Recombinant Escherichia coli cells immobilized in Ca-alginate beads for metabolite production

References

• Amsden B, Turner N. Diffusion characteristics of calcium alginate gels. Biotechnol Bioeng 1999; 65: 605–610
   PubMed Web of Science ®Google Scholar
• Barbotin J-N. Comportement physiologique et stabilite des cellules immobilisees. Biofutur 1994; 3: 22–27
   Google Scholar
• Barnes HJ, Arlotto MP, Waterman MR. Expression and enzymatic activity of recombinant cytochrome P450 17α-hydroxylase in Escherichia coli. Proc Natl Acad Sci U S A 1991; 88: 5591–5601
   Google Scholar
• Bienaime C, Barbotin JN, Nava-Saucedo JE. How to build an adapted and bioactive cell microenvironment? A chemical interaction study of the structure of Ca-alginate matrices and their repercussion on confined cells. J Biomed Mater Res 2002; 67A: 376–388
   Google Scholar
• Blaauboer BM. Biotransformation: detoxication and bioactivation. Toxicology, principles and applications, RJM Niesink, J de Vries, MA Hollinger. CRC Press, Inc. and Open University of The Netherlands, Boca Raton, (FL) 1996
   Google Scholar
• Blake JAR, Pritchard M, Ding S, Smith GCM, Burchell B, Wolf CR, Friedberg T. Coexpression of a human (CYP3A4) and P450 reductase generates a highly functional monooxygenase system in Escherichia coli. FEBS Lett 1996; 397: 210–214
   PubMed Web of Science ®Google Scholar
• Buters JTM, Korzekwa KR, Kunze KL, Omata Y, Hardwick JP, Gonzalez FJ. cDNA-directed expression of human cytochrome P450 CYP3A4 using Baculovirus. Drug Metab Dispos 1994; 22: 688–629
   PubMed Web of Science ®Google Scholar
• Cassidy MB, Lee H, Trevors JT. Environmental applications of immobilized microbial cells: a review. J Ind Microbiol 1996; 16: 79–101
   Google Scholar
• Clark BJ, Waterman MR. Functional expression of bovine 17α-hydroxylase in COS 1 cells is dependent upon the presence of an amino-terminal signal anchor sequence. J Biol Chem 1992; 267: 24568–24574
   PubMedGoogle Scholar
• Crespi CL, Penman BW, Steimel DT, Gelboin H, Gonzalez FJ. The development of a human cell line stably expressing human CYP3A4: role in the metabolic activation of aflatoxin B1 and comparison to CYP1A2 and CYP2A3. Drug Metab Dispos 1991; 22: 688–692
   Google Scholar
• Doehmer J, Schmalix WA, Greim H. Genetically engineered in vitro systems for biotransformation studies. Methods Find Exp Clin Pharmacol 1994; 16: 513–518
   PubMedGoogle Scholar
• Durieux A, Nicolay X, Simon J-P. Continuous malolactic fermentation by Oenococcus oeni entrapped in lentikats. Biotechnol Lett 2000; 22: 1679–1684
   Google Scholar
• Estape D, Godia F, Sola C. Determination of glucose and ethanol effective diffusion coefficients in Ca-alginate gel. Enzyme Microb Technol 1992; 14: 396–401
   PubMed Web of Science ®Google Scholar
• Ferrante AA, Augliera J, Lewis K, Klibanov AM. Cloning of an organic solvent-resistant gene in Escherichia coli: the unexpected role of alkylhydroperoxide reductase. Proc Natl Acad Sci U S A 1995; 92: 7617–7621
   PubMedGoogle Scholar
• Friedberg T, Wolf CR. Recombinant DNA technology as an investigative tool in drug metabolism research. Adv Drug Deliv Rev 1996; 22: 187–213
   Web of Science ®Google Scholar
• Friehs K, Reardon KF. Parameters influencing the productivity of recombinant E. coli cultivations. Adv Biochem Eng Biotechnol 1993; 48: 55–77
   Google Scholar
• Fujita K-I, Kamataki T. Genetically engineered bacterial cells co-expressing human cytochrome P450 with NADPH-cytochrome P450 reductase: prediction of metabolism and toxicity of drugs in humans. Drug Metabol Pharmacokinet 2002; 17: 1–22
   PubMedGoogle Scholar
• Gaserod O, Smidsrod O, Sjak-Braek G. Microcapsules of alginate–chitosan – I. A quantitative study of the interaction between alginate and chitosan. Biomaterials 1998; 19: 1815–1825
   PubMed Web of Science ®Google Scholar
• Gaserod O, Sannes A, Skjak-Braek G. Microcapsules of alginate–chitosan. II. A study of capsule stability and permeability. Biomaterials 1999; 20: 773–783
   PubMed Web of Science ®Google Scholar
• Gillam MJE. Human cytochrome P450 enzymes expressed in bacteria: reagents to probe molecular interactions in toxicology. Clin Exp Pharmacol Physiol 1998; 25: 877–886
   PubMed Web of Science ®Google Scholar
• Gonzalez FJ, Korzekwa KR. Cytochrome P450 expression systems. Annu Rev Pharmacol Toxicol 1995; 35: 369–390
   PubMed Web of Science ®Google Scholar
• Gosmann B, Rehm HJ. Oxygen uptake of microorganisms entrapped in Ca-alginate. Appl Microbiol Biotechnol 1986; 23: 163–167
   Web of Science ®Google Scholar
• Griffin DR, Yang F, Carta G, Gainer JL. Asymmetric reduction of acetophenone with calcium-alginate-entrapped baker's yeast in organic solvents. Biotechnol Prog 1998; 14: 588–593
   PubMed Web of Science ®Google Scholar
• Guengerich FP. Reactions and significance of cytochrome P450 enzymes. J Biol Chem 1991; 266: 10019–10022
   PubMed Web of Science ®Google Scholar
• Guengerich FP. Cytochrome P450 enzymes. Am Sci 1993; 81: 440–447
   Web of Science ®Google Scholar
• Hannoun BJM, Stephanopoulos G. Diffusion coefficients of glucose and ethanol in cell-free and cell-occupied calcium alginate membranes. Biotechnol Bioeng 1986; 28: 829–835
   PubMed Web of Science ®Google Scholar
• Ioannides C. Cytochrome P450, metabolic and toxicological aspects. CRC Press, Inc, Boca Raton, (FL) 1996
   Google Scholar
• Iwata H, Fujita K, Kushida H, Suzuki A, Konno Y, Nakamura K, Fujino A, Kamataki T. High catalytic activity of human cytochrome P450 co-expressed with human NADPH-cytochrome P450 reductase in Escherichia coli. Biochem Pharmacol 1998; 55: 1315–1325
   PubMed Web of Science ®Google Scholar
• Kanamori Y, Fujita K, Nakayama K, Kawai H, Kamataki T. Large-scale production of genetically engineered CYP3A4 in E. coli: application of a Jarfermenter. Drug Metab Pharmacokinet 2003; 18: 42–47
   PubMedGoogle Scholar
• Kawakami K, Abe T, Yoshida T. Silicone-immobilized biocatalysts effective for bioconversions in nonaqueous media. Enzyme Microb Technol 1992; 14: 371–375
   PubMed Web of Science ®Google Scholar
• Lee-Robichaud P, Kaderbhai MA, Wright JN, Akhtar M. Interaction of human CYP17 (P-450(14α),17α-hydroxylase-17,20-lyase) with cytochrome b5: importance of the orientation of the hydrophobic domain of cytochrome b5. Biochem J 1997; 321: 857–863
   PubMed Web of Science ®Google Scholar
• Li X. The use of chitosan to increase the stability of calcium alginate beads with entrapped yeast cells. Biotechnol Appl Biochem 1996; 23: 269–272
   PubMed Web of Science ®Google Scholar
• Makrides SC. Strategies for achieving high level expression of genes in Escherichia coli. Microbiol Rev 1996; 60: 512–538
   PubMedGoogle Scholar
• Maurel P. The CYP3A family. Cytochrome P450, metabolic and toxicological aspects, C Ioannides. CRC Press, Inc, Boca Raton, (FL) 1996; 241–270
   Google Scholar
• McGinnity DF, Griffin FJ, Moody GC, Voice M, Hanlon S, Friedberg T, Riley RJ. Rapid characterization of the major drug-metabolizing human hepatic cytochrome P-450 enzymes expressed in Escherichia coli. Drug Metab Dispos 1999; 27: 1017–1023
   PubMed Web of Science ®Google Scholar
• Nedovic VA, Durieux A, van Nedervelde L, Rosseels P, Vandegans J, Plaisant A-M, Simon J-P. Continuous cider fermentation with co-immobilized yeast and Leuconostoc oenos cells. Enzyme Microb Technol 2000; 26: 834–839
   PubMed Web of Science ®Google Scholar
• Omata T, Iida T, Tanaka A, Fukui S. Transformation of steroids by gel-entrapped Nocardia rhodocrous cells in organic solvents. Eur J Appl Microbiol Biotechnol 1979; 8: 143–155
   Google Scholar
• Omata T, Tanaka A, Fukui S. Bioconversion under hydrophobic conditions. Effect of solvent polarity on steroid transformations by gel-entrapped Nocardia rhodocrous cells. J Ferment Technol 1980; 58: 339–343
   Google Scholar
• Parikh A, Gillam EM, Guengerich FP. Drug metabolism by Eschericia coli expressing human cytochrome P450. Nat Biotechnol 1997; 15: 784–788
   PubMed Web of Science ®Google Scholar
• Parkinson A. Biotransformation of xenobiotics. Casarett & Doull's toxicology, the basic science of poisons5th edn, CD Klaassen. McGraw Hill), New York 1996; 6: 113–186
   Google Scholar
• Prakash S, Soe-Lin H. Strategy for cell therapy: polymers for live cell encapsulation and delivery. Trends Biomater Artif Organs 2004; 18: 24–25
   Google Scholar
• Pritchard MP, Ossetian R, Li DN, Henderson CJ, Burchell B, Wolf RC, Friedberg T. A general strategy for the expression of recombinant human cytochrome P450s in Escherichia coli using bacterial signal peptides: expression of CYP3A4, CYP2A6 and CYP2E1. Arch Biochem Biophys 1997; 345: 342–354
   PubMed Web of Science ®Google Scholar
• Pritchard MP, Glancey MJ, Blake JAR, Gilham DE, Burchell B, Wolf CR, Friedberg T. Functional co-expression of CYP2D6 and human NADPH-cytochrome P450 reductase in Escherichia coli. Pharmacogenetics 1998; 8: 33–42
   PubMedGoogle Scholar
• Pritchard MP, McLaughlin L, Friedberg T. Establishment of functional human cytochrome P450 monooxygenase systems in Escherichia coli. Methods Mol Biol 2006; 320: 19–29
   PubMedGoogle Scholar
• Renaud JP, Peyronneau MA, Urban P, Truan G, Cullin C, Pompon D, Beaune P, Mansuy D. Recombinant yeast in drug metabolism. Toxicology 1993; 82: 39–52
   PubMed Web of Science ®Google Scholar
• Sagara Y, Barnes HJ, Waterman MR. Expression in Escherichia coli of functional cytochrome P450c17 lacking its hydrophobic amino-terminal signal anchor. Arch Biochem Biophys 1993; 304: 272–278
   PubMedGoogle Scholar
• Sambrook J, Fritsch EF, Maniatis T. Molecular cloning: A laboratory manual2nd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, (NY) 1989; 1.8–1.9, 1.86
   Google Scholar
• Schneider A, Schmalix WA, Siruguri V, Groene EM, Harbach GJ, Kleingeist B, Lang D, Boker R, Belloc C, Beaune P, Greim H, Doehmer J. Stable expression of human cytochrome P450 3A4 in conjunction with human NADPH-cytochrome P450 oxidoreductase in V79 Chinese hamster cells. Arch Biochem Biophys 1996; 332: 295–304
   PubMedGoogle Scholar
• Serp D, Cantana E, Heinzen C, Von Stockar U, Marison IW. Characterization of an encapsulation device for the production of monodisperse alginate beads for cell immobilization. Biotechnol Bioeng 2000; 70: 41–53
   PubMed Web of Science ®Google Scholar
• Shimada T, Yamazaki H, Miura M, Inui Y, Guengerich FP. Interindividual variation in human liver cytochrome P450 enzyme involved in the oxidation of drugs: studies with liver microsomes of 30 Japanese and Caucasians. J Pharmacol Exp Ther 1994; 270: 414–423
   PubMed Web of Science ®Google Scholar
• Simon J-P. Facteurs affectant la productibite et la longevite d'un bioreacteur continu utilisant S. cerevisiae inclus dans une matrice d'alginate de calcium: limitation de la croissance cellulaire confine par la composition chimique du polymere utilize. Belg J Food Chem Biotechnol 1989a; 44: 6–16
   Google Scholar
• Simon J-P. Facteurs affectant la productivite et la longevite d'un bioreacteur continu utilisant Saccharomyces cerevisiae inclus dans une matrice d'alginate de calcium: 1. Effets des taux d'inoculation, des contre-ions de gelification et de la geometrie des matrices. Belg J Food Chem Biotechnol 1989b; 44: 183–191
   Google Scholar
• Steinig GH, Livingston AG, Stuckey DC. Bioconversion of hydrophobic compounds in a continuous closed-gas-loop-bioreactor: feasibility assessment and epoxide production. Biotechnol Bioeng 2000; 70: 553–563
   PubMedGoogle Scholar
• Trevan MD, Poltorak OM, Chukhrai ES. Stability in enzymes and cells. Molecular biology and biotechnology, JM Walker, EB Gingold. Royal Society of Chemistry, Cambridge 1993; 267–304
   Google Scholar
• Uno T, Okamoto S, Masuda S, Itoh A, Uno Y, Nakamura M, Kanamaru K, Yamagata H, Imaishi H. Bioconversion of small molecules by cytochrome P450 species expressed in Escherichia coli. Biotechnol Appl Biochem 2008; 50: 165–171
   PubMedGoogle Scholar
• Vail RB, Homann MJ, Hanna IH, Zaks A. Preparative synthesis of drug metabolites using human cytochrome P450s 3A4, 2C9 and 1A2 with NADPH-P450 reductase expressed in Escherichia coli. J Ind Microbiol Biotechnol 2005; 32: 67–74
   PubMed Web of Science ®Google Scholar
• Voice MW, Zhang Y, Wolf CR, Burchell B, Friedberg T. Effect of human cytochrome b5 on CYP3A4 activity and stability in vivo. Arch Biochem Biophys 1999; 366: 116–124
   PubMed Web of Science ®Google Scholar
• Waterman MR, Jenkins CM, Pikuleva I. Genetically engineered bacterial cells and applications. Toxicol Lett 1995; 82/83: 807–813
   Web of Science ®Google Scholar