舒必利分子印迹聚合物的制备及其性能研究
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摘要
舒必利(Sulpiride)是苯甲酰胺类抗精神病药,具有较强的抗木僵、退缩、幻觉、妄想及精神错乱作用,还有一定的抗抑郁作用,除此之外还具有很强的中枢性止吐作用。目前采用分子印技术制备各种分子印迹聚合物(Molecular Imprinted Polymers,MIPs)的报道逐年增加,MIPs是一种对特定模板分子及其结构类似物具有特异性识别和选择性吸附的高分子聚合材料,由于其独特的特异性吸附识别优势,现已广泛地应用于药物分离、固相萃取、缓控释给药系统、模拟酶催化等领域。
本文以舒必利为模板分子,甲基丙烯酸(Methacrylic Acid,MAA)和衣康酸(Itaconic Acid,ITA)分别作为单体,采用本体聚合法制备了对舒必利及其结构类似物具有选择吸附性能的MIPs,考察了不同制备条件对MIPs吸附性能的影响,并对其结构进行了表征;探讨了MIPs对舒必利选择性识别的机理,以它作为载体初步应用于舒必利与其他药物的特异性吸附识别和释放性能的研究,为更进一步地用于舒必利的分离、富集以及缓释控制剂型的载体材料等方面的研究奠定了基础。本文主要内容如下:
1、以MAA为功能单体,采用本体聚合法制备舒必利MIPs,通过优化确定其制备条件为:0.3 mmol舒必利和1.2 mmol MAA,溶于6 mL乙腈,再经交联聚合得到的聚合物,采用甲醇–乙酸(9:1)进行洗脱。对该条件下制备的MIPs采用静态平衡吸附实验测试了它的吸附性能,并采用FTIR和SEM对其结构进行了表征。结果表明:MIPs对舒必利有较好的特异性识别能力,其印迹因子α为3.77,在10 min内对舒必利的吸附量可达到88%;Scatchard的模拟结果发现MIPs的最大吸附量Qmax为178.39μmol/g,在低浓度范围和高浓度范围内,具有非均一性的特异性和非特异性两类不同的结合位点,FTIR图谱显示其印迹的主要结合位点是由MAA的?COOH与舒必利分子中酰胺基团形成氢键所产生;从SEM图可观察到MIPs的粒径明显比NIPs小,表面积更大。
2、以ITA为功能单体,优化了本体聚合法制备舒必利MIPs的实验条件,采用静态平衡吸附实验测试了聚合物的吸附性能,并采用FTIR和SEM对其结构进行了表征。结果表明:制备MIPs的优化条件为取0.3 mmol舒必利和1.2 mmol ITA溶于6 mL甲醇,加入4.5 mmol EDMA和60 mg AIBN,热引发聚合24 h即可;与MAA为单体制备的MIPs相比,其非特异性吸附量大大减小,特异性识别能力提高,其印迹因子α为5.58;MIPs在10 min内吸附速率快,吸附量能达到80%;Scatchard模拟表明MIPs的结合位点具有非均一性,FTIR对MIPs结构表征证实了舒必利与ITA间通过氢键结合识别,从SEM图可观察到MIPs的粒径明显比NIPs小,表面积更大。
3、以舒必利及其结构类似物阿米舒必利和泰必利分别作为底物,采用静态平衡吸附实验分别评价了以MAA和ITA为单体制备的MIPs对舒必利的选择性,并根据舒必利的化学结构,以对甲苯磺酰胺、甲酰胺和N-甲基吡咯烷为目标物探讨了MIPs的印迹识别的机理。结果表明:以ITA为单体制备的MIPs的选择性更高,其选择性因子S明显大于MAA制备的聚合物;且对目标物吸附能力的强弱顺序为甲酰胺> N-甲基吡咯烷>对甲苯磺酰胺,证明舒必利中酰胺基团上的O原子和N原子是识别舒必利的主要位点,其次是N-甲基吡咯烷上N原子的贡献。将MIPs用于对磺胺甲噁唑、对氨基苯磺酰胺、对甲苯磺酰胺、对硝基苯胺、乙酰苯胺、甲氧苄啶及舒必利混合溶液的特异性识别试验,结果表明,除甲氧苄啶有一定吸附外,MIPs对舒必利具有较好的特异性识别功能,可用作分离富集的材料。
4、以制备的MIPs作为载体,试验了载药后的MIPs粉末及加入辅料制成的MIPs-舒必利片剂的释药性能。结果表明:载药后MIPs粉末在pH 6.8的模拟肠液中,舒必利在100 min释放达到平衡;含有辅料的MIPs-舒必利片剂在250 min释放达到平衡,显示该材料作为载体后具有一定的缓释性能,因此可作为药物的载体材料,具有进一步开发为药物控释制剂的价值。
Sulpiride is a benzamide drugs that is used as an antipsychotic, which is effective in the treatment of stupor, withdrawal, hallucinations, delusion and mental disorder. It also has a role in antidepressant and central antiemetic. Recently,the molecularly imprinting technology (MIT) has recently arisen increasing attention, and various molecularly imprinted polymers (MIPs) has been prepared in many fields. MIPs are synthetic polymeric materials possessing specific cavities designed for a target molecule, which have specific recognition and selective adsorption to the molecular template and their structural analogues. As its unique advantages, it has been widely used in separation, solid phase extraction, controlled release drug delivery system, enzyme catalysis simulation, etc.
In this research, the MIPs of sulpiride was prepared by classical bulk polymerization method using methacrylic acid (MAA) and itaconic acid (ITA) as functional monomer, respectively. In order to obtain the optimum experimental conditions, the influence factors of preparing the MIPs were investigated for their adsorption properties, and then the structure of the MIPs optimized was characterized. The mechanism of MIPs obtained on the specific recognition and adsorption for sulpiride was also discussed. MIPs have been applied to the specific recognition and release characteristics in preliminary study used as carriers. All of this laid the foundation for further study in the separation and enrichment, and sustained release formulation materials for sulpiride. The research in this paper was carried out as following:
1. The MIPs of sulpiride was prepared by bulk polymerization method with MAA as functional monomer under the optimized experimental conditions. The optimum conditions were as following: 0.3 mmol sulpiride, 1.2 mmol MAA, 6 mL acetonitrile, then the obtained polymer after polymerization was eluted with methanol–acetic acid (9:1). The adsorptivity of the MIPs were measured by the static absorption test, and its structure was also characterized through Fourier transform infrared spectroscopy (FTIR) and scanning electron microscope (SEM). The obtained results showed that the MIPs had higher specific recognition capability to sulpiride, and its imprinted factor value was 3.77. The characteristic of adsorption kinetics of MIPs showed that adsorption ratio could achieve 88% within 10 min. Its maximum adsorption capacity reached 178.39μmol/g based on Scatchard simulation results. It was further found that imprinting sulpiride for MIPs appeared inhomogeneous with two different types of specific and non-specific binding sites. FTIR spectra proved that the primary binding site in the MIPs was structurally hydrogen bonding formed between carboxyl group of MAA and amide group of sulpiride. The results of SEM indicated that the particles of the MIPs were much smaller, larger surface area than its non–imprinted polymers (NIPs).
2. The sulpiride MIPs was prepared by bulk polymerization method with ITA as functional monomer, afterwards the experimental conditions was optimized, and then the adsorption properties of MIPs obtained were also measured through static absorption experiment. The structure of the MIPs was also investigated by means of FTIR and SEM. The results showed that the optimized conditions of preparing the MIPs were as follows: 0.3 mmol sulpiride and 1.2 mmol ITA were dissolved in methanol, then 4.5 mmol EDMA and 60 mg AIBN were added together for polymerization 24 hours initiated by heating. The MIPs indicated a higher specific recognition capability with imprinted factor 5.58, and its nonspecific adsorption capacity was greatly reduced comparing with the MIPs prepared by MAA as monomer. The MIPs exhibited a quick absorption rates to sulpiride, which adsorption ratio could reached 80% within 10 min, the Scatchard simulation results also showed that their binding sites was inhomogeneous. The characteristics spectra of FTIR for the MIPs also proved that ITA and sulpiride was bonded through hydrogen bonds. The results of SEM indicated that the particles of the MIPs were much smaller, larger surface area than its non–imprinted polymers (NIPs).
3. The selectivity of MIPs prepared with MAA and ITA as monomer was evaluated using the static absorption experiment, in which the analogs of sulpiride such as amisulpride and tiapride were chosen as the substrates. Based on the chemical structure of sulpiride, p-toluenesulfonamide, formamide and 1-methylpyrrolidine selected as substrates to investigate recognition mechanism of the MIPs. The results to the analogs revealed that using ITA as monomer exhibited higher selectivity; its selectivity factor was much larger than MAA. Through the adsorption test for several substrates composed of sulpiride, the results of their adsorptivity showed in following descending order: formamide>1-methylpyrrolidine>p-toluenesulfonamide, which proved that oxygen atom and nitrogen atom in the amide group were the main recognition sites and nitrogen atom in the 1-methylpyrrolidine was second. The MIPs prepared by ITA as special carrier was applied to recognize sulpiride from a mixture composed with sulfonamides, phenylamines, dicarboximides and sulpiride. The results showed that the MIPs has higher selectivity due to its specific recognition ability to sulpiride except TMP, therefore it can be used as separation and enrichment matierals.
4. For further application of MIPs, Drug-loaded MIPs and Drug-loaded tablet made by some excipients using the MIPs as carrier material to carried out release test. The results indicated that the release of sulpiride in pH 6.8 simulated intestinal fluid could be equilibrium within 100 min when using MIPs as carriers; the tablet pressed sulpiride reached equilibrium within 250 min with certain controlled release property. Thus the MIPs will be potentially valuable for development of drug delivery materials.
本文以舒必利为模板分子,甲基丙烯酸(Methacrylic Acid,MAA)和衣康酸(Itaconic Acid,ITA)分别作为单体,采用本体聚合法制备了对舒必利及其结构类似物具有选择吸附性能的MIPs,考察了不同制备条件对MIPs吸附性能的影响,并对其结构进行了表征;探讨了MIPs对舒必利选择性识别的机理,以它作为载体初步应用于舒必利与其他药物的特异性吸附识别和释放性能的研究,为更进一步地用于舒必利的分离、富集以及缓释控制剂型的载体材料等方面的研究奠定了基础。本文主要内容如下:
1、以MAA为功能单体,采用本体聚合法制备舒必利MIPs,通过优化确定其制备条件为:0.3 mmol舒必利和1.2 mmol MAA,溶于6 mL乙腈,再经交联聚合得到的聚合物,采用甲醇–乙酸(9:1)进行洗脱。对该条件下制备的MIPs采用静态平衡吸附实验测试了它的吸附性能,并采用FTIR和SEM对其结构进行了表征。结果表明:MIPs对舒必利有较好的特异性识别能力,其印迹因子α为3.77,在10 min内对舒必利的吸附量可达到88%;Scatchard的模拟结果发现MIPs的最大吸附量Qmax为178.39μmol/g,在低浓度范围和高浓度范围内,具有非均一性的特异性和非特异性两类不同的结合位点,FTIR图谱显示其印迹的主要结合位点是由MAA的?COOH与舒必利分子中酰胺基团形成氢键所产生;从SEM图可观察到MIPs的粒径明显比NIPs小,表面积更大。
2、以ITA为功能单体,优化了本体聚合法制备舒必利MIPs的实验条件,采用静态平衡吸附实验测试了聚合物的吸附性能,并采用FTIR和SEM对其结构进行了表征。结果表明:制备MIPs的优化条件为取0.3 mmol舒必利和1.2 mmol ITA溶于6 mL甲醇,加入4.5 mmol EDMA和60 mg AIBN,热引发聚合24 h即可;与MAA为单体制备的MIPs相比,其非特异性吸附量大大减小,特异性识别能力提高,其印迹因子α为5.58;MIPs在10 min内吸附速率快,吸附量能达到80%;Scatchard模拟表明MIPs的结合位点具有非均一性,FTIR对MIPs结构表征证实了舒必利与ITA间通过氢键结合识别,从SEM图可观察到MIPs的粒径明显比NIPs小,表面积更大。
3、以舒必利及其结构类似物阿米舒必利和泰必利分别作为底物,采用静态平衡吸附实验分别评价了以MAA和ITA为单体制备的MIPs对舒必利的选择性,并根据舒必利的化学结构,以对甲苯磺酰胺、甲酰胺和N-甲基吡咯烷为目标物探讨了MIPs的印迹识别的机理。结果表明:以ITA为单体制备的MIPs的选择性更高,其选择性因子S明显大于MAA制备的聚合物;且对目标物吸附能力的强弱顺序为甲酰胺> N-甲基吡咯烷>对甲苯磺酰胺,证明舒必利中酰胺基团上的O原子和N原子是识别舒必利的主要位点,其次是N-甲基吡咯烷上N原子的贡献。将MIPs用于对磺胺甲噁唑、对氨基苯磺酰胺、对甲苯磺酰胺、对硝基苯胺、乙酰苯胺、甲氧苄啶及舒必利混合溶液的特异性识别试验,结果表明,除甲氧苄啶有一定吸附外,MIPs对舒必利具有较好的特异性识别功能,可用作分离富集的材料。
4、以制备的MIPs作为载体,试验了载药后的MIPs粉末及加入辅料制成的MIPs-舒必利片剂的释药性能。结果表明:载药后MIPs粉末在pH 6.8的模拟肠液中,舒必利在100 min释放达到平衡;含有辅料的MIPs-舒必利片剂在250 min释放达到平衡,显示该材料作为载体后具有一定的缓释性能,因此可作为药物的载体材料,具有进一步开发为药物控释制剂的价值。
Sulpiride is a benzamide drugs that is used as an antipsychotic, which is effective in the treatment of stupor, withdrawal, hallucinations, delusion and mental disorder. It also has a role in antidepressant and central antiemetic. Recently,the molecularly imprinting technology (MIT) has recently arisen increasing attention, and various molecularly imprinted polymers (MIPs) has been prepared in many fields. MIPs are synthetic polymeric materials possessing specific cavities designed for a target molecule, which have specific recognition and selective adsorption to the molecular template and their structural analogues. As its unique advantages, it has been widely used in separation, solid phase extraction, controlled release drug delivery system, enzyme catalysis simulation, etc.
In this research, the MIPs of sulpiride was prepared by classical bulk polymerization method using methacrylic acid (MAA) and itaconic acid (ITA) as functional monomer, respectively. In order to obtain the optimum experimental conditions, the influence factors of preparing the MIPs were investigated for their adsorption properties, and then the structure of the MIPs optimized was characterized. The mechanism of MIPs obtained on the specific recognition and adsorption for sulpiride was also discussed. MIPs have been applied to the specific recognition and release characteristics in preliminary study used as carriers. All of this laid the foundation for further study in the separation and enrichment, and sustained release formulation materials for sulpiride. The research in this paper was carried out as following:
1. The MIPs of sulpiride was prepared by bulk polymerization method with MAA as functional monomer under the optimized experimental conditions. The optimum conditions were as following: 0.3 mmol sulpiride, 1.2 mmol MAA, 6 mL acetonitrile, then the obtained polymer after polymerization was eluted with methanol–acetic acid (9:1). The adsorptivity of the MIPs were measured by the static absorption test, and its structure was also characterized through Fourier transform infrared spectroscopy (FTIR) and scanning electron microscope (SEM). The obtained results showed that the MIPs had higher specific recognition capability to sulpiride, and its imprinted factor value was 3.77. The characteristic of adsorption kinetics of MIPs showed that adsorption ratio could achieve 88% within 10 min. Its maximum adsorption capacity reached 178.39μmol/g based on Scatchard simulation results. It was further found that imprinting sulpiride for MIPs appeared inhomogeneous with two different types of specific and non-specific binding sites. FTIR spectra proved that the primary binding site in the MIPs was structurally hydrogen bonding formed between carboxyl group of MAA and amide group of sulpiride. The results of SEM indicated that the particles of the MIPs were much smaller, larger surface area than its non–imprinted polymers (NIPs).
2. The sulpiride MIPs was prepared by bulk polymerization method with ITA as functional monomer, afterwards the experimental conditions was optimized, and then the adsorption properties of MIPs obtained were also measured through static absorption experiment. The structure of the MIPs was also investigated by means of FTIR and SEM. The results showed that the optimized conditions of preparing the MIPs were as follows: 0.3 mmol sulpiride and 1.2 mmol ITA were dissolved in methanol, then 4.5 mmol EDMA and 60 mg AIBN were added together for polymerization 24 hours initiated by heating. The MIPs indicated a higher specific recognition capability with imprinted factor 5.58, and its nonspecific adsorption capacity was greatly reduced comparing with the MIPs prepared by MAA as monomer. The MIPs exhibited a quick absorption rates to sulpiride, which adsorption ratio could reached 80% within 10 min, the Scatchard simulation results also showed that their binding sites was inhomogeneous. The characteristics spectra of FTIR for the MIPs also proved that ITA and sulpiride was bonded through hydrogen bonds. The results of SEM indicated that the particles of the MIPs were much smaller, larger surface area than its non–imprinted polymers (NIPs).
3. The selectivity of MIPs prepared with MAA and ITA as monomer was evaluated using the static absorption experiment, in which the analogs of sulpiride such as amisulpride and tiapride were chosen as the substrates. Based on the chemical structure of sulpiride, p-toluenesulfonamide, formamide and 1-methylpyrrolidine selected as substrates to investigate recognition mechanism of the MIPs. The results to the analogs revealed that using ITA as monomer exhibited higher selectivity; its selectivity factor was much larger than MAA. Through the adsorption test for several substrates composed of sulpiride, the results of their adsorptivity showed in following descending order: formamide>1-methylpyrrolidine>p-toluenesulfonamide, which proved that oxygen atom and nitrogen atom in the amide group were the main recognition sites and nitrogen atom in the 1-methylpyrrolidine was second. The MIPs prepared by ITA as special carrier was applied to recognize sulpiride from a mixture composed with sulfonamides, phenylamines, dicarboximides and sulpiride. The results showed that the MIPs has higher selectivity due to its specific recognition ability to sulpiride except TMP, therefore it can be used as separation and enrichment matierals.
4. For further application of MIPs, Drug-loaded MIPs and Drug-loaded tablet made by some excipients using the MIPs as carrier material to carried out release test. The results indicated that the release of sulpiride in pH 6.8 simulated intestinal fluid could be equilibrium within 100 min when using MIPs as carriers; the tablet pressed sulpiride reached equilibrium within 250 min with certain controlled release property. Thus the MIPs will be potentially valuable for development of drug delivery materials.
引文
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