Enhanced anaerobic degradation of polymeric azo compounds by Escherichia coli in the presence of low-molecular-weight redox mediators

Journal of Pharmacy and Pharmacology

Volumn 54, Issue 11, 2002, Pages 1471-1479

  Rau, J ^a   Maris, B ^b   Kinget, R ^b   Samyn, C ^b   Van Den Mooter, G ^b   Stolz, A ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

^b UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

16 HYDROXYHEXADECANOIC ACID; 4 (6 HYDROXYHEXYL)OXY PHENYLAZOBENZOIC ACID; AZO COMPOUND; AZOBENZENE DERIVATIVE; LAWSONE; POLY(METHACRYLATE CO 4,4' DIMETHACRYLOYLAMINOAZOBENZENE); POLYETHER DERIVATIVE; POLYMER; POLYMETHACRYLIC ACID DERIVATIVE; UNCLASSIFIED DRUG; 16 HYDROXYHEXADECANOATE; 16-HYDROXYHEXADECANOATE; 4 (6 HYDROXYHEXYL)OXY PHENYLAZOBENZOATE; 4-(6-HYDROXYHEXYL)OXY-PHENYLAZOBENZOATE; METHACRYLIC ACID METHYL ESTER; NAPHTHOQUINONE; PALMITIC ACID DERIVATIVE; WATER;

ANAEROBIC METABOLISM; ARTICLE; COLON; DRUG EFFECT; DRUG SOLUBILITY; DRUG TARGETING; ESCHERICHIA COLI; HYDROPHILICITY; HYDROPHOBICITY; MOLECULAR WEIGHT; NONHUMAN; OXIDATION REDUCTION REACTION; POLYMERIZATION; BIOREMEDIATION; CHEMISTRY; METABOLISM; TIME;

AZO COMPOUNDS; BIODEGRADATION, ENVIRONMENTAL; ESCHERICHIA COLI; HYDROPHOBICITY; METHYLMETHACRYLATES; MOLECULAR WEIGHT; NAPHTHOQUINONES; OXIDATION-REDUCTION; PALMITIC ACIDS; POLYMERS; POLYMETHACRYLIC ACIDS; TIME FACTORS; WATER;

EID: 0036847920     PISSN: 00223573     EISSN: None     Source Type: Journal    
DOI: 10.1211/002235702126     Document Type: Article

References (34)

1. Brown, J. P. (1981) Reduction of polymeric azo and nitro dyes by intestinal bacteria. Appl. Environ. Microbiol. 41: 1283-1286
2. Chung, K.-T., Stevens, S. E., Cerniglia, C. E. (1992) The reduction of azo dyes by the intestinal microflora. Crit. Rev. Microbiol. 18: 175-190
3. Dubin, P., Wright, K. L. (1975) Reduction of azo food dyes in cultures of Proteus vulgaris. Xenobiotica 5: 563-571
4. Field, J. A., Cervantes, F. J., Van der Zee, F. P., Lettinga, G. (2000) Role of quinones in the biodegradation of priority pollutants: a review. Water Sci. Technol. 42: 215-222
5. Florence, T. M. (2965) Polarography of aromatic azo compounds. II. Kinetic study of the disproportionation of 4-aminohydrazobenzene-4′-sulphonic acid. Aust. J. Chem. 18: 619-626
6. Ghandehari, H., Kopeckova, P., Kopecek, J. (1997) In vitro degradation of pH-sensitive hydrogels containing aromatic azo bonds. Biomaterials 18: 861-872
7. Honohan, T., Enderlin, F. E., Ryerson, B. A., Parkinson, T. M. (1977) Intestinal absorption of polymeric derivatives of the food dyes sunset yellow and tartrazine in rats. Xenobiotica 7: 765-774
8. Kakoulides, E. P., Smart, J. D., Tsibouklis, J. (1998) Azocrosslinked poly(acrylic acid) for colonic delivery and adhesion specificity: in vitro degradation and preliminary ex vivo bioadhesion studies. J. Control. Release 54: 95-109
9. Kimura, Y., Makita, Y., Kumagai, T., Yamane, H., Kitao, T., Sasatani, H., Kim, S. I. (1992) Degradation of azo containing polyurethane by the action of intestinal microflora. Polymer 33: 5294-5299
10. Kinget, R., Kalala, W., Vervoort, L., Van den Mooter, G. (1998) Colonic drug targeting. J. Drug Target. 6: 129-149
11. Kopecek, J., Kopeckova, P., Brondsted, H., Rathi, R., Rihova, B., Yeh, P.-Y., Ikesue, K. (1992) Polymers for colon-specific drug-delivery. J. Control. Release 19: 121-130
12. Kopeckova, P., Kopecek, J. (1990) Release of 5-aminosalicylic acid from bioadhesive N-(2-hydroxypropyl)methacrylamide copolymers by azoreductase in vitro. Makromol. Chem. 191: 2037-2045
13. Kopeckova, P., Rathi, R., Takada, S., Rihova, B., Berenson, M. M., Kopecek, J. (1994) Bioadhesive N-(2-hydroxypropyl)methacrylamide copolymers for colon-specific drug delivery. J. Control. Release 28: 211-222
14. Kudlich, M., Keck, A., Klein, J., Stolz, A. (1997) Localization of the enzyme system involved in the anaerobic reduction of azo dyes by Sphingomonas sp. BN6 and effect of artificial redox mediators on the rate of azo dye reduction. Appl. Environ. Microbiol. 63: 3691-3694
15. Lloyd, A. W., Martin, G. P., Soozandehfarm, S. H. (1994) Azopolymers: a means of colon specific drug delivery? Int. J. Pharmaceutics 106: 255-260
16. Madigan, M. T., Martinko, J. M., Parker, J. (2000) Brock biology of microorganisms. 9th edn, Prentice-Hall International, London, p. 267
17. Mechsner, K., Wuhrmann, K. (1982) Cell permeability as a rate limiting factor in the microbial reduction of sulfonated azo dyes. Eur. J. Appl. Microbiol. Biotechnol. 15. 123-126
18. Peppercorn, M. A., Goldman, P. (1972) The role of intestinal bacteria in the metabolism of salicylazosulfapyridine. J. Pharmacol. Exp. Ther. 181: 555-562
19. Rau, J., Knackmuss, H.-J., Stolz, A. (2002) Effects of different quinoide redox mediators on the anaerobic reduction of azo dyes by bacteria. Env. Sci. Technol. 36: 1497-1504
20. Russ, R., Rau, J., Stolz, A. (2000) The function of cytoplasmatic flavin reductases in the bacterial reduction of azo dyes. Appl. Environ. Microbiol. 66: 1429-1434
21. Ryan, A. J., Roxon, J. J., Sivayavirojana, A. (1968) Bacterial azo reduction: a metabolic reaction in mammals. Nature 219: 854-855
22. Samyn, C., Kalala, W., Van den Mooter, G., Kinget, R. (1995) Synthesis and in vitro biodegradation of poly(ether-ester)azo polymers designed for colon targeting. Int. J. Pharmaceutics 121: 211-216
23. Schacht, E., Gevaert, A., Kenawy, E. R., Molly, K., Verstraete, W., Adriaensens, P., Carleer, R., Gelan, J. (1996) Polymers for colon specific drug delivery. J. Control Release 39: 327-338
24. Schmidt, K., Jensen, S. L., Schlegel, H. G. (1963) Arch. Mikrobiol. 46: 117-126
25. Shanta, K. L., Ravichandran, P., Panduranga Rao, K. (1995) Azo polymeric hydrogels for colon targeted drug delivery. Biomaterials 16: 1313-1318
26. Stolz, A. (2001) Basic and applied aspects in the microbial degradation of azo dyes. Appl. Microbiol. Biotechnol. 56: 69-80
27. Ueda, T., Yamaoka, T., Miyamoto, M., Kimura, Y., Sasatani, H., Kim, S. I. (1996) Bacterial reduction of azo-compounds as a model reaction for the degradation of azo-containing polyurethane by the action of intestinal flora. Bull. Chem. Soc. Jpn. 69: 1139-1142
28. Van den Mooter, G. (1994) Contribution to oral colon-specific drug delivery: synthesis and evaluation of biodegradable azo polymers. PhD thesis, Katholieke Universiteit Leuven
29. Van den Mooter, G., Samyn, C., Kinget, R. (1993) Azo polymers for colon-specific drug delivery. II: influence of the type of azo polymer on the degradation by intestinal microflora. Int. J. Pharmaceutics 97: 133-139
30. Van den Mooter, G., Maris, B., Samyn, C., Augustijns, P., Kinget, R. (1997) Use of azo polymers for colon-specific drug delivery. J. Pharm. Sci. 86: 1321-1327
31. Van Hees, P. A. M., Tuinte, J. H. M., Van Rossum, J. M., Van Tongeren, J. H. M. (1979) Influence of intestinal transit time on azo reduction of salicylazosulphapyridine (salazopyrin). Gut 20: 300-304
32. Yamaoka, T., Makita, Y., Sasatani, H., Kim, S.-I., Kimura, Y. (2000) Linear type azo-containing polyurethane as drug-coating material for colon-specific delivery: its properties, degradation, behavior, and utilization for drug formulation. J. Control. Release 66: 187-197
33. Yamazaki, S., Kano, K., Ikeda, T., Isawa, K., Kaneko, T. (1998) Mechanistic study on the role of a bifidogenetic growth stimulator based on physicochemical characterization. Biochim. Biophys. Acta 1425: 516-526
34. + regeneration in Bifidobacterium longum. Biochim. Biophys. Acta 1428: 241-250