有机锡羧酸酯配合物的合成、结构表征及性质研究
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摘要
通过对大量文献调查研究作者发现,有机锡配合物具有多方面的作用,特别是在抗癌活性方面。自80年代初,Crowe等人发现有机锡配合物有抗癌活性以来,关于有机锡抗癌活性的研究成为继顺铂之后又一极为活跃的热点。在此基础上,作者合成了两大系列的化合物:卡铂型有机锡类维A酸酯配合物(16a - 16d和17a - 17d)和卡铂型芳香型有机锡羧酸酯配合物(32e - 32j)。
对于有机锡类维A酸酯配合物,作者发现类维A酸本身在癌症等治疗方面有着重要的表现,作者设想将类维A酸接到具有抗癌活性的有机锡上,充分利用药物协调原理,从而合成具有更好抗癌活性的有机锡配合物。生物活性显示此类化合物对宫颈癌细胞(Hela)、肝癌细胞(Liver Cancer Cell)、肺癌细胞(A549)都具有较好的抗癌活性。
而对于顺铂芳香型有机锡羧酸酯配合物,初步的生物活性显示它们具有较好的抗癌活性,而它们的生物活性又存在差别,为了研究分子结构与抗癌活性之间的关系,本论文用X射线单晶衍射测定了其中化合物32b和32e的晶体结构。化合物32b属于斜方晶系,R-3空间群, a = 25.388(3) A,b = 25.388(3) A,c = 19.081(4) A,β= 90°,V = 10651(3) A~3,Z = 12,R = 0.0492,wR = 0.1257,化合物32e属于单斜晶系,P2(1)/c空间群, a = 9.3215(8) A,b = 23.9936(19) A,c = 10.8225(9) A,β= 107.8480(10)°,V = 2304.0(3) A~3,Z = 4,R = 0.0585,wR = 0.1281。32b和32e晶体中锡原子配位数均为6,形成了严重扭曲八面体几何构型。32b和32e均存在分子内及分子间氢键作用,32b中氢键作用较弱,在生物体系中比32e更易释放出游离态R_2Sn~(2+),易与癌细胞的DNA结合,具有更好的抗癌生物活性。
为了进一步的探讨有机锡配合物的抗癌活性机理,合成了二全氟己基乙基二氯化锡(33),并同时运用循环伏安法、紫外光谱等手段,对二全氟己基乙基二氯化锡与小牛胸腺DNA(CT-DNA)作用机制进行了研究,结果表明:化合物二全氟己基乙基二氯化锡通过静电作用于DNA的骨架磷酸基团,从而与DNA发生作用。
本论文共合成化合物30个,其中新化合物15个。所有化合物都通过IR、1H NMR表征,部分化合物还用~(13)C NMR、~(19)F NMR和~(119)Sn NMR进行了表征。
The author have found that organotin compounds have many important significance in different fields especially anticancer activities based on reading a number of literatures. More and more organometallic scientists paid attention to the anticancer activities of organotin compounds since the scientists Crown and his coworks found organotin compounds exhibited better anticancer activity in the early 1980s. So two series of di-n-butyltin carboxylates(32e - 32j and 16a - 16d, 17a - 17d) were synthesized by the reaction of di-n-butyltin oxide with corresponding aromatic carboxylic acids.
The author also have found that retinoids play an essential role in vertebrate growth and development, supporting cell differentiation, embryonic development, vision, the immune response and reproduction especially anticancer activities. Therefore in order to enhance the activities of organotin compounds, we synthesized a series of di-n-butyltin retinoates by the reaction of di-n-butyltin oxide with corresponding retinoids in 1: 2(16a - 16d) and 1: 1 (17a - 17d) molar ratio. Study of their biological activity in Hela、Liver Cancer Cell(LCC)、A549 cancer cell showed that compound 17a had better anticancer activity.
A series of di-n-butyltin dicarboxylates[n-Bu_2Sn(OOCAr)_2(32a - 32j)] were synthesized by the reaction of di-n-butyltin oxide with corresponding aromatic carboxylic acids in 1: 2 molar ratio. The anticancer activities of these compounds indicated that all of them exhibited good activities. In order to research the relations between their structures and anticancer activities, compound 32b and 32e were determined by X-ray single crystal diffraction. The crystal 32b belongs to rhombohedral with space group R-3, a = 25.388(3) A, b = 25.388(3) A, c = 19.081(4) A,β= 90°, V = 10651(3) A~3, Z = 12, R = 0.0492, wR = 0.1257. The crystal 32e belongs to monoclinic with space group P2(1)/c, a = 9.3215(8) A, b = 23.9936(19) A, c = 10.8225(9) A,β= 107.8480(10)°, V = 2304.0(3) A~3, Z = 4, R = 0.0585, wR = 0.128. In the crystals of 32b and 32e each tin atom is six-coordinated in a distorted octahedron geometry structure. The structures of 32b and 32e exist in their crystals by intermolecular and intramolecular hydrogen bonds. 32b presented better anticancer activity than 32e because the hydrogen bonds in 32b are longer and weaker, so that the species R2Sn~(2+) of 32b in bio-system is released more easily to combine with DNA of cancer cells.
In order to reveal the anticancer mechanism of organotin compounds, di-trideca-fluorooctayltin dichloride[(C_6F_(13)CH_2CH_2)2SnCl_2] was synthesized and the cyclic voltammetric and spectrophotometric methods were used to study the interaction of (C_6F_(13)CH_2CH_2)_2SnCl_2 and DNA. The results suggested that compound (C_6F_(13)CH_2CH_2)_2SnCl_2 mainly reacts electrostatically with the phosphate backbone of DNA.
We have synthesized 30 compounds and 15 of them were not reported in literatures until now. Their structures were characterized and confirmed by IR, 1H NMR, 13C NMR, 19F NMR and 119Sn NMR spectra.
对于有机锡类维A酸酯配合物,作者发现类维A酸本身在癌症等治疗方面有着重要的表现,作者设想将类维A酸接到具有抗癌活性的有机锡上,充分利用药物协调原理,从而合成具有更好抗癌活性的有机锡配合物。生物活性显示此类化合物对宫颈癌细胞(Hela)、肝癌细胞(Liver Cancer Cell)、肺癌细胞(A549)都具有较好的抗癌活性。
而对于顺铂芳香型有机锡羧酸酯配合物,初步的生物活性显示它们具有较好的抗癌活性,而它们的生物活性又存在差别,为了研究分子结构与抗癌活性之间的关系,本论文用X射线单晶衍射测定了其中化合物32b和32e的晶体结构。化合物32b属于斜方晶系,R-3空间群, a = 25.388(3) A,b = 25.388(3) A,c = 19.081(4) A,β= 90°,V = 10651(3) A~3,Z = 12,R = 0.0492,wR = 0.1257,化合物32e属于单斜晶系,P2(1)/c空间群, a = 9.3215(8) A,b = 23.9936(19) A,c = 10.8225(9) A,β= 107.8480(10)°,V = 2304.0(3) A~3,Z = 4,R = 0.0585,wR = 0.1281。32b和32e晶体中锡原子配位数均为6,形成了严重扭曲八面体几何构型。32b和32e均存在分子内及分子间氢键作用,32b中氢键作用较弱,在生物体系中比32e更易释放出游离态R_2Sn~(2+),易与癌细胞的DNA结合,具有更好的抗癌生物活性。
为了进一步的探讨有机锡配合物的抗癌活性机理,合成了二全氟己基乙基二氯化锡(33),并同时运用循环伏安法、紫外光谱等手段,对二全氟己基乙基二氯化锡与小牛胸腺DNA(CT-DNA)作用机制进行了研究,结果表明:化合物二全氟己基乙基二氯化锡通过静电作用于DNA的骨架磷酸基团,从而与DNA发生作用。
本论文共合成化合物30个,其中新化合物15个。所有化合物都通过IR、1H NMR表征,部分化合物还用~(13)C NMR、~(19)F NMR和~(119)Sn NMR进行了表征。
The author have found that organotin compounds have many important significance in different fields especially anticancer activities based on reading a number of literatures. More and more organometallic scientists paid attention to the anticancer activities of organotin compounds since the scientists Crown and his coworks found organotin compounds exhibited better anticancer activity in the early 1980s. So two series of di-n-butyltin carboxylates(32e - 32j and 16a - 16d, 17a - 17d) were synthesized by the reaction of di-n-butyltin oxide with corresponding aromatic carboxylic acids.
The author also have found that retinoids play an essential role in vertebrate growth and development, supporting cell differentiation, embryonic development, vision, the immune response and reproduction especially anticancer activities. Therefore in order to enhance the activities of organotin compounds, we synthesized a series of di-n-butyltin retinoates by the reaction of di-n-butyltin oxide with corresponding retinoids in 1: 2(16a - 16d) and 1: 1 (17a - 17d) molar ratio. Study of their biological activity in Hela、Liver Cancer Cell(LCC)、A549 cancer cell showed that compound 17a had better anticancer activity.
A series of di-n-butyltin dicarboxylates[n-Bu_2Sn(OOCAr)_2(32a - 32j)] were synthesized by the reaction of di-n-butyltin oxide with corresponding aromatic carboxylic acids in 1: 2 molar ratio. The anticancer activities of these compounds indicated that all of them exhibited good activities. In order to research the relations between their structures and anticancer activities, compound 32b and 32e were determined by X-ray single crystal diffraction. The crystal 32b belongs to rhombohedral with space group R-3, a = 25.388(3) A, b = 25.388(3) A, c = 19.081(4) A,β= 90°, V = 10651(3) A~3, Z = 12, R = 0.0492, wR = 0.1257. The crystal 32e belongs to monoclinic with space group P2(1)/c, a = 9.3215(8) A, b = 23.9936(19) A, c = 10.8225(9) A,β= 107.8480(10)°, V = 2304.0(3) A~3, Z = 4, R = 0.0585, wR = 0.128. In the crystals of 32b and 32e each tin atom is six-coordinated in a distorted octahedron geometry structure. The structures of 32b and 32e exist in their crystals by intermolecular and intramolecular hydrogen bonds. 32b presented better anticancer activity than 32e because the hydrogen bonds in 32b are longer and weaker, so that the species R2Sn~(2+) of 32b in bio-system is released more easily to combine with DNA of cancer cells.
In order to reveal the anticancer mechanism of organotin compounds, di-trideca-fluorooctayltin dichloride[(C_6F_(13)CH_2CH_2)2SnCl_2] was synthesized and the cyclic voltammetric and spectrophotometric methods were used to study the interaction of (C_6F_(13)CH_2CH_2)_2SnCl_2 and DNA. The results suggested that compound (C_6F_(13)CH_2CH_2)_2SnCl_2 mainly reacts electrostatically with the phosphate backbone of DNA.
We have synthesized 30 compounds and 15 of them were not reported in literatures until now. Their structures were characterized and confirmed by IR, 1H NMR, 13C NMR, 19F NMR and 119Sn NMR spectra.
引文
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