聚古罗糖醛酸硫酸酯及其寡糖的制备、结构与活性研究
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摘要
尿路结石症是一种具有高复发率的常见疾病。尿大分子抑制物,特别是糖胺聚糖(Glycosaminoglycans,GAGs),在抑制尿路结石的形成中发挥着重要的作用,GAGs及其类似物在临床上潜在的应用前景受到了人们广泛的关注。本论文选择以海洋褐藻中分离得到的聚古罗糖醛酸(Polyguluronate,PG)为分子骨架,经硫酸酯化修饰成功制备了一种具有高电荷密度和强聚阴离子性质的GAGs类似物――聚古罗糖醛酸硫酸酯(Polyguluronate sulfate,PGS),并采用多种现代仪器分析方法对PGS的化学结构进行了确证。经对PGS的抗尿路结石活性和安全性进行评价,PGS在尿路结石症的预防和治疗方面显示出了良好的应用前景。另外,本论文还采用多种方法制备了具有不同硫酸基取代度和不同聚合度的PGS寡糖,并对PGS寡糖与成纤维细胞生长因子(FGF)及其受体(FGFR)的结合活性进行了评价。
本论文以褐藻酸为原料,经酸水解、pH分级和纯化制备得到了聚古罗糖醛酸,分别采用三氧化硫-三甲胺、三氧化硫-吡啶和氯磺酸-甲酰胺三种硫酸酯化方法制备得到了PGS。经对三种制备方法的特点进行比较,发现三氧化硫-吡啶法反应条件温和,操作简单、硫酸酯基的取代度高,适合于PGS的制备。经对PGS的结构分别采用UV、IR、GC、CD、1H-NMR、13C-NMR、1H-1H COSY、1H-13C HMQC等现代仪器分析技术并结合化学方法进行分析,证实硫酸酯化反应是发生在了聚古罗糖醛酸的C2和C3位;经采用SYBYL分子模拟软件对PGS的分子构象进行模拟,结果表明PGS是一个具有较大柔性的长链分子,在水溶液中分子形成卷曲状态,并可自由摆动。对PGS分别在高温、高湿和强光照射实验条件下的质量稳定性进行考察,结果表明PGS具有较好的质量稳定性,但提示PGS的保存应尽量避免高温和高湿环境。
本论文分别采用喂食乙二醇致大鼠肾结石和植入锌粒致大鼠膀胱结石两种动物模型,对PGS的抗尿路结石活性进行了评价。结果表明:PGS在50和100mg/Kg剂量下,可明显降低大鼠肾结石中肾草酸和肾钙的含量,对肾脏结石的沉积、肾脏病变具有明显的改善作用,对乙二醇致大鼠肾结石和植入性膀胱结石的形成均具有明显的预防和治疗作用。另外,采用棉球肉牙肿模型大鼠对PGS进行评价,结果表明PGS还具有明显的抗炎作用。急性毒性研究结果表明:PGS具有良好的安全性,对小鼠口服给药的最大耐受量为25g/kg;对小鼠静脉注射PGS的LD50为6.29g/kg。
本论文分别采用自由基降解法、固相酸解法和PG寡糖修饰法制备了具有不同硫酸酯基取代度的PGS寡糖。固相酸解法是首次将732#酸性树脂应用于硫酸多糖的降解,研究表明该方法不仅可对PGS进行有效降解,而且在降解过程中不产生无机盐杂质,避免了寡糖与无机盐二次的分离,但在降解过程中有较明显的硫酸酯基脱落,适合制备具有较低硫酸酯基取代度的PGS寡糖。自由基降解法和PG寡糖修饰法适合制备具有高硫酸酯基取代度的PGS寡糖,但这种高硫酸酯基取代度PGS寡糖的分离较为困难。采用Bio-Gel P6凝胶层析柱,可对固相酸解法制备的寡糖进行良好的分离,并得到了13个寡糖组分F1-F13。经采用ESI-MS分析,证实F1-F13分别为聚合度1-13的PGS寡糖。PGS寡糖与FGF-FGFR1c的结合活性研究结果表明:不同聚合度的PGS寡糖对FGF-FGFR1c具有不同的结合能力,其中与FGF1-FGFR1c和FGF19-FGFR1c结合的最小结构片段分别为PGS4糖和PGS12糖;与FGF7-FGFR1c的结合能力随PGS寡糖聚合度的增加而增加。
另外,为改善PGS的口服吸收和提高生物利用度,本论文还对PGS脂质体的制备方法进行了研究,采用反相蒸发法制备的PGS包封率可达39.13%。同时,本论文还建立了一种适合于PGS脂质体包封率测定的HPGPC方法。
本论文各项研究结果,对下一步PGS的临床应用研究具有较重要的指导意义和参考价值。不同聚合度PGS寡糖的制备及结构分析,不仅为PGS的构效关系研究提供了良好的基础,而且还为进一步探讨硫酸寡糖与和FGF-FGFR相关疾病如肿瘤等的相互关系研究提供了基础。
Urolithiasis is a common disorder with a high recurrence rate. Urinary macromolecules, especially glycosaminoglycans (GAGs) play important roles as inhibitors of urinary stone formation. GAGs and their analogues have attracted considerable interest as potential and promising drug candidates for the prevention and treatment of urolithiasis. Polyguluronate sulfate (PGS) as an analogue of GAGs, which has high charge density and strong polyanionic property, is prepared by chemical sulfation of polyguluronate (PG) that separated from alginate. The structure of PGS is characterized by modern analytical techniques. Results of antiurolithiatic activity and safety of PGS show a good prospect on the prevention and treatment of urolithiasis. PGS oligosaccharides with different degrees of sulfate substitution and different polymerization degrees are prepared by several methods, and their activities on the incorporation with fibroblast growth factors (FGF) and fibroblast growth factor receptors (FGFR) are assayed also in this paper.
PG is obtained by pH-fractionated precipitation from the hydrolysate of alginate. PGS is prepared by chemical sulfation of PG with sulfur trioxide trimethylamine complex (SO3-TMA) method, sulfur trioxide pyridine complex (SO3-Py) method and chlorosulfonic acid-foramide method, respectively. Compared with other methods, the reaction condition of SO3-Py method is mild, and it is simple and suitable to prepare PGS with high degree of sulfate substitution. The structure of PGS is characterized by UV, IR, GC, CD, 1H-NMR, 13C-NMR, 1H-1HCOSY, 1H-13C HMQC and other chemical analyses. Sulfation is demonstrated to occur at the C-2 and C-3 positions of the guluronic acid residues. Molecular conformation simulated by Sybyl software show that PGS is a flexible long chain molecule. PGS molecule is a random coil and can sway freely in water solution. The quality stability of PGS are tested under high temperature, high humidity and strong light, respectively. Results show that PGS exhibits a good quality stability, but it should keep away from high temperature and high humidity.
Antiurolithiatic activities of PGS are assayed on two experimental urolithiasis models in rats. The contents of renal oxalate and calcium in ethylene glycol-induced nephrolithiasic rats are decreased significantly, and the renal crystal deposition and pathological changes are improved after administration of PGS at dose-levels of 50 and 100 mg/kg. The formation of zinc disc implant-induced urinary bladder stones in rats are inhibited considerably after administration of PGS at dose-levels of 50 and 100 mg/kg. PGS exhibits good effects both on the prevention and the treatment of urolithiasis. In addition, PGS exhibits considerable anti-inflammatory activity in the cotton pellet-induced granuloma in rats. Acute toxicity results of PGS show that it is a safe drug candidate. The intravenous LD50 in mice is 6.29 g/kg, and the oral maximum tolerance values of LPGS in mice is 25 g/kg.
PGS oligosaccharides with different degrees of sulfate substitution and different polymerization degrees are prepared by free radical degradation, solid phase acid degradation and by chemical sulfation of PG oligosaccharides, respectively. 732# resin as a solid phase acid is used for the degradation of sulfated polysaccharides at firstly in this paper. Not only PGS can be degraded effectively by the solid phase acid method, but also there are no salt impurities exist in PGS oligosaccharides. The difficulty of separation between oligosaccharides and salt is avoided by the solid phase acid method, but the PGS oligosaccharides are desulfated obviously. So, the solid phase acid method is suitable to prepare PGS oligosaccharides with low degrees of sulfate substitution. The free radical degradation and chemical sulfation of PG oligosaccharides method are suitable to prepare PGS oligosaccharides with high degrees of sulfate substitution, but it is difficult to separate these PGS oligosaccharides. PGS oligosaccharides prepared by solid phase acid method are separated by Bio-Gel P6 column, and thirteen oligosaccharide fractions (F1-F13) are obtained. The polymerization degree of F1-F13 is one to thirteen, respectively, demonstrated by ESI-MS analysis. Results of PGS oligosaccharides incorporated with FGF-FGFR1c show that the least segments of PGS oligosaccharides to incorporate with FGF1-FGFR1c and FGF19-FGFR1c are PGS4 and PGS12, respectively. The ability of PGS oligosaccharides to incorporate with FGF7-FGFR1c is increased when the polymerization degree is increased.
In addition, PGS liposomes are prepared by different methods in order to improve oral absorption and bioavailability of PGS. The encapsulation efficiency of PGS liposomes prepared by reverse-phase evaporation is up to 39.13%. A HPGPC method is established also for the determination of encapsulation efficiency of PGS liposomes.
All results on PGS above are important and useful to guide the further clinical research of PGS. Preparation and structure analysis of PGS oligosaccharides with different polymerization degrees have provide a base not only for the research on structure-activity relationship of PGS, but also for further research on the relationship of sulfated oligosaccharides with some diseases, such as cancer, which are relevant to FGF-FGFR.
本论文以褐藻酸为原料,经酸水解、pH分级和纯化制备得到了聚古罗糖醛酸,分别采用三氧化硫-三甲胺、三氧化硫-吡啶和氯磺酸-甲酰胺三种硫酸酯化方法制备得到了PGS。经对三种制备方法的特点进行比较,发现三氧化硫-吡啶法反应条件温和,操作简单、硫酸酯基的取代度高,适合于PGS的制备。经对PGS的结构分别采用UV、IR、GC、CD、1H-NMR、13C-NMR、1H-1H COSY、1H-13C HMQC等现代仪器分析技术并结合化学方法进行分析,证实硫酸酯化反应是发生在了聚古罗糖醛酸的C2和C3位;经采用SYBYL分子模拟软件对PGS的分子构象进行模拟,结果表明PGS是一个具有较大柔性的长链分子,在水溶液中分子形成卷曲状态,并可自由摆动。对PGS分别在高温、高湿和强光照射实验条件下的质量稳定性进行考察,结果表明PGS具有较好的质量稳定性,但提示PGS的保存应尽量避免高温和高湿环境。
本论文分别采用喂食乙二醇致大鼠肾结石和植入锌粒致大鼠膀胱结石两种动物模型,对PGS的抗尿路结石活性进行了评价。结果表明:PGS在50和100mg/Kg剂量下,可明显降低大鼠肾结石中肾草酸和肾钙的含量,对肾脏结石的沉积、肾脏病变具有明显的改善作用,对乙二醇致大鼠肾结石和植入性膀胱结石的形成均具有明显的预防和治疗作用。另外,采用棉球肉牙肿模型大鼠对PGS进行评价,结果表明PGS还具有明显的抗炎作用。急性毒性研究结果表明:PGS具有良好的安全性,对小鼠口服给药的最大耐受量为25g/kg;对小鼠静脉注射PGS的LD50为6.29g/kg。
本论文分别采用自由基降解法、固相酸解法和PG寡糖修饰法制备了具有不同硫酸酯基取代度的PGS寡糖。固相酸解法是首次将732#酸性树脂应用于硫酸多糖的降解,研究表明该方法不仅可对PGS进行有效降解,而且在降解过程中不产生无机盐杂质,避免了寡糖与无机盐二次的分离,但在降解过程中有较明显的硫酸酯基脱落,适合制备具有较低硫酸酯基取代度的PGS寡糖。自由基降解法和PG寡糖修饰法适合制备具有高硫酸酯基取代度的PGS寡糖,但这种高硫酸酯基取代度PGS寡糖的分离较为困难。采用Bio-Gel P6凝胶层析柱,可对固相酸解法制备的寡糖进行良好的分离,并得到了13个寡糖组分F1-F13。经采用ESI-MS分析,证实F1-F13分别为聚合度1-13的PGS寡糖。PGS寡糖与FGF-FGFR1c的结合活性研究结果表明:不同聚合度的PGS寡糖对FGF-FGFR1c具有不同的结合能力,其中与FGF1-FGFR1c和FGF19-FGFR1c结合的最小结构片段分别为PGS4糖和PGS12糖;与FGF7-FGFR1c的结合能力随PGS寡糖聚合度的增加而增加。
另外,为改善PGS的口服吸收和提高生物利用度,本论文还对PGS脂质体的制备方法进行了研究,采用反相蒸发法制备的PGS包封率可达39.13%。同时,本论文还建立了一种适合于PGS脂质体包封率测定的HPGPC方法。
本论文各项研究结果,对下一步PGS的临床应用研究具有较重要的指导意义和参考价值。不同聚合度PGS寡糖的制备及结构分析,不仅为PGS的构效关系研究提供了良好的基础,而且还为进一步探讨硫酸寡糖与和FGF-FGFR相关疾病如肿瘤等的相互关系研究提供了基础。
Urolithiasis is a common disorder with a high recurrence rate. Urinary macromolecules, especially glycosaminoglycans (GAGs) play important roles as inhibitors of urinary stone formation. GAGs and their analogues have attracted considerable interest as potential and promising drug candidates for the prevention and treatment of urolithiasis. Polyguluronate sulfate (PGS) as an analogue of GAGs, which has high charge density and strong polyanionic property, is prepared by chemical sulfation of polyguluronate (PG) that separated from alginate. The structure of PGS is characterized by modern analytical techniques. Results of antiurolithiatic activity and safety of PGS show a good prospect on the prevention and treatment of urolithiasis. PGS oligosaccharides with different degrees of sulfate substitution and different polymerization degrees are prepared by several methods, and their activities on the incorporation with fibroblast growth factors (FGF) and fibroblast growth factor receptors (FGFR) are assayed also in this paper.
PG is obtained by pH-fractionated precipitation from the hydrolysate of alginate. PGS is prepared by chemical sulfation of PG with sulfur trioxide trimethylamine complex (SO3-TMA) method, sulfur trioxide pyridine complex (SO3-Py) method and chlorosulfonic acid-foramide method, respectively. Compared with other methods, the reaction condition of SO3-Py method is mild, and it is simple and suitable to prepare PGS with high degree of sulfate substitution. The structure of PGS is characterized by UV, IR, GC, CD, 1H-NMR, 13C-NMR, 1H-1HCOSY, 1H-13C HMQC and other chemical analyses. Sulfation is demonstrated to occur at the C-2 and C-3 positions of the guluronic acid residues. Molecular conformation simulated by Sybyl software show that PGS is a flexible long chain molecule. PGS molecule is a random coil and can sway freely in water solution. The quality stability of PGS are tested under high temperature, high humidity and strong light, respectively. Results show that PGS exhibits a good quality stability, but it should keep away from high temperature and high humidity.
Antiurolithiatic activities of PGS are assayed on two experimental urolithiasis models in rats. The contents of renal oxalate and calcium in ethylene glycol-induced nephrolithiasic rats are decreased significantly, and the renal crystal deposition and pathological changes are improved after administration of PGS at dose-levels of 50 and 100 mg/kg. The formation of zinc disc implant-induced urinary bladder stones in rats are inhibited considerably after administration of PGS at dose-levels of 50 and 100 mg/kg. PGS exhibits good effects both on the prevention and the treatment of urolithiasis. In addition, PGS exhibits considerable anti-inflammatory activity in the cotton pellet-induced granuloma in rats. Acute toxicity results of PGS show that it is a safe drug candidate. The intravenous LD50 in mice is 6.29 g/kg, and the oral maximum tolerance values of LPGS in mice is 25 g/kg.
PGS oligosaccharides with different degrees of sulfate substitution and different polymerization degrees are prepared by free radical degradation, solid phase acid degradation and by chemical sulfation of PG oligosaccharides, respectively. 732# resin as a solid phase acid is used for the degradation of sulfated polysaccharides at firstly in this paper. Not only PGS can be degraded effectively by the solid phase acid method, but also there are no salt impurities exist in PGS oligosaccharides. The difficulty of separation between oligosaccharides and salt is avoided by the solid phase acid method, but the PGS oligosaccharides are desulfated obviously. So, the solid phase acid method is suitable to prepare PGS oligosaccharides with low degrees of sulfate substitution. The free radical degradation and chemical sulfation of PG oligosaccharides method are suitable to prepare PGS oligosaccharides with high degrees of sulfate substitution, but it is difficult to separate these PGS oligosaccharides. PGS oligosaccharides prepared by solid phase acid method are separated by Bio-Gel P6 column, and thirteen oligosaccharide fractions (F1-F13) are obtained. The polymerization degree of F1-F13 is one to thirteen, respectively, demonstrated by ESI-MS analysis. Results of PGS oligosaccharides incorporated with FGF-FGFR1c show that the least segments of PGS oligosaccharides to incorporate with FGF1-FGFR1c and FGF19-FGFR1c are PGS4 and PGS12, respectively. The ability of PGS oligosaccharides to incorporate with FGF7-FGFR1c is increased when the polymerization degree is increased.
In addition, PGS liposomes are prepared by different methods in order to improve oral absorption and bioavailability of PGS. The encapsulation efficiency of PGS liposomes prepared by reverse-phase evaporation is up to 39.13%. A HPGPC method is established also for the determination of encapsulation efficiency of PGS liposomes.
All results on PGS above are important and useful to guide the further clinical research of PGS. Preparation and structure analysis of PGS oligosaccharides with different polymerization degrees have provide a base not only for the research on structure-activity relationship of PGS, but also for further research on the relationship of sulfated oligosaccharides with some diseases, such as cancer, which are relevant to FGF-FGFR.
引文
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