Bacterial reduction as means for colonic drug delivery: Can other chemical groups provide an alternative to the azo bond?

Journal of Medicinal Chemistry

Volumn 55, Issue 23, 2012, Pages 10781-10785

  Saphier, Sigal ^a   Haft, Avital ^b   Margel, Shlomo ^b  

^a ISRAEL INSTITUTE FOR BIOLOGICAL RESEARCH   (Israel)

^b BAR ILAN UNIVERSITY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

5 NITROSALICYLIC ACID; AROMATIC NITRO COMPOUND; AZO COMPOUND; DISULFIDE; OLSALAZINE; SALAZOSULFAPYRIDINE;

ARTICLE; BACTERIUM; CHEMICAL BOND; COLON; DISULFIDE BOND; DRUG DELIVERY SYSTEM; DRUG DESIGN; DRUG STRUCTURE; QUANTITATIVE STRUCTURE ACTIVITY RELATION; REDUCTION;

AZO COMPOUNDS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COLON; DRUG DELIVERY SYSTEMS;

EID: 84871006076     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm301381a     Document Type: Article

References (37)

1. Friend, D. R. New oral delivery systems for treatment of inflammatory bowl disease Adv. Drug Delivery Rev. 2005, 57, 247-265
2. Patel, M.; Shah, T.; Amin, A. Therapeutic opportunities in colon-specific drug-delivery systems Crit. Rev. Ther. Drug Carrier Syst. 2007, 24 (2) 147-202
3. McConnell, E. L.; Fadda, H. M.; Basit, A. Gut instincts: explorations in intestinal physiology and drug delivery Int. J. Pharm. 2008, 364, 213-226
4. Rajguru, V. V.; Gaikwad, P. D.; Bankar, V. H.; Pawar, S. P. An overview on colonic drug delivery system Int. J. Pharm. Sci. Rev. Res. 2011, 6 (2) 197-204
5. Das, S.; Chaudhury, A.; Ng, K.-Y. Preparation and evaluations of zinc-pectin-chitosan composite particles for drug delivery to the colon: role of chitosan in modifying in vitro and in vivo drug release Int. J. Pharm. 2011, 406, 11-20
6. Watts, P. J.; Illum, L. Colonic drug delivery Drug Dev. Ind. Pharm. 1997, 23 (9) 893-913
7. McConnell, E. L.; Short, M. D.; Basit, A. W. An in vivo comparison of intestinal pH and bacterial as physiological trigger mechanisms for colonic tergeting in man J. Controlled Release 2008, 130, 154-160
8. Patel, M.; Amin, A. Recent trends in microbially and/or enzymatically driven colon-specific drug delivery systems Crit. Rev. Ther. Drug Carrier Syst. 2011, 28 (6) 489-552
9. Sinha, V. R.; Kumria, R. Colonic drug delivery: prodrug approach Pharm. Res. 2001, 18 (5) 557
10. Sinha, V. R.; Kumria, R. Microbially triggered drug delivery to the colon Eur. J. Pharm. Sci. 2003, 18, 3-18
11. Chourasia, M. K.; Kain, S. K. Polysaccharides for colon targeted drug delivery Drug Delivery 2004, 11, 129-148
12. Larrosa, M.; Tome-Carneiro, J.; Yanez-Gascon, M. J.; Alcantara, D.; Selma, M. V.; Beltran, D.; Garcia-Conesa, M. T.; Urban, C.; Lucas, R.; Tomas-Barberan, F.; Morales, J. C.; Espin, J. C. Preventive oral treatment with resveratrol pro-prodrugs drastically reduce colon inflammation in rodents J. Med. Chem. 2010, 53, 7365-7376
13. Van-den-Mooter, G.; Maris, B.; Samyn, C.; Augustijns, P.; Kinget, R. Use of azo polymers for colon-specific drug delivery J. Pharm. Sci. 1997, 86 (12) 1321-1327
14. Saphier, S.; Karton, Y. Novel salicylazo polymers for colon drug delivery: dissolving polymers by means of bacterial degradation J. Pharm. Sci. 2010, 99 (2) 804-815
15. West, K. R.; Otto, S. Reversible covalent chemistry in drug delivery Curr. Drug Discovery Technol. 2005, 2, 123-160
16. Saito, G.; Swanson, J. A.; Lee, K.-D. Drug delivery strategy utilizing conjugation via reversible disulfide linkages: role and site of cellular reducing activities Adv. Drug Delivery Rev. 2003, 55, 199-215
17. Sarti, F.; Bernkop-Schnurch, A. Chitosan and thiolated chitosan Adv. Polym. Sci. 2011, 243, 93-110
18. Wilding, I. Site-specific drug delivery in the gasrtointestinal tract Crit. Rev. Ther. Drug Carrier Syst. 2000, 17 (6) 557-620
19. Schacht, E.; Wilding, I. Process for the Preparation of Azo and/or Disulfide Polymer Matrix Drug Delivery System for the Site Specific Delivery of an Active Agent in the Colon. US005,407,682, Apr 18, 1995.
20. Kudo, Y.; Ueshima, H.; Sakai, K. System for Release in Lower Digestive Tract. WO/2000/074720, 2000.
21. Pelkonen, K.; Hanninen, O. Interactions of xenobiotics with the gastrointestinal flora Gastrointest. Toxicol. 1986, 193-212 (Chapter 7)
22. Scheline, R. R. Metabolism of foreign compounds by gastrointestinal microorganisms Pharm. Rev. 1973, 25, 451-523
23. Pieper, I. A.; Bertau, M. Predictive tools for the evaluation of microbial effects on drugs during gastrointestinal passage Expert. Opin. Drug Metab. Toxicol. 2010, 6 (6) 747-760
24. Asche, C.; Dumy, P.; Carrez, D.; Croisy, A.; Demeunynck, M. Nitrobenzylcarbamate prodrugs of cytotoxic acridines for potential use with nitroreductase gene-directed enzyme prodrug therapy Bioorg. Med. Chem. Lett. 2006, 16, 1990-1994
25. Brown, J. P. Reduction of polymeric azo and nitro dyes by intestinal bacteria Appl. Environ. Microbiol. 1981, 41 (5) 1283-1286
26. Dubin, P.; Wright, L. Reduction of azo food dyes in cultures of Proteus vulgaris Xenobiotica 1975, 5 (9) 563-571
27. Walker, R.; Ryan, A. J. Some molecular parameters influencing rate of reduction of azo compounds by intestinal microflora Xenobiotica 1971, 1 (4/5) 483-486
28. Brown, M. A.; DeVito, S. C. Predicting azo dye toxicity Crit. Rev. Environ. Sci. Technol. 1993, 23 (3) 249-324
29. Ueda, T.; Yamakoa, T.; Miyamoto, M.; Kimura, Y.; Sasatani, H.; Kim, S.-I. 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. 1996, 69, 1139-1142
30. Bernkop-Schnurch, A. Mucoadhesive systems in oral drug delivery Drug Discovery Today: Technol. 2005, 2 (1) 83-86
31. Hansch, C.; Leo, A.; Taft, A. W. A survey of Hammett substituent constants and resonance and field parameters Chem. Rev. 1991, 91, 165-195
32. Hansch, C.; Leo, A. In Exploring QSAR, Fundamentals and Applications in Chemistry and Biology; American Chemical Society: Washington, DC, 1995.
33. Jaffe, H. H. A reexamination of the Hammett equation Chem. Rev. 1953, 53, 191
34. Paula, F. S. d.; Sales, E. M.; Vallaro, M.; Fruttero, R.; Goulart, M. O. F. The relationship between redox potentials and substituent constants in biologically active arylazoxy compounds J. Electroanal. Chem. 2005, 57 (1) 33-41
35. Lauwiner, M.; Rys, P.; Wissmann, J. Reduction of aromatic nitro compounds with hydrazine hydrate in the presence of an iron oxide hydroxide catalyst. I The reduction of monosubstituted nitrobenzens with hydrazine hydrate in the presence of ferrihydrite Appl. Catal., A 1998, 172, 141-148
36. Semde, R.; Pierre, D.; Geuskens, G.; Devleeschouwer, M.; Moes, A. J. Study of some important factors involved in azo derivative reduction by Clostridium perfringens Int. J. Pharm. 1998, 161, 45-54
37. Rau, J.; Maris, B.; Kinget, R.; Samyn, C.; Mooter, G. V. d.; Stoiz, A. Enhanced anaerobic degradation of polymeric azo compounds by Escherichia coli in the presence of low-molecular-weight redox mediators J. Pharm. Pharmacol. 2002, 54, 1471-1479