CN111320642A - 一种具有抗菌活性的萘普生锌配合物及其制备方法 - Google Patents
一种具有抗菌活性的萘普生锌配合物及其制备方法 Download PDFInfo
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- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 title claims abstract description 31
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- 239000003446 ligand Substances 0.000 claims abstract description 6
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims abstract description 4
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Abstract
本发明公开了一种具有抗菌活性的萘普生锌配合物及其制备方法,属于配合物合成及药物化学技术领域。本发明分别以萘普生和1,3‑丙二胺为主配体和第二配体,以锌离子为中心离子,利用溶剂挥发法,制备出单核结构的萘普生锌配合物。经检测发现,本发明所述配合物、萘普生及阳性对照药环丙沙星对金黄色葡萄球菌关于最小抑菌浓度的MIC值分别为:56.25、>225、1.76μg/mL,由此表明配合物的抑菌活性优于萘普生,具有一定的抗菌活性。
Description
技术领域
本发明涉及一种具有抗菌活性的萘普生锌配合物及其制备方法,属于配合物合成及药物化学技术领域。
背景技术
萘普生是一类具有抗炎、解热、镇痛作用的非甾体抗炎药,广泛应用于类风湿性关节炎、骨关节炎、强直性脊柱炎、痛风及轻、中度疼痛等的治疗。然而长期服用,会带来胃肠的不良反应,副作用表现如胃肠道溃疡、结肠病变等。因此,对传统的非甾体抗炎药进行结构修饰、改造,开发高效、副作用低且生物活性丰富的抗炎类药物具有非常重要的意义。
金属配合物药物以其优越的药理活性被认为是一种有效的药物开发设计手段。金属离子的引入,可以使配合物药物具有较好的抗菌、抗肿瘤、抗炎、抗氧化等活性。因此,以具有生物活性的小分子与金属离子反应合成非甾体抗炎药的配合物,是降低药物副作用、提高药物活性的有效方式。
发明内容
本发明目的在于提供一种具有抗菌活性的萘普生锌配合物及其制备方法。
本发明以非甾体抗炎药萘普生为主配体,以含N小分子1,3-丙二胺为第二配体,与锌离子反应制备配合物药物并培养其单晶。通过单晶X射线衍射表征了单晶结构,并测试了萘普生及其配合物以及阳性对照药环丙沙星对金黄色葡萄球菌的抗菌活性。萘普生没有抑菌活性,本发明的配合物表现出较好的抑菌性质,为传统抗炎类药物开拓了治疗领域及应用范围。
本发明技术方案如下:
步骤1.称量1mmol(0.23g)萘普生溶解于15mL氨水中,配置成萘普生溶液,将0.5mmol ZnO(0.0406g)加入到萘普生溶液中,室温混合搅拌30分钟。
步骤2.再将0.5mmol(41.67μL)1,3-丙二胺液体缓慢滴加入上述反应液中,室温搅拌3小时。
步骤3.过滤反应液至5ml小瓶。瓶口覆盖封口膜,封口膜用针扎数孔,室温静置,待缓慢挥发数天后有无色晶体析出。
步骤4.将小瓶溶液过滤,得无色透明柱状晶体,用母液冲洗,至真空干燥箱干燥。
步骤5.所得晶体用单晶X衍射仪进行结构表征,用微量肉汤稀释法测试其抗菌活性。
附图说明
【图1】是本发明实施所述配合物的单晶对称单元。
具体实施方式
通过以下实施案例详细说明本发明,但本发明的范围并不受这些实施例的任何限制。
实施例:
萘普生溶液的配置:准确称量萘普生0.23g(1mmol)溶解于15ml氨水溶液。
氧化锌的称量:准确称量氧化锌[ZnO]0.0406g(0.5mmol)。
1,3-丙二胺的称量:准确称量1,3-丙二胺41.67μL(0.5mmol)。
配置萘普生的氨水溶液(0.067mmol/mL)15mL,向其中加入0.5mmol氧化锌,室温混合搅拌30分钟,再缓慢滴加入1,3-丙二胺液体(0.5mmol)41.67μL,室温混合搅拌3小时。将反应液过滤至5ml玻璃小瓶中,瓶口用封口膜封装,封口膜用针扎数孔,室温静置,待缓慢挥发数天后有无色透明柱状晶体析出,溶液过滤,所得晶体用母液冲洗,置真空干燥箱干燥得到配合物晶体。经单晶X-射线衍射仪进行结构测试,晶体的对称结构单元如附图1所示,晶体数据见表1,分子式为C31H36N2O6Zn。
经测试,该配合物为单核结构,每个配合物单元含有2个萘普生分子、1个锌离子、一个1,3-丙二胺分子。
表1本发明所述配合物主要晶体结构数据
实施例:
萘普生锌配合物对金黄色葡糖球菌的抗菌活性测试
1)培养液的配制
取24g Mueller-Hinton肉汤培养基干粉溶于1000mL的蒸馏水中,121℃高压灭菌15分钟备用;配制TTC(氯化三苯基四氮唑,又称红四氮唑)溶液至10g/L,121℃高压灭菌15分钟备用。
2)试验菌的培养
在无菌室内,取金黄色葡萄球菌株,于酒精灯下用接种针分别在试验菌株斜面上,刮取少量斜面菌苔,用一定量的无菌水制成菌悬液,然后取一定量加到事先配制好的灭菌MH培养基中,摇匀,在37℃培养箱中培养过夜活化;次日,将活化的菌株接种到适量的上述培养基中,在37℃培养箱中培养,通过测OD600值监测菌种的生长状态,当OD600=0.5左右时菌株处于生长对数期,取该时期细菌备用。吸取菌液1mL,用MH培养基按1∶1000稀释,使菌液浓度约为1×104-1×105CFU/mL。
3)抗菌实验
取1.5mg的药物(包括合成的配合物、萘普生、环丙杀星)分别溶解在1mL含2%DMSO的水溶液中,配制成浓度为1.5mg/mL的药物存储液。取灭菌后的TTC溶液与MH培养基混合配制成混合培养基(TTC含量5%),加入到96孔培养板中,每行第一个孔140μL,剩余孔100μL。取60μL的药物存储液加入到第一个孔,然后用二倍稀释法将药品稀释成一定浓度梯度。即将第一个孔吹打均匀后吸取100μL到第二个孔,吹打三次后吸取100μL到后一个孔,反复至第11个孔。第十一个孔中弃去100μL混有药物的培养基,第12个孔设置为阴性对照,每个药物溶液浓度平行3次。将对数期的细菌用培养基稀释到OD600=0.1,依次在96孔培养板中加入100μL菌悬液。将处理完的药敏板放置在37℃培养箱中继续培养12-18h,等待结果。
4)抗菌活性检测
使用比浊法对已培养了12-18h后的96孔板进行统计,经过稀释之后第一个药物终浓度为225μg/mL,依次对半稀释。统计以在小孔内完全抑制细菌生长的最低药物浓度为MIC,即肉眼无菌生长的最低浓度孔。当对照孔(即不含抗生素)内细菌明显生长试验才有意义。重复三次,统计MIC平均值。
本发明所述配合物对金黄色葡萄球菌的MIC值为56.25μg/mL,阳性对照药环丙沙星的MIC值为1.76μg/mL,萘普生没有抑菌活性。由此说明,本发明所述配合物相比萘普生而言,对于金黄色葡萄球菌具有明显的抑菌效果,从而进一步拓展了抗炎药萘普生的治疗领域及应用范围。
Claims (3)
1.一种具有抗菌活性的萘普生锌配合物,其特征在于:该配合物分别以萘普生和1,3-丙二胺为主配体和第二配体,以锌离子为中心离子。
2.一种权利要求1所述的具有抗菌活性的萘普生锌配合物的制备方法,其特征在于:萘普生、氧化锌和1,3-丙二胺,按照摩尔比2∶1∶1,溶于氨水溶液,室温静置缓慢挥发制备而成。
3.一种权利要求1所述的具有抗菌活性的萘普生锌配合物的用途,其特征在于:对金黄色葡萄球菌具有较好的抑菌活性,开拓了传统抗炎药的治疗领域及应用范围。
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