Application of biocatalysis to drug metabolism: Preparation of mammalian metabolites of a biaryl-bis-sulfonamide ampa (α-amino-3-hydroxy-5- methylisoxazole-4-propionic acid) receptor potentiator using Actinoplanes missouriensis

Drug Metabolism and Disposition

Volumn 34, Issue 6, 2006, Pages 925-931

  Zmijewski, Milton ^a   Gillespie, Todd A ^a   Jackson, David A ^a   Schmidt, Douglas F ^a   Yi, Ping ^a   Kulanthaivel, Palaniappan ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMPA RECEPTOR; DRUG METABOLITE; LY 451395; SULFONAMIDE; UNCLASSIFIED DRUG; [2 PROPANESULFONAMIDE, N[2 [4' [2 (METHYLSULFONYL)AMINO]ETHYL][1,1' BIPHENYL] 4 YL]PROPYL];

ACTINOMYCETALES; ARTICLE; BIOCATALYST; BIOTRANSFORMATION; DEAMINATION; DRUG IDENTIFICATION; DRUG ISOLATION; DRUG METABOLISM; DRUG POTENTIATION; DRUG PURITY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VIVO STUDY; INCUBATION TIME; MAMMAL; MASS SPECTROMETRY; MICROBIAL METABOLISM; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

ACTINOMYCETALES; ACTINOPLANES MISSOURIENSIS; MAMMALIA;

EID: 33646787431     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.106.009522     Document Type: Article

References (22)

1. Azerad R (1999) Microbial models for drug metabolism. Adv Biochem Eng Biotech 63:169-218.
2. 14C] ruboxistaurin in dogs, mice and rats following oral administration and the structure determination of its metabolites by LC/MS and NMR spectroscopy. Drug Metab Dispos 34:213-224.
3. Baumbarger PJ, Muhlhauser M, Yang CR, and Nisenbaum ES (2001a) LY392098, a novel AMPA receptor potentiator: electrophysiological studies in prefrontal cortical neurons. Neuropharmacology 40:992-1002.
4. Baumbarger P, Muhlhauser M, Zhai J, Yang CR, and Nisenbaum ES (2001b) Positive modulation of a-amino-3-hydroxy-5-methyl-4-isoxazole propionic acid (AMPA) receptors in prefrontal cortical neurons by a novel allosteric potentiator. J Pharmacol Exp Ther 298:86-102.
5. Gates M, Ogden A, and Bleakman D (2001) Pharmacological effects of AMPA receptor potentiators LY392098 and LY404187 on rat neuronal AMPA receptors in vitro. Neuropharmacology 40:984-991.
6. Goodhue CT (1982) The methodology of microbial transformation of organic compounds, in Microbial Transformation of Bioactive Compounds (Rosazza JP ed) pp 1-133, CRC Press, Boca Raton, FL.
7. Lacroix I, Biton J, and Azerad (1999) Microbial models of drug metabolism: microbial transformations of trimegestone (RU27987), a 3-keto-D4, 9(10)-19-norsteroid drug. Bioorg Med Chem 7:2329-2341.
8. Li X, Tizzano JP, Griffey K, Clay M, Lindstrom T, and Skolnick P (2001) Antidepressant-like actions of an AMPA receptor potentiator (LY392098). Neuropharmacology 40:1028-1033.
9. Li X, Witkin JM, Need AB, and Skolnick P (2003) Enhancement of antidepressant potency by a potentiator of AMPA receptors. Cell Mol Neurobiol 23:419-430.
10. Miu P, Jarvie KR, Radhakrishnan V, Gates MR, Ogden A, Ornstein PL, Zarrinmayeh H, Ho K, Peters D, Grabell J, et al. (2001) Novel AMPA receptor potentiators LY392098 and LY404187: Effects on recombinant human AMPA receptors in vitro. Neuropharmacology 40:976-983.
11. O'Neill MJ, Bleakman D, Zimmerman DM, and Nisenbaum ES (2004) AMPA potentiators for the treatment of CNS disorders. Current drug targets. CNS Neurol Disord 3:181-194.
12. O'Neill MJ, Murray TK, Clay MP, Lindstrom T, Yang CR, and Nisenbaum ES (2005) LY503430: pharmacology, pharmacokinetics and effects in rodent models of Parkinson's disease. CNS Drug Rev 11:77-96.
13. Panke S and Wubbolts M (2005) Advances in biocatalytic synthesis of pharmaceutical intermediates. Curr Opin Chem Biol 9:188-194.
14. Parsons CG, Danysz W, and Lodge D (2002) Introduction to glutamate receptors, their function and pharmacology, in Ionotropic Glutamate Receptors as Therapeutic Targets (Danysz W, Lodge D, and Parsons CG eds) pp 1-30, Graham Publishing Co., Johnson City, TN.
15. Powell KA, Ramer SW, del Cardayre SB, Stemmer WPC, Tobin MB, Longchamp PF, and Huisman GW (2001) Directed evolution and biocatalysis. Angew Chem Int Ed 40:3948-3959.
16. Preisig CL, Laakso JA, Mocek UM, Wang PT, Baez J, and Byng G (2003) Biotransformations of the cardiovascular drugs mexrenone and canrenone. J Nat Prod 66:350-356.
17. Quirk JC and Nisenbaum ES (2002) A Novel positive allosteric modulator of AMPA receptors. CNS Drug Rev 8:255-282.
18. Schmid A, Dordick JS, Hauer B, Kiener A, Wubbolts M, and Witholt B (2001) Industrial biocatalysis today and tomorrow. Nature (Lond) 409:258-268.
19. Skolnick P, Leguko B, Li X, and Bymaster FP (2001) Current perspectives on the development of non-biogenic amine-based antidepressants. Pharmacol Res 43:411-423.
20. Smith RV and Rosazza JP (1975) Microbial models of mammalian metabolism. J Pharm Sci 64:1737-1759.
21. Vandergriff J, Huff K, Bond A, and Lodge D (2001) Potentiation of responses to AMPA on central neurons by LY392098 and LY404187 in vivo. Neuropharmacology 40:1003-1009.
22. Zhang D, Zhang H, Aranibar N, Hanson R, Huang Y, Cheng PT, Wu S, Bonacorsi S, Zhu M, Swaminathan A, et al. (2006) Structural elucidation of human oxidative metabolites of muraglitazar: use of microbial bioreactors in the biosynthesis of metabolite standards. Drug Metab Dispos 34:267-280.