemid 32925872)
58. Sato M, Furuike T, Sadamoto R, Fujitani N, Nakahara T, Niikura K, Monde K, Kondo H, Nishimura S (2004a) Glycoinsulins: dendritic sialyloligosaccharide- displaying insulins showing a prolonged blood-sugar-lowering activity. J Am Chem Soc 126:14013-14022 (Pubitemid 39447078)
59. Sato M, Sadamoto R, Niikura K, Monde K, Kondo H, Nishimura S (2004b) Site-specific introduction of sialic acid into insulin. Angew Chem Int Ed Engl 43:1516-1520 (Pubitemid 39257888)
60. Shao LH, Kumar G, Lenhart JL, Smith PJ, Payne GF (1999) Enzymatic modification of the synthetic polymer polyhydroxystyrene. Enzyme Microb Technol 25:660-668 (Pubitemid 29512401)
61. Shimba N, Yokoyama Y, Suzuki E (2002) J Agric Food Chem 50:1330-1334
62. Sorrentino A, Giosafatto CVL, Sirangelo I, De Simone C, Di Pierro P, Porta R, Mariniello L (2012) Higher susceptibility to amyloid fibril formation of the recombinant ovine prion protein modified by transglutaminase. Biochim Biophys Acta 1822:1509-1515
63. Tanaka T, Kamiya N, Nagamune T (2005) N-terminal glycine-specific protein conjugation catalyzed by microbial transglutaminase. FEBS Lett 579:2092-2096 (Pubitemid 40469676)
64. Tominaga J, Kemori Y, Tanaka Y, Maruyama T, Kamiya N, Goto M (2007) An enzymatic method for site-specific labeling of recombinant proteins with oligonucleotides. Chem Comm pp 401-403
65. Turgeon SL, Beaulieu M, Schmitt C, Sancez C (2003) Protein polysaccharide interactions: phase ordering kinetics thermodynamic and structural aspects. Curr Opin Colloid Interface Sci 8:401-414
66. Valdivia A, Villalonga R, Di Pierro P, Perez YP, Mariniello L, Gomez L, Porta R (2006) Transglutaminase-catalyzed site-specific glycosidation of catalase with aminated dextran. J Biotechnol 122:326-333 (Pubitemid 43327411)
67. Veronese FM, Mero A (2008) The impact of PEGylation on biological therapies. Biodrugs 22:315-329
68. Villalonga R, Fernandez M, Fragoso A, Cao R, Mariniello L, Porta R (2003a) Thermal stabilization of trypsin by enzymic modification with β-cyclodextrin derivatives. Biotechnol Appl Biochem 38:53-59 (Pubitemid 36976420)
69. Villalonga R, Fernandez M, Fragoso A, Cao R, Di Pierro P, Mariniello L, Porta R (2003b) Transglutaminase-catalyzed synthesis of trypsin-cyclodextrin conjugates. Kinetics and stability properties. Biotechnol Bioeng 81:732-737 (Pubitemid 36258527)
70. Villalonga ML, Villalonga R, Mariniello L, Gomez L, Di Pierro P, Porta R (2006) Transglutaminase-catalysed glycosidation of trypsin with aminated polysaccharides. World J Microbiol Biotechnol 22:595-602 (Pubitemid 43815116)
71. Washizu K, Ando K, Koiked S, Hiros S, Matsuura A, Akagi H, Motoki M, Takeuchi K (1994) Molecular cloning of the gene for microbial transglutaminase from Streptoverticillium and its expression in Streptomyces lividans. Biosci Biotechnol Biochem 58:82-87 (Pubitemid 2050099)
72. Wattendorf U, Merkle HP (2008) PEGylation as a tool for the biomedical engineering of surface modified microparticles. J Pharm Sci 97:4655-4669
73. Weinbreck F, De Kruif CG (2003) Complex coacervation of globular proteins and gum Arabic. In: Dickinson E, van Vliet T (eds) Food colloids biopolymers and materials. Royal Society of Chemistry, Cambridge, pp 337-344
74. Yang X, Liu Y, Payne GF (2009) Crosslinking lessons from biology: enlisting enzymes for macromolecular assembly. J Adhes 85:576-589
75. Ye A (2008) Complexation between milk proteins and polysaccharides via electrostatic interaction: principles and applications: a review. Int J Food Sci Technol 43:406-415
76. Yin W, Su R, Qi W, He Z (2012) A casein-polysaccharide hybrid hydrogel cross-linked by transglutaminase for drug delivery. J Mater Sci 47:2045-2055
77. Yokohama K, Nio N, Kikuchi Y (2004) Properties and applications of microbial transglutaminases. Appl Microbiol Biotechnol 64:447-454
78. Yoruk R, Marshall MR (2003) Physicochemical properties and function of plant polyphenol oxidase: a review. J Food Biochem 27:361-422 (Pubitemid 38034245)
79. Zalipsky S (1995) Functionalized poly(ethylene glycol) for preparation of biologically relevant conjugates. Bioconjugate Chem 6:150-165
80. Zhu Y, Rinzema A, Tramper J, Bol J (1995) Microbial transglutaminases: a review of its production and application in food processing. Appl Microbiol Biotechnol 44:277-282 (Pubitemid 26024346)