The objective of this study was to determine the sites and modes of interaction of the most common oligomers of B‐type procyanidins (PCs) with the active form of the matrix metalloproteinase‐7 (MMP‐7) and some molecular properties of the PCs by using theoretical methods. These data may provide useful insights into the ability of PCs to act as selective MMP‐7 inhibitors. Some stereoisomers that predominated in the analyzed PCs (PB2, PC1, tetramer) could act as selective inhibitors of MMP‐7 due to their interaction with amino acids of the subsites S2 and/or S1′ in the active site, and with some specific amino acids of MMP‐7 that bind to cholesterol sulfate to promote proteolysis of the cell membrane. Hydrogen bonding was the main interaction of PB2 and PC1 with MMP‐7, while in the tetramer, the van der Waals interactions prevailed. The determination of molecular properties such as chemical reactivity and stability by the highest occupied molecular orbital and lowest unoccupied molecular orbital gap, revealed that oligomers of PCs acquired very stable poses in their docking with MMP‐7. Polarizability seems to be an important factor for PCs with large molecular volume (PC1, tetramer) to establish contact with amino acids of narrow subsites in the active site (S2, S1′) and amino acids located outside the active site.

中文翻译：

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原花青素低聚物与基质金属蛋白酶-7活性形式之间的相互作用：理论上的见解

这项研究的目的是确定B型原花青素（PC）最常见的寡聚体与基质金属蛋白酶7（MMP-7）的活性形式的相互作用的位点和相互作用模式，以及PC的一些分子特性，使用理论方法。这些数据可能提供有用的见解，使PC发挥选择性MMP-7抑制剂的作用。在分析的PC中占主导地位的某些立体异构体（PB2，PC1，四聚体）可以作为MMP-7的选择性抑制剂，因为它们与活性位点S2和/或S1'的氨基酸相互作用，并且与某些特定的氨基酸相互作用与硫酸胆固醇结合的MMP-7酸，可促进细胞膜的蛋白水解。氢键是PB2和PC1与MMP-7的主要相互作用，而在四聚体中，范德华相互作用占优势。通过最高占据分子轨道和最低未占据分子轨道间隙来确定分子特性，例如化学反应性和稳定性，表明PC的低聚物在与MMP-7对接时获得了非常稳定的姿势。极化率似乎是大分子PC（PC1，四聚体）与活性位点（S2，S1'）中狭窄亚位的氨基酸和活性位点之外的氨基酸建立接触的重要因素。