摘要
氨基酸席夫碱其金属配合物被证实具有抗癌、抑菌、与DNA作用等生物活性及优良的载氧、催化性能，已成为生物无机化学与材料学领域的研究热点之一。泛素-蛋白酶体通路，作为真核细胞蛋白质降解的重要途径，控制着许多负责细胞周期和肿瘤生长的蛋白的降解。特异性的阻断该通路，会影响到细胞内众多关键蛋白的调控，进而影响到多个细胞内过程，最终导致细胞凋亡。蛋白酶体也因此成为了一个理想的抗肿瘤药物设计与开发的新靶点。近年来，席夫碱金属配合物的抗肿瘤活性已得到了人们的重视，但是对于含吲哚环的色氨酸类席夫碱金属配合物作为蛋白酶体抑制剂诱导肿瘤细胞凋亡的研究却是少有报道。因此，设计和合成新型的氨基酸类席夫碱金属配合物，研究其化学结构、生物活性及作用机制，特别是对肿瘤细胞内蛋白酶体的抑制作用及作用机理，对于抗肿瘤药物的开发具有重要的指导意义。
本文选择4种不同结构的杂环羰基化合物，使其与色氨酸缩合并与金属离子反应，得到了25种未见报道的席夫碱金属配合物，并培养了11个配合物的单晶。采用元素分析、红外光谱分析、紫外光谱分析、核磁共振氢谱分析、热重分析等分析测试方法对其结构进行了表征，推断出金属配合物可能的化学结构；采用X-射线单晶衍射分析对金属配合物的单晶进行结构测试和解析；对部分配合物与DNA的作用方式进行了研究；以蛋白酶体为靶点，研究了杂环-色氨酸类席夫碱镉配合物对肿瘤细胞内蛋白酶体活性的抑制作用及对肿瘤细胞的诱导凋亡作用。主要进行了以下几方面工作：
（1）合成并培养了2-乙酰基吡啶缩L-色氨酸席夫碱系列5个金属配合物单晶，其组成分别为M(C18H16N3O2)2·2CH3OH (M=Mg(II), Ni(II), Cu(II), Cd(II))、Zn(C18H16N3O2)2·2CH3CH2OH。单晶结构分析表明，上述五种配合物晶体均属四方晶系，空间群P43212。每一个金属原子都与两分子的2-乙酰基吡啶缩L-色氨酸配体相结合，并分别与每分子配体中吡啶上氮原子、羧基上羟基氧原子以及席夫碱>C=N-结构上氮原子配位，最终构成了一个4N+2O的六齿中性八面体配合物。此外，每分子金属配合物中都包含两个溶剂分子，其是晶体结构的一部分，但处于游离状态而不参与配位。以镁配合物Mg(C18H16N3O2)2·2CH3OH为代表，其晶胞参数（对I＞2(I)的衍射点）。通过N-H…O分子间氢键作用，配合物最终形成了一个二维的面状结构。
（2）合成了2-乙酰基吡嗪缩L-色氨酸席夫碱系列5种金属配合物，并培养了配合物Ni(C17H15N4O2)2·2CH3OH的单晶。单晶结构分析表明，该配合物晶体属四方晶系，空间群P43212，晶胞参数a=b=11.8069(10)，c=28.961(2)，最终偏差因子R1=0.0548，wR2=0.1466（对I＞2(I)的衍射点）。每一个镍原子都与两分子的2-乙酰基吡嗪缩L-色氨酸配体相结合，并分别与每分子配体中吡嗪环上氮原子、羧基上羟基氧原子以及席夫碱C=N结构上氮原子配位，形成了一个扭曲的八面体结构。在外界，每分子镍金属配合物中均包含两个游离状态的溶剂甲醇分子。镍配合物均通过N-H…O分子间氢键的作用形成一维链状结构，链之间通过同样的N-H…O分子间氢键形成了二维网状结构。
该系列其余4种配合物的化学组成分别为：M(C17H15N4O2)2·2CH3OH (M=Mn(II), Cu(II), Cd(II))、Zn(C17H15N4O2)2·4CH3OH。
（3）合成了5-甲基呋喃-2-甲醛缩L-色氨酸席夫碱系列5种金属配合物，配合物的化学组成为：M(C17H15N2O3)2·2CH3OH (M=Mn(II), Ni(II), Cu(II), Cd(II))、Zn(C17H15N2O3)2·4CH3OH。
（4）合成了5-溴噻吩-2-甲醛缩L-色氨酸席夫碱系列5种金属配合物，配合物的化学组成为：M(C16H12N2O2SBr)2·2CH3OH (M=Mn(II), Ni(II), Cu(II), Zn(II),Cd(II))。
（5）合成并培养了2-乙酰基吡嗪缩D-色氨酸席夫碱镍金属配合物单晶，其组成为Ni (C17H15N4O2)2·2CH3OH。单晶结构分析表明，该配合物属单斜晶系，空间群C2/c，晶胞参数a=17.4878(17)，b=11.3696(12)，c=18.6213(18)，最终偏差因子R1=0.0356，wR2=0.0866（对I＞2(I)的衍射点）。每一个镍原子都与两分子的2-乙酰基吡嗪缩D-色氨酸配体相结合，并分别与每分子配体中吡嗪环上氮原子、羧基上羟基氧原子以及席夫碱C=N结构上氮原子配位，形成了一个扭曲的八面体结构。在外界，每分子镍金属配合物中均包含两个游离状态的溶剂甲醇分子。
（6）合成并培养了2-乙酰基吡啶缩D-色氨酸席夫碱系列4个金属配合物单晶，其组成分别为M(C18H16N3O2)2·2CH3OH (M=Mg(II), Ni(II), Cd(II))、Zn(C18H16N3O2)2·4CH3OH。单晶结构分析表明，上述四种金属配合物均属四方晶系，空间群P41212。每一个金属原子都与两分子的2-乙酰基吡啶缩D-色氨酸配体相结合，并分别与每分子配体中吡啶上氮原子、羧基上羟基氧原子以及席夫碱>C=N-亚胺基结构上氮原子配位，最终均形成一个扭曲的六齿八面体配合物。
(7)以2-乙酰基吡啶缩L-色氨酸席夫碱镁金属配合物Mg(C18H16N3O2)2·2CH3OH的晶体结构为基础，运用Gaussian03量子化学程序包，采用密度泛函理论B3LYP方法，在6-31+G*水平上对分子进行结构优化。计算了分子稳定构型的总能量、前线分子轨道能量、原子自然电荷分布、静电势等。计算结果表明，理论值与实验值基本相符，证明了计算模型的稳定性。
（8）利用紫外吸收光谱、荧光发射光谱及粘度测定等方法，研究了2-乙酰基吡啶缩L-色氨酸席夫碱镁金属配合物Mg(C18H16N3O2)2·2CH3OH及2-乙酰基吡嗪缩L-色氨酸席夫碱镍金属配合物Ni(C17H15N4O2)2·2CH3OH与小牛胸腺DNA之间的相互作用。实验表明，上述两种金属配合物是通过静电结合而与CT-DNA发生作用。其它的结合方式，例如氢键结合，亦可能同时存在于体系中。研究表明，配合物中配体共面性差，配合物与DNA发生静电结合的可能性大。
（9）以蛋白酶体为靶点，研究了杂环-色氨酸类席夫碱镉配合物的抗肿瘤活性及作用机制。
以人乳腺癌MDA-MB-231细胞为作用对象，利用MTT法对前文合成的25种色氨酸类席夫碱金属配合物进行了抗肿瘤活性初筛。实验结果显示，与同系列铜、锌金属配合物相比，2-乙酰基吡啶缩L-色氨酸席夫碱镉金属配合物Cd1、2-乙酰基吡嗪缩L-色氨酸席夫碱镉金属配合物Cd2以及5-甲基呋喃-2-甲醛缩L-色氨酸席夫碱镉金属配合物Cd3对人乳腺癌MDA-MB-231细胞增殖的抑制效果更佳。结合蛋白酶体活性测试、蛋白质免疫印迹及细胞形态学研究等方法证明了金属配合物Cd1、Cd2、Cd3均可以通过抑制人乳腺癌MDA-MB-231细胞细胞内类糜蛋白酶体活性来诱导其发生细胞凋亡。
5-溴噻吩-2-甲醛缩L-色氨酸席夫碱镉金属配合物Cd4在噻吩环位上连有的溴原子增大了配合物的空间位阻，致使其不能自由穿过人乳腺癌MDA-MB-231细胞的细胞膜进入细胞体内，无法有效抑制细胞内类糜蛋白酶体活性，进而导致Cd4对人乳腺癌MDA-MB-231细胞的凋亡诱导效果不明显。
金属配合物Cd1、Cd2、Cd3、Cd4均能不同程度的抑制人前列腺癌LN-CaP细胞及人多发性骨髓瘤ANBL6-V10R细胞的细胞增殖，且这种抑制作用随药物浓度的增大而逐渐增强。以金属配合物Cd4为代表，研究表明，Cd4可以通过抑制细胞内类糜蛋白酶体活性来诱导人前列腺癌LN-CaP细胞及人多发性骨髓瘤ANBL6-V10R细胞发生凋亡。
Bortezomib与Cd4的联合作用能够更好地抑制人多发性骨髓瘤ANBL6-V10R细胞细胞内类糜蛋白酶体活性，进而高效诱导其发生细胞凋亡。
It has been proved that amino acid Schiff bases and amino acid Schiff basecomplexes have good biological activities (such as anticancer, antibacterial andinteractions with DNA), oxygen-carrying properties and catalytic performances,which has been a hot topic in the field of biological inorganic chemistry and materialsscience. As an important way for the protein degradation of eukaryotic cells,Ubiquitin-proteasome pathway (UPP) plays a critical role in the degradation of theproteins involve in the cell cycle control and tumor growth. Specified block thispathway will affect the regulation of many key proteins in cells, and then affect manyimportant cellular processes, eventually leading to cell apoptosis. Hence, theproteasome becomes an ideal target for the design and development of new anticancerdrugs. In recent years, the anticancer activities of Schiff base metal complexesreceived much attention. However, the study of tryptophan Schiff base metalcomplexes as proteasome inhibitors induce apoptosis in cancer cells is rarely reported.Therefore, it has an important guiding significance for the development of antitumordrugs to design and synthesize some novel amino acid Schiff base metal complexes,and study chemical structures, biological activity and mechanism, especially theinhibitory effect and mechanism on tumor cells by targeting cellular proteasome.
In this paper, four carbonyl heterocyclic compounds with multiple structureshave been used to react with tryptophan and then coordinate with metal ions,preparing25different heterocycle-tryptophan Schiff base metal complexes, including11single crystals. The structures of these metal complexes were characterized byelemental analysis, IR spectrum, UV spectrum,1H NMR, and TG-DTG analysis, etc.Furthermore, the crystal structures were detected by X-ray crystal diffraction. Theinteraction mode between two complexes and calf thymus DNA has been tested, too. Moreover, the inhibition of proteasomal chymotrypsin-like activity and induction ofapoptosis in various types of tumor cells by heterocycle-tryptophan Schiff base metalcomplexes have also been studied by targeting the cellular proteasome. The mainresearches of this paper are as follows:
(1) Five metal complex crystals with Schiff base2-acetylpyridine-L-tryptophanwere obtained, which were composed of M(C18H16N3O2)2·2CH3OH (M=Mg(II),Ni(II), Cu(II), Cd(II)), Zn(C18H16N3O2)2·2CH3CH2OH. The crystallographic structuralanalysis reveals that all five crystals crystallize in the tetragonal crystal system, spacegroup P43212. Each metal atom coordinates with two Schiff base ligands. It iscoordinated by six atoms, namely, two nitrogen atoms from C=N, two nitrogen atomsfrom pyridine rings and two carboxylic oxygen atoms in different ligands, forming atype of the4N+2O neutrality complex. In addition, there are two solvent moleculesin the crystalline lattice which are not bound to the metal ions. Take the complexMg(C18H16N3O2)2·2CH3OH for example. The cell parameters are as follows: a=b=11.6532(14), c=29.025(3),===90, V=3941.5(8)3, F(000)=1480,
calcd=1.181g/cm3, the final R1=0.0670and wR2=0.1763(I>2(I)). As a result ofthe alternate arrangement of chains through inter-chained N-H…O hydrogen bondinginteractions, a2-D fabricated layer.
(2) Five metal complexes with Schiff base ligand2-acetylpyrazine-L-tryptophanwere synthesized. The single crystal of Ni(C17H15N4O2)2·2CH3OH was also obtained.The crystallographic structural analysis reveals that the crystal crystallizes in thetetragonal crystal system, space group P43212with cell parameters a=b=11.8069(10)
, c=28.961(2),===90, V=4037.2(6)3, F(000)=1544,calcd=1.213g/cm3, the final R1=0.0548and wR2=0.1466(I>2(I)). Each nickel atomcoordinates with two Schiff base ligands. It is coordinated by six atoms, namely, twonitrogen atoms from C=N, two nitrogen atoms from pyrazine rings and twocarboxylic oxygen atoms in different ligands, forming a neutral4N+2O complex. Inaddition, there are two free solvent methanol molecules in the crystalline lattice. Eachligand bridges two Ni(II) centers through N–H…O intermolecular hydrogen bonds,leading to a one-dimensional coordination polymer. Two adjacent chains are bridged by one type of hydrogen bond, involving N–H…O interactions. As a result of thealternate arrangement of chains through inter-chained hydrogen bonding interactions,a2-D layer is formed.
The chemical compositions of the remaining four metal complexes are as follows:M(C17H15N4O2)2·2CH3OH (M=Mn(II), Cu(II), Cd(II)), Zn(C17H15N4O2)2·4CH3OH.
(3) Five metal complexes with Schiff base ligand5-methylfurfural-L-tryptophanwere synthesized. The chemical compositions of these metal complexes are as follows:M(C17H15N2O3)2·2CH3OH (M=Mn(II), Ni(II), Cu(II), Cd(II)),Zn(C17H15N2O3)2·4CH3OH.
(4) Five metal complexes with Schiff base5-bromo-2-thiophenecarbaldehyde-L-tryptophan were synthesized. The chemical compositions of these metal complexesare as follows: M(C16H12N2O2SBr)2·2CH3OH (M=Mn(II), Ni(II), Cu(II), Zn(II),Cd(II)).
(5) The crystal of2-acetylpyridine-D-tryptophan nickel complexNi(C17H15N4O2)2·2CH3OH was obtained. The crystallographic structural analysisreveals that the crystal crystallizes in the monoclinic crystal system, space group C2/cwith cell parameters a=17.4878(17), b=11.3696(12), c=18.6213(18),==90,=106.0470(10), V=3558.2(6)3, F(000)=1544,calcd=1.377g/cm3, thefinal R1=0.0356，wR2=0.0866(I>2(I)).
(6) Four metal complex crystals with Schiff base2-acetylpyridine-D-tryptophanwere obtained, which were composed of M(C18H16N3O2)2·2CH3OH (M=Mg(II),Ni(II), Cd(II)), Zn(C18H16N3O2)2·4CH3OH. The crystallographic structural analysisreveals that all four crystals crystallize in the tetragonal crystal system, space groupP41212. Each metal atom coordinates with two Schiff base ligands. It is coordinatedby six atoms, namely, two nitrogen atoms from C=N, two nitrogen atoms frompyridine rings and two carboxylic oxygen atoms in different2-acetylpyridine-D-tryptophan ligands, forming a type of the4N+2O neutralitycomplex.
(7) The energies and components of molecular orbital, natural chargesdistribution and electrostatic potential of Mg(C18H16N3O2)2·2CH3OH were calculated by the density functional theory with the gradient corrected B3LYP method usingGaussian03program package based on the crystal structure. All the data obtainedfrom quantum chemistry calculation are consistent with those from determination,indicating that the calculation model is stabilized.
(8) The interactions between complexes Mg(C18H16N3O2)2·2CH3OH,Ni(C17H15N4O2)2·2CH3OH and calf thymus DNA were studied by UV absorptionspectra, fluorescence emission spectra and viscometric method. The nature of thebinding seems to be mainly an electrostatic interaction between DNA and the complex.However, other binding modes, such as hydrogen bonding, may also be present in thissystem. It has been demonstrated that when ligand is less coplanar, it is morefavorable to interact with DNA in the way of electrostatic binding.
(9) Anticancer activities and mechanism of heterocycle-tryptophan Schiff basecadimum complexes as the proteasome inhibitor were studied. The antiproliferaionactivities of25tryptophan Schiff base complexes were studied by MTT method inhuman breast cancer MDA-MB-231cells. It shows that2-acetylpyridine-L-tryptophan cadimium complex Cd1,2-acetylpyrazine-L-tryptophan cadimiumcomplex Cd2and5-methylfurfural-L-tryptophan cadimium complex Cd3are moreeffective than the other metal complexes with same series in the inhibition of cellproliferation of human breast cancer MDA-MB-231cells. According to theproteasomal chymotrypsin-like activity assay, western blotting analysis and cellularapoptotic morphology assay, we proved that inhibition of proteasomal activity(especially, CT-like activity) by these three complexes, can strongly induce apoptosisin cultured breast cancer MDA-MB-231cells.
5-Bromo-2-thiophenecarbaldehyde-L-tryptophan cadimium comples Cd4, whichhas a-Br atom in the thiophene ring, cannot actually enter cancer cells. Although itcould inhibit CT-like activity of the cell-free proteasome in vitro, it cannot inhibitcellular proteasome activity, as a result, Cd4cannot induce apoptosis in culturedMDA-MB-231cells.
Cadimium complexes Cd1, Cd2, Cd3and Cd4could inhibit cancer cellproliferation of LN-CaP human prostate cancer cells and ANBL6-V10R human multiple myeloma cancer cells in a concentration-dependent manner. Take Cd4as anexample, it shows that Cd4is a potent inhibitor of proteasomal chymotrypsin-likeactivity, further capable of inducing apoptosis of LN-CaP human prostate cancer cellsand ANBL6-V10R human multiple myeloma cancer cells in a cancer cell-specificmanner.
The combination of Cd4and Bortezomib could highly inhibit the activity ofproteasome and then induce apotosis of ANBL6-V10R human multiple myelomacancer cells compared with Cd4or Bortezomib alone.
引文
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