CN104910212B - 一种席夫碱铂配合物及其制备方法和应用 - Google Patents
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Abstract
本发明提供了一种席夫碱铂(II)配合物及其制备方法,以及该配合物的应用。本发明席夫碱铂(II)配合物化学式为:Pt[X‑PMP][DMSO]Cl,其中X‑PMP=4‑X‑2‑[(苯基亚胺)甲基]‑苯酚(X=Cl或者NO2)。其制备方法:称取反应物X‑PMP溶于甲醇溶液中,向其中滴加摩尔量为该反应物1~2倍的三乙胺,搅拌下,将与X‑PMP等摩尔量的Pt(DMSO)2Cl2加入到上述反应溶液中,反应溶液避光且通氮气保护,加热回流反应1~4小时,析出固体产物。本发明配合物制备方法简单,原料易得,成本较低。生物活性实验检测表明,该配合物不仅能够有效抑制可作为抗肿瘤药物靶点的PTP1B活性,而且对乳腺癌细胞增殖有显著的抑制作用,可在制备抗肿瘤药物中应用。
Description
技术领域:
本发明涉及铂(II)配合物,具体涉及一种席夫碱铂(II)配合物及其制备方法和应用。
背景技术:
近年来,癌症已经成为严重威胁人类生命健康的主要疾病之一,在癌症的最有效治疗过程中,铂类抗癌药物起着举足轻重的作用,它们已经成为癌症化疗中不可或缺的药物,然而,目前上市的铂类药物也存许多各种各样的毒副作用,这些缺点限制了该类药物更广泛的应用,同时也促进了人们对铂类抗癌药物机理的深入研究,通过寻找不同于经典的顺铂类药物的可能的抗癌机理,对大量合成的具有新型结构的抗癌铂配合物进行深入研究,期望得到高效、低毒、水溶性好,选择性高、与顺铂无交叉耐药的候选药物。
众所周知,以顺铂为主的传统铂类抗癌药物的研究大多是以DNA为作用靶点,然而随着生命科学技术的不断深入,科学家们逐渐认识到铂配合物也可能通过作用于某些蛋白抑制癌细胞的生长、繁殖。其中,蛋白酪氨酸磷酸酶(PTPs)由于其活性异常与癌症发生和发展有着密切联系,已经成为目前抗癌药物的一个新靶点。为此我们选择具有较强生物活性的席夫碱类化合物为配体合成结构简单的新型铂(II)配合物,从全新的角度研究了该配合物对PTPs活性的抑制作用及其抗肿瘤效果,本发明铂(II)配合物结构在国内外尚未见报道。
发明内容:
本发明的目的在于提供一种席夫碱铂(II)配合物及其制备方法,以及该配合物作为蛋白酪氨酸磷酸酶1B抑制剂的应用,和在制备抗肿瘤药物中的应用。
本发明提供的一种席夫碱铂(II)配合物,其化学式为:Pt[X-PMP][DMSO]Cl,其中X-PMP=4-X-2-[(苯基亚胺)甲基]-苯酚(其中,X为Cl或者NO2),其结构式为:
本发明提供的一种席夫碱铂(II)配合物的制备方法,包括如下步骤:
(1)合成4-X-2-[(苯基亚胺)甲基]-苯酚配体(X为Cl或者NO2)(合成方法参照:韩虹,山西大学硕士学位论文,2012,p11-p12);
(2)合成Pt(DMSO)2Cl2前体铂配合物(合成方法参照:Jerold H.Price,et.al.Inorganic Chemistry,1972,11(6),1280-1284);
(3)合成席夫碱铂(II)配合物:按每毫摩尔反应物加入50~100mL甲醇的量,将4-X-2-[(苯基亚胺)甲基]-苯酚配体溶于甲醇溶液中,向其中滴加摩尔量为该反应物1~2倍的三乙胺,使其完全溶解,搅拌下,将与反应物等摩尔量的Pt(DMSO)2Cl2加入到上述反应溶液中,反应溶液避光并且通N2保护,加热回流反应1~4小时,停止反应,冷却有沉淀生成,抽滤,产物依次用水和甲醇各洗涤至少3次,真空干燥,得黄色固体粉末。
步骤中所述的X为Cl或者NO2。
本发明制得的席夫碱铂(II)配合物能够有效地抑制蛋白酪氨酸磷酸酶1B,可以用作高效的蛋白酪氨酸磷酸酶1B抑制剂;同时该类配合物具有较强的体外抑制肿瘤生长的活性,在相同实验条件下,抑制乳腺癌MCF-7细胞增殖的能力强于顺铂,可以在制备抗肿瘤药物中的应用。
本发明的优点和效果:本发明的席夫碱铂(II)配合物制备方法简单,原料易得,成本较低,在一般化学实验室均可完成,且生产过程对环境无污染;该配合物不仅能够有效地抑制蛋白酪氨酸磷酸酶1B活性,可作为高效的蛋白酪氨酸磷酸酶1B抑制剂,而且具有比顺铂更强的抑制MCF-7细胞增殖的作用,可为肿瘤治疗提供一种新的药物开发途径。
附图说明
图1本发明席夫碱铂(II)配合物抑制PTP1B活性的IC50值测定图
图2本发明席夫碱铂(II)配合物和顺铂分别对MCF-7细胞增殖的影响比较
具体实施方式
下面结合附图和实例对本发明作进一步说明。
实施例1
配合物的制备:
(1)配体4-X-2-[(苯基亚胺)甲基]-苯酚(X为Cl或者NO2)按照文献方法(韩虹,山西大学硕士学位论文,2012,p11-p12)制备。
(2)参照文献(Jerold H.Price,et.al.,Inorganic Chemistry,1972,11(6),1280-1284)方法合成前体铂配合物Pt(DMSO)2Cl2。
(3)合成本发明席夫碱铂(II)配合物Pt[Cl-PMP][DMSO]Cl:将0.5mmol(0.116g)4-氯-2-[(苯基亚胺)甲基]-苯酚溶于50mL甲醇溶液,向其中滴加0.67mmol(100μL)三乙胺,使其完全溶解,搅拌下,将0.5mmol(0.211g)的Pt(DMSO)2Cl2加入到上述反应溶液中,反应溶液避光并且通氮气保护,加热回流反应1~4小时,停止反应后冷却,抽滤,产物依次用蒸馏水和甲醇多次洗涤,真空干燥,得黄色固体粉末,产率约为59%。元素分析测定结果为:C15H15Cl2NO2PtS,括号内为理论值(%):C,33.58(33.40);H,2.85(2.80);N,2.56(2.60)。部分红外光谱数据(ν/cm-1):3048(C-H),1608(C=N),1305(C-O),1126(S=O),668(C-S),547(Pt-N),450(Pt-O);紫外光谱数据(λ/nm):418,307,243。
用0.5mmol(0.121g)4-硝基-2-[(苯基亚胺)甲基]-苯酚代替0.5mmol(0.116g)4-氯-2-[(苯基亚胺)甲基]-苯酚,在同样条件下合成铂(II)配合物Pt[NO2-PMP][DMSO]Cl,黄褐色固体产物,产率约为58%。元素分析结果按C15H15ClN2O4PtS计算:C,32.91(32.76);H,2.83(2.75);N,5.14(5.09);部分红外光谱数据(ν/cm-1):3035(C-H),1608(C=N),1321(C-O),1132(S=O),704(C-S),562(Pt-N),443(Pt-O);紫外光谱数据UV(λ/nm):414,332,204,267。
实施例2 本发明配合物抑制PTP1B活性的测定
IC50即半数抑制浓度,是指被抑制酶的活性达到一半时所用抑制剂的浓度,IC50值的大小是抑制剂对酶活性抑制能力强弱的评判标准之一,该值越小表明抑制剂的抑制能力就越强。IC50测定实验中以对硝基苯磷酸二钠盐(pNPP)为反应底物,该底物在PTP1B催化下易分解为黄色的对硝基苯酚(pNP),而pNP在405nm处有较强紫外吸收,所以通过测定该吸收值可以得知PTP1B作为催化剂已经反应的量,用该原理通过酶标仪检测得到一系列405nm波长下的吸光度值,并利用Origin程序处理数据,拟合得到配合物抑制酶的IC50值。
具体的实验步骤为:将83μL含PTP1B酶的MOPS缓冲溶液(50mM NaCl,20mM MOPS,pH=7.2)加入96孔板,再按照浓度梯度递增依次加入10μL抑制剂,于37℃恒温水浴锅中反应30min,然后用2μL pNPP(0.1M)启动反应,待颜色梯度出现后用5μL NaOH(2mM)终止反应,最后用酶标仪测量其紫外吸收强度,处理数据得到配合物抑制PTP1B活性的IC50值(附图1)。从图中可以看出本发明配合物Pt[Cl-PMP][DMSO]Cl和Pt[NO2-PMP][DMSO]Cl对PTP1B酶抑制的IC50值的范围分别为0.1~0.5和3~7μM,其中Pt[Cl-PMP][DMSO]Cl对PTP1B酶的抑制能力是顺铂(IC50为0.6~3.7μM)对PTP1B抑制能力的6倍左右,由此可见,该类席夫碱配合物能够有效地抑制PTP1B活性,而且不同结构的席夫碱铂(II)配合物对PTPs活性的抑制能力不同。
实施例3 本发明席夫碱铂配合物体外抗肿瘤活性测定
将人乳腺癌细胞(MCF-7)在含有10%胎牛血清的培养基中37℃、5%CO2培养箱中培养,用MTT法检测了本发明席夫碱铂(II)配合物对肿瘤细胞MCF-7增殖的影响,同时以顺铂为阳性对照,分析比较了相同条件下这两种配合物与顺铂抑制MCF-7增殖的能力。实验取对数生长期的MCF-7细胞经消化、离心收集后配制成1mL的细胞悬液,由血球计数板测得细胞悬液内的细胞个数,取适量体积的该细胞悬液将其稀释成细胞密度约为1×10-4个/mL的细胞悬液,均匀接种于96孔板,每孔200μL,将96孔板放置在CO2培养箱中孵化,至细胞单层铺满孔低,加入7个浓度梯度的席夫碱铂(II)配合物,每组设6个复孔。细胞继续在CO2培养箱中孵化48小时后,倒置显微镜下观察细胞形态变化,然后每孔加入20μLMTT(5mg/mL)溶液,继续孵育4小时,小心吸去上清液,每孔加入150的DMSO溶液,振荡10min,待底部蓝色结晶状固体完全溶解,用酶标仪测得各孔溶液490nm处的吸光度值A。以药物浓度为横坐标,细胞存活率为纵坐标绘制细胞生长曲线。
细胞存活率(%)=(A实验组/A对照组)×100
附图2为相同浓度梯度的席夫碱铂(II)配合物(Pt[Cl-PMP][DMSO]Cl和Pt[NO2-PMP][DMSO]Cl)和顺铂分别与MCF-7作用48小时后,它们抑制肿瘤细胞增殖情况的比较,实验结果表明,本发明席夫碱铂(II)配合物对人乳腺癌细胞(MCF-7)有显著的抑制作用,它们抑制MCF-7细胞增殖的IC50值分别为0.31~0.41和0.26~0.87μM,抑制效果明显优于顺铂(IC50=1.43~9.56μM),因此,本发明的铂类配合物可用作预防和治疗乳腺癌的潜在药物。
Claims (4)
1.一种席夫碱铂(II)配合物,其特征在于,结构式为:
2.如权利要求1所述的一种席夫碱铂(II)配合物的制备方法,其特征在于,包括如下步骤:
(1)合成4-X-2-[(苯基亚胺)甲基]-苯酚配体,X=Cl或者NO2;
(2)合成Pt(DMSO)2Cl2前体铂配合物;
(3)合成席夫碱铂(II)配合物:称取一定量反应物4-X-2-[(苯基亚胺)甲基]-苯酚溶于甲醇溶液中,向其中滴加摩尔量为该反应物1~2倍的三乙胺,使其完全溶解,搅拌下,将与反应物等摩尔量的前体铂配合物Pt(DMSO)2Cl2加入到上述反应溶液中,反应溶液避光并且通氮气保护,加热回流反应1~4小时,停止反应,冷却有沉淀生成,抽滤,产物依次用水和甲醇各洗涤至少3次,真空干燥得固体粉末产品。
3.如权利要求1所述的席夫碱铂(II)配合物作为蛋白酪氨酸磷酸酶1B抑制剂的应用。
4.如权利要求1所述的席夫碱铂(II)配合物在制备抗肿瘤药物中的应用。
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