A novel azoanthraquinone dye made through innovative enzymatic process

Dyes and Pigments

Volumn 85, Issue 3, 2010, Pages 99-108

  Enaud, Estelle ^a   Trovaslet, Marie ^a   Bruyneel, Frédéric ^a   Billottet, Ludovic ^a   Karaaslan, Rezzan ^b   Sener, Mehmet E ^b   Coppens, Paul ^c   Casas, Ana ^d   Jaeger, Ismene J ^e   Hafner, Christof ^e   Onderwater, Rob C A ^f   Corbisier, Anne Marie ^a   Marchand Brynaert, Jacqueline ^a   Vanhulle, Sophie ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

^b Setas Kimya San AS   (Turkey)

^c Ovelacq ^*  (Belgium)

^d BLC Leather Technology Centre   (United Kingdom)

^e Hydrotox GmbH   (Germany)

^f Wetlands Engineering SPRL   (Belgium)

Author keywords

Anthraquinone; Azo dye; Biosynthesis; Laccase; Sustainable process

Indexed keywords

ACID RED 1; ANTHRAQUINONE; AROMATIC AMINES; DYEING PROPERTIES; ECOTOXICITY; ENVIRONMENTAL-FRIENDLY; ENZYMATIC PROCESS; ENZYMATIC SYNTHESIS; INDUSTRIAL POTENTIALS; IR ANALYSIS; LACCASE; LACCASES; RED DYES; SCALE-UP; SUSTAINABLE PROCESS; TRAMETES VERSICOLOR;

ACIDS; AMINES; BIOCHEMISTRY; BIOSYNTHESIS; KETONES; TOXICITY;

AZO DYES;

ANTHRAQUINONE DYE; AZO DYE; COLOR; COUPLING; DYEING; SYNTHESIS; SYNTHETIC POLYAMIDE; TOXICITY;

EID: 72149099130     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2009.10.010     Document Type: Article

References (57)

1. Clarke E.A., and Anliker R. Organic dyes and pigments. The handbook of environmental chemistry (1980), Springer Verlag, New York 181-215
2. Jäger I., Hafner C., and Schneider K. Mutagenicity of different textile dye products in Salmonella typhimurium and mouse lymphoma cells. Mutation Research/Genetic Toxicology and Environmental Mutagenesis 561 1-2 (2004) 35-44
3. Jäger I., Schneider K., Janak P., and Huet M. Mutagenic dyes in textile finishing. Melliand English (2005) E12-E14
4. Schneider K., Hafner C., and Jäger I. Mutagenicity of different textile dye products. Journal of Applied Toxicology 24 (2004) 83-91
5. Xu F. Applications of oxidoreductases: recent progress (novozymes). Industrial Biotechnology 1 1 (2005) 38-50
6. Hadzhiyska H., Calafell M., Gibert J.M., Daga J.M., and Tzanov T. Laccase-assisted dyeing of cotton. Biotechnology Letters 28 10 (2006) 755-759
7. Wandrey C., Liese A., and Kihumbu D. Industrial biocatalysis: past, present, and future. Organic Process Research & Development 4 4 (2000) 286-290
8. Hoh C., and Villela Filho M. Enzyme classification in industrial biotransformation (2000), Wiley-VCH Verlag GmbH
9. Hasan F., Shah A., and Hameed A. Industrial applications of microbial lipases. Enzyme and Microbial Technology 39 2 (2006) 235-251
10. Panda T., and Gowrishankar B.S. Production and applications of esterases. Applied Microbiology and Biotechnology V67 2 (2005) 160-169
11. Zaks A. Industrial biocatalysis. Current Opinion in Chemical Biology 5 (2001) 130-136
12. Burton S.G. Laccases and phenol oxidases in organic synthesis - a review. Current Organic Chemistry (2003) 1317-1331
13. Solomon E.I., Sundaram U.M., and Machonkin T.E. Multicopper oxidases and oxygenases. Chemical Review 96 7 (1996) 2563-2606
14. Collins P.J., and Dobson A. Regulation of laccase gene transcription in Trametes versicolor. Applied and Environmental Microbiology 63 9 (1997) 3444-3450
15. Leonowicz A., Trojanowski J., and Orlicz B. Induction of laccase in basidiomycetes: apparent activity of the inducible and constitutive forms of the enzyme with phenolic substrates. Acta Biochimica Polonica 25 4 (1978) 369-378
16. Call H.P., and Mucke I. History, overview and applications of mediated lignolytic systems, especially laccase-mediator-systems (lignozym(R)-process). Journal of Biotechnology 53 2-3 (1997) 163-202
17. Dubroca J., Brault A., Kollmann A., Touton I., Jolivalt C., Kerhoas L., et al. Biotransformation of nonylphenol surfactants in soils amended with contaminated sewage sludges. Environmental chemistry: green chemistry and pollutants in ecosystems (2005), Springer 305-315
18. Torres E., Bustos-Jaimes I., and Le Borgne S. Potential use of oxidative enzymes for the detoxification of organic pollutants. Applied Catalysis B: Environmental 46 1 (2003) 1-15
19. Wesenberg D., Kyriakides I., and Agathos S.N. White-rot fungi and their enzymes for the treatment of industrial dye effluents. Biotechnology Advances 22 1-2 (2003) 161-187
20. Xu F. Laccase. Encyclopedia of bioprocessing technology: fermentation, biocatalysis and bioseparation (1999), Wiley, New York
21. Yadav JS, Quensen III JF, Tiedje JM, Reddy CA. Degradation of polychlorinated biphenyl mixtures (Aroclors 1242, 1254, and 1260) by the white rot fungus Phanerochaete chrysosporium as evidenced by congener-specific analysis. 1995;61(7):2560-5.
22. Mayer A.M., and Staples R.C. Laccase: new functions for an old enzyme. Phytochemistry 60 6 (2002) 551-565
23. Nagai M., Kawata M., Watanabe H., Ogawa M., Saito K., Takesawa T., et al. Important role of fungal intracellular laccase for melanin synthesis: purification and characterization of an intracellular laccase from Lentinula edodes fruit bodies. Microbiology 149 Pt 9 (2003) 2455-2462
24. Ridgway T., Tucker G., and Wiseman H. Novel bioconversion for the production of designer antioxidant and colourant flavonoids using polyphenol oxidases. Biotechnology and Engineering Reviews 14 (1997) 165-190
25. Taylor A., and Clydesdale F. Potential of oxidised phenolics as food colourants. Food Chemistry 24 (1987) 301-313
26. Taylor A., and Clydesdale F. Assessment of tinctorial power of food colourants. Food Chemistry 26 (1987) 1-10
27. Mustafa R., Muniglia L., Rovel B., and Girardin M. Phenolic colorants obtained by enzymatic synthesis using a fungal laccase in a hydro-organic biphasic system. Food Research International 38 8-9 (2005) 995-1000
28. Vanhulle S., Enaud E., Trovaslet M., Billottet L., Kneipe L., Habib Jiwan J.-L., et al. Coupling occur before breakdown during WRF biotransformation of ABu62. Chemosphere 70 6 (2007) 1097-1107
29. Vanhulle S., Enaud E., Trovaslet M., Nouaimeh N., Bols C.-M., Keshavarz T., et al. Overlap of laccases/cellobiose dehydrogenase activities during the decolourisation of anthraquinonic dyes with close chemical structure by Pycnoporus strains. Enzyme and Microbial Technology 40 7 (2007) 1723-1731
30. Robinson P.J., Dunnill P., and Lilly M.D. Porous glass as a solid support for immobilisation or affinity chromatography of enzymes. Biochimica et Biophysica Acta 242 (1971) 659-661
31. Maron D., and Ames B. Revised methods for the Salmonella mutagenicity test. Handbook of mutagenicity test procedures (1984), Elsevier, Amsterdam, New York, Oxford 93-141
32. Commission Directive 2000/32/ECB.13/14. Mutagenicity - reverse mutation test bacteria. Official Journal of the European Communities (2000)
33. OECD Guideline 471. OECD guidelines for the testing of chemicals, section 4 - health effects. Bacterial reverse mutation test (1997), OECD, Paris
34. Flamand N., Meunier J.-R., Meunier P.-A., and Agapakis-Caussè C. Mini mutagenicity test: a miniaturized version of the Ames test used in a prescreening assay for point mutagenesis assessment. Toxicology in Vitro 15 (2001) 105-114
35. Din EN 15088, 2006. German standard methods for the examination of water, waste water and sludge - subanimal testing (group T) - part 6: toxicity to fish. Determination of the non-acute-poisonous effect of waste water to fish eggs by dilution limits (T 6) (2001), German Standardization Organization
36. Din En Iso 11348 (1-3). Water quality - determination of the inhibitory effect of water samples on the light emission of Vibrio fisherii (luminescent bacteria test) - part 3: method using freeze-dried bacteria (1998), German Standardization Organization
37. Klein B. Möglichkeiten und Grenzen der Farbkorrektur im Leuchtbakterientest mit Hilfe von Absorptions-Korrektur-Küvetten. Zeitschrift für Wasser- und Abwasser-Forschung 23 (1990) 70-74
38. Lange D. Correcting absorptive inhibition in the luminescent bacteria test by means of a combined luminometric/photometric procedure. 13. January 1998.
39. Lange D. LUMISsoft4 Manual, Version 1.001. 2000.
40. EC Directive 92/69/EWG Part C: C.2. Acute toxicity for daphnia. 2000.
41. OECD Guideline 202 OECD guideline for testing of chemicals. Daphnia sp., acute immobilisation test and reproduction test (2004), Organisation for Economic Co-operation and Development, Paris
42. OECD guideline 201. Freshwater alga and cyanobacteria, growth inhibition test (2006), Organisation for Economic Co-operation and Development, Paris
43. 2 evolution (modified Sturm test) (1992), Organisation for Economic Co-operation and Development, Paris
44. Setti L., Giuliani S., Spinozzi G., and Pifferi P.G. Laccase catalyzed-oxidative coupling of 3-methyl 2-benzothiazolinone hydrazone and methoxyphenols. Enzyme and Microbial Technology 25 3-5 (1999) 285-289
45. Gasowska B., Frackowiak B., and Wojtasek H. Indirect oxidation of amino acid phenylhydrazides by mushroom tyrosinase. Biochimica et Biophysica Acta (BBA) - General Subjects 1760 9 (2006) 1373-1379
46. Glanzel M., Bultmann R., Starke K., and Frahm A.W. Structure-activity relationships of novel P2-receptor antagonists structurally related to reactive blue 2. European Journal of Medicinal Chemistry 40 12 (2005) 1262-1276
47. Zhang Y., and Hou W. The influence of methyl groups on the colour and dyeing properties of acid dyes derived from 1-amino-4-bromo-anthraquinone-2-sulphonic acid and arylamines. Dyes and Pigments 30 4 (1996) 283-289
48. Zhang Y., Hou W., and Tan Y. Structure and dyeing properties of some anthraquinone violet acid dyes. Dyes and Pigments 34 1 (1997) 25-35
49. Zollinger H. Color chemistry: syntheses, properties and applications of organic dyes and pigments (2003), VCH, Weinheim
50. Hooker J., Hinks D., Montero G., and Conlee C. Synthesis of N, N-diethyl-N-{4-[(E)-(4-nitrophenyl)diazenyl]phenyl}amine via in situ diazotisation and coupling in supercritical carbon dioxide. Coloration Technology 118 6 (2002) 273-276
51. Nagel R. DarT: the embryo test with the zebrafish (Danio rerio) - a general model in ecotoxicology and toxicology. ALTEX 19 (2002) 38-48
52. Oberemm A. The use of a refined zebra fish embryo bioassay for the assessment of aquatic toxicity. Lab Animal 29 (2000) 32-40
53. OECD Guideline. OECD guideline for testing of chemicals - draft proposal for a new guideline - fish embryo toxicity (FET) test (2006), OECD
54. Law K.-Y., and Tarnawskyj I. Azo pigments and their intermediates. On the anomalous optical absorption of bisazo pigments from 4,4′-diamino-1,1′-dianthrimide and 2-hydroxy-3-naphthanilides. Journal of Photochemistry and Photobiology A: Chemistry 57 (1991) 217-230
55. Hawari J., Beaudet S., Halasz A., Thiboutot S., and Ampleman G. Microbial degradation of explosives: biotransformation versus mineralization. Applied Microbiology and Biotechnology 54 5 (2000) 605-618
56. Esteve-Nunez A., Caballero A., and Ramos J.L. Biological degradation of 2,4,6-trinitrotoluene. Microbiology and Molecular Biology Reviews 65 3 (2001) 335-352
57. Enaud E, Marchand-Brynaert J, Bols C-M, Groslambert S, Tron T, Iacazio G, Sener M, Karaaslan R, Jager JI, Hercher C, Vanhulle S. New azo dyes. 2008; US 61/078,675.