苯并噻唑抗肿瘤药物的合成、筛选及其作用机理
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摘要
肿瘤的发生与肿瘤细胞本身凋亡信号的抑制息息相关,因此细胞凋亡在肿瘤的化疗中起着重要的作用,很多的药物都是通过重建细胞凋亡来达到治疗肿瘤的目的。过量的ROS(intracellular reactive oxygen species)可以诱导线粒体膜电位(MMP)崩溃,使线粒体中的死亡因子释放,诱导细胞死亡;同时ROS的积累会造成脂质过氧化,蛋白质、酶的氧化失活和DNA的氧化损伤。研究表明,肿瘤细胞具有比正常细胞更高的ROS水平,对ROS的攻击更敏感,因此ROS相关的药物开发成为抗肿瘤药物研究开发的一个热点。
苯并噻唑是药物研究中的一个重要母核。一些苯并噻唑化合物被研究证实具有拓扑异构酶Ⅱ抑制剂的作用,有些被证实具有激酶抑制剂的作用,大量的研究表明,苯并噻唑类药物具有抗氧化作用,而且其生物活性与ROS相关。
因此,我们设计合成了一系列以2.(1,3-diphenyl-1H-pyrazol-4-y1)benzo[d]thiazole(DPB)为母环的苯并噻唑类化合物,并筛选了它们的抗肿瘤活性。筛选得到3-(4-(benzo[d]thiazol-2-y1)-1-phenyl-1H-pyrazol-3-y1)phenyl acetate(DPB-5)具有较高的细胞毒性。进一步研究发现DPB-5通过ROS介导的AIF信号通路诱导细胞凋亡。
本实验的主要结论如下:
1.本实验成功设计合成了10个苯并噻唑的衍生物,并用碳谱、氢谱和质谱等方法对其结构进行表征。本实验采用邻氨基硫酚的缩合反应合成苯并噻唑,并对反应条件进行了优化。最佳反应条件:溶剂,乙醇;原料配比吡唑:邻氨基苯硫酚=1:1.1;以浓度为5%(mmol体积比)的对甲苯磺酸为催化剂,室温反应,反应得率80%～90%。
2.本实验用肝癌细胞Hep G2、乳腺癌细胞MCF-7和喉癌细胞Hep 2筛选所合成的苯并噻唑药物,得到细胞毒性最高的DPB-5,其对Hep G2的IC_(50)为4.6μM。进一步研究表明DPB-5对正常肝细胞LO2的细胞毒性较低,IC_(50) 9.6μM,为Hep G2的2.1倍,DPB-5对肝癌细胞的选择性表明DPB-5具有开发成抗肿瘤药物的潜力。通过Hoechst染色,Annexin V-FITC和PI双染,DNALadder片段分析以及细胞周期凋亡峰分析等多种方法分析确定,DPB-5具有诱导Hep G2细胞凋亡的作用。DPB-5诱导Hep G2细胞凋亡的同时伴随着ROS的增加和GSH的减少,然而对于正常细胞LO2细胞,ROS的增加大大减弱同时GSH未明显减少。我们推测DPB-5显著的细胞毒性作用与Hep G2对ROS的敏感性有关。
3.抗氧化剂(N-acetyl-L-cysteine和过氧化氢酶)在抑制Hep G2细胞ROS爆发和GSH减少的同时,成功的阻滞了MMP的减少,并且抑制了细胞凋亡,减少了细胞的死亡率。因此,ROS爆发是MMP崩溃与细胞凋亡的前提。
4.在ROS诱导的细胞凋亡中,通常MMP崩溃就会引发细胞色素C的释放,而在DPB-5诱导的细胞凋亡中,并没有明显的细胞色素C释放,同时细胞色素C下游的caspase-9和caspase-3也没有活性增加。相对的,AIF(apoptosis inducingfactor),另一个细胞死亡信号却在细胞质中积累,因此我们推测DPB-5通过AIF信号通路诱导细胞凋亡。进一步的研究表明,虽然在细胞凋亡过程中caspase-9和caspase-3没有被激活,但是其他caspase的活化对于细胞凋亡却是必须的,因为当用caspase抑制剂zVADfmk抑制所有caspase的活性时,细胞凋亡率和细胞死亡率都明显降低。
综上所述,DPB-5对肝癌细胞具有很好的杀伤效果,而对正常肝细胞低毒性,因此其具有较好的抗肿瘤活性。DPB-5通过caspase依赖的ROS介导的AIF信号通路诱导细胞凋亡。由于通过细胞色素C-caspase诱导的抗肿瘤药物在临床上经常会碰到药物抗性,因此,AIF途径的抗肿瘤药物可以做一个有效的补充,这使得DPB系列的抗肿瘤药物的研究开发更具有价值。这些工作为发展新型的苯并噻唑类抗肿瘤药物做了一定的基础性的研究。
Apoptosis is important in chemotherapy-induced tumor-cell killing,and many anticancer drugs induce restoration of apoptosis.Many tumors have been associated with the inhibition of apoptosis,and the disruption of apoptotic function which contribute substantially to the transformation of a normal cell into a tumor cell. Intracellular reactive oxygen species(ROS) is considered to be a death signal in apoptosis.ROS induces disruption of the mitochondrial membrane potential(MMP) and release of cell death signals to trig cell death.Accumulation of excessive ROS leads to lipid peroxidation,protein oxidation,enzyme inactivation,oxidative DNA damage.Cancer cells are more sensitive to ROS than normal cells;therefore,ROS is a hotpoint for anti-cancer drug research.
Thiazole,an important heterocyclic ring,is widely used in anticancer drug development.Many natural chemotherapeutic agents containing thiazole moiety have been discovered and studied,like tiazofurin,distamycin,bleomycin and netropsin. Among the thiazole derivatives,benzothiazole is an important scaffold of drugs,and it has been studied extensively.Benzothiazole derivatives are known as inhibitors of topoisomeraseⅡ,tyrosine kinase and ubiquitin proteasome system.Some studies reported the antioxidant properties of benzothiazole derivatives,and their biological activity was indicated to be strongly related to ROS.
In this respect,a new serious of benzothiazole derivatives based on 2-(1,3-diphenyl-1H-pyrazol-4-yl)benzo[d]thiazole(DPB) were designed and synthesized.Next,we evaluated their anti-cancer effects and found 3-(4-(benzo[d]thiazol-2-yl)-1-phenyl-1H-pyrazol-3-yl) phenyl acetate(DPB-5). Further more the molecular mechanism of DPB-5 for its anticancer effect was studied.We found that DPB-5 induced apoptosis in human liver cancer cells through a caspase-dependent and ROS-mediated AIF pathway.
The main results of this study are as follows:
1.10 benzothiazole derivates based on DPB-5 were designed and synthesized, the structures was determined by NMR and MS.The optimum reaction conditions: solvent,ethanol;raw materials ratio pyrazole:2-aminophenyl mercaptan=1:1.1; p-toluene sulfonic acid as catalyst,with the concentration of 5%(mmol volume ratio). The reaction conditions can be at room temperature,with the yields at 80%～90%.
2.The anti-cancer effects of benzothiazoles were evaluated by MTT method using Hep G2,MCF-7,Hep 2 cell lines.The results showed that DPB-5 was the highest cytotoxic to these cancer cell lines and Hep G2 was most sensitive to the cytotoxicity of benzothiazole.Hep G2 cells were shown to be much more sensitive to DPB-5-induced cytotoxicity with an IC_(50) of 4.6μM while LO2 normal liver cells with an IC_(50) of 9.6μM.The cytotoxic effect of DPB-5 caused apoptotic cell death,as determined by DNA fragmentation,morphological change of the nucleus,increase of pro-G1 DNA content,and externalization of phosphatidylserine.The apoptotic effect was associated with an early elevated level of ROS and significant decrease of GSH, however DPB-5 induced less change of ROS and GSH on normal liver cells LO2. The higher vulnerability to ROS of Hep G2 cells than LO2 cells lead to the higher cytotoxicity of Hep G2 cells on DPB-5 than that of LO2 cells.
3.ROS burst was a prerequisite for mitochondrial membrane potential(MMP) collapse and cell death induced by DPB-5.Anti-oxidants(N-acetyl-L-cysteine and catalase) blocked the MMP depolarization,inhibited the cytotoxicity of DPB-5, decreased cell apoptosis and enhanced cell survival associating with suppressed ROS generation and GSH depletion.
4.Considering the death signal trigged by MMP collapse,there was no significantly release of cytochrome C,which was supported by no activation of caspase-9 or caspase-3.However,apoptosis inducing factor(AIF,another death signal molecular) was clearly increased in cytoplasm.It is suggested DPB-5 induced Hep G2 cell apoptosis via AIF/Endo G pathway.Although no need of caspase-9 or caspase-3 activated,DPB-5 induced Hep G2 cells apoptosis in a caspase dependent pathway.Pan-caspase inhibitor zVADfmk significantly reduced cell death rate and inhibited cell apoptosis.
Taken together,DPB-5 showed a good anti-cancer activity while low cytotoxicity to normal cells.And DPB-5 induced Hep G2 cell apoptosis in a ROS-mediated AIF pathway which was caspase dependent.These findings will contribute to develop of new serious of benzothiazole anti-cancer drugs.
苯并噻唑是药物研究中的一个重要母核。一些苯并噻唑化合物被研究证实具有拓扑异构酶Ⅱ抑制剂的作用,有些被证实具有激酶抑制剂的作用,大量的研究表明,苯并噻唑类药物具有抗氧化作用,而且其生物活性与ROS相关。
因此,我们设计合成了一系列以2.(1,3-diphenyl-1H-pyrazol-4-y1)benzo[d]thiazole(DPB)为母环的苯并噻唑类化合物,并筛选了它们的抗肿瘤活性。筛选得到3-(4-(benzo[d]thiazol-2-y1)-1-phenyl-1H-pyrazol-3-y1)phenyl acetate(DPB-5)具有较高的细胞毒性。进一步研究发现DPB-5通过ROS介导的AIF信号通路诱导细胞凋亡。
本实验的主要结论如下:
1.本实验成功设计合成了10个苯并噻唑的衍生物,并用碳谱、氢谱和质谱等方法对其结构进行表征。本实验采用邻氨基硫酚的缩合反应合成苯并噻唑,并对反应条件进行了优化。最佳反应条件:溶剂,乙醇;原料配比吡唑:邻氨基苯硫酚=1:1.1;以浓度为5%(mmol体积比)的对甲苯磺酸为催化剂,室温反应,反应得率80%～90%。
2.本实验用肝癌细胞Hep G2、乳腺癌细胞MCF-7和喉癌细胞Hep 2筛选所合成的苯并噻唑药物,得到细胞毒性最高的DPB-5,其对Hep G2的IC_(50)为4.6μM。进一步研究表明DPB-5对正常肝细胞LO2的细胞毒性较低,IC_(50) 9.6μM,为Hep G2的2.1倍,DPB-5对肝癌细胞的选择性表明DPB-5具有开发成抗肿瘤药物的潜力。通过Hoechst染色,Annexin V-FITC和PI双染,DNALadder片段分析以及细胞周期凋亡峰分析等多种方法分析确定,DPB-5具有诱导Hep G2细胞凋亡的作用。DPB-5诱导Hep G2细胞凋亡的同时伴随着ROS的增加和GSH的减少,然而对于正常细胞LO2细胞,ROS的增加大大减弱同时GSH未明显减少。我们推测DPB-5显著的细胞毒性作用与Hep G2对ROS的敏感性有关。
3.抗氧化剂(N-acetyl-L-cysteine和过氧化氢酶)在抑制Hep G2细胞ROS爆发和GSH减少的同时,成功的阻滞了MMP的减少,并且抑制了细胞凋亡,减少了细胞的死亡率。因此,ROS爆发是MMP崩溃与细胞凋亡的前提。
4.在ROS诱导的细胞凋亡中,通常MMP崩溃就会引发细胞色素C的释放,而在DPB-5诱导的细胞凋亡中,并没有明显的细胞色素C释放,同时细胞色素C下游的caspase-9和caspase-3也没有活性增加。相对的,AIF(apoptosis inducingfactor),另一个细胞死亡信号却在细胞质中积累,因此我们推测DPB-5通过AIF信号通路诱导细胞凋亡。进一步的研究表明,虽然在细胞凋亡过程中caspase-9和caspase-3没有被激活,但是其他caspase的活化对于细胞凋亡却是必须的,因为当用caspase抑制剂zVADfmk抑制所有caspase的活性时,细胞凋亡率和细胞死亡率都明显降低。
综上所述,DPB-5对肝癌细胞具有很好的杀伤效果,而对正常肝细胞低毒性,因此其具有较好的抗肿瘤活性。DPB-5通过caspase依赖的ROS介导的AIF信号通路诱导细胞凋亡。由于通过细胞色素C-caspase诱导的抗肿瘤药物在临床上经常会碰到药物抗性,因此,AIF途径的抗肿瘤药物可以做一个有效的补充,这使得DPB系列的抗肿瘤药物的研究开发更具有价值。这些工作为发展新型的苯并噻唑类抗肿瘤药物做了一定的基础性的研究。
Apoptosis is important in chemotherapy-induced tumor-cell killing,and many anticancer drugs induce restoration of apoptosis.Many tumors have been associated with the inhibition of apoptosis,and the disruption of apoptotic function which contribute substantially to the transformation of a normal cell into a tumor cell. Intracellular reactive oxygen species(ROS) is considered to be a death signal in apoptosis.ROS induces disruption of the mitochondrial membrane potential(MMP) and release of cell death signals to trig cell death.Accumulation of excessive ROS leads to lipid peroxidation,protein oxidation,enzyme inactivation,oxidative DNA damage.Cancer cells are more sensitive to ROS than normal cells;therefore,ROS is a hotpoint for anti-cancer drug research.
Thiazole,an important heterocyclic ring,is widely used in anticancer drug development.Many natural chemotherapeutic agents containing thiazole moiety have been discovered and studied,like tiazofurin,distamycin,bleomycin and netropsin. Among the thiazole derivatives,benzothiazole is an important scaffold of drugs,and it has been studied extensively.Benzothiazole derivatives are known as inhibitors of topoisomeraseⅡ,tyrosine kinase and ubiquitin proteasome system.Some studies reported the antioxidant properties of benzothiazole derivatives,and their biological activity was indicated to be strongly related to ROS.
In this respect,a new serious of benzothiazole derivatives based on 2-(1,3-diphenyl-1H-pyrazol-4-yl)benzo[d]thiazole(DPB) were designed and synthesized.Next,we evaluated their anti-cancer effects and found 3-(4-(benzo[d]thiazol-2-yl)-1-phenyl-1H-pyrazol-3-yl) phenyl acetate(DPB-5). Further more the molecular mechanism of DPB-5 for its anticancer effect was studied.We found that DPB-5 induced apoptosis in human liver cancer cells through a caspase-dependent and ROS-mediated AIF pathway.
The main results of this study are as follows:
1.10 benzothiazole derivates based on DPB-5 were designed and synthesized, the structures was determined by NMR and MS.The optimum reaction conditions: solvent,ethanol;raw materials ratio pyrazole:2-aminophenyl mercaptan=1:1.1; p-toluene sulfonic acid as catalyst,with the concentration of 5%(mmol volume ratio). The reaction conditions can be at room temperature,with the yields at 80%～90%.
2.The anti-cancer effects of benzothiazoles were evaluated by MTT method using Hep G2,MCF-7,Hep 2 cell lines.The results showed that DPB-5 was the highest cytotoxic to these cancer cell lines and Hep G2 was most sensitive to the cytotoxicity of benzothiazole.Hep G2 cells were shown to be much more sensitive to DPB-5-induced cytotoxicity with an IC_(50) of 4.6μM while LO2 normal liver cells with an IC_(50) of 9.6μM.The cytotoxic effect of DPB-5 caused apoptotic cell death,as determined by DNA fragmentation,morphological change of the nucleus,increase of pro-G1 DNA content,and externalization of phosphatidylserine.The apoptotic effect was associated with an early elevated level of ROS and significant decrease of GSH, however DPB-5 induced less change of ROS and GSH on normal liver cells LO2. The higher vulnerability to ROS of Hep G2 cells than LO2 cells lead to the higher cytotoxicity of Hep G2 cells on DPB-5 than that of LO2 cells.
3.ROS burst was a prerequisite for mitochondrial membrane potential(MMP) collapse and cell death induced by DPB-5.Anti-oxidants(N-acetyl-L-cysteine and catalase) blocked the MMP depolarization,inhibited the cytotoxicity of DPB-5, decreased cell apoptosis and enhanced cell survival associating with suppressed ROS generation and GSH depletion.
4.Considering the death signal trigged by MMP collapse,there was no significantly release of cytochrome C,which was supported by no activation of caspase-9 or caspase-3.However,apoptosis inducing factor(AIF,another death signal molecular) was clearly increased in cytoplasm.It is suggested DPB-5 induced Hep G2 cell apoptosis via AIF/Endo G pathway.Although no need of caspase-9 or caspase-3 activated,DPB-5 induced Hep G2 cells apoptosis in a caspase dependent pathway.Pan-caspase inhibitor zVADfmk significantly reduced cell death rate and inhibited cell apoptosis.
Taken together,DPB-5 showed a good anti-cancer activity while low cytotoxicity to normal cells.And DPB-5 induced Hep G2 cell apoptosis in a ROS-mediated AIF pathway which was caspase dependent.These findings will contribute to develop of new serious of benzothiazole anti-cancer drugs.
引文
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