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RESEARCH FRONT
Contents Vol 63(11)

A Bioorganometallic Chemistry Overview: From Cytochrome P450 Enzyme Metabolism of Organotin Compounds to Organorhodium-Hydroxytamoxifen Complexes with Potential Anti-Cancer Properties; A 37 Year Perspective at the Interface of Organometallic Chemistry and Biology

Richard H. Fish A
+ Author Affiliations
- Author Affiliations

A Lawrence Berkeley National Laboratory, University of California, Berkeley, CA 94708, USA. Email: rhfish@lbl.gov

Australian Journal of Chemistry 63(11) 1505-1513 https://doi.org/10.1071/CH10239
Submitted: 10 June 2010  Accepted: 16 October 2010   Published: 11 November 2010

Abstract

A 37 year perspective on bioorganometallic chemistry studies, which included metabolism of organotin compounds with cytochrome P450 enzymes, and their biomimics; reactions of organorhodium aqua complexes with nucleobases, nucleosides, and nucleotides; supramolecular organorhodium-nucleobase complexes as hosts for aromatic amino acid and aromatic carboxylic acid guests; regioselective reduction of NAD+ biomimics with an organorhodium hydride; tandem catalysis of an organorhodium hydride reduction to provide a 1,4-NADH biomimic for horse liver dehydrogenase stereoselective reduction of achiral ketones to chiral alcohols, and oxidation reactions with cytochrome P450 enzymes; and organorhodium-hydroxytamoxifen pharmaceuticals, will be presented. Each of these areas of bioorganometallic chemistry will be briefly discussed in this personal synopsis of the new, important, and exciting field of bioorganometallic chemistry, and its impact on metal-based drug research.


References

[1]  (a) R. H. Fish, E. C. Kimmel, J. E. Casida, J. Organomet. Chem. 1975, 93, C1.
         | Crossref | GoogleScholarGoogle Scholar |
      (b) R. H. Fish, E. C. Kimmel, J. E. Casida, J. Organomet. Chem. 1976, 118, 41.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) R. H. Fish, J. E. Casida, E. C. Kimmel, ACS Symp. Ser. 1978, 82, 82.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) D. de Vos, R. Willem, M. Gielen, K. E. van Wingerden, K. Nooter, Metal-Based Drugs 1998, 5, 179.
         | Crossref | GoogleScholarGoogle Scholar |

[2]  R. H. Fish, R. T. Price, Organometallics 1989, 8, 225.
         | Crossref | GoogleScholarGoogle Scholar |

[3]  (a) R. H. Fish, J. E. Casida, E. C. Kimmel, Tetrahedron Lett. 1977, 18, 3515.
         | Crossref | GoogleScholarGoogle Scholar |
      (b) R. H. Fish, B. M. Broline, J. Organomet. Chem. 1977, 136, C41.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) R. H. Fish, B. M. Broline, J. Organometal. Chem. 1978, 159, 255.
         | Crossref | GoogleScholarGoogle Scholar |

[4]  D. P. Smith, E. B. Baralt, B. Morales, M. M. Olmstead, M. F. Maestre, R. H. Fish, J. Am. Chem. Soc. 1992, 114, 10647.
         | Crossref | GoogleScholarGoogle Scholar |

[5]  (a) H. Chen, M. M. Olmstead, M. F. Maestre, R. H. Fish, Angew. Chem. Int. Ed. Engl. 1995, 34, 1514.
         | Crossref | GoogleScholarGoogle Scholar |
      (b) D. P. Smith, M. M. Olmstead, M. F. Maestre, R. H. Fish, Organometallics 1993, 12, 593.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) H. Chen, M. M. Olmstead, M. F. Maestre, R. H. Fish, J. Am. Chem. Soc. 1995, 117, 9097.
         | Crossref | GoogleScholarGoogle Scholar |

[6]  H. Chen, M. F. Maestre, R. H. Fish, J. Am. Chem. Soc. 1995, 117, 3631.
         | Crossref | GoogleScholarGoogle Scholar |

[7]  (a) H. Chen, S. Ogo, R. H. Fish, J. Am. Chem. Soc. 1996, 118, 4993.
         | Crossref | GoogleScholarGoogle Scholar |
      (b) S. Ogo, S. Nakamura, H. Chen, K. Isobe, Y. Watanabe, R. H. Fish, J. Org. Chem. 1998, 63, 7151.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) R. Bakhtiar, H. Chen, S. Ogo, R. H. Fish, Chem. Commun. 1997, 2135.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) A. Elduque, D. Carmona, L. A. Oro, M. Eisenstein, R. H. Fish, J. Organomet. Chem. 2003, 668, 123.
         | Crossref | GoogleScholarGoogle Scholar |

[8]  (a) H. C. Lo, O. Buriez, J. B. Kerr, R. H. Fish, Angew. Chem. Int. Ed. 1999, 38, 1429.
         | Crossref | GoogleScholarGoogle Scholar |
      (b) H. C. Lo, C. Leiva, O. Buriez, J. B. Kerr, M. M. Olmstead, R. H. Fish, Inorg. Chem. 2001, 40, 6705.
         | Crossref | GoogleScholarGoogle Scholar |

[9]  H. C. Lo, R. H. Fish, Angew. Chem. Int. Ed. 2002, 41, 478.
         | Crossref | GoogleScholarGoogle Scholar |

[10]  (a) J. D. Ryan, R. H. Fish, D. S. Clark, ChemBioChem 2008, 9, 2579.
         | Crossref | GoogleScholarGoogle Scholar | 18816544PubMed |
      (b) J. Lutz, F. Hollmann, T. V. Ho, A. Schnyder, R. H. Fish, A. Schmid, J. Organomet. Chem. 2004, 689, 4783.
         | Crossref | GoogleScholarGoogle Scholar |

[11]  R. H. Fish, G. Jaouen, Organometallics 2003, 22, 2166 and references therein. 10.1021/OM0300777
      (b) C. S. Allardyce, P. J. Dyson, D. J. Ellis, S. L. Heath, Chem. Commun. 2001, 1396.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) C. S. Allardyce, P. J. Dyson, D. J. Ellis, P. A. Salter, R. Scopelliti, J. Organomet. Chem. 2003, 668, 35.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) R. E. Morris, R. E. Aird, P. D. Murdoch, H. M. Chen, J. Cummings, N. D. Hughes,, R. E. Morris, R. E. Aird, P. D. Murdoch, H. M. Chen, J. Cummings, N. D. Hughes,, J. Med. Chem. 2001, 44, 3616.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) H. Chen, J. A. Parkinson, S. Parsons, R. A. Coxall, R. O. Gould, P. J. Sadler, J. Am. Chem. Soc. 2002, 124, 3064.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) F. Wang, H. Chen, J. A. Parkinson, P. D. Murdoch, P. J. Sadler, Inorg. Chem. 2002, 41, 4509.
         | Crossref | GoogleScholarGoogle Scholar |
      G. Jaouen, S. Top, A. Vessières, R. Alberto, J. Organomet. Chem. 2000, 600, 23 and references therein. 10.1016/S0022-328X(00)00036-X
      (h) G. Jaouen, Chem. Br. 2001, 36.
      (i) P. Köpf-Maier, Eur. J. Clin. Pharmacol. 1994, 47, 1.
         | Crossref | GoogleScholarGoogle Scholar |
      M. Melchart, P. J. Sadler, in Bioorganometallics 2005, Ch. 2, p. 39 (Ed. G. Jaouen) (Wiley-VCH: Weinheim).
      G. Jaouen, S. Top, A. Vessières, in Bioorganometallics 2005, Ch. 3, p. 65 (Ed. G. Jaouen) (Wiley-VCH: Weinheim).
      R. Alberto, in Bioorganometallics 2005, Ch. 4, p. 97 (Ed. G. Jaouen) (Wiley-VCH: Weinheim).
      (m) R. Dagani, Chem. Engineer. News 2002, 80, 23.
      (n) A. Dorcier, C. G. Hartinger, R. Scopelliti, R. H. Fish, B. K. Keppler, P. J. Dyson, J. Inorg. Biochem. 2008, 102, 1066.
         | Crossref | GoogleScholarGoogle Scholar |
      (o) A. F. A. Peacock, P. J. Sadler, Chem. Asian J. 2008, 11, 1886.
      (p) C. G. Hartinger, P. J. Dyson, Chem. Soc. Rev. 2009, 38, 391.
         | Crossref | GoogleScholarGoogle Scholar |
      (q) K. Strohfeldt, M. Tacke, Chem. Soc. Rev. 2008, 37, 1174.
         | Crossref | GoogleScholarGoogle Scholar |

[12]  S. Top, A. Vessières, G. Jaouen, R. H. Fish, Organometallics 2006, 25, 3293.
         | Crossref | GoogleScholarGoogle Scholar |

[13]  S. Top, I. Efremenko, N.-M. Rager, A. Vessières, G. Jaouen, R. H. Fish, Inorg. Chem. 2010, in press.

[14]  I. Efremenko, S. Top, J. M. L. Martin, R. H. Fish, Dalton Trans. 2009, 4334.
         | Crossref | GoogleScholarGoogle Scholar |

[15]  A. Volbeda, M. H. Charon, C. Piras, E. C. Hatchikian, M. Frey, J. Fontecilla-Camps, Nature 1995, 373, 580.
         | Crossref | GoogleScholarGoogle Scholar |