新型糖基氨基酸衍生物的合成及初步生物活性研究
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摘要
蛋白质酪氨酸磷酸酶1B (PTP1B)作为治疗糖尿病,肥胖症及特定癌症的潜在药物靶标,近年来受到人们的广泛关注。课题组前期工作发现通过点击化学合成的糖基氨基酸和芳香碳糖苷类化合物均对PTP1B显示出一定的抑制活性。本论文希望结合二者优势,设计并合成了如下化合物系列：以糖环为骨架,在其1位异头碳引入对甲氧基苯基,而6位通过点击化学引入苯丙氨酸或酪氨酸片段,作为潜在PTP1B小分子抑制剂。体外生物活性测试表明：化合物18,19,20,21对PTP1B有较好的抑制效果,其中化合物20不仅对PTP1B的IC50(半数抑制浓度)值达到5.6μM,还对与PTP1B同源性较高的蛋白酪氨酸磷酯酶SHP-1, SHP-2及TCPTP显示出一定的选择性。
氨氧酸型多肽是在普通多肽的基础上,通过化学手段在氨基酸中的氨基与碳原子之间引入氧原子得到。由于比普通多肽更具刚性,氨氧酸型多肽作为药物用于临床治疗颇具前景。本论文设计以丝氨酸为骨架,对其进行结构改造引入氨氧基官能团,并希望通过酰胺键的链接模式形成不同长度的肽链,然后引入糖基,获得一类新型的糖基氨氧酸拟肽化合物。本工作顺利合成相关氨氧酸链接单元,通过后续酰胺化及糖基的引入可获最终目标多肽结构。
PTP1B(Protein Tyrosine Phosphatase 1B) is a potential target for treating diabetes, obesity and some cancers, and thus it has been attached great importance in recent years. Triazolyl glycosyl amino acids synthesized via click chemistry and aryl C-glycosides have been found to display exciting PTPIB inhibitory efficacy in the previous work of our lab. In this paper, we expected to take advantage of the two natural-like products, and thereby designed and synthesized a series of compounds with the sugar as the skeleton, a 2, 4-dimethoxy phenyl introduced to the anomeric carbon, and a phenylalanine or a tyrosine introduced to the C-6 position. Also we gauged their inhibition activity in vitro. The results show that compound 18,19,20,21 are modest PTP1B inhibitors, and compound 20 has moderate selectivities over SHP-1, SHP-2 and TCPTP, which are also protein tyrosine phosphatases and share high sequence homology with PTP1B yet play distinct physiological roles.
Peptides of aminoxy acids are oxa-analogues of peptides where an oxygen atom is introduced between the nitrogen atom of the amino and its adjacent carbon atom. They form more stable turn and helix structures than peptides, and are, therefore, of more pharmaceutical interest. In this work, we design a glycopeptide molecular of aminoxy acid, and expect to evaluate its potential biological activity. This molecule takes the serine as the building block, which is first modified to an aminoxy acid, and then converted to reacting blocks with the carboxyl and amino group bared respectively. These reacting blocks are combined with each other to yield the peptide of aminoxy acid through N-terminal acetylation and C-Terminal Amidation. The resulting peptide is then linked to the sugars to give the final product. In current, those partly protected aminoxy acids have already been successfully synthesized.
氨氧酸型多肽是在普通多肽的基础上,通过化学手段在氨基酸中的氨基与碳原子之间引入氧原子得到。由于比普通多肽更具刚性,氨氧酸型多肽作为药物用于临床治疗颇具前景。本论文设计以丝氨酸为骨架,对其进行结构改造引入氨氧基官能团,并希望通过酰胺键的链接模式形成不同长度的肽链,然后引入糖基,获得一类新型的糖基氨氧酸拟肽化合物。本工作顺利合成相关氨氧酸链接单元,通过后续酰胺化及糖基的引入可获最终目标多肽结构。
PTP1B(Protein Tyrosine Phosphatase 1B) is a potential target for treating diabetes, obesity and some cancers, and thus it has been attached great importance in recent years. Triazolyl glycosyl amino acids synthesized via click chemistry and aryl C-glycosides have been found to display exciting PTPIB inhibitory efficacy in the previous work of our lab. In this paper, we expected to take advantage of the two natural-like products, and thereby designed and synthesized a series of compounds with the sugar as the skeleton, a 2, 4-dimethoxy phenyl introduced to the anomeric carbon, and a phenylalanine or a tyrosine introduced to the C-6 position. Also we gauged their inhibition activity in vitro. The results show that compound 18,19,20,21 are modest PTP1B inhibitors, and compound 20 has moderate selectivities over SHP-1, SHP-2 and TCPTP, which are also protein tyrosine phosphatases and share high sequence homology with PTP1B yet play distinct physiological roles.
Peptides of aminoxy acids are oxa-analogues of peptides where an oxygen atom is introduced between the nitrogen atom of the amino and its adjacent carbon atom. They form more stable turn and helix structures than peptides, and are, therefore, of more pharmaceutical interest. In this work, we design a glycopeptide molecular of aminoxy acid, and expect to evaluate its potential biological activity. This molecule takes the serine as the building block, which is first modified to an aminoxy acid, and then converted to reacting blocks with the carboxyl and amino group bared respectively. These reacting blocks are combined with each other to yield the peptide of aminoxy acid through N-terminal acetylation and C-Terminal Amidation. The resulting peptide is then linked to the sugars to give the final product. In current, those partly protected aminoxy acids have already been successfully synthesized.
引文
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