Production of a new pyridine N-oxide by bioconversion with Cunninghamella echinulata var. elegans

Journal of Bioscience and Bioengineering

Volumn 114, Issue 5, 2012, Pages 497-499

  Zeng, Jia ^a   Gage, David ^a   Zhan, Jixun ^a  

^a Utah State University   (United States)

Author keywords

Biotransformation; Cunninghamella echinulata var. elegans; Efficient; N Oxidation; Pyridine; Selective

Indexed keywords

BIOTRANSFORMATION; EFFICIENT; ELEGANS; N-OXIDATION; SELECTIVE;

PYRIDINE; VALUE ENGINEERING;

BIOCONVERSION;

3 (N TERT BUTOXYCARBONYL AMINOMETHYL) 5 BROMOPYRIDINE; PYRIDINE 1 OXIDE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOTRANSFORMATION; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CUNNINGHAMELLA ECHINULATA; NONHUMAN; OXIDATION; SPECTROSCOPY;

BIOTRANSFORMATION; CUNNINGHAMELLA; OXIDATION-REDUCTION; PYRIDINES;

CUNNINGHAMELLA ECHINULATA;

EID: 84866408874     PISSN: 13891723     EISSN: 13474421     Source Type: Journal    
DOI: 10.1016/j.jbiosc.2012.06.006     Document Type: Article

References (20)

1. Lee K.J., Kim D.H. Synthesis and inhibitory study of N-oxide containing substrate analog inhibitors of carboxypeptidase A. Bull. Korean Chem. Soc. 1997, 18:1100-1104.
2. Youssif S. Recent trends in the chemistry of pyridine N-oxides. ARKIVOC 2001, 2:242-268.
3. Stevens M., Pannecouque C., De C.E., Balzarini J. Inhibition of human immunodeficiency virus by a new class of pyridine oxide derivatives. Antimicrob. Agents Chemother. 2003, 47:2951-2957.
4. Balzarini J., Stevens M., De C.E., Schols D., Pannecouque C. Pyridine N-oxide derivatives: unusual anti-HIV compounds with multiple mechanisms of antiviral action. J. Antimicrob. Chemother. 2005, 55:135-138.
5. Lustosa K.R.M.D., Menegatti R., Braga R.C., Liao L.M., de Oliveira V. Microbial β-glycosylation of entacapone by Cunninghamella echinulata ATCC 9245. J. Biosci. Bioeng. 2012, 13:611-613.
6. Asha S., Vidyavathi M. Cunninghamella - a microbial model for drug metabolism studies - a review. Biotechnol. Adv. 2009, 27:16-29.
7. Zi J., Valiente J., Zeng J., Zhan J. Metabolism of quercetin by Cunninghamella elegans ATCC 9245. J. Biosci. Bioeng. 2011, 112:360-362.
8. Zhang D., Evans F.E., Freeman J.P., Duhart B., Cerniglia C.E. Biotransformation of amitriptyline by Cunninghamella elegans. Drug Metab. Dispos. 1995, 23:1417-1425.
9. Moody J.D., Freeman J.P., Fu P.P., Cerniglia C.E. Biotransformation of mirtazapine by Cunninghamella elegans. Drug Metab. Dispos. 2002, 30:1274-1279.
10. Moody J.D., Freeman J.P., Cerniglia C.E. Biotransformation of doxepin by Cunninghamella elegans. Drug Metab. Dispos. 1999, 27:1157-1164.
11. Cerniglia C.E., Hansen E.B., Lambert K.J., Korfmacher W.A., Miller D.W. Fungal transformations of antihistamines: metabolism of methapyrilene, thenyldiamine and tripelennamine to N-oxide and N-demethylated derivatives. Xenobiotica 1988, 18:301-312.
12. Hansen E.B., Cerniglia C.E., Korfmacher W.A., Miller D.W., Heflich R.H. Microbial transformation of the antihistamine pyrilamine maleate. Formation of potential mammalian metabolites. Drug Metab. Dispos. 1987, 15:97-106.
13. Badgujar D.M., Talawar M.B., Asthana S.N., Mahulikar P.P. Studies of antimicrobial activity of picryl amino pyridine N-oxides. Indian J. Chem. B Org. 2010, 49:1675-1677.
14. Wiley R.H., Slaymaker S.C. Pyrimidine N-oxides and their infrared absorption characteristics. J. Am. Chem. Soc. 1957, 79:2233-2236.
15. Gao L.-M., Han Y.-X., Wang Y.-P., Li Y.-H., Shan Y.-Q., Li X., Peng Z.-G., Bi C.-W., Zhang T., Du N.-N., Jiang J.-D., Song D.-Q. Design and synthesis of oxymatrine analogues overcoming drug resistance in hepatitis B virus through targeting host heat stress cognate 70. J. Med. Chem. 2011, 54:869-876.
16. Ling Q., Xu X., Wei X., Wang W., Zhou B., Wang B., Zheng S. Oxymatrine induces human pancreatic cancer PANC-1 cells apoptosis via regulating expression of Bcl-2 and IAP families, and releasing of cytochrome c. J. Exp. Clin. Cancer Res. 2011, 30:66.
17. Jana N.K., Verkade J.G. Phase-vanishing methodology for efficient bromination, alkylation, epoxidation, and oxidation reactions of organic substrates. Org. Lett. 2003, 5:3787-3790.
18. Rajanarendar E., Raju S., Reddy M.N., Krishna S.R., Kiran L.H., Reddy A.R.N., Reddy Y.N. Multi-component synthesis and in vitro and in vivo anticancer activity of novel arylmethylene bis-isoxazolo[4,5-b]pyridine-N-oxides. Eur. J. Med. Chem. 2012, 50:274-279.
19. 2. Catal. Sci. Technol. 2012, 2:1140-1145.
20. Tan Y., Barrios-Landeros F., Hartwig J.F. Mechanistic studies on direct arylation of pyridine N-oxide: evidence for cooperative catalysis between two distinct palladium centers. J. Am. Chem. Soc. 2012, 134:3683-3686.