Derivatization of the azole 1-aminobenzotriazole using laccase of Pycnoporus cinnabarinus and Myceliophthora thermophila: Influence of methanol on the reaction and biological evaluation of the derivatives

Biotechnology and Applied Biochemistry

Volumn 56, Issue 2, 2010, Pages 43-48

  Hahn, Veronika ^a   Mikolasch, Annett ^a   Wende, Kristian ^a   Bartrow, Hannelore ^a   Lindequist, Ulrike ^a   Schauer, Frieder ^a  

^a UNIVERSITY OF GREIFSWALD   (Germany)

Author keywords

Amination; Antimicrobial; Biotransformation; Cytostatic; Laccase; Solvent

Indexed keywords

ANTI-FUNGAL; ANTI-MICROBIAL ACTIVITY; ANTIMICROBIAL; BIOLOGICAL EVALUATION; BIOTRANSFORMATION; COSOLVENTS; CYTOTOXIC ACTIVITIES; DERIVATIZATION OF; DIHYDROXYBENZOIC ACIDS; ETHYL ESTERS; EXTRACELLULAR ENZYMES; LACCASES; METHYL ESTERS; MYCELIOPHTHORA THERMOPHILA; ONE POT; PROTEIN STABILITY; PYCNOPORUS CINNABARINUS; SOLVENT CONCENTRATION;

ACIDS; AMINES; DIMERS; ESTERIFICATION; ESTERS; METHANOL; MICROORGANISMS; SYNTHESIS (CHEMICAL);

ORGANIC SOLVENTS;

1 AMINOBENZOTRIAZOLE; 2 (BENZOTRIAZOL 1 YLAMINO) 3,6 DIOXOCYCLOHEXA 1,4 DIENECARBOXYLIC ACID ETHYL ESTER; 2 (BENZOTRIAZOL 1 YLAMINO) 3,6 DIOXOCYCLOHEXA 1,4 DIENECARBOXYLIC ACID METHYL ESTER; 2,5 BIS (BENZOTRIAZOL 1 YLAMINO) 3,6,3',6' TETRAOXOBICYCLOHEXYL 1,4,1',4' TETRAENE 4,4' DICARBOXYLIC ACID DIETHYL ESTER; 2,5 DIHYDROXYBENZOIC ACID ETHYL ESTER; 2,5 DIHYDROXYBENZOIC ACID METHYL ESTER; 2,5,5' TRIS (BENZOTRIAZOL 1 YLAMINO) 3,6,3',6' TETRAOXOBICYCLOHEXYL 1,4,1',4' TETRAENE 4,4' DICARBOXYLIC ACID DIETHYL ESTER; AMPHOTERICIN B; AMPICILLIN; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; BENZOTRIAZOLE DERIVATIVE; CYTOTOXIC AGENT; ETOPOSIDE; FLUCONAZOLE; FUNGAL ENZYME; GENTAMICIN; LACCASE; METHANOL; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOTOXICITY; DRUG ISOLATION; FUNGUS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MYCELIOPHTHORA THERMOPHILA; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PYCNOPORUS CINNABARINUS; SYNTHESIS;

BACILLUS SUBTILIS; CELL LINE, TUMOR; CELL PROLIFERATION; GENTISATES; HUMANS; LACCASE; METHANOL; MICROBIAL SENSITIVITY TESTS; MITOSPORIC FUNGI; PYCNOPORUS; STAPHYLOCOCCUS AUREUS; TRIAZOLES;

CORYNASCUS HETEROTHALLICUS; PYCNOPORUS CINNABARINUS;

EID: 77954828271     PISSN: 08854513     EISSN: None     Source Type: Journal    
DOI: 10.1042/BA20100078     Document Type: Article

References (34)

1. Baldrian, P. (2006) FEMS Microbiol. Rev. 30, 215-242
2. Bhalerao, U. T., Muralikrishna, C. and Rani, B. R. (1994) Tetrahedron 50, 4019-4024
3. Schäfer, A., Specht, M., Hetzheim, A., Francke, W. and Schauer, F. (2001) Tetrahedron 57, 7693-7699
4. Vanden Bossche, H., Willemsens, G., Marichal, P., Cools, W. and Lauwers, W. (1984) in Mode of Action of Antifungal Agents (Trinci, A. P. J. and Ryley, J. F., eds), Cambridge University Press, Cambridge, pp. 321-341
5. Sheehan, D. J., Hitchcock, C. A. and Sibley, C. M. (1999) Clin. Microbiol. Rev. 12, 40-79
6. Kale, P. and Johnson, L. B. (2005) Drugs Today (Barcelona) 41, 91-105
7. Agematu, H., Tsuchida, T., Kominato, K., Shibamoto, N., Yoshioka, T., Nishida, H., Okamoto, R., Shin, T. and Murao, S. (1993) J. Antibiotics 46, 141-148
8. Mikolasch, A., Niedermeyer, T. H. J., Lalk, M., Witt, S., Seefeldt, S., Hammer, E., Schauer, F., Gesell, M., Hessel, S., Jülich, W.-D. and Lindequist, U. (2006) Chem. Pharm. Bull. 54, 632-638
9. Agematu, H., Kominato, K., Shibamoto, N., Yoshioka, T., Nishida, H., Okamoto, R., Shin, T. and Murao, S. (1993) Biosci. Biotech. Biochem. 8, 1387-1388
10. Mikolasch, A., Niedermeyer, T. H. J., Lalk, M., Witt, S., Seefeldt, S., Hammer, E., Schauer, F., Salazar, M., Hessel, S., Jülich, W.-D. and Lindequist, U. (2007) Chem. Pharm. Bull. 55, 412-416
11. Manda, K., Hammer, E., Mikolasch, A., Gördes, D., Thurow, K. and Schauer, F. (2006) Amino Acids 31, 409-419
12. Hahn, V., Mikolasch, A., Manda, K., Gördes, D., Thurow, K. and Schauer, F. (2009) Amino Acids 37, 315-321
13. Lugaro, G., Carrea, G., Cremonesi, P., Casellato, M. M. and Antonini, E. (1973) Arch. Biochem. Biophys. 159, 1-6;
14. Nicotra, S., Intra, A., Ottolina, G., Riva, S. and Danieli, B. (2004) Tetrahedron 15, 2927-2931
15. Nicotra, S., Cramarossa, M. R., Mucci, A., Pagnoni, U. M., Riva, S. and Forti, L. (2004) Tetrahedron 60, 595-600
16. Ncanana, S., Baratto, L., Roncaglia, L., Riva, S. and Burton, S. G. (2007) Adv. Synth. Catal. 349, 1507-1513
17. Agematu, H., Tsuchida, T., Kominato, K., Shibamoto, N., Yoshioka, T., Nishida, H., Okamoto, R., Shin, T. and Murao, S. (1993) J. Antibiot. 46, 141-148
18. Ponzoni, C., Beneventi, E., Cramarossa, M. R., Raimondi, S., Trevisi, G., Pagnoni, U. M., Riva, S. and Forti, L. (2007) Adv. Synth. Catal. 349, 1497-1506
19. Ottolina, G., Gianinetti, F., Riva, S. and Carrea, G. (1994) J. Chem. Soc. Chem. Commun. 4, 535-536
20. Wescott, C. R. and Klibanov, A. M. (1994) Biochim. Biophys. Acta 1206, 1-9
21. Carrea, G. and Riva, S. (2000) Angew. Chem. Int. Ed. 39, 2226-2254
22. Jonas, U., Hammer, E., Schauer, F. and Bollag, J. M. (1997) Biodegradation 8, 321-328
23. Eggert, C., Temp, U. and Eriksson, K. E. L. (1996) Appl. Environ. Microbiol. 62, 1151-1158
24. Feng, B. B., Voehler, M., Zhou, L., Passarelli, M., Harris, C. M., Harris, T. M. and Stone, M. P. (1996) Biochemistry 35, 7316-7329
25. Berka, R. M., Schneider, P., Golightly, E. J., Brown, S. H., Madden, M., Brown, K. M., Halkier, T., Mondorf, K. and Xu, F. (1997) Appl. Environ. Microbiol. 63, 3151
26. Bourbonnais, R. and Paice, M. G. (1990) FEBS Lett. 267, 99-102
27. Rodríguez-Tudela, J. L., Barchiesi, F., Bille, J., Chryssanthou, E., Cuenca-Estrella, M., Denning, D., Donnelly, J. P., Dupont, B., Fegeler, W., Moore, C. et al. (2003) Clin. Microbiol. Infect. Dis. 9, 1-8
28. Hahn, V., Mikolasch, A., Wende, K., Bartrow, H., Lindequist, U. and Schauer, F. (2009) Biotechnol. Appl. Biochem. 54, 187-195
29. European Pharmacopoeia (1997) Mikrobiologische Wertbestimmung von Antibiotika, Diffusionsmethode, 6th Ed., section 2.7.2., Deutscher-Apotheker- Verlag, Stuttgart
30. Comment to the European Pharmacopeia (2008) Mikrobiologische Wertbestimmung von Antibiotika, Diffusionsmethode, section 2.7.2., Wissenschaftliche Verlagsgesellschaft mbH, Stuttgart
31. Niedermeyer, T. H. J., Mikolasch, A. and Lalk, M. (2005) J. Org. Chem. 70, 2002-2008
32. Hahn, V., Mikolasch, A., Manda, K., Gördes, D., Thurow, K. and Schauer, F. (2009) J. Mol. Catal. B Enzym. 60, 76-81
33. Schroeder, M., Pereira, L., Couto, S. R., Erlacher, A., Schoening, K.-U., Cavaco-Paulo, A. and Guebitz, G. M. (2007) Enzyme Microbiol. Technol. 40, 1748-1752
34. Osiadacz, J., Al-Adhami, A. J. H., Bajraszewska, D., Fischer, P. and Peczynska-Czoch, W. (1999) J. Biotechnol. 72, 141-149