Syntheses and photodynamic properties of glucopyranoside-conjugated indium(III) porphyrins as a bifunctional agent
Syntheses and photodynamic properties of glucopyranoside-conjugated indium(III) porphyrins as a bifunctional agent
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DOI：
10.1142/s1088424613500934
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发表时间：
2013-12
影响因子：
1.5
通讯作者：
Misaki Nakai;T. Maeda;Tsuyoshi Mashima;S. Yano;S. Sakuma;Eriko Otake;A. Morita;Y. Nakabayashi
中科院分区：
文献类型：
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作者：
Misaki Nakai;T. Maeda;Tsuyoshi Mashima;S. Yano;S. Sakuma;Eriko Otake;A. Morita;Y. Nakabayashi
合成了吡喃葡萄糖苷类共轭卟啉：H_2TPP{p-O-(CH_2)_2-O-O-AcGlc}(1)、[InTPP{p-O-(CH_2)_2-O-O-AcGlc}]NO_3(2)、H_2TPP{p-O-(CH_2)_2-O-GLC}(3)、[InTPP{p-O-(CH_2)_2-O-GLC]-NO_3(4)和ZnTPP{p-O-(CH_2)_2-O-O-AcGlc}(5)。UV-Vis光谱和元素分析。在2的~1H核磁共振谱中，观察到了两组卟啉苯基上的H原子的信号，表明2由于NO_3离子与铟原子配位而具有轴向手性。用1，3-二苯基异苯并呋喃(DPBF)作为猝灭剂考察了它们的单线态氧产生能力，表明它们的单线态氧产生能力高于自由基和锌基的，反映了重原子效应。研究了这些卟啉类化合物对Colo 679的光动力学性质。所有吡喃葡萄糖苷偶联的卟啉都表现出比Laserporrin®更高的光细胞毒性。最重要的是，4显示出最高的光细胞毒性，这与该络合物产生单线态氧和细胞通透性的高能力相一致。
The glucopyranoside-conjugated porphyrins, H2TPP{p-O-(CH2)2-O-OAcGlc} (1), [InTPP{p-O-(CH2)2-O-OAcGlc}]NO3 (2), H2TPP{p-O-(CH2)2-O-Glc} (3), [InTPP{p-O-(CH2)2-O-Glc]-NO3 (4) and ZnTPP{p-O-(CH2)2-O-OAcGlc} (5) were synthesized, and characterized by 1H NMR, 13C NMR, ESI-MS, UV-vis spectroscopies and elemental analyses. In the 1H NMR spectrum of 2, two sets of signals were observed for H-atoms of the phenyl group of porphyrin, indicating that 2 has the axial chirality due to a NO3 ion coordinating to the indium atom. Abilities of the singlet oxygen production of these porphyrins, investigated by using 1,3-diphenylisobenzofuran (DPBF) as a quencher, were higher than those of the free-based and zinc porphyrins, reflecting the heavy atom effect. The photodynamic properties of these porphyrin derivatives were investigated against COLO 679. All of the glucopyranoside-conjugated porphyrins exhibited the high photocytotoxicity compared with Laserphyrin®. Above all, 4 exhibited the highest photocytotoxicity, coinciding with the high abilities of this complex for the singlet oxygen production and the cell permeability.