抗非特异性蛋白质吸附多肽的合成、表征及体外酶降解性能研究
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摘要
生物材料与普通的材料的一个根本区别在于其生物相容性。生物相容性不仅包括组织相容性,不会使组织产生炎症甚至免疫原性；而且包括血液相容性,即不会产生凝血和血栓现象。聚乙二醇(PEG)是为数不多的经过美国食品药品监督管理局(FDA)批准能够应用于临床的医用生物材料,但是已经证明其在长期体内环境条件下容易氧化,失效甚至引起血栓等严重后果。传统两性离子材料如聚甲基丙烯酰氧基乙基磷酰胆碱(pMPC)、聚磺基甜菜碱甲基丙烯酸酯(pSBMA)和聚羧基甜菜碱甲基丙烯酸酯(pCBMA)具有优良的抗非特异性吸附性能和生物相容性,但是由于其甲基丙烯酸酯类的聚合物骨架不能生物降解,这限制了它们在药物与基因载体等领域的应用。因此,我们开发了若干具有优异抗非特异性蛋白质吸附性能的多肽,并综合考察了它们的各种性能,尤其是酶降解性能。主要的内容和结论包括以下几个部分：
1、以Nε-苄氧羰基-α-叔丁基-L-赖氨酸盐酸盐(H-Lys (Z)-OtBu.HCl)和δ-苄基-N-叔丁氧羰基-L-谷氨酸(Boc-Glu(Z)-OH)作为起始原料,合成了具有均一正负电荷分布的多肽(poly(EK),对应二聚体称dimer1)抗非特异性蛋白质吸附材料,解决了N-羧基环状酸酐(NCA)单体混聚所产生的不均一性和PEG类和甲基丙烯酸酯类材料的生物不可降解性问题。核磁共振图谱(1HNMR)和凝胶渗透色谱(GPC)检测结果表明已经成功得到不同分子量的poly(EK).以dimer1作为原料,典型的poly(EK)收率为45%左右。衰减全反射傅立叶转换红外光谱(ATR-FTIR)、X-射线光电子谱(XPS)以及椭圆偏振光谱仪(Ellipsometer, ELL)检测结果表明在金片表面存在多肽的自组装单分子膜(SAMs). ELL测定的SAMs膜厚大约只有几纳米,且随着多肽的分子量呈非线性增加。以TCPS表面作为对照,SAMs表面对anti-IgG和Fg的最低相对吸附量只有5.1±1.6%和7.3±1.8%,表明该多肽具有良好的抗非特异性蛋白质吸附性能。没有发现明显的细菌和细胞吸附。在5mg/mL情况下,poly(EK)没有发现明显的细胞毒性和溶血现象。
2、以α-苄基-Nε-苄氧羰基-L-赖氨酸盐酸盐(H-Lys(Z)-OBzl.HCl)和α-叔丁基-N-叔丁氧羰基-L-谷氨酸(BOC-Glu-O'Bu)作为起始原料,我们合成了一种具有聚谷氨酸骨架带赖氨酸侧链的多肽(poly(E)-K,对应二聚体称dimer2)。1HNMR和GPC的检测结果表明得到了不同分子量的目标多肽。以dimer2作为原料,典型的poly(E)-K的收率为40%左右。ATR-FTIR、XPS以及ELL的检测结果都证实了金片表面存在多肽SAMs.以TCPS表面作为对照,该多肽SAMs (3.5kDa)对anti-IgG和Fg的最低吸附量只有3.3±1.8%和4.4±1.6%,具有比poly(EK)更好的抗非特异性蛋白质吸附性能。在5mg/mL的情况下,poly(E)-K也没有发现明显的细胞毒性和溶血性能。在溶血性实验中,poly(E)-K的吸光度甚至低于阴性对照组PBS的吸光度,表明它对细胞膜的作用很小,甚至可能还有一定的保护作用。
3、预备实验发现,由a-氨基和α-羧基正常接肽的poly(EK)可以被胰蛋白酶降解；而聚合物骨架与侧链之间通过γ-羧基与a-氨基非正常接肽而成的poly(E)-K,则不能被胰蛋白酶降解。在此基础上,通过调节两种二聚体的比例,缩合得到不同比例的混聚多肽。]HNMR的检测结果表明,已经成功得到不同比例的混聚多肽。初步酶降解实验结果显示,随着poly(E)-K的比例不断增加,混聚多肽的酶降解时间有一定程度的延长。因此,通过调节混聚多肽的组成,可以方便调控其酶降解速度和时间,这在药物／基因控制释放,以及组织工程等方面有广阔的应用前景。
The inherent difference between the biomaterials and common materials is their biocompatibility. Biocompatibility includes not only organ compatibility, but also blood compatibility. Organ compatibility means that biomaterials doesn't cause inflammation immunogenicity for the organ, and blood compatibility means that biomaterials doesn't cause coagulation or thrombosis. PEG is one of the few biomaterials approved by the Food and Drug Adiministration (FDA) for clinical use, but researchers demonstrated that it can be easily oxidized, becoming failure or causing thrombosis under long exposure to the blood. Traditional zwitterionic materials, such as poly(2-methacryloyloxyethyl phosphorylcholine)(pMPC), poly(sulfobetaine methacylate)(pSBMA) and poly(carboxybetaine methacylate)(pCBMA) are ideal candidates for nonfouling materials due to their excellent anti-nonspecific protein adsorption property and biocompatibility. But their methacrylic backbones cannot biodegrade, which hinders their further applications. Herein, we developed several polypeptide-based antifouling biomaterials and intensive investigations were done for their properties especially for their enzymatic degradation property. The main contents and conclusions of the dissertation are presented as follows:
1. Using H-Lys(Z)-O\Bu.HCl and Boc-Glu(Z)-OH as starting materials, antifouling polypeptide with alternative uniform charges (poly(EK), its corresponding dimer is designated as dimer1) were synthesized by polycondesation. We have resolved the dilemma of ununiformity or local defects caused by the random ring opening polymerzation(ROP) of glutamic acid and lysine N-carboxyanhydrate (NCA) and the unbiodegradability of poly(ethylene glycol)(PEG) or methacrylic materials. Results from Nuclear Magnetic Resonance (1HNMR) and Gel Permeation Chromatography (GPC) demonstrated successful synthesis of the target polymer. Typical yield of the polypeptide is about45%from the dimer1. Successful formation of self-assembly monolayers (SAMs) on gold chips were demonstrated by ATR-FTIR, XPS and ELL. The thicknesses of the SAMs determined by ELL are several nanometers and the thicknesses don't linearly increase with the molecular weights (MWs) increase. The lowest relative nonspecific adsorption of the polypeptide SAMs for anti-IgG and Fg is5.1±1.6%and7.3±1.8%, respectively, when tissue cultural polystyrene (TCPS) surface adsorption is set as control. No obvious cell attachment or bacterium adhesion were observed on the SAMs surfaces. When the feeding concentration of the polypeptide is about5mg/mL, no toxicity or hemolytic activity were detected for the polypeptide.
2. Using H-Lys(Z)-OBzl.HCl and BOC-Glu-O'Bu as starting materials, polypeptide of poly(glutamic acid) backbone with lysine side chains (poly(E)-K, its corresponding dimer is designated as dimer2) were synthesized. Results from1HNMR and GPC show that poly(E)-K with different molecular weights(MWs) were obtained. Typical yield of the polypeptide is about40%from the dimer2. Results from ATR-FTIR, XPS and ELL demonstrate the formation of the polypeptide SAMs on gold surface. The lowest relative protein adsorption for anti-IgG and Fg were observed for the3.5kDa polypeptide SAMs, for which the values are3.3±1.8%and4.4±1.6%, respectively, indicating this kind of polypeptide owns better antifouling property than poly(EK). No toxicity and no hemolytic activity were detected for the polypeptide. In hemolytic assay, the absorbance of polypeptide is even lower than the negative control PBS, indicating the low interactions between the polypeptide and the cell membranes or even the protection of the polypeptide for the cells.
3. In preparatory enzymatic degradation experiments, we found that poly(EK) can degrade while poly(E)-K can't. Thus, we synthesized several copolypeptide by adjusting the ratios of dimer1to dimer2. Results from1HNMR demonstrate that we have successfully synthesized the co-polypeptides with different ingredients. The enzymatic degradation results indicate that the enzymatic degradation time of the copolypeptide become longer when the ratios of the poly(E)-K increase. Consequently, the enzymatic degradation speed and time of the copolypeptide can be easily manipulated by adjusting the proportions of the two dimmers. We are sure to believe that this kind of technology will have a wide range of applications in drug/gene controlled release or tissue engineering in future.
1、以Nε-苄氧羰基-α-叔丁基-L-赖氨酸盐酸盐(H-Lys (Z)-OtBu.HCl)和δ-苄基-N-叔丁氧羰基-L-谷氨酸(Boc-Glu(Z)-OH)作为起始原料,合成了具有均一正负电荷分布的多肽(poly(EK),对应二聚体称dimer1)抗非特异性蛋白质吸附材料,解决了N-羧基环状酸酐(NCA)单体混聚所产生的不均一性和PEG类和甲基丙烯酸酯类材料的生物不可降解性问题。核磁共振图谱(1HNMR)和凝胶渗透色谱(GPC)检测结果表明已经成功得到不同分子量的poly(EK).以dimer1作为原料,典型的poly(EK)收率为45%左右。衰减全反射傅立叶转换红外光谱(ATR-FTIR)、X-射线光电子谱(XPS)以及椭圆偏振光谱仪(Ellipsometer, ELL)检测结果表明在金片表面存在多肽的自组装单分子膜(SAMs). ELL测定的SAMs膜厚大约只有几纳米,且随着多肽的分子量呈非线性增加。以TCPS表面作为对照,SAMs表面对anti-IgG和Fg的最低相对吸附量只有5.1±1.6%和7.3±1.8%,表明该多肽具有良好的抗非特异性蛋白质吸附性能。没有发现明显的细菌和细胞吸附。在5mg/mL情况下,poly(EK)没有发现明显的细胞毒性和溶血现象。
2、以α-苄基-Nε-苄氧羰基-L-赖氨酸盐酸盐(H-Lys(Z)-OBzl.HCl)和α-叔丁基-N-叔丁氧羰基-L-谷氨酸(BOC-Glu-O'Bu)作为起始原料,我们合成了一种具有聚谷氨酸骨架带赖氨酸侧链的多肽(poly(E)-K,对应二聚体称dimer2)。1HNMR和GPC的检测结果表明得到了不同分子量的目标多肽。以dimer2作为原料,典型的poly(E)-K的收率为40%左右。ATR-FTIR、XPS以及ELL的检测结果都证实了金片表面存在多肽SAMs.以TCPS表面作为对照,该多肽SAMs (3.5kDa)对anti-IgG和Fg的最低吸附量只有3.3±1.8%和4.4±1.6%,具有比poly(EK)更好的抗非特异性蛋白质吸附性能。在5mg/mL的情况下,poly(E)-K也没有发现明显的细胞毒性和溶血性能。在溶血性实验中,poly(E)-K的吸光度甚至低于阴性对照组PBS的吸光度,表明它对细胞膜的作用很小,甚至可能还有一定的保护作用。
3、预备实验发现,由a-氨基和α-羧基正常接肽的poly(EK)可以被胰蛋白酶降解；而聚合物骨架与侧链之间通过γ-羧基与a-氨基非正常接肽而成的poly(E)-K,则不能被胰蛋白酶降解。在此基础上,通过调节两种二聚体的比例,缩合得到不同比例的混聚多肽。]HNMR的检测结果表明,已经成功得到不同比例的混聚多肽。初步酶降解实验结果显示,随着poly(E)-K的比例不断增加,混聚多肽的酶降解时间有一定程度的延长。因此,通过调节混聚多肽的组成,可以方便调控其酶降解速度和时间,这在药物／基因控制释放,以及组织工程等方面有广阔的应用前景。
The inherent difference between the biomaterials and common materials is their biocompatibility. Biocompatibility includes not only organ compatibility, but also blood compatibility. Organ compatibility means that biomaterials doesn't cause inflammation immunogenicity for the organ, and blood compatibility means that biomaterials doesn't cause coagulation or thrombosis. PEG is one of the few biomaterials approved by the Food and Drug Adiministration (FDA) for clinical use, but researchers demonstrated that it can be easily oxidized, becoming failure or causing thrombosis under long exposure to the blood. Traditional zwitterionic materials, such as poly(2-methacryloyloxyethyl phosphorylcholine)(pMPC), poly(sulfobetaine methacylate)(pSBMA) and poly(carboxybetaine methacylate)(pCBMA) are ideal candidates for nonfouling materials due to their excellent anti-nonspecific protein adsorption property and biocompatibility. But their methacrylic backbones cannot biodegrade, which hinders their further applications. Herein, we developed several polypeptide-based antifouling biomaterials and intensive investigations were done for their properties especially for their enzymatic degradation property. The main contents and conclusions of the dissertation are presented as follows:
1. Using H-Lys(Z)-O\Bu.HCl and Boc-Glu(Z)-OH as starting materials, antifouling polypeptide with alternative uniform charges (poly(EK), its corresponding dimer is designated as dimer1) were synthesized by polycondesation. We have resolved the dilemma of ununiformity or local defects caused by the random ring opening polymerzation(ROP) of glutamic acid and lysine N-carboxyanhydrate (NCA) and the unbiodegradability of poly(ethylene glycol)(PEG) or methacrylic materials. Results from Nuclear Magnetic Resonance (1HNMR) and Gel Permeation Chromatography (GPC) demonstrated successful synthesis of the target polymer. Typical yield of the polypeptide is about45%from the dimer1. Successful formation of self-assembly monolayers (SAMs) on gold chips were demonstrated by ATR-FTIR, XPS and ELL. The thicknesses of the SAMs determined by ELL are several nanometers and the thicknesses don't linearly increase with the molecular weights (MWs) increase. The lowest relative nonspecific adsorption of the polypeptide SAMs for anti-IgG and Fg is5.1±1.6%and7.3±1.8%, respectively, when tissue cultural polystyrene (TCPS) surface adsorption is set as control. No obvious cell attachment or bacterium adhesion were observed on the SAMs surfaces. When the feeding concentration of the polypeptide is about5mg/mL, no toxicity or hemolytic activity were detected for the polypeptide.
2. Using H-Lys(Z)-OBzl.HCl and BOC-Glu-O'Bu as starting materials, polypeptide of poly(glutamic acid) backbone with lysine side chains (poly(E)-K, its corresponding dimer is designated as dimer2) were synthesized. Results from1HNMR and GPC show that poly(E)-K with different molecular weights(MWs) were obtained. Typical yield of the polypeptide is about40%from the dimer2. Results from ATR-FTIR, XPS and ELL demonstrate the formation of the polypeptide SAMs on gold surface. The lowest relative protein adsorption for anti-IgG and Fg were observed for the3.5kDa polypeptide SAMs, for which the values are3.3±1.8%and4.4±1.6%, respectively, indicating this kind of polypeptide owns better antifouling property than poly(EK). No toxicity and no hemolytic activity were detected for the polypeptide. In hemolytic assay, the absorbance of polypeptide is even lower than the negative control PBS, indicating the low interactions between the polypeptide and the cell membranes or even the protection of the polypeptide for the cells.
3. In preparatory enzymatic degradation experiments, we found that poly(EK) can degrade while poly(E)-K can't. Thus, we synthesized several copolypeptide by adjusting the ratios of dimer1to dimer2. Results from1HNMR demonstrate that we have successfully synthesized the co-polypeptides with different ingredients. The enzymatic degradation results indicate that the enzymatic degradation time of the copolypeptide become longer when the ratios of the poly(E)-K increase. Consequently, the enzymatic degradation speed and time of the copolypeptide can be easily manipulated by adjusting the proportions of the two dimmers. We are sure to believe that this kind of technology will have a wide range of applications in drug/gene controlled release or tissue engineering in future.
引文
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