CN112079853A - 一种以2-吡啶甲醛缩氨基硫脲为配体的锌配合物及其合成方法和应用 - Google Patents
一种以2-吡啶甲醛缩氨基硫脲为配体的锌配合物及其合成方法和应用 Download PDFInfo
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Abstract
本发明公开了一种以2‑吡啶甲醛缩氨基硫脲为配体的锌配合物及其合成方法和应用。本发明合成了两个以2‑吡啶甲醛缩氨基硫脲为配体的锌(II)配合物,通过实验证明合成的两个锌配合物对人肝癌细胞株BEL‑7404具有很强的抗肿瘤活性,可用于制备抗肿瘤的药物,特别是治疗肝癌的药物。
Description
技术领域
本发明涉及锌配合物,具体是一种以2-吡啶甲醛缩氨基硫脲为配体的锌配合物及其合成方法和应用。
背景技术
肝癌是消化系统常见的恶性肿瘤之一,其发病率正在逐年增加。我国是肝癌高发病率国家,肝癌死亡率高居所有癌症的第二位。近年来,以索拉非尼为代表的分子靶向药物为肝癌的治疗带来了重大的突破,但近年来临床观察发现,有将近70%的患者对索拉非尼产生耐药性或一系列严重的不良反应。因此,开发新型、低毒的抗肝癌药物迫在眉睫。
锌席夫碱配合物被广泛应用于抗肿瘤研究,也有少量报道以缩氨基硫脲为配体合成锌配合物用于肿瘤治疗和抑制细菌生长的研究,目前以2-吡啶甲醛缩氨基硫脲为配体的锌配合物尚无报道。
发明内容
本发明的目的是提供一种以2-吡啶甲醛缩氨基硫脲为配体的锌配合物及其合成方法和应用。本发明合成了两个以2-吡啶甲醛缩氨基硫脲为配体的锌(II)配合物,通过实验证明合成的锌配合物对人肝癌细胞株BEL-7404具有很强的抗肿瘤活性,可用于制备抗肿瘤的药物。
实现本发明目的的技术方案是:
一种以2-吡啶甲醛缩氨基硫脲为配体的锌配合物,其结构式如下式C1-C2所示:
上述式C1-C2所示锌配合物的合成路线为:
上述式C1所示锌配合物的合成方法为:
取0.1mmol 4,4-二甲基-3-氨基硫脲和0.1mmol的ZnCl2溶于总体积为5ml的无水甲醇和二氯甲烷的混合液中,再加入0.26mmol 2-吡啶甲醛液体混合均匀,混均后将混合溶液于65℃鼓风干燥箱中静置,数小时后,逐渐析出棕色晶体,即目标配合物C1;
所述无水甲醇和二氯甲烷的体积比为1:1。
上述式C2所示锌配合物的合成方法,包括如下步骤:
(1)取3mmol 4-(2-甲基苯基)-3-氨基硫脲溶解于20ml的无水甲醇中,再加入3mmol的2-吡啶甲醛液体混合均匀,混均后将混合溶液于65℃回流搅拌6~8h,溶液中产生白色沉淀物,再将混合液冷却至室温,过滤沉淀物,将所得白色沉淀物用无水乙醇洗涤,干燥,收集得到配体L2;
(2)取0.1mmol步骤(1)得到的配体L2和0.05mmol的ZnCl2溶于总体积为5ml的无水甲醇中,再缓慢滴加氨水,直至溶液中的沉淀溶解,放置于65℃鼓风干燥箱中,数小时后,逐渐析出棕色晶体,即目标配合物C2。
本发明的有益效果:
1.合成的2-吡啶甲醛缩4,4-二甲基-3-氨基硫脲锌配合物、2-吡啶甲醛缩4-(2-甲基苯基)-3-氨基硫脲锌配合物为新结构,这些结构为第一次公布;
2.合成的锌配合物对人肝癌细胞株BEL-7404具有很强的抗肿瘤活性;
3.合成的锌配合物可以有效抑制人肝癌细胞株BEL-7404细胞的迁移;
4.与纯配体相比,锌配合物对肿瘤细胞的活性更强,可用于制备抗肿瘤的药物。
附图说明
图1为实施例1合成的C1锌配合物的单晶结构图;
图2为实施例2合成的C2锌配合物的单晶结构图;
图3为锌配合物C1、C2、L2对人肝癌细胞BEL-7404的抑制迁移率图。
具体实施方式
下面结合具体实施例和附图对本发明内容作进一步的详述,以更好地理解本发明的内容,但本发明并不限于以下实施例。
实施例1:
C1锌配合物的合成,具体合成方法为:
取0.1mmol 4,4-二甲基-3-氨基硫脲和0.1mmol的ZnCl2溶于总体积为5ml的无水甲醇和二氯甲烷的混合液中(V无水甲醇:V二氯甲烷=1:1)溶液中,再加入0.26mmol 2-吡啶甲醛混合均匀,于65℃鼓风干燥箱中静置,数小时后,逐渐析出棕色晶体,即目标配合物C1,产率53%,其晶体结构和数据保存至剑桥晶体数据中心(CCDC数据库)申请号:No.2019291;利用单晶衍射仪获取衍射数据,应用OLEX 2软件解析锌配合物C1晶体结构,如图1所示;
对锌配合物C1进行表征:
元素分析:Anal.Calcd(%)for:C10H14ClN4OSZn.C,35.41;H,4.16;Cl,10.45;N,16.52;O,4.72;S,9.45;Zn,19.28.Found:C,33.15;H,3.65;Cl,10.82;N,17.16;O,4.85;S,9.81;Zn,20.08。
实施例2:
C2锌配合物的合成,具体合成方法为:
(1)将3mmol 4-(2-甲基苯基)-3-氨基硫脲溶解于20ml的无水甲醇中,再加入3mmol的2-吡啶甲醛,混均后将混合溶液于65℃回流搅拌6~8h,溶液中产生白色沉淀物.将混合液冷却至室温,过滤沉淀物,将所得白色沉淀用无水乙醇洗涤,干燥,收集得到配体L2;
(2)取0.1mmol配体L2和0.05mmol的ZnCl2溶于总体积为5ml的无水甲醇中,此时溶液中有未溶解完的沉淀物,用3ml的巴氏滴管滴加3滴氨水(约250ul)混合,沉淀物溶解,放置于65℃鼓风干燥箱中,数小时后,逐渐析出棕色晶体,即目标配合物C2,产率55%,其晶体结构和数据保存至剑桥晶体数据中心(CCDC数据库)申请号:No.2019159;利用单晶衍射仪获取衍射数据,应用OLEX 2软件解析锌配合物C1晶体结构,如图2所示;
对锌配合物C2进行表征:
元素分析:Anal.Calcd(%)for:C29H29N8S2Zn:C,56.26;H,4.72;N,18.10;S,10.36;Zn,10.56..Found:C,56.22;H,4.69;N,18.01;S,10.30;Zn,10.55。
实验例:
对锌配合物进行体外抗肿瘤活性实验,实验过程如下:
1.选用肝癌细胞株BEL-7404和人正常肝细胞株HL-7702进行了体外细胞毒性实验;
2.噻唑蓝(MTT)实验。于96孔板中每孔加入180μL浓度为5×104个细胞/mL细胞,37℃,5%CO2培养箱培养16h后;每孔加入20μL不同浓度的锌配合物,继续培养48h,每孔加入10uL MTT(浓度5mg/mL),孵育4h,弃去培养基,每孔加入100μl DMSO,溶解,用震荡机震荡均匀;利用酶标仪测试波长为570nm/630nm时的吸光度,导出测量差值,利用Bliss算法计算IC50值,如表1所示。
表1.配体以及锌配合物对人肝癌细胞株BEL-7404和正常肝细胞株HL-7702的IC50值(μM);
从测试结果可知:对于这两株癌细胞,单纯的配体L1、L2的活性较低,而配合物C1,C2具有较好的抗肿瘤活性,对抑制人肝癌细胞株BEL-7404的增殖表现出良好的效果。此外,C1,C2配合物对正常肝细胞HL-7702的毒副作用较小。
3.细胞划痕实验。将人肝癌细胞株BEL-7404细胞种植于6孔板中,待细胞贴壁;使用灭菌过的牙签划线,可获得无细胞的空白区域,弃去含有悬浮细胞的培养基,加入2mL新的培养基,生理盐水作为对照组,在培养箱中继续培养,于24h和48h时观察拍照。
实验结果表明:对照组在划线24h和48h后,细胞会继续向空白处生长,空白的比例越来越小;而加入锌配合物后空白的区域比对照组的大,说明锌配合物可以有效抑制细胞的迁移,得到锌配合物C1,C2,L2对人肝癌细胞BEL-7404的抑制迁移率,如附图3所示,抑制迁移率(%)=空白区域面积(24h/48h时)/空白区域面积(0h时)。
Claims (5)
3.根据权利要求2所述的锌配合物的合成方法,其特征在于,C1所示锌配合物的合成方法为:
取0.1mmol 4,4-二甲基-3-氨基硫脲和0.1mmol的ZnCl2溶于总体积为5ml的无水甲醇和二氯甲烷的混合液中,再加入0.26mmol 2-吡啶甲醛液体混合均匀,混均后将混合溶液于65℃鼓风干燥箱中静置,数小时后,逐渐析出棕色晶体,即目标锌配合物C1;
所述无水甲醇和二氯甲烷的体积比为1:1。
4.根据权利要求2所述的锌配合物的合成方法,其特征在于,C2所示锌配合物的合成方法,包括如下步骤:
(1)取3mmol 4-(2-甲基苯基)-3-氨基硫脲溶解于20ml的无水甲醇中,再加入3mmol 2-吡啶甲醛液体混合均匀,混均后将混合溶液于65℃回流搅拌6~8h,溶液中产生白色沉淀物,再将混合液冷却至室温,过滤沉淀物,将所得白色沉淀物用无水乙醇洗涤,干燥,收集得到配体L2;
(2)取0.1mmol配体L2和0.05mmol的ZnCl2溶于总体积为5ml的无水甲醇中,再滴加氨水,直至溶液中的沉淀溶解,放置于65℃鼓风干燥箱中静置,数小时后,逐渐析出棕色晶体,即目标锌配合物C2。
5.权利要求1所述的锌配合物在制备治疗肝癌药物中的应用。
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