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      Common and Uncommon Cytochrome P450 Reactions Related to Metabolism and Chemical Toxicity

      Chemical Research in Toxicology

      American Chemical Society (ACS)

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          Abstract

          Cytochrome P450 (P450) enzymes catalyze a variety of reactions and convert chemicals to potentially reactive products as well as make compounds less toxic. Most of the P450 reactions are oxidations. The majority of these can be rationalized in the context of an FeO(3+) intermediate and odd electron abstraction/rebound mechanisms; however, other iron-oxygen complexes are possible and alternate chemistries can be considered. Another issue regarding P450-catalyzed reactions is the delineation of rate-limiting steps in the catalytic cycle and the contribution to reaction selectivity. In addition to the rather classical oxidations, P450s also catalyze less generally discussed reactions including reduction, desaturation, ester cleavage, ring expansion, ring formation, aldehyde scission, dehydration, ipso attack, one-electron oxidation, coupling reactions, rearrangement of fatty acid and prostaglandin hydroperoxides, and phospholipase activity. Most of these reactions are rationalized in the context of high-valent iron-oxygen intermediates and Fe(2+) reductions, but others are not and may involve acid-base catalysis. Some of these transformations are involved in the bioactivation and detoxication of xenobiotic chemicals.

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          Author and article information

          Journal
          Chemical Research in Toxicology
          Chem. Res. Toxicol.
          American Chemical Society (ACS)
          0893-228X
          1520-5010
          June 2001
          June 2001
          : 14
          : 6
          : 611-650
          11409933
          © 2001
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