喜树碱细胞毒性的DFT研究Ⅳ——伊立替康的活性和非活性形式

IF 0.9 Q4 CHEMISTRY, MULTIDISCIPLINARY Acta Chimica Slovaca Pub Date : 2023-01-01 DOI:10.2478/acs-2023-0001
M. Štekláč, M. Breza
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引用次数: 0

摘要

采用B3LYP/6-311G*处理,优化了伊立替康(CPT-11)单重态中性内酯、中性羧基和阴离子羧酸盐形态及其与Cu(II)双重态配合物的结构。评价了金属离子亲和力(MIA)、Cu电荷和CPT可能活性位点的Cu-配体键临界点laplacian。铜(II)配合物与阴离子羧酸配体的形成导致二氧化碳的释放,由于药物的所有形式之间的平衡,二氧化碳的释放会导致活性内酯形式的浓度降低。内酯<中性羧基<阴离子羧酸盐的MIA值和向Cu转移的电子密度增大。两种中性形式的伊立替康表现出比喜树碱更低的MIA值,不像阴离子羧酸形式。
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DFT studies of camptothecins cytotoxicity IV — active and inactive forms of irinotecan
Abstract Structures of irinotecan (CPT-11) in neutral lactone, neutral carboxyl, and anionic carboxylate forms in singlet ground states and of their complexes with Cu(II) in doublet ground states are optimized using B3LYP/6-311G* treatment. Metal ion affinities (MIA), Cu charges and Laplacians of Cu-ligand bond critical points of possible CPT active sites are evaluated. The formation of Cu(II) complexes with the anionic carboxylate ligand leads to the release of CO2 that can cause a decrease in the concentration of the active lactone form due to equilibria between all forms of the drug. MIA values and electron density transfer to Cu increase in the sequence lactone < neutral carboxyl < anionic carboxylate. Both neutral forms of irinotecan exhibit lower MIA values than those of camptothecin, unlike the anionic carboxylate form.
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Acta Chimica Slovaca
Acta Chimica Slovaca CHEMISTRY, MULTIDISCIPLINARY-
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