Generation of new protein kinase inhibitors utilizing cytochrome P450 mutant enzymes for indigoid synthesis

Journal of Medicinal Chemistry

Volumn 47, Issue 12, 2004, Pages 3236-3241

  Guengerich, F Peter ^a   Sorrells, Jennifer L ^a,c   Schmitt, Sophie ^b   Krauser, Joel A ^a   Aryal, Pramod ^a   Meijer, Laurent ^b  

^a VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b STATION BIOLOGIQUE   (France)

^c EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5 METHOXYINDOLE; 5,5' DIMETHOXYINDIRUBIN; CYCLIN DEPENDENT KINASE 1; CYCLIN DEPENDENT KINASE 5; CYTOCHROME P450; CYTOCHROME P450 2A6; GLYCOGEN SYNTHASE KINASE 3; INDIGOID DERIVATIVE; INDIRUBIN; INDOLE DERIVATIVE; PROTEIN KINASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CONCENTRATION RESPONSE; DRUG SCREENING; DRUG SYNTHESIS; ENZYME INHIBITOR INTERACTION; ESCHERICHIA COLI; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; NONHUMAN; OXIDATION; REACTION ANALYSIS;

ARYL HYDROCARBON HYDROXYLASES; CDC2 PROTEIN KINASE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYCLIN-DEPENDENT KINASE 5; CYCLIN-DEPENDENT KINASES; ESCHERICHIA COLI; GLYCOGEN SYNTHASE KINASE 3; HUMANS; INDOLES; MIXED FUNCTION OXYGENASES; MUTATION; PROTEIN KINASE INHIBITORS;

EID: 2542635063     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm030561b     Document Type: Article

References (36)

1. Miller, C. P.; Collini, M. D.; Tran, B. D.; Harris, H. A.; Kharode, Y. P.; et al. Design, synthesis, and preclinical characterization of novel, highly selective indole estrogens. J. Med. Chem. 2001, 44, 1654-1657.
2. Hoessel, R.; Leclerc, S.; Endicott, J. A.; Nobel, M. E. M.; Lawrie, A.; et al. Indirubin, the active constituent of a Chinese antileukaemia medicine, inhibits cyclin-dependent kinases. Nat. Cell Biol. 1999, 1, 60-67.
3. Tang, W.; Eisenbrand, G. Chinese Drugs of Plant Origin: Chemistry, Pharmacology, and Use in Traditional and Modern Medicine; Springer-Verlag: Heidelberg, 1992.
4. Xiao, Z.; Hao, Y.; Liu, B.; Qian, L. Indirubin and meisoindigo in the treatment of chronic myelogenous leukemia in China. Leuk. Lymphoma 2002, 43, 1763-1768.
5. Damiens, E.; Baratte, B.; Marie, D.; Eisenbrand, G.; Meijer, L. Anti-mitotic properties of indirubin-3′-monoxime, a CDK/GSK-3 inhibitor: induction of endoreplication following prophase arrest. Oncogene 2001, 20, 3786-3797.
6. Leclerc, S.; Garnier, M.; Hoessel, R.; Marko, D.; Bibb, J. A.; et al. Indirubins inhibit glycogen synthase kinase-3β and CDK5/P25, two protein kinases involved in abnormal tau phosphorylation in Alzheimer's disease. A property common to most cyclin-dependent kinase inhibitors? J. Biol. Chem. 2001, 276, 251-260.
7. Adachi, J.; Mori, Y.; Matsui, S.; Takigami, H.; Fujino, J.; et al. Indirubin and indigo are potent aryl hydrocarbon receptor ligands present in human urine. J. Biol. Chem. 2001, 276, 31475-31478.
8. Bradfield, C. A.; Bjeldanes, L. F. Dietary modification of xenobiotic metabolism: contribution of indolylic compounds present in Brassica oleracea. J. Agric. Food Chem. 1987, 35, 896-900.
9. Song, J.; Clagett-Dame, M.; Peterson, R. E.; Hahn, M. E.; Westler, W. M. ; et al. A ligand for the aryl hydrocarbon receptor isolated from lung. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 14694-14699.
10. Riby, J. E.; Feng, C.; Chang, Y.; Schaldach, C. M.; Firestone, G. L.; et al. The major cyclic trimeric product of indole-3-carbinol is a strong agonist of the estrogen receptor signaling pathway. Biochemistry 2000, 39, 910-918.
11. Bittinger, M. A.; Nguyen, L. P.; Bradfield, C. A. Aspartate aminotransferase generates proagonists of the aryl hydrocarbon receptor. Mol. Pharmacol. 2003, 64, 550-556.
12. Denison, M. S.; Nagy, S. R. Activation of the aryl hydrocarbon receptor by structurally diverse exogenous and endogenous chemicals. Annu. Rev. Pharmacol. Toxicol. 2003, 43, 309-334.
13. Koehler, C. S. W. Synthetic dyes and the German chemical industry. Today's Chemist Work 1999, 8, 85-91.
14. Bäyer, A. Synthese des Indigblaus. Chem. Ber. 1878, 11, 1296-1297.
15. Huxtable, R. J. The mutability of blue. Mol. Interventions 2001, 1,141-144.
16. Ensley, B. D.; Ratzkin, B. J.; Osslund, T. D.; Simon, M. J.; Wackett, L. P.; et al. Expression of naphthalene oxidation genes in Escherichia coli results in the biosynthesis of indigo. Science 1983, 222, 167-169.
17. Murdock, D.; Ensley, B. D.; Serdar, C.; Thalen, M. construction of metabolic operons catalyzing the de novo biosynthesis of indigo in Escherichia coli. Bio/Technol. 1993, 11, 381-386.
18. Bialy, H. Biotechnology, bioremediation, and blue genes. Nat. Biotechnol. 1997, 15, 110.
19. Gillam, E. M. J.; Aguinaldo, A. M.; Notley, L. M.; Kim, D.; Mundkowski, R. G.; et al. Formation of indigo by recombinant mammalian cytochrome P450. Biochem. Biophys. Res. Commun. 1999, 265, 469-472.
20. Gillam, E. M. J.; Notley, L. M.; Cai, H.; DeVoss, J. J.; Guengerich, F. P. Oxidation of indole by cytochrome P450 enzymes. Biochemistry 2000, 39, 13817-13824.
21. Li, Q. S.; Schwaneberg, U.; Fischer, P.; Schmid, R. D. Directed evolution of the fatty-acid hydroxylase P450 BM-3 into an indolehydroxylating catalyst. Chem. Eur. J. 2000, 6, 1531-1536.
22. Nakamura, K.; Martin, M. V.; Guengerich, F. P. Random mutagenesis of cytochrome P450 2A6 and screening with indole oxidation products. Arch. Biochem. Biophys. 2001, 395, 25-31.
23. Nettekoven, M. Combinatorial synthesis of libraries of indole derivatives. Bioorg. Med. Chem. 2001, 11, 2169-2171.
24. Ozawa, T.; Kinae, N. Formation of new crystallizable pigments from D-glucose or D-fructose and p-toluidine. Chem. Pharm. Bull. 1970, 18, 1293-1294.
25. Ozawa, T.; Kinae, N. Studies on the autoxidation of carbohydrate and its derivatives. VII. Formation of the pigments in amino-carbonyl reaction of glucose. Yakugaku Zasshi 1973, 93, 8-13.
26. Shim, J.-Y.; Chang, Y.-J.; Kim, S.-U. Indigo and indirubin derivatives from indoles in Polygonum tinctorium tissue cultures. Biotechnol. Lett. 1998, 20, 1139-1143.
27. Kim, S.-Y.; Song, K.-S.; Jung, D.-S.; Chae, Y.-A.; Lee, H. J. Production of indoxyl derivatives in indole-suppemented tissue cultures of Polygonum tinctorium. Planta Med. 1996, 62, 54-56.
28. Guengerich, F. P. Cytochrome P450 enzymes in the generation of commercial products. Nat. Rev. Drug Discovery 2002, 1, 359-366.
29. Schmidt-Dannert, C. Molecular breeding of carotenoid biosynthetic pathways. Nat. Biotechnol. 2000, 18, 750-753.
30. Müller-Kuhrt, L. Putting nature back into drug discovery. Nat. Biotechnol. 2003, 21, 602.
31. Knockaert, M.; Greengard, P.; Meijer, L. Pharmacological inhibitors of cyclin-dependent kinases. Trends Pharmacol. Sci. 2002, 23, 417-425.
32. Soucek, P. Expression of cytochrome P450 2A6 in Escherichia coli: Purification, spectral and catalytic characterization, and preparation of polyclonal antibodies. Arch. Biochem. Biophys. 1999, 370, 190-200.
33. Primot, A.; Baratte, B.; Gompel, M.; Borgne, A.; Liabeuf, S.; et al. Purification of GSK-3 by affinity chromatography on immobilized axin. Protein Expression Purif. 2000, 20, 394-404.
34. cdc2 on Thr-14 and Tyr-15 at the prophase/metaphase transition. J. Biol. Chem. 1996, 271, 27847-27854.
35. Parikh, A.; Gillam, E. M. J.; Guengerich, F. P. Drug metabolism by Escherichia coli expressing human cytochromes P450. Nat. Biotechnol. 1997, 15, 784-788.
36. Sandhu, P.; Baba, T.; Guengerich, F. P. Expression of modified cytochrome P450 2C10 (2C9) in Escherichia coli, purification, and reconstitution of catalytic activity. Arch. Biochem. Biophys. 1993, 306, 443-450.