Sansen Stefaan, Yano Jason K, Reynald Rosamund L, Schoch Guillaume A, Griffin Keith J, Stout C David, Johnson Eric F
Department of Molecular and Experimental Medicine, The Scripps Research Institute, La Jolla, CA 92037, USA.
J Biol Chem. 2007 May 11;282(19):14348-55. doi: 10.1074/jbc.M611692200. Epub 2007 Feb 20.
Microsomal cytochrome P450 family 1 enzymes play prominent roles in xenobiotic detoxication and procarcinogen activation. P450 1A2 is the principal cytochrome P450 family 1 enzyme expressed in human liver and participates extensively in drug oxidations. This enzyme is also of great importance in the bioactivation of mutagens, including the N-hydroxylation of arylamines. P450-catalyzed reactions involve a wide range of substrates, and this versatility is reflected in a structural diversity evident in the active sites of available P450 structures. Here, we present the structure of human P450 1A2 in complex with the inhibitor alpha-naphthoflavone, determined to a resolution of 1.95 A. alpha-Naphthoflavone is bound in the active site above the distal surface of the heme prosthetic group. The structure reveals a compact, closed active site cavity that is highly adapted for the positioning and oxidation of relatively large, planar substrates. This unique topology is clearly distinct from known active site architectures of P450 family 2 and 3 enzymes and demonstrates how P450 family 1 enzymes have evolved to catalyze efficiently polycyclic aromatic hydrocarbon oxidation. This report provides the first structure of a microsomal P450 from family 1 and offers a template to study further structure-function relationships of alternative substrates and other cytochrome P450 family 1 members.
微粒体细胞色素P450 1家族酶在异源物解毒和前致癌物激活过程中发挥着重要作用。P450 1A2是人类肝脏中表达的主要细胞色素P450 1家族酶,广泛参与药物氧化反应。该酶在诱变剂的生物激活过程中也具有重要意义,包括芳胺的N-羟基化反应。P450催化的反应涉及多种底物,这种多功能性体现在现有P450结构活性位点明显的结构多样性上。在此,我们展示了与抑制剂α-萘黄酮结合的人P450 1A2的结构,分辨率为1.95 Å。α-萘黄酮结合在血红素辅基远端表面上方的活性位点中。该结构揭示了一个紧凑、封闭的活性位点腔,高度适合相对较大的平面底物的定位和氧化。这种独特的拓扑结构明显不同于P450 2和3家族酶已知的活性位点结构,展示了P450 1家族酶如何进化以高效催化多环芳烃氧化。本报告提供了第一个来自1家族的微粒体P450的结构,并为进一步研究替代底物和其他细胞色素P-450 1家族成员的结构-功能关系提供了一个模板。