斑蝥素及其类似物:抗肿瘤及丝氨酸/苏氨酸蛋白质磷酸酶抑制活性

摘要/Abstract

摘要：

本文主要叙述了斑蝥素结构经过改造后, 在抗癌活性和对丝氨酸苏氨酸蛋白质磷酸酶抑制活性方面的研究进展。

关键词: 斑蝥素类似物, 斑蝥素类似物, 斑蝥素类似物, 抗肿瘤活性, 抗肿瘤活性, 抗肿瘤活性, 丝氨酸苏氨酸蛋白质磷酸酶抑制活性, 丝氨酸苏氨酸蛋白质磷酸酶抑制活性, 丝氨酸苏氨酸蛋白质磷酸酶抑制活性

Abstract: This paper mainly describes the anticancer activities and Ser/Thr protein phosphatase inhibitory activities of cantharidin and its analogues.

Key words: cantharidin analogues, cantharidin analogues, anticancer activity, anticancer activity, Ser/Thr protein phosphatase inhibitory activity, Ser/Thr protein phosphatase inhibitory activity

中图分类号:

R916.696

Supporting: ^*Corresponding author. Tel.: 86-24-23986443

史清华, 王玉玲, 宋宏锐^*, 程卯生. 斑蝥素及其类似物:抗肿瘤及丝氨酸/苏氨酸蛋白质磷酸酶抑制活性[J]. .

SHI Qing-hua, WANG Yu-ling, SONG Hong-rui^*, CHENG Mao-sheng. Cantharidin and Its Analogues:Anticancer and Ser/Thr Protein Phosphatase Inhibitory Activities[J]. .

[1] Wang GS. Medical uses of Mylabris in ancient China and recent studies [J]. J Ethnoparmacol, 1989, 26 : 147-162.
[2] McCluskey A, Taylor C, Quinn RJ, Inhibition of protein phosphatase 2A by cantharidin analoges [J]. Bioorg Med Chem Lett, 1996, 6 (9) : 1025-1028.
[3] Lin PY, Shi SJ, Shu HL, et al. A simple procedure for preparation of N-thiazolyl and N-thiadiazolyl cantharidinimides and evaluation of their cytotoxicities against human hepatocellular carcinoma cells [J]. Bioorg Chem, 2000, 28 (5) : 266-272.
[4] Tian SL, Zhao SW, Fang Y. Antitumor drug studies III: the synthesis and anticancer activities of norcantharidin amino acid analogues [J]. Pharm J, 1993, 28 (11) : 870-875.
[5] Li TH, Tang ZG, Huang YH. The synthesis and distribution in animals of their 125 I labeled compounds of 5, 6-dibrom-onorcantharidinimides analogues [J]. J Chin Pharm, 1999, 9 (1) : 46-47.
[6] Kawamura N, Li YM, Engel JL, et al. Endothall thioanhydride : structural aspects of unusually high mouse toxicity and specific binding site in liver [J]. Chem Res Toxicol, 1990, 3 (4) : 318-24.
[7] Kihara N, Morimoto T, Nakanishi T. Platinum-dioxolane analogue complexes as antineoplas2tics [P]. J P : 6137796, 1986-02-22.
[8] Zou FA, Dou PY, Wang K. Synthesis, antitumor activity and acute toxicity of diamine/diaminocyclohexane platinum (II) complexes with oxygen-ligating leaving group [J]. J Inorg Biochem, 1997, 65 (2) : 145-149.
[9] Li JS, Ma YQ, Liu RC, et al. Synthesis, antitumor activity and crystal structure of the triphenyltin analogue of exo-7-oxabicyclo [2. 2. 1] hept-5-ene-3-N-p-tolylamide222acid [J]. Appl Organomet Chem, 2001,15 (3) : 227-232.
[10] Lee SM, Choi WM, Syntheses and antitumor activities of medium molecular weight polymers containing α-ethoxy-exo-3,6-epoxy-1, 2, 3, 6-tetrahydrophthaloyl-5-fluorouracil [J]. J Polym Sci, Part A : Polym Chem, 1999, 37 (14) : 2619-2627.
[11] McCluskey A, Bowyer MC, Collins E, et al. Anhydride modified cantharidin analogues : synthesis, inhibition of protein phosphatases 1 and 2A and anticancer activity [J]. Bioorg Med Chem Lett, 2000, 10 (15) : 1687-1690.
[12] McCluskey A, Ackland S, Bowyer MC. Cantharidin analogues : synthesis and evaluation of growth inhibition in a panel of selected tumor cell lines [J]. Bioorg Chem, 2003, 31 : 68-79.
[13] Cohen P. The structure and regulation of protein phosphatases [J]. Annu Rev Biochem, 1989, 58 : 453-508.
[14] McCluskey A, Ackland SP, Cardiner E, et al. The inhibition of protein phosphatases 1 and 2A: a new target for rational anti-cancer drug design [J]. Anti Cancer Drugs Des, 2001, 16 (6) : 291-303.
[15] Ghosh S, Schroeter D, Paweletz N. Okadaic acid overrides the S-phase checkpoint and accelerates progression of G2-phase to induce premature mitosis in HeLa cells [J]. Exp Cell Res, 1996, 227 : 165-169.
[16] Roberge M, Tudan C, Hung SM, et al. Antitumor drug fostriecin inhibits the mitotic entry checkpoint and protein phosphatases 1 and 2A [J]. Cancer Res, 1994, 54 : 6115-6121.
[17] Yamashita K, Yasuda H, Pines J, et al. Okadaic acid, a potent inhibitor of type 1 and 2A protein phosphatases, acti-vates cdc2/H1 kinase and transiently induces a premature mitosis-like state in BHK21 cells [J]. EMBO J, 1990, 9 : 4331-4338.
[18] Lazzereschi D, Coppa A, Mincione G, et al. The phosphatase inhibitor okadaic acid stimulates the TSH-induces G1-Sphase transition in thyroid cells [J]. Exp Cell Res, 1997, 234 : 425-433.
[19] Sassoon I, Severin FF, Andrews PD, et al. Regulation of Saccharomyces cerevisiae kinetochores by the type 1 phosphatase Glc7p [J]. Genes Dev, 1999, 13 : 545-555.
[20] Giese G, Weigers W, Kubbies M, et al. Okadaic acid co-induces vimentin expression and cell cycle arrest in MPC-11 mouse plasmacytoma cells [J]. J Cell Physiol, 1995, 163 : 145-154.
[21] McCluskey A, Keane M, Walkom C, et al. The first two cantharidin analogues displaying PP1 selectivity [J]. Bioorg Med Chem Lett, 2002, 12 : 391-393.
[22] Suzanne B, Buck CH, Satoshi I, et al. Fundamental role of the fostriecin unsaturated lactone and implications for selective protein phosphatase inhibition [J]. J Am Chem Soc, 2003, 125 : 15694-15695.
[23] McCluskey A, Bowyer MC, Collins E, et al. Anhydride modified cantharidin analogues : synthesis, inhibition of protein phosphatases 1 and 2A and anticancer activity [J]. Bioorg Med Chem Lett, 2000, 10 (15) : 1687-1690.
[24] McCluskey A, Walkom C, Bowyer MC, et al. Cantharimides : a new class of modified cantharidin analogues inhibiting protein phosphatase 1 and 2A [J]. Bioorg Med Chem Lett, 2001, 11 (22) : 2941-2946.
[25] McCluskey A, Mirella AK, Mudgee LM, et al. Anhydride modified cantharidin analogues. Is ring opening important in the inhibition of protein phosphatase 2A [J]. Eur J Med Chem, 2000, 35 : 957-964.
[26] Laidcey CW, Dauben WG, Guo IR, et al. 2-Carboxymethylendothall analogues as affinity probes for stabilized PP2A [J]. Bioorg Med Chem, 1999, 7 : 2937-2944.
[27] Gauss CM, James E, Sheppeck J E, et al. A molecular modeling analysis of the binding interactions between the okadaic acid class of natural product inhibitors and the SerPThr phosphthatases, PP1 and PP2A [J]. Bioorg Med Chem Lett, 1997, 5 (9) : 1751-1773.
[28] Baba Y, Hirukawa N, Tanohira N, et al. Structure-based design of a highly selective catalytic site directed inhibition of Ser/Thr protein phosphatase 2B [J]. J Am Chem Soc, 2003, 125 : 9740-9749.

斑蝥素及其类似物:抗肿瘤及丝氨酸/苏氨酸蛋白质磷酸酶抑制活性

Cantharidin and Its Analogues:Anticancer and Ser/Thr Protein Phosphatase Inhibitory Activities

PDF (PC)

可视化

被引次数

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价

[1]	许士琪, 朱礼岩, 郝超, 刘文倩, 陈成龙, 陈泳怡, 刘爱芹. 一种新型含氨基酸基团替加氟前药的合成及其抗肿瘤活性评价[J]. 中国药学(英文版), 2021, 30(9): 743-753.
[2]	周北斗, 俞紫涵, 童玉贵, 李佳莉, 黄堡城, 魏蓉蓉, 翁智敏, 王欣, 阮志鹏, 林健, 许彩红, 刘建波. 异戊烯基和香叶基取代的呫吨酮的合成与生物活性研究[J]. 中国药学(英文版), 2020, 29(8): 564-576.
[3]	雷丽, 陈宇, 杨思敏, 孟祥豹, 余四旺. 一个新型氮杂萘醌类化合物通过诱导细胞凋亡来抑制肿瘤生长[J]. 中国药学(英文版), 2018, 27(9): 600-607.
[4]	梁晓霞, 孔令茜, 何敏. 从卵叶蜘蛛抱蛋中分离得到的一个具有潜在抗菌活性的高异黄酮类化合物[J]. 中国药学(英文版), 2016, 25(9): 700-703.
[5]	周代营, 赵肃清, 郑希, 杜志云, 张焜. 哌啶酮类姜黄素类似物的合成及抗肿瘤活性研究[J]. 中国药学(英文版), 2015, 24(8): 524-529.
[6]	郭亮, 范文玺, 甘紫云, 陈伟, 马芹, 曹日晖. 1-取代-β-咔啉衍生物的设计、合成与初步的抗肿瘤作用研究[J]. 中国药学(英文版), 2015, 24(12): 801-808.
[7]	章俊麟, 金武, 王学清, 王坚成, 张烜, 张强^*. 奥曲肽修饰的PEG隐形脂质体用于改善阿霉素对生长抑素受体II阳性肿瘤的抗癌效果[J]. , 2010, 19(5): 363-370.
[8]	李功, 孙崎^, 崔景荣, 李润涛^. 螺环季铵盐修饰的苯丁酸氮芥类抗肿瘤化合物[J]. , 2010, 19(5): 346-352.
[9]	杨青, 朱继让, 孙崎^, 崔景荣, 李润涛, 葛泽梅^. 新型环磷酰胺前药: 环磷酰胺哌嗪季铵盐的构效关系[J]. , 2010, 19(1): 24-33.
[10]	刘墨, 葛泽梅^, 程铁明, 李润涛^. 一类环磷酰胺双哌嗪季铵盐类抗肿瘤化合物的合成[J]. , 2009, 18(4): 320-325.
[11]	闫星, 马玉卓, 陈静波, 刘鹰翔^* . 2-(E)-(3-甲氧基-4-环戊氧基苯基亚甲基)环戊酮衍生物的合成及抗肿瘤活性[J]. , 2007, 16(4): 268-271.
[12]	向蓉, 张辅民, 倪京满^*, 田瑄. 5-FU-乙酸鬼臼酯的合成及稳定性研究[J]. , 2007, 16(1): 47-50.
[13]	严俊, 邓声菊, 况斌, 贺飞, 刘涛, 曾慧慧^*. 新型有机硒化合物Eb抗肿瘤, 免疫活性及硒组织分布特点[J]. , 2004, 13(3): 199-204.
[14]	李树春, 李辉, 张法, 李中军^, 崔景荣^^*. 取代肉桂酸苯乙酯的抗肿瘤活性研究[J]. , 2003, 12(4): 184-187.
[15]	徐志栋, 刘河, 王敏, 肖苏龙, 杨铭^*, 卜显和. 具有抗肿瘤活性的6,7-二氰基-二吡啶基[2,2-d:2',3'-f]喹喔啉合钴(II)配合物的合成、晶体结构及与DNA结合的研究[J]. , 2002, 11(4): 125-131.