水杨醛席夫碱金属配合物的合成、表征及PTP1B抑制活性研究
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摘要
属于重大疾病之一的糖尿病,对人类危害十分严重,迄今为止还没有彻底治疗的有效方法。糖尿病发病的关键因素是胰岛素分泌不足和胰岛素抵抗,众多研究表明,蛋白酪氨酸磷酸酶1B(PTP1B)对胰岛素信号传导具有负性调节作用,PTP1B的表达水平在糖尿病或发生胰岛素抵抗时明显增高,而且PTP1B与肿瘤的发生发展也有密切关系。因此开展对蛋白酪氨酸磷酸酶1B抑制剂的研究,并探索抑制剂与酶作用机理,不仅对于研究生物体中的信号传导具有重要的理论价值,也有利于开发新型抗糖尿病及抗癌药物。
目前国内外关于PTP1B抑制剂的报道很多,其中以有机小分子居多,但是无机小分子抑制剂的研究却非常少。大量研究表明微量金属元素如V、Cr、Cu、Zn等特别是V与糖尿病的预防和治疗密切相关,但其作用机制仍不明确。一些研究表明钒配合物可能通过抑制PTP活性发挥降血糖作用。为了进一步深入探讨钒配合物的降血糖活性和机理,我们选择了一些具有广泛生物活性的配体,设计合成了各种新的金属配合物,研究了这些配合物对PTP1B活性的抑制作用,并进行了初步的选择性和作用机理研究。本论文的主要研究成果如下:
1.合成了一系列新型的水杨醛及其衍生物缩邻氨基苯甲酸-多吡啶-氧钒三元配合物,运用元素分析、晶体衍射、红外光谱、电子顺磁共振光谱、密度泛函理论计算、摩尔电导、紫外光谱、电喷雾质谱、电位滴定等手段对其结构进行了表征,结果表明,这是一类稳定的具有六配位变形八面体结构的中性氧钒(Ⅳ)配合物。在配合物结构特性研究的基础上,首次研究了这类三元氧钒配合物对PTP1B活性的抑制作用及模式,初步探讨了配合物与PTP1B作用的机理。配合物对PTP1B的半数抑制浓度(ICso)只有几十纳摩尔,而且相对于SHP-1和TCPTP来说,这类配合物对PTP1B有适度的选择性。另外,稳态动力学实验也表明这类配合物以竞争模式与PTP1B相互作用,所以该类配合物是高效的、适度选择性的、典型的竞争型PTP1B抑制剂。结合配合物竞争型的作用模式,利用分子模拟的方法初步探索了该类配合物与PTP1B活性位点相互作用的可能模式,即配合物凭借其比较适合的结构进入PTP1B酶的催化域口袋并且主要通过其钒氧及邻近基团与PTP1B活性位点作用。
文献报道苯环上引入不同取代基时,由于电子效应、空间效应的影响,这些取代基会对其合成的化合物生物活性有一定的影响,为了比较取代基对抑制活性的影响,我们进一步在水杨醛的苯环上引入溴或者将苯环用萘环取代,然后与邻氨基苯甲酸缩合而成两种新的席夫碱,5-溴水杨醛缩邻氨基苯甲酸席夫碱和2-羟基-1-萘醛缩邻氨基苯甲酸席夫碱,利用这两种席夫碱和多吡啶配体合成一系列类似的新型氧钒配合物,研究了配合物与PTP1B的相互作用,结果表明,该类配合物的抑制活性要略低于没有取代基的相应配合物,这可能是由于取代基的引入对配合物进入酶的催化域口袋产生一些位阻作用,但是在这个空间结构中位阻还没有足够大到阻止配合物进入酶的催化域口袋,所以与没有取代基的配合物抑制活性相比,该类配合物对PTP1B活性的抑制作用变化不明显。
2.动物实验已经表明,配位形式为VO(N_2O_2)的配合物有非常显著的抗糖作用,所以我们选择含有N_2O_2配位基的水杨醛双席夫碱作为配体,合成一系列新的水杨醛及其衍生物缩芳胺双席夫碱氧钒配合物,利用元素分析、红外光谱、摩尔电导、紫外光谱、电子顺磁共振光谱和密度泛函理论计算等手段对其结构进行了表征,并用紫外光谱测定了配合物在缓冲溶液中的稳定性动力学。结果表明这是一类稳定的具有五配位扭曲四方锥结构的中性氧钒(Ⅳ)配合物。同样,我们也首次研究了该类配合物与PTP1B的相互作用,发现所合成的这些配合物对PTP1B都具有很好的抑制活性,半数抑制浓度IC_(50)值在15～133nM范围内,从IC_(50)值结果可以看出,配合物中不同部位取代基的改变对配合物的PTP1B抑制作用有不同的影响结果。其中席夫碱配体中水杨醛上取代基的引入主要是对配合物进入PTP1B活性区域时产生一定的空间位阻,而且取代基越大,位阻也就越大,而席夫碱配体中邻苯二胺上取代基的引入可能主要是通过电子的推拉效应影响氧钒离子与PTP1B活性部位的相互作用,结果还表明吸电子基的引入能够提高配合物的抑制活性。另外,以水杨醛缩邻苯二胺双席夫碱氧钒配合物为例,酶动力学实验研究表明,该类配合物是典型的竞争型抑制剂。根据实验结果并结合分子模拟计算,推测配合物也是以钒氧端与PTP1B活性部位结合的。
3.铜和锌是重要的生命金属元素,以DNA为作用靶点的铜配合物抗肿瘤活性的研究已有很多报道,但是以PTP1B为作用靶点的铜配合物的各种生物活性研究还没见文献报道,我们课题组以PTP1B为作用靶点,首次探索了铜配合物以及席夫碱锌配合物对PTP1B活性的抑制作用。本文中,合成了分别以水杨醛缩芳胺席夫碱和1,10-邻菲哕啉为配体的铜、锌配合物,运用元素分析、晶体衍射、红外光谱、摩尔电导、紫外光谱等手段对其结构进行了表征,并研究了这些配合物对PTP1B的抑制作用。实验结果表明,这些配合物都能很好的抑制PTP1B酶的活性,它们的IC_(50)值在10~(-6)～10~(-7)M数量级范围。进一步的研究表明,还原型谷胱甘肽的存在一定程度上降低了席夫碱铜配合物对PTP1B抑制的作用,氧气的存在增强邻菲哕啉铜配合物对PTP1B的抑制,我们推测铜配合物抑制PTP1B酶活性的过程可能存在氧化机理。我们初步认为这个机理可能不同于产生羟基自由基的氧化机理,因为还原剂GSH的去除对铜配合物的抑制活性没有明显的影响,更进一步的机理研究还在继续中。另外,值得一提的是双核铜配合物[Cu(phen)_2(μ-IDA)Cu(phen)(NO_3)]NO_3·4H_2O是以一种很少见的反竞争方式来抑制PTP1B活性的,而且比较配合物对PTP1B、TCPTP和SHP-1活性的抑制能力可以发现,该配合物对TCPTP活性的抑制有一定的选择性。
4.尝试用浸泡法观察在金属配合物中浸泡24小时后PTP1B的蛋白晶体的变化,比较浸泡前后PTP1B晶体的初步结构发现,金属抑制剂作用之前PTP1B活性区域口袋形状比较明显,活性位点Cys215上的巯基向上伸展,当金属抑制剂作用之后PTP1B活性区域口袋形状就变得有些不太清楚了,活性位点Cys215上的巯基也都向袋子口方向伸展,这可能是由于金属抑制抑制剂与活性位点发生作用的原因。特别值得一提的是,从经过铜配合物溶液浸泡后的PTP1B晶体结构中我们发现活性位点Cys215上的巯基有部分被氧化和成环的趋势,这一现象与prof.H.Jhoti等2003年在Nature上报道的双氧水氧化PTP1B的机理有点类似,为我们今后更深入地研究PTP1B铜配合物抑制剂奠定了坚实的理论基础。
本论文创新之处:获得一系列新型的金属配合物,首次研究了这些配合物对PTP1B活性的抑制作用,并进行了初步的机理探索,为金属配合物作为胰岛素模拟物方面的探索积累了一些研究基础,同时获得一些高效且有一定选择性的PTP1B金属抑制剂;首次以PTP1B作为靶点来研究铜配合物的生物活性,这些有意义的研究结果将对今后开发基于金属化合物的抗糖尿病和抗肿瘤药物提供理论和实验依据,同时也进一步丰富了相关金属的生物无机化学内容。
The number of patients suffering from diabetes mellitus(DM) is increasing throughout the world,with this disease becoming most significant disease in the century.Up to now,there are not still potent methods to cure the disease thoroughly.DM is a disease that results in chronic hyperglycemia due to an absolute or relative lack of insulin and/or insulin resistance.It is proved that protein-tyrosine phosphatase 1B(PTP1B) is an important negative regulator of insulin and leptin signaling in vivo.PTP1B can associate with and dephosphorylate activated insulin receptor(IR) or insulin receptor substrates.Overexpression of PTP1B in cell cultures decreases insulin-stimulated phosphorylation of nsulin receptor(IR) or insulin receptor substrates.So it is very important to study the inhibitors'interaction with PTP1B and their mechanism.Furthermore,the potent and specificity PTP1B inhibitors may be promising candidates for novel anti-diabetic drug development.
Currently,a large number of the studies on PTP1B inhibitors have been reported.While most of the inhibitors are organic moleculars,the inorganic metal-complex PTP1B inhibitors have been few reported.Many experiments in vivo have shown the close relation of the trace metal elements to diabetes precaution and treatment.However,the mechanism for the insulin-sensitizing of metal effects has not been well understood by far,though the activities of decreasing the blood sugar by metal compounds had been associated with protein tyrosine phosphatase inhibition.Therefore,how metal compounds directly inhibit PTP1B and then influence metabolism need more investigation.
In this thesis,we design and synthesis a series novel metal compounds employing the ligands with wide biological activities,and their inhibition effect and mechanism against PTP1B were investigated.The main results are as follows:
1.A new series of oxovanadium complexes with mixed ligands,a tridentate ONO donor Schiff base ligand[viz.,salicylidene anthranilic acid(SAA)]and a bidentate polypyridyle ligand,have been synthesized and characterized by elemental analysis,FT-IR,EPR,DFT calculations,X-ray crystallography, ESI-MS,UV-vis,Molar conductivity measurment and potentiometric pH titrations.The results show that this kind of oxovanadium complex with a distorted octahedral geometry is stable and neutral,and the center vanadium atom is the oxidation state ofⅤ(Ⅳ) with d~1 configuration.The complexes have been found to be potent inhibitors against PTP1B(IC_(50) approximate 10~(-8)M) in vitro.This kind of complex selectively inhibits PTP1B over the other two phosphatases(approximate 4～9-fold selectivity against SHP-1 and about 2-fold selectivity against TCPTP).Kinetics assays suggest that these complexes inhibit PTP1B in a competitive manner.The binding model of the kind of complex with PTP1B is predicted by using molecular docking techniques.The putative mode of interaction of the kind of complex with PTP1B suggests that the complex is capable of binding to the catalytic site of PTP1B.In the model,the vanadyl oxygen is close to the sulphur atom of the active site cysteine(Cys 215).
In order to test the substitution of ligands effects on the PTP1B-inhibition activities,we replaced "salicylaldehyde" with "5-bromo-salicylaldehyde" and "2-hydroxy naphthalene-1-carbaldehyde",respectively,then synthesize and characterized a series of new similar mixed oxovanadium complexes.The results of inhibition assays show the PTP1B-inhibition activities of these oxovanadium complexes of derivatives are slightly lower than the corresponding complexes.It appears that the spatial bulk of substitute of Schiff base weakly diminishes the PTP1B-inhibition activities in these complexes.
2.Based on the good activities of decreasing blood sugar by the oxovanadium complex with N_2O_2 coordination form.A tetradentate donor Schiff base ligand and derivatives with N_2O_2 coordination form were chosen to synthesize a series of oxovanadium complexes.These complexes were characterized by elemental analysis,FT-IR,EPR,DFT,UV-vis,conductivity measurment.The results show this kind of oxovanadium complex is five-coordinated neutral complex with distorted tetragonal pyramid geometry. The center vanadium atom is V(IV) with d~1 configuration.The complexes have been shown to be potent inhibitors of PTP1B.Kinetics assays suggest that the complex VO(sal-BDA) inhibits PTP1B in a competitive manner and inhibition constant of 31nM,was determined for the inhibition of PTP1B. The binding model of the complex VO(sal-BDA) with PTP1B is studied by using molecular docking techniques.The putative mode of interaction of the complex with PTP1B suggests that the vanadyl oxygen of the complex is close to the sulphur atom of cysteine(Cys 215) at the active site.
3.Copper and zinc are essential trace elements that play some central roles in the biochemistry of every living organism.The antitumor activity of copper complexes based on DNA cleavage has been studied extensively. However,the investigation of copper complexes interaction with PTP1B, which is regared as the target of antitumor drugs,is not reported.Our group first explores PTP1B-inhibitory activities of copper complexes and zinc complexes with Schiff base ligands.In this thesis,the copper complexes with Schiff base.or 1,10-phenanthroline ligands are synthesized and nsulin receptor(IR) or insulin receptor substratesthen characterized by elemental analysis,FT-IR,X-ray crystallography,UV-vis,conductivity measurement. The results of inhibition assays show these copper complexes are potent PTP1B inhibitors.IC_(50) values ranged from 10~(-6) to 10~(-7)M.More studies show that PTP1B inhibitory activities of copper complexes with Schiff base ligands decrease in the presence of GSH and PTP1B inhibitory activities of the copper complex[Cu(phen)_3]~(2+) increase in the presence of oxygen,implying the existence of oxidation mechanism during the PTP1B-inhibition process by copper complexes.Noted that the binuclear copper complex [Cu(phen)_2(μ-IDA)Cu(phen)(NO_3)]NO_3 inhibits PTP1B in a uncompetitive manner.And the complex selectively inhibits TCPTP over the other two phosphatases SHP-1 and TCPTP.
4.Using oxovanadium complex VO(SAA)(phen) and copper complex [Cu(phen)_2(μ-IDA)Cu(phen)(NO_3)]NO_3 as the representatives,we attempt to cultivate and PTP1B/inhibitor compound crystals by the soaking method and obtain two X-ray crystal structures of PTP1B soaked in the copper complex and oxovanadium complex.In comparison with the native PTP1B,the structures in PTP1B soaked in the copper complex and oxovanadium complex have some difference,and it is mainly obvious for the SH group of Cys 215,which indicates the ever happened interactions between the inhibitors and active region of PTP1B.Remarkably,the SH of catalytic cysteine of PTP1B is partially oxidized in the PTP1B/(copper complex) compound crystal,and the phenomenon is similar to that reported by the reference published in Nature.
目前国内外关于PTP1B抑制剂的报道很多,其中以有机小分子居多,但是无机小分子抑制剂的研究却非常少。大量研究表明微量金属元素如V、Cr、Cu、Zn等特别是V与糖尿病的预防和治疗密切相关,但其作用机制仍不明确。一些研究表明钒配合物可能通过抑制PTP活性发挥降血糖作用。为了进一步深入探讨钒配合物的降血糖活性和机理,我们选择了一些具有广泛生物活性的配体,设计合成了各种新的金属配合物,研究了这些配合物对PTP1B活性的抑制作用,并进行了初步的选择性和作用机理研究。本论文的主要研究成果如下:
1.合成了一系列新型的水杨醛及其衍生物缩邻氨基苯甲酸-多吡啶-氧钒三元配合物,运用元素分析、晶体衍射、红外光谱、电子顺磁共振光谱、密度泛函理论计算、摩尔电导、紫外光谱、电喷雾质谱、电位滴定等手段对其结构进行了表征,结果表明,这是一类稳定的具有六配位变形八面体结构的中性氧钒(Ⅳ)配合物。在配合物结构特性研究的基础上,首次研究了这类三元氧钒配合物对PTP1B活性的抑制作用及模式,初步探讨了配合物与PTP1B作用的机理。配合物对PTP1B的半数抑制浓度(ICso)只有几十纳摩尔,而且相对于SHP-1和TCPTP来说,这类配合物对PTP1B有适度的选择性。另外,稳态动力学实验也表明这类配合物以竞争模式与PTP1B相互作用,所以该类配合物是高效的、适度选择性的、典型的竞争型PTP1B抑制剂。结合配合物竞争型的作用模式,利用分子模拟的方法初步探索了该类配合物与PTP1B活性位点相互作用的可能模式,即配合物凭借其比较适合的结构进入PTP1B酶的催化域口袋并且主要通过其钒氧及邻近基团与PTP1B活性位点作用。
文献报道苯环上引入不同取代基时,由于电子效应、空间效应的影响,这些取代基会对其合成的化合物生物活性有一定的影响,为了比较取代基对抑制活性的影响,我们进一步在水杨醛的苯环上引入溴或者将苯环用萘环取代,然后与邻氨基苯甲酸缩合而成两种新的席夫碱,5-溴水杨醛缩邻氨基苯甲酸席夫碱和2-羟基-1-萘醛缩邻氨基苯甲酸席夫碱,利用这两种席夫碱和多吡啶配体合成一系列类似的新型氧钒配合物,研究了配合物与PTP1B的相互作用,结果表明,该类配合物的抑制活性要略低于没有取代基的相应配合物,这可能是由于取代基的引入对配合物进入酶的催化域口袋产生一些位阻作用,但是在这个空间结构中位阻还没有足够大到阻止配合物进入酶的催化域口袋,所以与没有取代基的配合物抑制活性相比,该类配合物对PTP1B活性的抑制作用变化不明显。
2.动物实验已经表明,配位形式为VO(N_2O_2)的配合物有非常显著的抗糖作用,所以我们选择含有N_2O_2配位基的水杨醛双席夫碱作为配体,合成一系列新的水杨醛及其衍生物缩芳胺双席夫碱氧钒配合物,利用元素分析、红外光谱、摩尔电导、紫外光谱、电子顺磁共振光谱和密度泛函理论计算等手段对其结构进行了表征,并用紫外光谱测定了配合物在缓冲溶液中的稳定性动力学。结果表明这是一类稳定的具有五配位扭曲四方锥结构的中性氧钒(Ⅳ)配合物。同样,我们也首次研究了该类配合物与PTP1B的相互作用,发现所合成的这些配合物对PTP1B都具有很好的抑制活性,半数抑制浓度IC_(50)值在15～133nM范围内,从IC_(50)值结果可以看出,配合物中不同部位取代基的改变对配合物的PTP1B抑制作用有不同的影响结果。其中席夫碱配体中水杨醛上取代基的引入主要是对配合物进入PTP1B活性区域时产生一定的空间位阻,而且取代基越大,位阻也就越大,而席夫碱配体中邻苯二胺上取代基的引入可能主要是通过电子的推拉效应影响氧钒离子与PTP1B活性部位的相互作用,结果还表明吸电子基的引入能够提高配合物的抑制活性。另外,以水杨醛缩邻苯二胺双席夫碱氧钒配合物为例,酶动力学实验研究表明,该类配合物是典型的竞争型抑制剂。根据实验结果并结合分子模拟计算,推测配合物也是以钒氧端与PTP1B活性部位结合的。
3.铜和锌是重要的生命金属元素,以DNA为作用靶点的铜配合物抗肿瘤活性的研究已有很多报道,但是以PTP1B为作用靶点的铜配合物的各种生物活性研究还没见文献报道,我们课题组以PTP1B为作用靶点,首次探索了铜配合物以及席夫碱锌配合物对PTP1B活性的抑制作用。本文中,合成了分别以水杨醛缩芳胺席夫碱和1,10-邻菲哕啉为配体的铜、锌配合物,运用元素分析、晶体衍射、红外光谱、摩尔电导、紫外光谱等手段对其结构进行了表征,并研究了这些配合物对PTP1B的抑制作用。实验结果表明,这些配合物都能很好的抑制PTP1B酶的活性,它们的IC_(50)值在10~(-6)～10~(-7)M数量级范围。进一步的研究表明,还原型谷胱甘肽的存在一定程度上降低了席夫碱铜配合物对PTP1B抑制的作用,氧气的存在增强邻菲哕啉铜配合物对PTP1B的抑制,我们推测铜配合物抑制PTP1B酶活性的过程可能存在氧化机理。我们初步认为这个机理可能不同于产生羟基自由基的氧化机理,因为还原剂GSH的去除对铜配合物的抑制活性没有明显的影响,更进一步的机理研究还在继续中。另外,值得一提的是双核铜配合物[Cu(phen)_2(μ-IDA)Cu(phen)(NO_3)]NO_3·4H_2O是以一种很少见的反竞争方式来抑制PTP1B活性的,而且比较配合物对PTP1B、TCPTP和SHP-1活性的抑制能力可以发现,该配合物对TCPTP活性的抑制有一定的选择性。
4.尝试用浸泡法观察在金属配合物中浸泡24小时后PTP1B的蛋白晶体的变化,比较浸泡前后PTP1B晶体的初步结构发现,金属抑制剂作用之前PTP1B活性区域口袋形状比较明显,活性位点Cys215上的巯基向上伸展,当金属抑制剂作用之后PTP1B活性区域口袋形状就变得有些不太清楚了,活性位点Cys215上的巯基也都向袋子口方向伸展,这可能是由于金属抑制抑制剂与活性位点发生作用的原因。特别值得一提的是,从经过铜配合物溶液浸泡后的PTP1B晶体结构中我们发现活性位点Cys215上的巯基有部分被氧化和成环的趋势,这一现象与prof.H.Jhoti等2003年在Nature上报道的双氧水氧化PTP1B的机理有点类似,为我们今后更深入地研究PTP1B铜配合物抑制剂奠定了坚实的理论基础。
本论文创新之处:获得一系列新型的金属配合物,首次研究了这些配合物对PTP1B活性的抑制作用,并进行了初步的机理探索,为金属配合物作为胰岛素模拟物方面的探索积累了一些研究基础,同时获得一些高效且有一定选择性的PTP1B金属抑制剂;首次以PTP1B作为靶点来研究铜配合物的生物活性,这些有意义的研究结果将对今后开发基于金属化合物的抗糖尿病和抗肿瘤药物提供理论和实验依据,同时也进一步丰富了相关金属的生物无机化学内容。
The number of patients suffering from diabetes mellitus(DM) is increasing throughout the world,with this disease becoming most significant disease in the century.Up to now,there are not still potent methods to cure the disease thoroughly.DM is a disease that results in chronic hyperglycemia due to an absolute or relative lack of insulin and/or insulin resistance.It is proved that protein-tyrosine phosphatase 1B(PTP1B) is an important negative regulator of insulin and leptin signaling in vivo.PTP1B can associate with and dephosphorylate activated insulin receptor(IR) or insulin receptor substrates.Overexpression of PTP1B in cell cultures decreases insulin-stimulated phosphorylation of nsulin receptor(IR) or insulin receptor substrates.So it is very important to study the inhibitors'interaction with PTP1B and their mechanism.Furthermore,the potent and specificity PTP1B inhibitors may be promising candidates for novel anti-diabetic drug development.
Currently,a large number of the studies on PTP1B inhibitors have been reported.While most of the inhibitors are organic moleculars,the inorganic metal-complex PTP1B inhibitors have been few reported.Many experiments in vivo have shown the close relation of the trace metal elements to diabetes precaution and treatment.However,the mechanism for the insulin-sensitizing of metal effects has not been well understood by far,though the activities of decreasing the blood sugar by metal compounds had been associated with protein tyrosine phosphatase inhibition.Therefore,how metal compounds directly inhibit PTP1B and then influence metabolism need more investigation.
In this thesis,we design and synthesis a series novel metal compounds employing the ligands with wide biological activities,and their inhibition effect and mechanism against PTP1B were investigated.The main results are as follows:
1.A new series of oxovanadium complexes with mixed ligands,a tridentate ONO donor Schiff base ligand[viz.,salicylidene anthranilic acid(SAA)]and a bidentate polypyridyle ligand,have been synthesized and characterized by elemental analysis,FT-IR,EPR,DFT calculations,X-ray crystallography, ESI-MS,UV-vis,Molar conductivity measurment and potentiometric pH titrations.The results show that this kind of oxovanadium complex with a distorted octahedral geometry is stable and neutral,and the center vanadium atom is the oxidation state ofⅤ(Ⅳ) with d~1 configuration.The complexes have been found to be potent inhibitors against PTP1B(IC_(50) approximate 10~(-8)M) in vitro.This kind of complex selectively inhibits PTP1B over the other two phosphatases(approximate 4～9-fold selectivity against SHP-1 and about 2-fold selectivity against TCPTP).Kinetics assays suggest that these complexes inhibit PTP1B in a competitive manner.The binding model of the kind of complex with PTP1B is predicted by using molecular docking techniques.The putative mode of interaction of the kind of complex with PTP1B suggests that the complex is capable of binding to the catalytic site of PTP1B.In the model,the vanadyl oxygen is close to the sulphur atom of the active site cysteine(Cys 215).
In order to test the substitution of ligands effects on the PTP1B-inhibition activities,we replaced "salicylaldehyde" with "5-bromo-salicylaldehyde" and "2-hydroxy naphthalene-1-carbaldehyde",respectively,then synthesize and characterized a series of new similar mixed oxovanadium complexes.The results of inhibition assays show the PTP1B-inhibition activities of these oxovanadium complexes of derivatives are slightly lower than the corresponding complexes.It appears that the spatial bulk of substitute of Schiff base weakly diminishes the PTP1B-inhibition activities in these complexes.
2.Based on the good activities of decreasing blood sugar by the oxovanadium complex with N_2O_2 coordination form.A tetradentate donor Schiff base ligand and derivatives with N_2O_2 coordination form were chosen to synthesize a series of oxovanadium complexes.These complexes were characterized by elemental analysis,FT-IR,EPR,DFT,UV-vis,conductivity measurment.The results show this kind of oxovanadium complex is five-coordinated neutral complex with distorted tetragonal pyramid geometry. The center vanadium atom is V(IV) with d~1 configuration.The complexes have been shown to be potent inhibitors of PTP1B.Kinetics assays suggest that the complex VO(sal-BDA) inhibits PTP1B in a competitive manner and inhibition constant of 31nM,was determined for the inhibition of PTP1B. The binding model of the complex VO(sal-BDA) with PTP1B is studied by using molecular docking techniques.The putative mode of interaction of the complex with PTP1B suggests that the vanadyl oxygen of the complex is close to the sulphur atom of cysteine(Cys 215) at the active site.
3.Copper and zinc are essential trace elements that play some central roles in the biochemistry of every living organism.The antitumor activity of copper complexes based on DNA cleavage has been studied extensively. However,the investigation of copper complexes interaction with PTP1B, which is regared as the target of antitumor drugs,is not reported.Our group first explores PTP1B-inhibitory activities of copper complexes and zinc complexes with Schiff base ligands.In this thesis,the copper complexes with Schiff base.or 1,10-phenanthroline ligands are synthesized and nsulin receptor(IR) or insulin receptor substratesthen characterized by elemental analysis,FT-IR,X-ray crystallography,UV-vis,conductivity measurement. The results of inhibition assays show these copper complexes are potent PTP1B inhibitors.IC_(50) values ranged from 10~(-6) to 10~(-7)M.More studies show that PTP1B inhibitory activities of copper complexes with Schiff base ligands decrease in the presence of GSH and PTP1B inhibitory activities of the copper complex[Cu(phen)_3]~(2+) increase in the presence of oxygen,implying the existence of oxidation mechanism during the PTP1B-inhibition process by copper complexes.Noted that the binuclear copper complex [Cu(phen)_2(μ-IDA)Cu(phen)(NO_3)]NO_3 inhibits PTP1B in a uncompetitive manner.And the complex selectively inhibits TCPTP over the other two phosphatases SHP-1 and TCPTP.
4.Using oxovanadium complex VO(SAA)(phen) and copper complex [Cu(phen)_2(μ-IDA)Cu(phen)(NO_3)]NO_3 as the representatives,we attempt to cultivate and PTP1B/inhibitor compound crystals by the soaking method and obtain two X-ray crystal structures of PTP1B soaked in the copper complex and oxovanadium complex.In comparison with the native PTP1B,the structures in PTP1B soaked in the copper complex and oxovanadium complex have some difference,and it is mainly obvious for the SH group of Cys 215,which indicates the ever happened interactions between the inhibitors and active region of PTP1B.Remarkably,the SH of catalytic cysteine of PTP1B is partially oxidized in the PTP1B/(copper complex) compound crystal,and the phenomenon is similar to that reported by the reference published in Nature.
引文
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