微波辅助的功能糖复合物的合成；三氮唑糖配基水溶性荧光探针的合成与应用
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摘要
糖类是生物体内的三大营养物质之一,参与了生命中新陈代谢的诸多环节。近年来,许多与糖相关的交叉学科如糖化学(Carbohydrate Chemistry)、n糖生物学(Glycobiology)、糖免疫学、糖组学等均得到了迅速发展。联用化学和生物学的方法、手段研究糖的结构与功能、糖与生物分子间的相互作用,探明糖类物质在生命过程中发挥作用的机制,进而以糖分子为“载体”或“探针”,将对生命过程的调控发挥重大作用。本文主要基于单糖在糖骨架药物及糖分子探针两个方面的应用对其进行拓展探究,按学术内容分为两个章节：
第一章节蛋白酪氨酸磷酸酯酶(PTP)是一类信号传导调节酶,通过调节细胞内的酪氨酸磷酸化水平来控制细胞的成长、分化和代谢,其调节紊乱可导致多种疾病的发生,如糖尿病、肥胖症、癌症和骨质疏松症等。PTP1B和CDC25B是PTP家族的重要成员,已经成为了Ⅱ型糖尿病、肥胖症及恶性肿瘤潜在的治疗靶点。发展具有高催化活性、高生物利用度和高选择性的小分子抑制剂,近年来已成为一种良好的药物研发策略。
本章在单糖这一核心骨架基础上,结合模块化、专一性的点击化学(铜催化的叠氮与炔1,3-偶极环加成反应),并引入微波辅助合成手段成功构建了两个系列三氮唑连接的功能糖复合物,对部分目标化合物进行了PTP族多种酶靶点的生物活性筛选,得到了一系列活性数据,并对部分化合物进行计算机辅助docking对接模拟,根据得到的构效关系信息,提出了合理的活性分析,为后续的研究和结构修饰提供了一定的参考价值：
1、将C1-炔基化的苄基糖和叠氮化的天然氨基酸经点击化学构建第一系列糖氨基酸系列衍生物。所合成的三氮唑糖基氨基酸衍生物均具有微摩尔级别的PTP1B和CDC25B抑制活性,并显示了一定的同源PTP选择性。化合物27对于PTP1B的抑制效果最佳(IC50=5.1μM),而28则显示了更好的CDC25B抑制活性(ICso=3.9μM)。其中16个化合物未见文献报道。
2、将C1-炔基化的五乙酰基糖和叠氮化的极性(羟基)苯甲酸衍生物经点击化学构建了第二系列糖水杨酸系列衍生物。化合物41对于PTP1B的IC50值为36.6μM,显示了比其余同源PTP至少4倍的抑制活性(IC50>160μM)。而化合物51(50.5μM,98.4%抑制率)也对其C-4位差向异构体54(35.3%抑制率)显示了良好的选择性。其中21个化合物未见文献报道。
第二章节荧光探针技术在重金属离子、有毒有害气体及有机化学污染物的检测方面具有广泛的应用,并越来越多的应用于水环境及生物体内的离子和小分子探测。糖类以其独特的立体结构、灵活的可修饰性、良好的生物利用度和强大的水溶性成为了研究者在构建水溶性或生物性荧光探针分子时经常用到的结构骨架。
本章利用单糖这一核心骨架,将C2,3-或4,6-双炔基化的1-甲氧基葡萄糖、半乳糖和甘露糖与荧光淬灭的3-叠氮香豆素衍生物经由微波辅助的双点击化学以较高的反应转化率和收率构建了一系列荧光恢复的双齿型糖三氮唑香豆素复合物。随后将脱去糖环苄基保护的具良好水溶性的化合物84、85在纯水中做了初步的紫外和荧光检测,得到了一些有意义的结果,为后续的深入光学测试提供了一定的数据基础,期待将其用于水环境中的选择性离子探测；同时设计了基于半乳糖的环氨氧基肽模拟物荧光探针分子,得到了一些初步的结果。其中18个化合物未见文献报道。
Carbohydrate is one of the three nutriments in organism attending many parts of metabolism. Recently, varieties of interdisciplines related with carbohydrate have being rapidly developed including glycochemistry, glycobiology, glycoimmunology and glycomics. It would be critical for regulation in life process to use carbohydrate molecules as carrier or probe through studying structure and function of carbohydrate and molecular interactions combining chemical approaches and biological approaches and proving up the mechanism of carbohydrate in life process, and then,. This thesis is based on exploring of application of monosaccharide on both of drugs of carbohydrate as skeleton and sugar probe, it could be divided into two parts:
Part1
Protein Tyrosine Phosphatase (PTP) is an important regulator of signal transduction which control growth, differentiation and metabolism of cells by regulating tyrosine phosphorylation level. Varieties of diseases including diabets, obesity, cancer and osteoporosis may happen because of improper regulating. PTP1B and CDC25B are two important members in PTP family who have been potential therapeutic targets of type2diabets, obesity and cancer. Development of smaller molecular inhibitors with high catalytic activity, higher bioavailability and high selectivity has been positive strategy of drug discovery.
In this part, two series of compounds of triazole-linked functional glycosyl have been constructed on the basis of monosaccharide as skeleton combining with both modularized specific'Click'(Cu-catalyzed cycloaddition reactions between azides and alkynes) and microwave-assisted synthesis, a set of activity data obtained by selecting bioactivity of enzyme targets in PTP family of some target compound and reasonable activity analysis resulting from structure-activity relationship gained through computer-assisted docking all contributing to reference of following research and structural modification:
1. The1st series of glycosyl amino acid derivatives were generated by'click'chemistry between C1-propargyl benzyl sugar and azido natural amino acid. The synthesized glycosyl triazoloamino acid derivatives all have inhibition activity of PTP IB and CDC25B with micro-mole level and show specified selectivity of homologous PTP.27has the best PTP1B inhibitory effect (IC50=5.1μM),while28shows better CDC25B inhibitory effect (IC50= 3.9μM).16compounds among them have not yet been reported in the literature so far.
2. The2nd series of glycosyl salicylic acid derivatives was generated by'click'reactions between C1-propargyl acetyl sugar and azido polar(hydroxy)benzoates. IC50value to PTP1B of41was36.6μM demonstrating4-time inhibitory activity of other homologous PTP(IC50>160μM).51(50.5μM,98.4%inhibition rate) shows better selectivity comparing with it's epimer54(35.3%inhibition rate).21compounds among them have not yet been reported in the literature.
Part2
Fluorescence probe technique is widely used in detecting heavy metal ions, toxic gases and organic contaminants and is applied in detecting aquatic environmental, iron and smaller molecules in creatures more and more. Carbohydrate has been usually used as structural skeleton when generating water-soluble and biological fluorescence probe molecule because of it's unique stereochemical structure, flexible bioavailability and strong water solubility.
In this part, monosaccharide was used as key skeleton to synthesize a series of fluorescent recovering bis-triazolocoumarin glycosyl conjugates by microwave-assisted dual click chemistry between C2,3-or4,6-bis-propargyl1-methoxy glucose, galactose and mannose with fluorescence quenched3-azido coumarin derivative with high conversion and yield. Then, benzyl dropped84and85which have good water-solubility were initially tested by UV and fluorescence in pure water resulting in some significative conclusions providing basic data for further optical test, and it would be used to detect ion-selecting in aquatic environmental; on the other side, galactose-based aminoxy peptide analog fluorescence probe molecule was successfully designed and some preliminary results were presented.16compounds among them have not yet been reported in the literature.
第一章节蛋白酪氨酸磷酸酯酶(PTP)是一类信号传导调节酶,通过调节细胞内的酪氨酸磷酸化水平来控制细胞的成长、分化和代谢,其调节紊乱可导致多种疾病的发生,如糖尿病、肥胖症、癌症和骨质疏松症等。PTP1B和CDC25B是PTP家族的重要成员,已经成为了Ⅱ型糖尿病、肥胖症及恶性肿瘤潜在的治疗靶点。发展具有高催化活性、高生物利用度和高选择性的小分子抑制剂,近年来已成为一种良好的药物研发策略。
本章在单糖这一核心骨架基础上,结合模块化、专一性的点击化学(铜催化的叠氮与炔1,3-偶极环加成反应),并引入微波辅助合成手段成功构建了两个系列三氮唑连接的功能糖复合物,对部分目标化合物进行了PTP族多种酶靶点的生物活性筛选,得到了一系列活性数据,并对部分化合物进行计算机辅助docking对接模拟,根据得到的构效关系信息,提出了合理的活性分析,为后续的研究和结构修饰提供了一定的参考价值：
1、将C1-炔基化的苄基糖和叠氮化的天然氨基酸经点击化学构建第一系列糖氨基酸系列衍生物。所合成的三氮唑糖基氨基酸衍生物均具有微摩尔级别的PTP1B和CDC25B抑制活性,并显示了一定的同源PTP选择性。化合物27对于PTP1B的抑制效果最佳(IC50=5.1μM),而28则显示了更好的CDC25B抑制活性(ICso=3.9μM)。其中16个化合物未见文献报道。
2、将C1-炔基化的五乙酰基糖和叠氮化的极性(羟基)苯甲酸衍生物经点击化学构建了第二系列糖水杨酸系列衍生物。化合物41对于PTP1B的IC50值为36.6μM,显示了比其余同源PTP至少4倍的抑制活性(IC50>160μM)。而化合物51(50.5μM,98.4%抑制率)也对其C-4位差向异构体54(35.3%抑制率)显示了良好的选择性。其中21个化合物未见文献报道。
第二章节荧光探针技术在重金属离子、有毒有害气体及有机化学污染物的检测方面具有广泛的应用,并越来越多的应用于水环境及生物体内的离子和小分子探测。糖类以其独特的立体结构、灵活的可修饰性、良好的生物利用度和强大的水溶性成为了研究者在构建水溶性或生物性荧光探针分子时经常用到的结构骨架。
本章利用单糖这一核心骨架,将C2,3-或4,6-双炔基化的1-甲氧基葡萄糖、半乳糖和甘露糖与荧光淬灭的3-叠氮香豆素衍生物经由微波辅助的双点击化学以较高的反应转化率和收率构建了一系列荧光恢复的双齿型糖三氮唑香豆素复合物。随后将脱去糖环苄基保护的具良好水溶性的化合物84、85在纯水中做了初步的紫外和荧光检测,得到了一些有意义的结果,为后续的深入光学测试提供了一定的数据基础,期待将其用于水环境中的选择性离子探测；同时设计了基于半乳糖的环氨氧基肽模拟物荧光探针分子,得到了一些初步的结果。其中18个化合物未见文献报道。
Carbohydrate is one of the three nutriments in organism attending many parts of metabolism. Recently, varieties of interdisciplines related with carbohydrate have being rapidly developed including glycochemistry, glycobiology, glycoimmunology and glycomics. It would be critical for regulation in life process to use carbohydrate molecules as carrier or probe through studying structure and function of carbohydrate and molecular interactions combining chemical approaches and biological approaches and proving up the mechanism of carbohydrate in life process, and then,. This thesis is based on exploring of application of monosaccharide on both of drugs of carbohydrate as skeleton and sugar probe, it could be divided into two parts:
Part1
Protein Tyrosine Phosphatase (PTP) is an important regulator of signal transduction which control growth, differentiation and metabolism of cells by regulating tyrosine phosphorylation level. Varieties of diseases including diabets, obesity, cancer and osteoporosis may happen because of improper regulating. PTP1B and CDC25B are two important members in PTP family who have been potential therapeutic targets of type2diabets, obesity and cancer. Development of smaller molecular inhibitors with high catalytic activity, higher bioavailability and high selectivity has been positive strategy of drug discovery.
In this part, two series of compounds of triazole-linked functional glycosyl have been constructed on the basis of monosaccharide as skeleton combining with both modularized specific'Click'(Cu-catalyzed cycloaddition reactions between azides and alkynes) and microwave-assisted synthesis, a set of activity data obtained by selecting bioactivity of enzyme targets in PTP family of some target compound and reasonable activity analysis resulting from structure-activity relationship gained through computer-assisted docking all contributing to reference of following research and structural modification:
1. The1st series of glycosyl amino acid derivatives were generated by'click'chemistry between C1-propargyl benzyl sugar and azido natural amino acid. The synthesized glycosyl triazoloamino acid derivatives all have inhibition activity of PTP IB and CDC25B with micro-mole level and show specified selectivity of homologous PTP.27has the best PTP1B inhibitory effect (IC50=5.1μM),while28shows better CDC25B inhibitory effect (IC50= 3.9μM).16compounds among them have not yet been reported in the literature so far.
2. The2nd series of glycosyl salicylic acid derivatives was generated by'click'reactions between C1-propargyl acetyl sugar and azido polar(hydroxy)benzoates. IC50value to PTP1B of41was36.6μM demonstrating4-time inhibitory activity of other homologous PTP(IC50>160μM).51(50.5μM,98.4%inhibition rate) shows better selectivity comparing with it's epimer54(35.3%inhibition rate).21compounds among them have not yet been reported in the literature.
Part2
Fluorescence probe technique is widely used in detecting heavy metal ions, toxic gases and organic contaminants and is applied in detecting aquatic environmental, iron and smaller molecules in creatures more and more. Carbohydrate has been usually used as structural skeleton when generating water-soluble and biological fluorescence probe molecule because of it's unique stereochemical structure, flexible bioavailability and strong water solubility.
In this part, monosaccharide was used as key skeleton to synthesize a series of fluorescent recovering bis-triazolocoumarin glycosyl conjugates by microwave-assisted dual click chemistry between C2,3-or4,6-bis-propargyl1-methoxy glucose, galactose and mannose with fluorescence quenched3-azido coumarin derivative with high conversion and yield. Then, benzyl dropped84and85which have good water-solubility were initially tested by UV and fluorescence in pure water resulting in some significative conclusions providing basic data for further optical test, and it would be used to detect ion-selecting in aquatic environmental; on the other side, galactose-based aminoxy peptide analog fluorescence probe molecule was successfully designed and some preliminary results were presented.16compounds among them have not yet been reported in the literature.
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