新型药物缓释材料的制备及性能
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摘要
聚酯类和聚酸酐类材料在临床医学领域的应用越来越受到重视。为了寻找对亲水性药物具有良好缓释性能,在体内可降解吸收的生物相容性好的新型药物缓释材料,本文采用C12-C15脂肪二酸和其它相关单体合成了几种新型聚酸酐和一类新的可注射药物缓释材料—改性不饱和聚酯材料,研究了这些材料的降解、释药性能和在与药物配伍后的生物活性。包括以下主要内容:
1、以二聚酸和C12-C15脂肪二酸为单体两两共聚,制备得到了聚(二聚酸-月桂二酸)共聚酸酐、聚(二聚酸-十三烷二酸)共聚酸酐、聚(二聚酸-十四烷二酸)共聚酸酐、聚(二聚酸-十五烷二酸)共聚酸酐、聚(月桂二酸-十四烷二酸)共聚酸酐和聚(十三烷二酸-十五烷二酸)共聚酸酐。所有聚酸酐用FT-IR、GPC、DSC和广角X-射线衍射进行了表征,并研究了聚酸酐的体外降解及其对亲水性模型药物盐酸环丙沙星的释放性能。实验结果表明合成的聚酸酐具有分子量高、熔点低、热稳定性好等特点, 在0.1mol/L pH7.4PBS中可降解,对盐酸环丙沙星和硫酸庆大霉素有较好的释放性能,总体上表现出一级释放动力学特征,在一定的配比条件下的药物释放呈0级释放动力学行为,材料降解和药物释放速率与疏水性单体二聚酸含量及结晶度成反比。用小鼠做的组织学试验结果表明,聚酸酐材料在皮下植入部位周围所引起的局部刺激反应比明胶海绵稍轻,表现出较好的生物相容性。小鼠皮下植入实验结果表明,盐酸阿霉素-聚酸酐缓释片可被完全吸收,心脏血液中未检出药物,具有良好的生物可降解吸收特性和释药安全性。
2、初步研究了硫酸庆大霉素-聚酸酐缓释药丸的抑菌活性和盐酸阿霉素-聚酸酐缓释片的体内抗癌活性。硫酸庆大霉素-聚酸酐控释片对大肠杆菌、金黄色葡萄球菌的抑菌试验表明,控释片对作用菌有长达50~60天的持续抑菌活性,可望用于骨髓炎的定点治疗。对小鼠S180鼠肉瘤模型的研究表明,盐酸阿霉素-聚酸酐缓释制剂能显著延长小鼠S180鼠肉瘤的体积倍增时间,当该制剂为150mg时倍增时间从对照组的7天延长至24~35天,表现出强的抑癌作用,在实体瘤治疗方面展示出良好的应用前景。
3、以马来酸酐或富马酸为不饱和酸单体,以癸二酸、十二烷二酸、十三烷二酸之一为饱和酸单体,与乙二醇共聚,制备得到了新型不饱和聚酯材料:聚(马来酸-乙二醇-癸二酸)、聚(富马酸-乙二醇-癸二酸)、聚(富马酸-乙二醇-月桂二酸)、聚(富马酸-乙二醇-十三烷二酸)。一些不饱和聚酯材料用聚酸酐进行了改性以改善
降解性能,得到了聚(二聚酸-十三烷二酸)共聚酸酐改性的聚(富马酸-乙二醇)共聚物和聚(月桂二酸-十四烷二酸)共聚酸酐改性的聚(富马酸-乙二醇)共聚物。实验结果表明所有新合成的不饱和聚酯具有可注射、体温下固化速度快等特点。降解及释药实验结果表明,合成的不饱和聚酯材料在0.1mol/L pH7.4 PBS中可降解,对盐酸环丙沙星有好的缓释性能。用小鼠做的组织学试验结果表明,在皮下注射植入新合成的不饱和聚酯材料后,材料在注射植入部位所引起的局部刺激反应比明胶海绵稍轻并可降解,表明该类新型新合成的不饱和聚酯材料在皮下具有较好的生物相容性和生物可降解吸收特性,适合用作药物缓释载体。
4、以盐酸阿霉素和5-氟尿嘧啶为模型药物,研究了这些药物与不饱和聚酯制成的缓释剂体内的抗癌活性。对小鼠S180鼠肉瘤模型的瘤内注射给药治疗研究表明,以盐酸阿霉素-不饱和聚酯缓释剂能显著延长小鼠S180鼠肉瘤的体积倍增时间,从对照组的7天延长至17~22天,间隔14~17天二次瘤内注射给药治疗效果更好(24~35天),表现出强的抑癌活性。间隔11天二次瘤内注射5-氟尿嘧啶-不饱和聚酯缓释剂给药治疗效果最好,肿瘤几乎消失,表现出良好的抑癌作用,在实体瘤治疗方面呈现出很好的应用前景。
Polyesters and polyanhydrides come under an increasingly recognition in medical application. In this article a new kind of injectable drug controlled release material of unsaturated polyester and several new type of polyanhydrides have been prepared by using C12~15 dibasic acids and other corresponding monomers, they have desired biocompatibility, absorbable biodegradability in vivo and bioactivity after mixed drugs. The main results are as follows:
.1. Poly(dimer acid-dodecanedioic acid) copolymer, poly(dimer acid-brassylic acid) copolymer, poly(dimer acid-tetradecanedioic acid) copolymer and poly(dimer acid-pentadecanedioic acid) copolymer were prepared by melt polycondensation by using C12~15 dibasic acid copolymerized with dimer acid respectively, poly(dodecanedioic acid- tetradecanedioic acid) copolymer and poly(brassylic acid - pentadecanedioic acid) copolymer were also prepared by using prepolymer of C12~15 dibasic acid respectively. The copolymers in vitro degradation, drug release profiles of hydrophilic model drug, ciprofloxacin hydrochloride, from the copolyanhydrides in 0.1mol/L pH7.4 PBS at 37℃ were also investigated. The copolymers were characterized by FT-IR, gel permeation chromatography (GPC), differential scanning calorimetry (DSC), wide angle X-ray powder-diffraction, and thermal gravimetric analysis (TGA) etc. In vitro degradation, drug release profiles of hydrophilic model drug, ciprofloxacin hydrochloride,from the copolyanhydrides in 0.1mol/L pH 7.4PBS at 37℃ were also investigated. It showed that all the prepared copolyanhydrides meet the essential requirement for polyanhydrides as drug delivery material including high molecular weights, low melting points, and desired thermal stability. In vitro release profiles of gentamicin sulfate and ciprofloxacin hydrochloride from the copolyanhydrides showed relatively steady drug release rate, and followed first order release kinetics as a whole,in some definite monomer ratio conditions the release profiles followed zero order release kinetics,The in vitro degradable characterization of all the copolymers showed the desired erosion rate for drug release. The erosion rate and drug release rate seems in reverse to the content of DA and the degree of crystallinity. The synthesized polyanhydrides were preliminarily injected under mice skin, and the microscopically histopathologic observations revealed that the copolymers produced responses gently than the control, absorbable gelatin sponge. Preliminary in vivo studies under mice skin showed that adriamycin hydrochloride-polyanhydride controlled release preparation can be absorbed completely
and no drugs can be checked out in blood of heart. The polymers possess good tissue compatibility,animal degradability and have proper standing drug release profiles and good security of drug release.
2. In vitro bacteriostatic activity of gentamicin sulfate-polyanhydride and in vivo anti-tumor activity of adriamycin hydrochloride-polyanhydride wafer were preliminarily determined. In vitro bacteriostatic activity studies demonstrated that the beads containing 5% gentamicin sulfate possessed desired bacteriostatic activity, and lasted for 45-60 days for staphylococcus aureus and escherichia coli, which are common bacteria for infections in bone, suggest that the biodegradable sustained-release beads may be promise as a new treatment device for osteomyelitis treatment. In vivo studies showed that antitumor efficacy of polyanhydride(150mg) containing 5% adriamycin hydrochloride in Sarcoma-180 mice bearing tumor exhibited increased volume doubling time between 24~35 days compared to plain subcutaneous injection of adriamycin hydrochloride (7days). All above demonstrated that the novel sustained-release wafer may be promising for the treatment of noumenon tumor.
3. The new unsaturated polyester resins were prepared by melt polycondensation of the corresponding mixed monomers: sebacic acid or C12~13 dibasic acid, fumaric acid or maleic anhydride and glycol. They were Poly(maleic anhydride-glycol-sebacic acid) cop
1、以二聚酸和C12-C15脂肪二酸为单体两两共聚,制备得到了聚(二聚酸-月桂二酸)共聚酸酐、聚(二聚酸-十三烷二酸)共聚酸酐、聚(二聚酸-十四烷二酸)共聚酸酐、聚(二聚酸-十五烷二酸)共聚酸酐、聚(月桂二酸-十四烷二酸)共聚酸酐和聚(十三烷二酸-十五烷二酸)共聚酸酐。所有聚酸酐用FT-IR、GPC、DSC和广角X-射线衍射进行了表征,并研究了聚酸酐的体外降解及其对亲水性模型药物盐酸环丙沙星的释放性能。实验结果表明合成的聚酸酐具有分子量高、熔点低、热稳定性好等特点, 在0.1mol/L pH7.4PBS中可降解,对盐酸环丙沙星和硫酸庆大霉素有较好的释放性能,总体上表现出一级释放动力学特征,在一定的配比条件下的药物释放呈0级释放动力学行为,材料降解和药物释放速率与疏水性单体二聚酸含量及结晶度成反比。用小鼠做的组织学试验结果表明,聚酸酐材料在皮下植入部位周围所引起的局部刺激反应比明胶海绵稍轻,表现出较好的生物相容性。小鼠皮下植入实验结果表明,盐酸阿霉素-聚酸酐缓释片可被完全吸收,心脏血液中未检出药物,具有良好的生物可降解吸收特性和释药安全性。
2、初步研究了硫酸庆大霉素-聚酸酐缓释药丸的抑菌活性和盐酸阿霉素-聚酸酐缓释片的体内抗癌活性。硫酸庆大霉素-聚酸酐控释片对大肠杆菌、金黄色葡萄球菌的抑菌试验表明,控释片对作用菌有长达50~60天的持续抑菌活性,可望用于骨髓炎的定点治疗。对小鼠S180鼠肉瘤模型的研究表明,盐酸阿霉素-聚酸酐缓释制剂能显著延长小鼠S180鼠肉瘤的体积倍增时间,当该制剂为150mg时倍增时间从对照组的7天延长至24~35天,表现出强的抑癌作用,在实体瘤治疗方面展示出良好的应用前景。
3、以马来酸酐或富马酸为不饱和酸单体,以癸二酸、十二烷二酸、十三烷二酸之一为饱和酸单体,与乙二醇共聚,制备得到了新型不饱和聚酯材料:聚(马来酸-乙二醇-癸二酸)、聚(富马酸-乙二醇-癸二酸)、聚(富马酸-乙二醇-月桂二酸)、聚(富马酸-乙二醇-十三烷二酸)。一些不饱和聚酯材料用聚酸酐进行了改性以改善
降解性能,得到了聚(二聚酸-十三烷二酸)共聚酸酐改性的聚(富马酸-乙二醇)共聚物和聚(月桂二酸-十四烷二酸)共聚酸酐改性的聚(富马酸-乙二醇)共聚物。实验结果表明所有新合成的不饱和聚酯具有可注射、体温下固化速度快等特点。降解及释药实验结果表明,合成的不饱和聚酯材料在0.1mol/L pH7.4 PBS中可降解,对盐酸环丙沙星有好的缓释性能。用小鼠做的组织学试验结果表明,在皮下注射植入新合成的不饱和聚酯材料后,材料在注射植入部位所引起的局部刺激反应比明胶海绵稍轻并可降解,表明该类新型新合成的不饱和聚酯材料在皮下具有较好的生物相容性和生物可降解吸收特性,适合用作药物缓释载体。
4、以盐酸阿霉素和5-氟尿嘧啶为模型药物,研究了这些药物与不饱和聚酯制成的缓释剂体内的抗癌活性。对小鼠S180鼠肉瘤模型的瘤内注射给药治疗研究表明,以盐酸阿霉素-不饱和聚酯缓释剂能显著延长小鼠S180鼠肉瘤的体积倍增时间,从对照组的7天延长至17~22天,间隔14~17天二次瘤内注射给药治疗效果更好(24~35天),表现出强的抑癌活性。间隔11天二次瘤内注射5-氟尿嘧啶-不饱和聚酯缓释剂给药治疗效果最好,肿瘤几乎消失,表现出良好的抑癌作用,在实体瘤治疗方面呈现出很好的应用前景。
Polyesters and polyanhydrides come under an increasingly recognition in medical application. In this article a new kind of injectable drug controlled release material of unsaturated polyester and several new type of polyanhydrides have been prepared by using C12~15 dibasic acids and other corresponding monomers, they have desired biocompatibility, absorbable biodegradability in vivo and bioactivity after mixed drugs. The main results are as follows:
.1. Poly(dimer acid-dodecanedioic acid) copolymer, poly(dimer acid-brassylic acid) copolymer, poly(dimer acid-tetradecanedioic acid) copolymer and poly(dimer acid-pentadecanedioic acid) copolymer were prepared by melt polycondensation by using C12~15 dibasic acid copolymerized with dimer acid respectively, poly(dodecanedioic acid- tetradecanedioic acid) copolymer and poly(brassylic acid - pentadecanedioic acid) copolymer were also prepared by using prepolymer of C12~15 dibasic acid respectively. The copolymers in vitro degradation, drug release profiles of hydrophilic model drug, ciprofloxacin hydrochloride, from the copolyanhydrides in 0.1mol/L pH7.4 PBS at 37℃ were also investigated. The copolymers were characterized by FT-IR, gel permeation chromatography (GPC), differential scanning calorimetry (DSC), wide angle X-ray powder-diffraction, and thermal gravimetric analysis (TGA) etc. In vitro degradation, drug release profiles of hydrophilic model drug, ciprofloxacin hydrochloride,from the copolyanhydrides in 0.1mol/L pH 7.4PBS at 37℃ were also investigated. It showed that all the prepared copolyanhydrides meet the essential requirement for polyanhydrides as drug delivery material including high molecular weights, low melting points, and desired thermal stability. In vitro release profiles of gentamicin sulfate and ciprofloxacin hydrochloride from the copolyanhydrides showed relatively steady drug release rate, and followed first order release kinetics as a whole,in some definite monomer ratio conditions the release profiles followed zero order release kinetics,The in vitro degradable characterization of all the copolymers showed the desired erosion rate for drug release. The erosion rate and drug release rate seems in reverse to the content of DA and the degree of crystallinity. The synthesized polyanhydrides were preliminarily injected under mice skin, and the microscopically histopathologic observations revealed that the copolymers produced responses gently than the control, absorbable gelatin sponge. Preliminary in vivo studies under mice skin showed that adriamycin hydrochloride-polyanhydride controlled release preparation can be absorbed completely
and no drugs can be checked out in blood of heart. The polymers possess good tissue compatibility,animal degradability and have proper standing drug release profiles and good security of drug release.
2. In vitro bacteriostatic activity of gentamicin sulfate-polyanhydride and in vivo anti-tumor activity of adriamycin hydrochloride-polyanhydride wafer were preliminarily determined. In vitro bacteriostatic activity studies demonstrated that the beads containing 5% gentamicin sulfate possessed desired bacteriostatic activity, and lasted for 45-60 days for staphylococcus aureus and escherichia coli, which are common bacteria for infections in bone, suggest that the biodegradable sustained-release beads may be promise as a new treatment device for osteomyelitis treatment. In vivo studies showed that antitumor efficacy of polyanhydride(150mg) containing 5% adriamycin hydrochloride in Sarcoma-180 mice bearing tumor exhibited increased volume doubling time between 24~35 days compared to plain subcutaneous injection of adriamycin hydrochloride (7days). All above demonstrated that the novel sustained-release wafer may be promising for the treatment of noumenon tumor.
3. The new unsaturated polyester resins were prepared by melt polycondensation of the corresponding mixed monomers: sebacic acid or C12~13 dibasic acid, fumaric acid or maleic anhydride and glycol. They were Poly(maleic anhydride-glycol-sebacic acid) cop
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