Skip to main content

Microbial Models for Drug Metabolism

  • Chapter
  • First Online:
Biotransformations

Part of the book series: Advances in Biochemical Engineering/Biotechnology ((4143,volume 63))

Abstract

This review describes microbial transformation studies of drugs, comparing them with the corresponding metabolism in animal systems, and providing technical methods for developing microbial models. Emphasis is laid on the potential for selected microorganisms to mimic all patterns of mammalian biotransformations and to provide preparative methods for structural identification and toxicological and pharmacological studies of drug metabolites.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 39.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 54.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Velluz L, Bellet P (1959) C R Acad Sci 248:3453

    CAS  Google Scholar 

  2. Rosi D, Peruzotti G, Dennis EW, Berberian DA, Freele H, Archer S (1965) Nature 208:1005

    Article  CAS  Google Scholar 

  3. Rosi D, Peruzotti G, Dennis EW, Berberian DA, Freele H, Tullar BF, Archer S (1967) J Med Chem 10:867

    Article  CAS  Google Scholar 

  4. Fonken GS, Johnson RA (1972) Chemical oxidations with microorganisms. Marcel Dekker, New York

    Google Scholar 

  5. Karim A, Brown EA (1972) Steroids 20:41

    Article  CAS  Google Scholar 

  6. Ozaki M, Kariya T, Kato H, Kimura T (1972) Agr Biol Chem 36:451

    CAS  Google Scholar 

  7. Beukers R, Marx AF, Zuidweg MHJ (1972) Microbial conversion as a tool in the preparation of drugs. In: Ariëns EJ (ed) Drug design, vol 3. Academic Press, New york, p 1

    Google Scholar 

  8. Marschek WJ, Karim A (1973) Appl Microbiol 25:647

    Google Scholar 

  9. Sebek OK (1975) Acta Microbiol 22:381

    CAS  Google Scholar 

  10. Smith RV, Rosazza JP (1974) Arch Biochem Biophys 161:551

    Article  CAS  Google Scholar 

  11. Smith RV, Rosazza JP (1975) J Pharm Sci 64:1737

    Article  CAS  Google Scholar 

  12. Smith RV, Rosazza JP (1975) Biotech Bioeng 17:785

    Article  CAS  Google Scholar 

  13. Smith RV, Acosta DJ, Rosazza JP (1977) Adv Biochem Eng 5:69

    Article  CAS  Google Scholar 

  14. Rosazza JP (1978) Lloydia 41:279

    Google Scholar 

  15. Rosazza JP, Smith RV (1979) Adv Appl Microbiol 25:169

    Article  CAS  Google Scholar 

  16. Smith RV, Davis PJ (1980) Adv Biochem Eng. 14:61

    Article  CAS  Google Scholar 

  17. Smith RV, Rosazza JP (1982) Microbial transformations as a mean of preparing mammalian drug metabolites. In: Rosazza JP (ed) Microbial transformations of bioactive compounds. CRC, Boca Raton, FL, p 1

    Google Scholar 

  18. Smith RV, Rosazza JP (1983) J Nat Prod 46:79

    Article  CAS  Google Scholar 

  19. Clark AM, McChesney JD, Hufford CD (1985) Med Res Rev 5:231

    Article  CAS  Google Scholar 

  20. Reighard JB, Knapp JE (1986) Pharm Int 7:92

    CAS  Google Scholar 

  21. Davis PJ (1988) Dev Indust Microbiol (J Indust Microbiol suppl No 3) 29:197

    CAS  Google Scholar 

  22. Clark AM, Hufford CD (1991) Med Res Rev 11:473

    Article  CAS  Google Scholar 

  23. Griffiths DA, Best DJ, Jezequel SG (1991) Appl Microbiol Biotechnol 35:373

    Article  CAS  Google Scholar 

  24. Kieslich K (1976) Microbial transformation of non-steroid cyclic compounds. Wiley Interscience, New York

    Google Scholar 

  25. Csuk R, Glanzer Br (199) Chem Rev 91:49

    Article  Google Scholar 

  26. Santaniello E, Ferraboschi P, Grisenti P, Manzocchi A (1992) Chem Rev 92:1071

    Article  CAS  Google Scholar 

  27. Sariaslani FS, Rosazza JP (1984) Enzyme Microb Technol 6:242

    Article  CAS  Google Scholar 

  28. Sebek OK (1983) Mycologia 75:383

    Article  CAS  Google Scholar 

  29. Servi S (1990) Synthesis 1

    Google Scholar 

  30. Servi S (ed) (1992) Microbial reagents in organic synthesis. Kluwer Acad Publ, Dordrecht, The Netherlands

    Google Scholar 

  31. Sih CJ, Chen C-S (1984) Angew Chem Int Ed Engl 23:570

    Article  Google Scholar 

  32. Yamada H, Shimizu S (1988) Angew Chem Int Ed Engl 27:622

    Article  Google Scholar 

  33. Peterson DH, Murray HC, Eppstein SH, Reineke LM, Weintraub A, Meister PD, Leigh HM (1952) J Am Chem Soc 74:5933

    Article  CAS  Google Scholar 

  34. Peterson DH, Murray HC (1952) J Am Chem Soc 74:1871

    Article  CAS  Google Scholar 

  35. Auret BJ, Boyd DR, Robinson PM, Watson CG, Daly DW, Jerina DM (1971) J Chem Soc Chem Commun p 1585

    Google Scholar 

  36. Ferris JP, Fasco MJ, Stylianopoulou FL, Jerina DM, Daly JW, Jeffrey AM (1973) Arch Biochem Biophys 156:97

    Article  CAS  Google Scholar 

  37. Borchert HH (1991) Arch Pharm 324:401

    Google Scholar 

  38. Sebek OK, Perlman D (1971) Adv Appl Microbiol 14:123

    Article  CAS  Google Scholar 

  39. Sebek OK (1974) Lloydia 37:115

    CAS  Google Scholar 

  40. Iizuka H, Naito A (1981) Microbial conversion of steroids and alkaloids. University of Tokyo Press-Springer, Berlin Heidelberg New York

    Google Scholar 

  41. Mahato SB, Mukherjee A (1984) Phytochemistry 23:2131

    Article  CAS  Google Scholar 

  42. Mahato SB, Banerjee S (1985) Phytochemistry 24:1403

    Article  CAS  Google Scholar 

  43. Mahato SB, Banerjee S, Podder S (1989) Phytochemistry 28:7

    Article  CAS  Google Scholar 

  44. Mahato SB, Majumdar I (1993) Phytochemistry 34:883

    Article  CAS  Google Scholar 

  45. Holland HL (1981) Microbial and in vitro enzymic transformation of alkaloids (chap. 5). In: Manske RHF, Rodrigo RGA (eds) The alkaloids, vol 18. Academic Press, New York; p 323

    Google Scholar 

  46. Davis PJ (1984) Natural and semi-synthetic alkaloids. In: Kieslich K (ed) Biotechnology, vol 6 a. Verlag Chemie, Weinheim, p 207

    Google Scholar 

  47. Rosazza JPN, Duffel W (1986) The Alkaloids 27:323

    CAS  Google Scholar 

  48. Betts RE, Walters DE, Rosazza JP (1974) J Med Chem 17:599

    Article  CAS  Google Scholar 

  49. Brannon DR, Horton HR, Svoboda GH (1974) J Med Chem 17:653

    Article  CAS  Google Scholar 

  50. Knaggs AR, Cable KM, Cannell RJP, Sidebottom PJ, Wells GN, Sutherland DR (1995) Tetrahedron Lett 36:477

    Article  CAS  Google Scholar 

  51. Rao GP, Davis PJ (1997) Drug Metab Dispos 25:709

    CAS  Google Scholar 

  52. Schwartz H, Licht R-E, Radunz H-E (1993) Appl Microbiol Biotechnol 40:382

    Article  CAS  Google Scholar 

  53. Umezawa H, Takahashi Y, Fujii A, Saino T, Shirai T, Takita T (1973) J Antibiot 26:1117

    Google Scholar 

  54. El-Marakby SA, Clark AM, Baker JK, Hufford CD (1986) J Pharm Sci 75:614

    Article  CAS  Google Scholar 

  55. Kittelmann M, Lattmann R, Ghisalba O (1993) Biosci Biotechnol Biochem 57:1589

    CAS  Google Scholar 

  56. Gibson M, Soper CJ, Parfitt RT, Sewell GJ (1984) Enzyme Microb Technol 6:471

    Article  CAS  Google Scholar 

  57. Sewell GJ, Soper CJ, Parfitt RT (1984) Appl Microbiol Biotechnol 19:247

    Article  CAS  Google Scholar 

  58. Kunz DA, Reddy GS, Vatvars A (1985) Appl Environ Microbiol 50:831

    CAS  Google Scholar 

  59. Zeitler H-J, Niemer H (1969) Hoppe-Seyler’s Z Physiol Chem 350:366

    CAS  Google Scholar 

  60. Hufford CD, Collins CC, Clark AM (1979) J Pharm Sci 68:1239

    Article  CAS  Google Scholar 

  61. Hufford CD, El-Sharkawy SH, Jurgens TM, Mikell JR (1992) Pharmaceut Res 9:623

    Article  CAS  Google Scholar 

  62. Zhang D, Hansen EB, Deck J, Heinze TM, Henderson A, Korfmacher WA, Cerniglia CE (1997) Xenobiotica 27:301

    Article  CAS  Google Scholar 

  63. Griffiths DA, Brown DE, Jezequel SG (1993) Xenobiotica 23:1085

    Article  CAS  Google Scholar 

  64. Schwartz H, Liebieg-Weber A, Hochstatter H, Bottcher H (1996) Appl Microbiol Biotechnol 44:731

    Article  CAS  Google Scholar 

  65. Chien MM, Rosazza JP (1979) Drug Metabol Dispos 7:211

    CAS  Google Scholar 

  66. Chien MM, Rosazza JP (1980) Appl Environ Microbiol 40:741

    CAS  Google Scholar 

  67. Marshall VP, Cialdella JI, Baczynski LA, Liggett WF, Johnson RA (1989) J Antibiot 42:132

    CAS  Google Scholar 

  68. Kuo M-S, Chirby DG, Argoudelis AD, Cialdella JI, Coats JH, Marshall VP (1989) Anti-microb Ag Chemother 33:2089

    CAS  Google Scholar 

  69. Hezari M, Davis PJ (1992) Drug Metab Dispos 20:882

    CAS  Google Scholar 

  70. Hezari M, Davis PJ (1992) Drug Metab Dispos 21:259

    Google Scholar 

  71. Cannell RJP, Knaggs AR, Dawson MJ, Manchee GR, Eddershaw PJ, Waterhouse I, Sutherland DR, Bowers GD, Sidebottom PJ (1995) Drug Metab Dispos 23:724

    CAS  Google Scholar 

  72. Hanlon GW, Kooloobandi A, Hutt AJ (1994) J Appl Microbiol 76:442

    Article  CAS  Google Scholar 

  73. Hansen Jr EB, Cerniglia CE, Korfmacher WA, Miller DW, Heflich RH (1987) Drug Metab Dispos 15:97

    CAS  Google Scholar 

  74. Chen TS, Doss GA, Hsu A, Lingham RB, White RF, Monaghan RL (1993) J Nat Prod-Lloydia 56:755

    Article  CAS  Google Scholar 

  75. Otten S, Rosazza JP (1978) Appl Environ Microbiol 35:554

    CAS  Google Scholar 

  76. Otten S, Rosazza JP (1979) Appl Environ Microbiol 38:311

    CAS  Google Scholar 

  77. Otten SL, Rosazza JP (1981) J Nat Prod 44:562

    Article  CAS  Google Scholar 

  78. Otten SL, Rosazza JP (1983) J Biol Chem 258:1610

    CAS  Google Scholar 

  79. David L, Gayet J-C, Veschambre H (1985) Agr Biol Chem 49:2693

    CAS  Google Scholar 

  80. Davis PJ, Glade JC, Clark AM, Smith RV (1979) Appl Environ Microbiol 38:891

    CAS  Google Scholar 

  81. Zedan HH, El-Tayeb OM, Walash MN (1983) J Gen Microbiol 129:1035

    CAS  Google Scholar 

  82. Freitag DG, Foster RT, Coutts RT, Pickard MA, Pasutto FM (1997) Drug Metab Dispos 25:685

    CAS  Google Scholar 

  83. Chen TS, Doss G (1992) Merk and Co: Europ Patent 92/02,519

    Google Scholar 

  84. Chen TS, White LSR, Monaghan RL (1993) J Antibiot 46:131

    CAS  Google Scholar 

  85. Jones DE, Moore RH, Crowley GC (1970) J Chem Soc C 1725

    Google Scholar 

  86. Sebek OK, Dolak LA (1984) J Antibiot 37:136

    CAS  Google Scholar 

  87. Kuo MS, Yurek DA, Chirby DG, Cialdella JI, Marshall VP (1991) J Antibiot 44:1096

    CAS  Google Scholar 

  88. Raju MS, Wu GS, Gard A, Rosazza JP (1982) J Nat Prod 45:321

    Article  CAS  Google Scholar 

  89. Schmitz H, Claridge CA (1977) J Antibiot 30:635

    CAS  Google Scholar 

  90. Rosazza JP, Kammer M, Youel L, Smith RV, Erhardt PW, Truong DH, Leslie SW (1977) Xenobiotica 7:133

    CAS  Google Scholar 

  91. Verdeil JL, Bister-Miel F, Agier C, Plat M, Guignard JL, Viel C (1985) Compt Rend Acad Sci Paris 300, Série III:305

    Google Scholar 

  92. Dunn GL, Gallagher G, Davis D, Hoover RE, Stedman J (1973) J Med Chem 16:996

    Article  CAS  Google Scholar 

  93. Valenta JR, Dicuollo CJ, Fare LR, Miller JA, Pagano JF (1974) Appl Microbiol 28:995

    CAS  Google Scholar 

  94. Davis PJ, Yang S-K, Smith RV (1984) Appl Environ Microbiol 48:327

    CAS  Google Scholar 

  95. Davis PJ, Yang S-K, Smith RV (1985) Xenobiotica 15:1001

    Article  CAS  Google Scholar 

  96. Smith RV, Davis PJ, Kerr KM (1983) J Pharm Sci p 733

    Google Scholar 

  97. Reddy CSG, Acosta D, Davis PJ (1990) Xenobiotica 20:1281

    Article  CAS  Google Scholar 

  98. Foster BC, Thomas BH, Zamecnik J, Dawson BA, Wilson DL, Duhaime R, Solomonraj G, McGilveray IJ, Lodge BA (1991) Can J Microbiol 37:504

    Article  CAS  Google Scholar 

  99. Hufford CD, Baker JK, Clark AM (1981) J Pharm Sci 70:155

    Article  CAS  Google Scholar 

  100. Baker JK, Wohlford JG, Bradbury BJ, Wirth PW (1981) J Med Chem 24:666

    Article  CAS  Google Scholar 

  101. Caroll FI, Brine GA, Boldt KG, Cone EJ, Yousefnejad D, Vaupel DB, Buchwald WF (1981) J Med Chem 24:1047

    Article  Google Scholar 

  102. Foster GR, Coutts RT, Pasutto FM, Mozayani A (1988) Life Sci 42:285

    Article  CAS  Google Scholar 

  103. Hansen EB, Cho BP, Korfmacher WA, Cerniglia CE (1995) Xenobiotica 25:1081

    Article  CAS  Google Scholar 

  104. Clark AM, Hufford CD, McChesney JD (1981) Antimicrob Ag Chemother 19:337

    CAS  Google Scholar 

  105. Clark AM, Evans SL, Hufford CD, McChesney JD (1982) J Nat Prod 45:574

    Article  CAS  Google Scholar 

  106. Hufford CD, Clark AM, Quinones JK, Baker JK, MacChesney JD (1983) J Pharm Sci 72:92

    Article  CAS  Google Scholar 

  107. Clark AM, Hufford CD, Puri RK, McChesney JD (1984) Appl Environ Microbiol 47:540

    CAS  Google Scholar 

  108. Clark AM, Hufford CD, Gupta RC, Puri RK, McChesney JD (1984) Appl Environ Microbiol 47:537

    CAS  Google Scholar 

  109. Clark AM, McChesney JD, Hufford CD (1986) Pharm Res 3:170

    Article  CAS  Google Scholar 

  110. Foster BC, Buttar HS, Qureshi SA, McGilveray IJ (1989) Xenobiotica 19:539

    Article  CAS  Google Scholar 

  111. Foster BC, Litster DL, Wilson DL, Ormsby E, Dawson BA (1992) Xenobiotica 22:1221

    Article  CAS  Google Scholar 

  112. Lancini GC, Thiemann JE, Sartori G, Sensi P (1967) Experientia 23:899

    Article  CAS  Google Scholar 

  113. Banerjee UC (1993) Enzyme Microb Technol 15:1037

    Article  CAS  Google Scholar 

  114. Davis PJ, Guenthner L (1985) Xenobiotica 15:845

    Article  CAS  Google Scholar 

  115. El-Sharkawy SH, Abul-Hajj Y (1987) Pharmacol Res 4:353

    Article  CAS  Google Scholar 

  116. El-Sharkawy SH (1991) Appl Microbiol Biotechnol 35:436

    Article  CAS  Google Scholar 

  117. Davis PJ, Rosazza JP (1976) J Org Chem 41:2548

    Article  CAS  Google Scholar 

  118. Davis PJ, Wiese D, Rosazza JP (1977) Lloydia 40:239

    CAS  Google Scholar 

  119. Moussa C, Houziaux P, Danrée B, Azerad R (1997) Drug Metab Dispos 25:301

    CAS  Google Scholar 

  120. Moussa C, Houziaux P, Danrée B, Azerad R (1997) Drug Metab Dispos 25:311

    CAS  Google Scholar 

  121. Foster GR, Litster DL, Zamecnik J, Coutts RT (1991) Can J Microbiol 37:791

    Article  CAS  Google Scholar 

  122. Hansen Jr EB, Heflich RH, Korfmacher WA, Miller DW, Cerniglia CE (1988) J Pharm Sc 77:259

    Article  CAS  Google Scholar 

  123. Rosazza JP, Nicholas AW, Gustafson ME (1978) Steroids 31:671

    Article  CAS  Google Scholar 

  124. Fuska J, Prousek J, Rosazza JP, Budesinsky M (1982) Steroids 40:157

    Article  CAS  Google Scholar 

  125. Fuska J, Khandlova A, Sturdikova M, Rosazza JP (1985) Folia Microbiol 30:427

    Article  CAS  Google Scholar 

  126. El-Sharkawy S, Abul-Haii YJ (1988) Xenobiotica 18:365

    CAS  Google Scholar 

  127. El-Sharkawy S, Abul-Haiu YJ (1988) J Org Chem 53:515

    Article  CAS  Google Scholar 

  128. Kamimura H (1986) Appl Environ Microbiol 52:515

    CAS  Google Scholar 

  129. El-Sharkawy S, Abul-Hajj YJ (1987) J Nat Prod 50:520

    Article  CAS  Google Scholar 

  130. El-Sharkawy SH (1989) Acta Pharm Jugosl 39:303

    CAS  Google Scholar 

  131. El-Sharkawy SH, Selim MI, Afifi MS, Halaweish FT (1991) Appl Environ Microbiol 57:549

    CAS  Google Scholar 

  132. Abul-Hajj YJ (1986) J Nat Prod 49:244

    Article  CAS  Google Scholar 

  133. Fiorentino A, Pinto G, Pollio A, Previtera L (1991) Bioorg Med Chem Lett 1:673

    Article  CAS  Google Scholar 

  134. Pollio A, Pinto G, Della Greca M, De Maio A, Fiorentino A, Previtera L (1994) Phyto-chemistry 37:1269

    CAS  Google Scholar 

  135. Kutney JP (1993) Acc Chem Res 26:559

    Article  CAS  Google Scholar 

  136. Coutts RT, Foster GR, Jones GR, Meyers GE (1979) Appl Environ Microbiol 37:429

    CAS  Google Scholar 

  137. Foster BC, Coutts RT, Pasutto FM (1989) Xenobiotica 19:531

    Article  CAS  Google Scholar 

  138. Foster BC, Nantais LM, Wilson DL, By AW, Zamecnik J, Lodge BA (1990) Xenobiotica 20:583

    CAS  Google Scholar 

  139. Coutts RT, Foster GR, Pasutto FM (1981) Life Sci 29:1951

    Article  CAS  Google Scholar 

  140. Foster BC, Wilson DL, McGilveray IJ (1989) Xenobiotica 19:445

    Article  CAS  Google Scholar 

  141. Cerniglia CE, Hansen EBJr, Lambert KJ, Korfmacher WA, Miller DW (1988) Xenobiotica 18:301

    CAS  Google Scholar 

  142. Gorrod JW, Damani LA (1985) Biological oxidation of nitrogen in organic molecules. Ellis Horwood & VCH, Chichester & Weinheim

    Google Scholar 

  143. Holland HL (1992) Organic synthesis with oxidative enzymes. VCH, New York

    Google Scholar 

  144. Hartman RE, Kraus EF, Andres WW, Patterson EL (1964) Appl Microbiol 12:138

    CAS  Google Scholar 

  145. Chen X-J, Archelas A, Furstoss R (1993) J Org Chem 58:5528

    Article  CAS  Google Scholar 

  146. Pedragosa-Moreau S, Archelas A, Furstoss R (1993) J Org Chem 58:5533

    Article  CAS  Google Scholar 

  147. Sheehan D, Casey JP (1993) Comp Biochem Physiol 104B: 1

    CAS  Google Scholar 

  148. Sheehan D, Casey JP (1993) Comp Biochem Physiol 104B:7

    CAS  Google Scholar 

  149. Hu S-H, Genain G, Azerad R (1995) Steroids 60:337

    Article  CAS  Google Scholar 

  150. Cerniglia CE, Freeman JP, Mitchum RK (1982) Appl Environ Microbiol 43:1070

    CAS  Google Scholar 

  151. Petzoldt K, Kieslich K, Steinbeck H (1974) German Pat. Deutsch Offen 2,326,084 (19 May 1973)

    Google Scholar 

  152. Kieslich K, Vidic HJ, Petzoldt K, Hoyer JA (1976) Chem Ber 109:2259

    Article  CAS  Google Scholar 

  153. Neef G, Eder U, Petzoldt K, Seeger A, Wieglep P (1982) J Chem Soc Chem Commun 366

    Google Scholar 

  154. Vigne B, Archelas A, Fourneron J-D, Furstoss R (1986) Tetrahedron 42:2451

    Article  CAS  Google Scholar 

  155. Lacroix I, Biton J, Azerad R (1997) Bioorg Med Chem 5:1369

    Article  CAS  Google Scholar 

  156. Dowd CA, Sheehan D (1993) Biochem Soc Trans 22:58 S

    Google Scholar 

  157. Wong YWJ, Davis PJ (1989) Pharm Res 6:982

    Article  CAS  Google Scholar 

  158. Davila JC, Hseih GC, Acosta D, Davis PJ (1990) Toxicol Lett 54:23

    Article  CAS  Google Scholar 

  159. Krasnobajew V (1984) Terpenoids. In: Kieslich K (ed) Biotechnology, vol 6 a. Verlag Chemie, Weinheim, p 31

    Google Scholar 

  160. Tramper J, VanderPlas HC, Linko P (eds) (1985) Biocatalysis in organic synthesis. Elsevier, Amsterdam

    Google Scholar 

  161. Sedlacæk L (1988) CRC Crit Rev Biotechnol 7:187

    Article  Google Scholar 

  162. Lamare V, Furstoss R (1990) Tetrahedron 46:4109

    Article  CAS  Google Scholar 

  163. Hamada H, Fuchikami Y, Jansing RL, Kaminsky LS (1993) Phytochemistry 33:599

    Article  CAS  Google Scholar 

  164. Faber K (1992) Biotransformations in organic chemistry. Springer, Berlin-Heidelberg New York

    Google Scholar 

  165. Margolin AL (1993) Enzyme Microb Technol 15:266

    Article  CAS  Google Scholar 

  166. Crout DHG, Roberts SM, Jones JB (eds) (1993) Enzymes in organic synthesis. In: Tetrahedron: Asymmetry, Special Issues 4:757

    Google Scholar 

  167. Crout DHG, Griengl H, Faber K, Roberts SM (eds) (1994) Proceedings of the European Symposium on Biocatalysis, September 12–17, 1993, Graz, Austria. In: Biocatalysis, Special Issues 9:722

    Google Scholar 

  168. Wong C-H, Whitesides GM (1994) Enzymes in synthetic organic chemistry. Pergamon, Oxford

    Google Scholar 

  169. Dahl ML, Nordin C, Bertilsson L (1991) Ther Drug Monit 13:189

    Article  CAS  Google Scholar 

  170. Drauz K, Waldmann H (eds) (1995) Enzyme catalysis in organic synthesis. VCH, Weinheim

    Google Scholar 

  171. Hanson JR (1995) An introduction to biotransformation in organic chemistry. WH Freeman, Oxford

    Google Scholar 

  172. Azerad R (1995) Bull Soc Chim 132:17

    CAS  Google Scholar 

  173. Cannell RJP, Rashid T, Ismail IM, Sidebottom PJ, Kaggs AR, Marshall PS (1997) Xenobiotica 27:147

    Article  CAS  Google Scholar 

  174. Sariaslani FS, Kunz DA (1986) Biochem Biophys Res Commun 141:405

    Article  CAS  Google Scholar 

  175. Byrne GS, Ward OP (1989) Biotechnol Bioeng 33:912

    Article  CAS  Google Scholar 

  176. Hermans JJR, Thijssen HHW (1989) Biochem Pharmacol 38:3365

    Article  CAS  Google Scholar 

  177. Hermans JJR, Thijssen HHW (1992) Drug Metab Dispos 20:268

    CAS  Google Scholar 

  178. Kaminsky LS, Zhang ZY (1997) Pharmacol Ther 73:67

    Article  CAS  Google Scholar 

  179. Thonnart N, Vanhaelen M, Vanhaelen-Fastre R (1977) J Med Chem 20:604

    Article  CAS  Google Scholar 

  180. Thonnart N, Vanhaelen M, Vanhaelen-Fastre R (1979) Drug Metab Dispos 7:449

    CAS  Google Scholar 

  181. Rizzo JD, Davis PJ (1988) Xenobiotica 18:1425

    Article  CAS  Google Scholar 

  182. Davis PJ, Rizzo JD (1982) Appl Environ Microbiol 43:884

    CAS  Google Scholar 

  183. Rizzo JD, Davis PJ (1989) J Pharm Sci 78:183

    Article  CAS  Google Scholar 

  184. Wong YWJ, Davis PJ (1991) J Pharm Sci 80:305

    Article  CAS  Google Scholar 

  185. Griffiths DA, Brown DE, Jezequel SG (1992) Appl Microbiol Biotechnol 37:169

    Article  CAS  Google Scholar 

  186. Mandal NC, Chakrabartty PK, Jash SS, Basu K, Bhattacharyya P (1990) Ind J Exp Biol 28:189

    CAS  Google Scholar 

  187. Takeshita M, Miura M, Unuma Y, Iwai S, Sato I, Arai T, Kosaka K (1995) Res Commun Mol Pathol Pharmacol 88:123

    CAS  Google Scholar 

  188. Holland HL, Riemland E (1985) Can J Chem 63:1121

    Article  CAS  Google Scholar 

  189. Lacroix I, Biton J, Azerad R, unpublished results

    Google Scholar 

  190. Biton J, Azerad R, Lacroix I, Marchandeau JP (1997) Eur Pat 0,808,845 A2

    Google Scholar 

  191. Potter WZ, Calil HM (1981) Metabolites of tricyclic antidepressants: biological activity and clinical implications. In: Usdin E (ed) Clinical pharmacology in psychiatry. Elsevier, New York, p 311

    Google Scholar 

  192. Breyerpfaff U, Nill K (1995) Xenobiotica 25:1311

    Article  CAS  Google Scholar 

  193. Zeugin TB, Brosen K, Meyer UA (1990) Anal Biochem 189:99

    Article  CAS  Google Scholar 

  194. Nordin C, Bertilsson L (1995) Clin Pharmacokinet 28:26

    Article  CAS  Google Scholar 

  195. Clark AM, Clinton RT, Baker JK, Hufford CD (1983) J Pharm Sci 72:1288

    Article  CAS  Google Scholar 

  196. Hufford CD, Capiton GA, Clark AM, Baker JK (1981) J Pharm Sci 70:151

    Article  CAS  Google Scholar 

  197. Zhang DL, Evans FE, Freeman JP, Duhart B, Cerniglia CE (1995) Drug Metab Dispos 23:1417

    CAS  Google Scholar 

  198. Grislain L, Gelé P, Bromet N, Luijten W, Volland JP, Mocaer E, Kamoun A (1990) Eur J Drug Metab Pharmacokinetics 15:339

    Article  CAS  Google Scholar 

  199. Beaumal JY, Lefoulon F, Azerad R, unpublished results

    Google Scholar 

  200. Azerad R (1997) Hydroxylations at saturated carbons. In: Katsuki T (ed) Asymmetric oxydation reactions. A practical approach. Oxford Univ Press, in press

    Google Scholar 

  201. Lee IS, Hufford CD (1990) Pharmacol Therap 48:345

    Article  CAS  Google Scholar 

  202. Lee I-S, ElSohly HL, Croom EM, Hufford CD (1989) J Nat Prod 52:337

    Article  CAS  Google Scholar 

  203. Lee I-S, ElSohly HL, Hufford CD (1990) Pharm Res 7:199

    Article  CAS  Google Scholar 

  204. Hufford CD, Lee I-S, ElSohly HL, Chi HT, Baker JK (1990) Pharm Res 7:923

    Article  CAS  Google Scholar 

  205. Johnson RA, Herr ME, Murray HC, Fonken GS (1968) J Org Chem33:3217

    Article  CAS  Google Scholar 

  206. Furstoss R, Archelas A, Waegell B (1980) Tetrahedron Lett 21:451

    Article  CAS  Google Scholar 

  207. Fourneron J-D, Archelas A, Vigne B, Furstoss R (1987) Tetrahedron 43:2273

    Article  CAS  Google Scholar 

  208. Hu YL, Highet RJ, Marion D, Ziffer H (1991) J Chem Soc Chem Commun 1176

    Google Scholar 

  209. Ziffer H, Hu Y, Pu Y (1992) Beauveria sulfurescens mediated oxidation of dihydroarte-misinin derivatives. In: Servi S (ed) Microbial reagents in organic synthesis. Kluwer Academic Publ, Dordrecht, p 361

    Google Scholar 

  210. Hu YL, Ziffer H, Li GY, Yeh HJC (1992) Bioorg Chem 20:148

    Article  CAS  Google Scholar 

  211. Hufford CD, Khalifa SI, Orabi KI, Wiggers FT, Kumar R, Rogers RD, Campana CF (1995) J Nat Prod 58:751

    Article  CAS  Google Scholar 

  212. Khalifa SI, Baker JK, Jung M, Mcchesney JD, Hufford CD (1995) Pharmaceut Res 12:1493

    Article  CAS  Google Scholar 

  213. Gueritte-Voegelein F, Guénard D, Potier P (1987) J Nat Prod 50:9

    Article  CAS  Google Scholar 

  214. Kingston DGI, Samaranayake G, Ivey CA (1990) J Nat Prod 53:1

    Article  CAS  Google Scholar 

  215. Kingston DGI (1991) Pharmac Ther 52:1

    Article  CAS  Google Scholar 

  216. Montsarrat B, Mariel E, Cros S, Garès M, Guénard D, Guéritte-Voegelein F, Wright M (1990) Drug Metab Dispos 18:895

    Google Scholar 

  217. Walle T, Kumar GN, Mcmillan JM, Thornburg KR, Walle UK (1993) Biochem Pharmacol 46:1661

    Article  CAS  Google Scholar 

  218. Harris JW, Katki A, Anderson LW, Chmurny GN, Paukstelis JV, Collins JW (1994) J Med Chem 37:706

    Article  CAS  Google Scholar 

  219. Kumar GN, Oatis JE, Thornburg KR, Heldrich FJ, Hazard ES, Walle T (1994) Drug Metab Dispos 22:177

    CAS  Google Scholar 

  220. Monegier B, Gaillard C, Sable S, Vuilhorgne M (1994) Tetrahedron Lett 35:3715

    Article  CAS  Google Scholar 

  221. Commercon A, Bourzat JD, Bezard D, Vuilhorgne M (1994) Tetrahedron 50:10,289

    Article  CAS  Google Scholar 

  222. Hamada H, Sanada K, Furuya T, Kawabe S, Jaziri M (1996) Nat Prod Lett 9:47

    Article  CAS  Google Scholar 

  223. Hanson RL, Wasylyk JM, Nanduri VB, Cazzulino DL, Patel RN, Szarka LJ (1994) J Biol Chem 269:22,145

    CAS  Google Scholar 

  224. Hu SH, Tian XF, Zhu WH, Fang QC (1996) Tetrahedron 52:8739

    Article  CAS  Google Scholar 

  225. Hu SH, Tian XF, Zhu WH, Fang QC (1998) J Nat Prod, in press

    Google Scholar 

  226. Hu S, Tian X, Zhu W, Fang Q (1997) Biocat Biotransform 14:241

    Article  CAS  Google Scholar 

  227. Stone R (1993) Science 260:154

    Article  CAS  Google Scholar 

  228. Stierle A, Strobel G, Stierle D (1993) Science 260:214

    Article  CAS  Google Scholar 

  229. Stierle A, Strobel G, Stierle D, Grothaus P, Bignami G (1995) J Nat Prod-Lloydia 58:1315

    Article  CAS  Google Scholar 

  230. Strobel G, Yang XS, Sears J, Kramer R, Sidhu RS, Hess WM (1996) Microbiology-UK 142:435

    Article  CAS  Google Scholar 

  231. Greene S, Watanabe K, Braatz-Trulson J, Lou L (1995) Biochem Pharmacol 50:861

    Article  CAS  Google Scholar 

  232. Williamson R, Yea CM, Robson PA, Curnock AP, Gadher S, Hambleton AB, Woodward K, Bruneau JM, Hambleton P, Moss D, Thomson AT, Spinella-Jaegle S, Morand P, Courtin O, Sautès C, Westwood R, Hercend T, Kuo EA, Ruuth E (1995) J Biol Chem 270:22,467

    CAS  Google Scholar 

  233. Dupront A (1995) personal communication

    Google Scholar 

  234. Brodie BB, Baer JE, Craig LC (1951) J Biol Chem 188:567

    CAS  Google Scholar 

  235. Palmer KH, Martin B, Baggett B, Wall ME (1969) Biochem Pharmacol 18:1845

    Article  CAS  Google Scholar 

  236. Caroll FI, Smith D, Wall ME (1974) J Med Chem 17:985

    Article  Google Scholar 

  237. Caroll FI, Philip A, Coleman MC (1976) Tetrahedron Lett 21:1757

    Article  Google Scholar 

  238. Beerman B, Leander K, Lindstrom B (1976) Acta Chem Scand B 30:465

    Article  Google Scholar 

  239. Flouvat B, Resplandy G, Roux A, Friocourt P, Viel C, Plat M (1988) Therapie 43:255

    CAS  Google Scholar 

  240. Caroll FI, Abraham P, Gaetano K, Mascarella SW, Wohl RA, Lind J, Petzoldt K (1991) J Chem Soc Perkin Trans 1,3017

    Google Scholar 

  241. Fenard S, Koenig J-J, Jaillon P, Jarreau FX (1982) J Pharmacol 13:129

    Google Scholar 

  242. Eckenrode FM (1984) J Nat Prod 47:882

    Article  CAS  Google Scholar 

  243. Siebers-Wolff S, Arfmann H-A, Abraham W-R, Kieslich K (1993) Biocatalysis 8:47

    Article  CAS  Google Scholar 

  244. Jarreau FX, Herré L, Azerad R, Ogerau T (1985) Fr Pat No 85/11,221

    Google Scholar 

  245. Azerad R(1993) Chimia 47:93

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1999 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Azerad, R. (1999). Microbial Models for Drug Metabolism. In: Faber, K. (eds) Biotransformations. Advances in Biochemical Engineering/Biotechnology, vol 63. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-69791-8_8

Download citation

  • DOI: https://doi.org/10.1007/3-540-69791-8_8

  • Received:

  • Published:

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-540-64496-5

  • Online ISBN: 978-3-540-69791-6

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics