CN102276633B - 槲皮素-谷氨酸Cu(Ⅱ)配合物及其制备方法和用途 - Google Patents
槲皮素-谷氨酸Cu(Ⅱ)配合物及其制备方法和用途 Download PDFInfo
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Abstract
槲皮素-谷氨酸Cu(Ⅱ)配合物,其结构式为:
Description
技术领域
本发明涉及一种槲皮素-谷氨酸Cu(Ⅱ)配合物制备方法及其抗癌的应用,属于化学及医药技术领域。
背景技术
槲皮素是一种具有多种生物活性黄酮类化合物,是黄酮类化学物的主要成分,化学命名为3,3’,4’,5,7-五羟基黄酮,又名栎精、槲皮黄素,具有很高的药用价值。在植物界中约有100种中草药含有槲皮素,广泛分布于多种植物花,果实,叶中,如中药槐米干燥花蕾、地耳草、银杏叶、番石榴叶、贯叶连翘、菟丝子、洋葱、槐花、地锦草、刺五加、满山红等。
槲皮素具有抗氧化、抗过敏、抗炎、抗菌、抗病毒,清除体内自由基、抑制恶性肿瘤生长和转移等多方面药理作用,改善脑循环和抗血小板活化因子、祛痰止咳、降低毛细血管通透性和脆性等多种生物活性,能提高免疫能力、降低胆固醇、增强心肌收缩力、舒张长平滑肌、降低血压、免疫抑制和抗过敏作用,是近年来国内外学者研究热门课题。
铜作为人体必需的微量元素,在人体内有多种生理功能,它形成酶具有促进生长发育的作用,维持神经系统的功能,保证内分泌功能的正常化,清除人体内有毒的自由基,防止集体发生肿瘤及动脉硬化等疾病。由于槲皮素不溶于水、难于吸收,极大地影响了槲皮素的生物利用度,国内外学者在槲皮素分子中导入亲水性基团、增加溶解度,从而增强其药理作用。槲皮素分子具有较高的超离域度,完整大π键的共轭体系,强配位能力的氧原子以及利于络合物形成的合适的空间构型,可作为金属离子的良好络合配体,且络合后大大增加了槲皮素在水中的溶解度。
发明内容
本发明的目的在于提供一种槲皮素-谷氨酸Cu(Ⅱ)配合物;
本发明的另一个目的,是提供槲皮素-谷氨酸Cu(Ⅱ)配合物的制备方法和应用;
为实现这一目的而进行了深入应用研究,本发明人的研究结果证明,槲皮素-谷氨酸Cu(Ⅱ)配合物对肝癌细胞7721,宫颈癌细胞Hela,胃癌细胞A549,有明显的抑制作用。
本发明给出了一个水溶性的槲皮素制备技术及应用新方案,主要是通过水溶性谷氨酸与槲皮素同时Cu(II),显著提高了槲皮素金属配合物的水溶性。
本发明通过补充铜来达到抗癌目的。
本发明槲皮素和铜与一个水溶性解离基配合提高水溶性。
本发明给出了一个具有抗癌作用的药物制备技术及应用新方案是采用现代制备合成方法得到单体,并用体外MTT显色实验方法测定单体体外药理活性。
本发明体外药理实验方法为MTT法。
本发明的发明人根据临床的需要将槲皮素-谷氨酸Cu(Ⅱ)配合物制备为各个剂型并可添加药学上可接受的辅剂及载体供临床选择应用。
槲皮素-谷氨酸Cu(Ⅱ)配合物及各个剂型作为一种有效的抗癌药物,在应用于临床中的有效剂量可以根据日常常用处方剂量及患者病情酌量增减。
槲皮素-谷氨酸Cu(Ⅱ)配合物的分子结构式为:
分子量为:510.01。
本发明的槲皮素-谷氨酸Cu(Ⅱ)配合物的制备方法是:
精密称定CuCl2·2H2O 3.4096g和谷氨酸钠3.7424g分别用10ml蒸馏水溶解,两者物质的量之比为1:1。将谷氨酸钠水溶液缓慢注入氯化铜水溶液中,边加边搅拌,得到亮蓝色水溶液。将溶液转移至100ml容量瓶中,加蒸馏水标定,制得0.002mol/ml谷氨酸铜溶液。
在30℃~80℃甲醇或乙醇50溶液中,加入0.6049g(2mmol)槲皮素,溶解的黄色溶液,然后加入到10ml谷氨酸铜溶液中(2mmol),得到黄绿色溶液。
把得到的溶液在50℃旋蒸,得到绿色固体。用甲醇水溶液洗涤3次,真空干燥,得到固体产物,即得
根据我们测定该产物在室温时,在水溶液中溶解度为14.30mg/ml,是槲皮素的2900倍。
槲皮素-谷氨酸Cu(Ⅱ)能制成口服剂或注射液。口服剂为颗粒剂、囊剂、片剂、丸剂或口服液。
具有抑制癌细胞增长功能,可应用于包括肝癌、胃癌、宫颈癌多种癌症的治疗。
本发明通过槲皮素与金属铜配合物的合成,增强槲皮素的溶解度,所合成槲皮素-谷氨酸Cu(Ⅱ)配合物在水中溶解度为14.29758 mg/ml,比原槲皮素的溶解度增大了至少2900倍。所合成槲皮素-谷氨酸Cu(Ⅱ)配合物通过体外MTT法测定其药理活性,结果证明其在体外有较强的抗肿瘤活性。
槲皮素铜氨基酸对人肝癌细胞SMMC-7721、宫颈癌细胞Hela、胃癌细胞A549的体外细胞抑制作用研究。
体外抑制癌细胞实验:
A:制备癌细胞悬液,取对数生长期的各肿瘤细胞,用0.25%胰蛋白酶消化,用培养基配制成 5×104个细胞/ml的细胞悬液 ,接种于96孔培养板中,每孔100μL。
B:37℃,5%CO2及饱和湿度下培养细胞24h。
C:将待测药液,及阳性对照环磷酰胺,经0.45μm滤膜过滤,分别以不同的量加入到已经制备好的殖有癌细胞的96孔板中,最后补加培养液至200μL,设5个复孔,将正常癌细胞组作为阴性对照组,阴性对照组加等量新鲜培养液。37℃,5%CO2及饱和湿度下培养细胞。
D:培养72 h后,加人新配制的MTT,每孔20μL,置37℃ CO2 培养箱内培养作用4h,小心吸去上清液,加入二甲亚砜(DMSO)150μL ,在振荡器上轻轻振荡5 min后,用酶标仪于492 nm处测吸光度值(A值).取5孔平均值,计算抑制率.根据公式:
细胞抑制率=(1一实验组A值/对照组A值)×100%
实验重复三次,实验结果见表1。
表1 槲皮素铜氨基酸对不同人肿瘤细胞的抑制作用
结果表明,槲皮素铜氨基酸络合物对人肿瘤细胞有明显的抑制作用。由于其颜色为绿色,当药物浓度过大时,药物挂在96孔板得孔壁上,影响了MTT实验结果的测定。
Claims (2)
1.槲皮素-谷氨酸Cu(Ⅱ)配合物,其特征在于制备方法是:
精密称定CuCl2·2H2O 3.4096g和谷氨酸钠3.7424g分别用10ml蒸馏水溶解,两者物质的量之比为1:1,将谷氨酸钠水溶液缓慢注入氯化铜水溶液中,边加边搅拌,得到亮蓝色水溶液,将溶液转移至100ml容量瓶中,加蒸馏水标定,制得0.0002mol/ml谷氨酸铜溶液;
在30℃~80℃甲醇50ml溶液中,加入2mmol槲皮素,得到黄色溶液,然后加入到10ml浓度为0.2mmol/ml谷氨酸铜溶液中,得到黄绿色溶液;
把得到的溶液在50℃旋蒸,得到绿色固体,用甲醇水溶液洗涤3次,真空干燥,得到固体产物,即得;
槲皮素-谷氨酸Cu(Ⅱ)制成口服剂或注射液,口服剂为颗粒剂、胶囊剂、片剂、丸剂或口服液。
2.根据权利要求1所述的槲皮素-谷氨酸Cu(Ⅱ)配合物,其特征是具有抑制癌细胞增长功能,应用于肝癌、胃癌、宫颈癌的治疗。
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CN1817896A (zh) * | 2006-03-10 | 2006-08-16 | 中山大学 | 槲皮素类化合物及其糖苷的金属配合物及其应用 |
CN101220014A (zh) * | 2008-01-18 | 2008-07-16 | 重庆大学 | 具有细胞凋亡诱导效应的槲皮素类及其糖苷化合物的金属配合物 |
CN101671263A (zh) * | 2009-10-12 | 2010-03-17 | 北京中国科学院老专家技术中心 | 新型氨基酸螯合物制备方法 |
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CN101220014A (zh) * | 2008-01-18 | 2008-07-16 | 重庆大学 | 具有细胞凋亡诱导效应的槲皮素类及其糖苷化合物的金属配合物 |
CN101671263A (zh) * | 2009-10-12 | 2010-03-17 | 北京中国科学院老专家技术中心 | 新型氨基酸螯合物制备方法 |
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