Structures of human cytochrome P450 2B6 and rabbit cytochrome P450 2B4 in complex with two molecules of the calcium channel blocker amlodipine have been determined by X-ray crystallography. The presence of two drug molecules suggests clear substrate access channels in each P450. According to a previously established nomenclature, amlodipine molecules were trapped in access pathway 2f in P450 2B6 and in pathway 2a or 2f in P450 2B4. These pathways overlap for part of the length and then diverge as they extend toward the protein surface. A previously described solvent channel was also found in each enzyme. The results indicate that key residues located on the surface and at the entrance of the substrate access channels in each of these P450s may play a crucial role in guiding substrate entry. In addition, the region of P450 2B6 and 2B4 involving helices B', F, F', and G' and part of helix G is substantially more open in the amlodipine complexes than in the corresponding 4-(4-chlorophenyl)imidazole complexes. The increased active site volume observed results from the major retraction of helices F, F', and B' and the β4 sheet region located close to the binding cavity to accommodate amlodipine. These structures demonstrate novel insight into distinct conformational states not observed with previous P450 2B structures and provide clear evidence of the substrate access channels in two drug-metabolizing P450s. In addition, the structures exhibit the versatility that can be exploited via in silico studies with other P450 2B6 ligands as large as raloxifene and itraconazole.

译文

已通过x射线晶体学确定了人细胞色素P450 2B6和兔细胞色素P450 2B4与钙通道阻滞剂氨氯地平的两个分子复合物的结构。两个药物分子的存在表明每个p450中有清晰的底物进入通道。根据先前建立的命名法,氨氯地平分子被捕获在P450 2B6的通路2f和P450 2B4的通路2a或2f中。这些途径在部分长度上重叠,然后在向蛋白质表面延伸时发散。在每种酶中也发现了先前描述的溶剂通道。结果表明,这些p450中每个p450中位于基板进入通道的表面和入口处的关键残留物可能在引导基板进入中起关键作用。此外,涉及螺旋B',F,F' 和G' 和部分螺旋G的P450 2B6和2B4的区域在氨氯地平络合物中比在相应的4-(4-氯苯基) 咪唑络合物中基本上更开放。观察到的活性位点体积增加是由于螺旋F的主要回缩导致的,f' 和B' 以及靠近结合腔的 β4片区域以容纳氨氯地平。这些结构展示了对先前P450 2B结构未观察到的不同构象状态的新见解,并提供了两个药物代谢P450中底物进入通道的明确证据。此外,该结构具有通用性,可以通过与雷洛昔芬和伊曲康唑等其他P450 2B6配体进行计算机研究来利用。

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