留言板

尊敬的读者、作者、审稿人, 关于本刊的投稿、审稿、编辑和出版的任何问题, 您可以本页添加留言。我们将尽快给您答复。谢谢您的支持!

姓名
邮箱
手机号码
标题
留言内容
验证码

应中央军委要求,2022年9月起,《药学实践杂志》将更名为《药学实践与服务》,双月刊,正文96页;2023年1月起,拟出版月刊,正文64页,数据库收录情况与原《药学实践杂志》相同。欢迎作者踊跃投稿!

聚乙二醇衍生物及其蛋白药物修饰研究进展

张羽 连治国 徐明波 冯芳

张羽, 连治国, 徐明波, 冯芳. 聚乙二醇衍生物及其蛋白药物修饰研究进展[J]. 药学实践与服务, 2018, 36(4): 301-306,328. doi: 10.3969/j.issn.1006-0111.2018.04.004
引用本文: 张羽, 连治国, 徐明波, 冯芳. 聚乙二醇衍生物及其蛋白药物修饰研究进展[J]. 药学实践与服务, 2018, 36(4): 301-306,328. doi: 10.3969/j.issn.1006-0111.2018.04.004
ZHANG Yu, LIAN Zhiguo, XU Mingbo, FENG Fang. Advances in the development of PEG derivatives and pegylated protein drugs[J]. Journal of Pharmaceutical Practice and Service, 2018, 36(4): 301-306,328. doi: 10.3969/j.issn.1006-0111.2018.04.004
Citation: ZHANG Yu, LIAN Zhiguo, XU Mingbo, FENG Fang. Advances in the development of PEG derivatives and pegylated protein drugs[J]. Journal of Pharmaceutical Practice and Service, 2018, 36(4): 301-306,328. doi: 10.3969/j.issn.1006-0111.2018.04.004

聚乙二醇衍生物及其蛋白药物修饰研究进展

doi: 10.3969/j.issn.1006-0111.2018.04.004

Advances in the development of PEG derivatives and pegylated protein drugs

  • 摘要: 聚乙二醇及其衍生物因其出色的亲水性、生物相容性、生物学惰性等特性而被广泛应用于蛋白药物修饰,其修饰可有效降低蛋白药物的免疫原性并延长体内半衰期。聚乙二醇衍生物的发展经历了第一代随机修饰,第二代特异性和功能性修饰,以及第三代分支型结构的应用。其应用也从简单的药物修饰扩展到生物传感、药物传输等方面。
  • [1] LAWRENCE P B, PRICE J L. How PEGylation influences protein conformational stability[J]. Curr Opin Chem Biol, 2016, 34:88-94.
    [2] PFISTER D, BOURGEAUX E, MORBIDELLI M. Kinetic modeling of protein PEGylation[J]. Chem Engin Sci, 2015, 137:816-827.
    [3] YANG Z, WANG J, LU Q, et al. PEGylation confers greatly extended half-life and attenuated immunogenicity to recombinant methioninase in primates[J]. Cancer Res, 2004, 64(18):6673-6678.
    [4] RODR GUEZMART NEZ JA, RIVERARIVERA I, SOL RJ, et al. Enzymatic activity and thermal stability of PEG-α-chymotrypsin conjugates[J]. Biotechnol Lett, 2009, 31(6):883-887.
    [5] 姜忠义, 许松伟, 王艳强. 蛋白质和肽类分子的聚乙二醇化化学[J]. 有机化学, 2003, 23(12):1340-1347.
    [6] ZALIPSKY S, SELTZER R, MENONRUDOLPH S. Evaluation of a new reagent for covalent attachment of polyethylene glycol to proteins[J]. Biotechnol Appl Biochem, 1992, 15(1):100-114.
    [7] MIRON T, WILCHEK M. A simplified method for the preparation of succinimidyl carbonate polyethylene glycol for coupling to proteins[J]. Bioconjug Chem, 1993, 4(6):568-569.
    [8] ABUCHOWSKI A, KAZO GM, JR VC, et al. Cancer therapy with chemically modified enzymes. I. Antitumor properties of polyethylene glycol-asparaginase conjugates[J]. Cancer Biochem Biophys, 1984, 7(2):175-186.
    [9] ABUCHOWSKI A,VAN ES T,PALCZUK NC,et al. Alteration of immunological properties of bovine serum albumin by covalent attachment of polyethylene glycol[J]. J Biol Chem,1977,252(11):3578-3581.
    [10] GAIS H J, RUPPERT S. Modification and immobilization of proteins with polyethylene glycol tresylates and polysaccharide tresylates:Evidence suggesting a revision of the coupling mechanism and the structure of the polymer-polymer linkage[J]. Tetrahedron Lett, 1995, 36(22):3837-3838.
    [11] ZALIPSKY S, LEE C. Use of functionalized poly(ethylene glycol)s for modification of polypeptides[M]//Poly(Ethylene Glycol) Chemistry. Springer US, 1992:1-15.
    [12] WANG J, HU T, LIU Y, et al. Kinetic and stoichiometric analysis of the modification process for N-terminal PEGylation of staphylokinase[J]. Anal Biochem, 2011, 412(1):114-116.
    [13] KINSTLER OB, BREMS DN, LAUREN SL, et al. Characterization and stability of N-terminally PEGylated rhG-CSF[J]. Pharm Res, 1996, 13(7):996-1002.
    [14] KINSTLER OB, GABRIEL NE, FARRAR CE, et al. N-terminally chemically modified protein-compositions and method:, DE 69509628 D1[P]. 1999.
    [15] FEE C J, DAMODARAN VB. Production of PEGylated proteins[M]//Biopharmaceutical Production Technology. 2012:199-222.
    [16] BROCCHINI S, GODWIN A, BALAN S, et al. Disulfide bridge based PEGylation of proteins[J]. Adv Drug Deliv Rev, 2008, 60(1):3-12.
    [17] TSUTSUMI Y, ONDA M, NAGATA S, et al. Site-specific chemical modification with polyethylene glycol of recombinant immunotoxin anti-Tac(Fv)-PE38(LMB-2) improves antitumor activity and reduces animal toxicity and immunogenicity[J]. Proc Natl Acad Sci USA, 2000, 97(15):8548-8553.
    [18] BANGALORE S, KUMAR S, FUSARO M, et al. Outcomes with various drug eluting or bare metal stents in patients with diabetes mellitus:mixed treatment comparison analysis of 22844 patient years of follow-up from randomised trials[J]. BMJ, 2012, 345:e5170.
    [19] PASUT G, VERONESE FM. State of the art in PEGylation:The great versatility achieved after forty years of research[J]. J Control Release, 2012, 161(2):461-472.
    [20] MORGENSTERN J, BAUMANN P, BRUNNER C, et al. Effect of PEG molecular weight and PEGylation degree on the physical stability of PEGylated lysozyme[J]. Int J Pharm, 2017, 519(1-2):408-417.
    [21] ROBERTS MJ, HARRIS JM. Attachment of degradable poly(ethylene glycol) to proteins has the potential to increase therapeutic efficacy[J]. J Pharm Sci, 1998, 87(11):1440-1445.
    [22] ANDREW J. GARMAN S,BARRET KALINDJIAN. The preparation and properties of novel reversible polymer-protein conjugates 2-ω-Methoxypolyethylene (5000) glycoxymethylene-3-methylmaleyl conjugates of plasminogen activators[J]. Febs Lett, 1987, 223(2):361-365.
    [23] 田浤, 金宇灏, 陈阳建,等. 聚乙二醇氨基酸衍生物的合成及其对紫杉醇的修饰[J]. 中国药科大学学报, 2011, 42(1):78-82.
    [24] KIZILEL S, SCAVONE A, LIU X, et al. Encapsulation of pancreatic islets within nano-thin functional polyethylene glycol coatings for enhanced insulin secretion[J]. Tissue Engin Part A, 2010, 16(7):2217.
    [25] YOO MK, PARK IK, LIM HT, et al. Folate PEG superparamagnetic iron oxide nanoparticles for lung cancer imaging[J]. Acta Biomater, 2012, 8(8):3005-3013.
    [26] ZHANG C, YANG XL, YUAN YH, et al. Site-specific PEGylation of therapeutic proteins via optimization of both accessible reactive amino acid residues and PEG derivatives[J]. Biodrugs, 2012, 26(4):209. 209-215.
    [27] RYAN SIN AD M, MANTOVANI GIUSEPPE, WANG XUEXUAN, et al. Advances in PEGylation of important biotech molecules:delivery aspects[J]. Expert Opin Drug Deliv,2008,5(4):371-383.
    [28] VUGMEYSTER Y,ENTRICAN C A,JOYCE AP,et al.Pharmacokinetic,biodistribution and biophysical profiles of TNF nanobodies conjugated to linear or branched poly (ethylene glycol)[J].Bioconjug Chem,2012,23(7):1452-1462.
    [29] DAVIS, FF.The origin of pegnology[J]. Adv Drug Deliv Rev,2002,54(4):457-458.
    [30] DAVIS FF, VAN EST, PALCZUK NC. Non-immunogenic polypeptides:US, US 4179337 A[P]. 1979.
    [31] ABUCHOWSKI A,MCCOY JR,PALCZUK NC,et al. Effect of covalent attachment of polyethylene glycol on immunogenicity and circulating life of bovine liver catalase[J]. J Biol Chem,1977,252(11):3582-3586.
    [32] LEE CR,MCKENZIE CA,WEBSTER KD,et al. Pegademase bovine:replacement therapy for severe combined immunodeficiency disease[J]. DICP, 1991, 25(10):1092-1095
    [33] "Amgen 2016 Annual Report to Stockholders"[www.amgen.com/~/media/amgen/full/www-amgen-com/downloads/investors/2016-annual-report-letter-and-10k_restrict.ashx?la=en] 2016-annual-report-letter-and-10.pdf, 2017, p. 55
    [34] DE GRAAF AJ, KOOIJMAN M, HENNINK WE, et al. Nonnatural amino acids for site-specific protein conjugation[J]. Bioconjug Chem, 2009, 20(7):1281.
    [35] YANG BB, KIDO MA, MS MMS, et al. Pharmacokinetics and pharmacodynamics of pegfilgrastim in subjects with various degrees of renal function[J]. J Clin Pharmacol, 2011, 50(5):295-306.
    [36] TURECEK PL, BOSSARD MJ, GRANINGER M,et al. BAX 855, a PEGylated rFVⅢ product with prolonged half-life. Development, functional and structural characterisation[J]. Hamostaseologie, 2012, 32(Suppl 1):S29-S38.
    [37] WORLD HEALTH ORGANIZATION. WHO Guidelines on the Quality, Safety, and Efficacy of Biological Medicinal Products Prepared by Recombinant DNA Technology. Switzerland:WHO Press, 2013. 91-92.
    [38] LI XL, LIU L, GAO JP, et al. Methods for identification of conjugation site on PEGylated protein[J]. Pharmaceutical Biotechnology, 2013.
    [39] YU W, YU C, WU L, et al. PEGylated recombinant human interferon-ω as a long-acting antiviral agent:structure, antiviral activity and pharmacokinetics[J]. Antiviral Res, 2014, 108:142-147.
    [40] JOHN B, SWAPAN C, JOHNSTON D. Characterization of poly(ethylene glycol)-modified superoxide dismutase:Comparison of capillary electrophoresis and matrix-assisted laser desorption/ionization mass spectrometry[J]. Analytical Chemistry, 1996, 68(18):3258-3264.
    [41] 李晶, 何辉, 程速远,等. 荧光胺衍生化法测定3种聚乙二醇化重组人生长激素的平均修饰率[J]. 药物分析杂志, 2014(8):1368-1373.
  • [1] 李锐, 张倩倩, 王瑞冬, 高小峰.  国家集中带量采购政策下样本医院良性前列腺增生治疗药物使用情况分析 . 药学实践与服务, 2025, 43(2): 1-6. doi: 10.12206/j.issn.2097-2024.202408031
    [2] 宋雨桐, 夏德润, 顾珩, 唐少文, 易洪刚, 沃红梅.  帕博利珠单抗与铂类化疗方案在晚期非小细胞肺癌一线治疗中的药物经济学评价 . 药学实践与服务, 2024, 42(8): 334-340. doi: 10.12206/j.issn.2097-2024.202303023
    [3] 何亚伦, 祁智, 常杰.  消胀通便膏在晚期肝癌患者阿片类药物相关性便秘的应用研究 . 药学实践与服务, 2024, 42(12): 1-4. doi: 10.12206/j.issn.2097-2024.202309009
    [4] 夏哲炜, 曾垣烨, 朱海菲, 李育, 陈啸飞.  核磁共振磷谱法测定磷酸氢钙咀嚼片中药物含量 . 药学实践与服务, 2024, 42(9): 399-401, 406. doi: 10.12206/j.issn.2097-2024.202404063
    [5] 孙丹倪, 黄勇, 张嘉宝, 王培.  代谢相关脂肪性肝病的无创诊断与药物治疗 . 药学实践与服务, 2024, 42(10): 411-418. doi: 10.12206/j.issn.2097-2024.202403049
    [6] 陈怡君, 王卓, 何苗, 张宇, 田泾.  泌尿系统碎石术抗菌药物预防使用合理管控实践 . 药学实践与服务, 2024, 42(): 1-5. doi: 10.12206/j.issn.2097-2024.202402034
    [7] 张岩, 李炎君, 刘家荟, 邓娇, 原苑, 张敬一.  药物性肝损伤不良反应分析 . 药学实践与服务, 2024, 42(): 1-5. doi: 10.12206/j.issn.2097-2024.202404034
    [8] 张元林, 宋凯, 孙蕊, 舒飞, 舒丽芯, 杨樟卫.  基于真实世界数据的药物利用研究综述 . 药学实践与服务, 2024, 42(6): 238-243. doi: 10.12206/j.issn.2097-2024.202312010
    [9] 刘汝雄, 杨万镇, 涂杰, 盛春泉.  铁死亡调控蛋白GPX4的小分子抑制剂研究进展 . 药学实践与服务, 2024, 42(9): 375-378. doi: 10.12206/j.issn.2097-2024.202312075
    [10] 毛智毅, 王筱燕, 陈晓颖, 汤逸斐.  度拉糖肽联合二甲双胍对肥胖型2型糖尿病患者机体代谢、体脂成分及血清脂肪因子的影响 . 药学实践与服务, 2024, 42(7): 305-309. doi: 10.12206/j.issn.2097-2024.202305032
    [11] 迟文雅, 袁艳, 李伟林, 吴茼妤, 俞媛.  负载骨髓间充质干细胞/白藜芦醇脂质体的水凝胶支架用于创伤性脑损伤治疗 . 药学实践与服务, 2024, 42(): 1-8. doi: 10.12206/j.issn.2097-2024.202406034
    [12] 陈炳辰, 佟达丰, 万苗, 闫飞虎, 姚建忠.  UPLC-MS/MS法测定小鼠血浆中紫杉醇脂肪酸酯前药及其药代动力学研究 . 药学实践与服务, 2024, 42(8): 341-345. doi: 10.12206/j.issn.2097-2024.202404082
    [13] 冯婷婷, 张景翔, 王彦, 许维恒, 张俊平.  ANXA3基因及蛋白的研究进展 . 药学实践与服务, 2024, 42(): 1-5. doi: 10.12206/j.issn.2097-2024.202309023
    [14] 李想, 陆鸿远, 张明玉, 高欢, 姚东, 许子华.  米格列醇激活UCP1介导棕色脂肪对冷暴露小鼠损伤的研究 . 药学实践与服务, 2024, 42(): 1-6. doi: 10.12206/j.issn.2097-2024.202404005
    [15] 戴菲菲, 傅翔, 陈琼年, 俞苏纯.  上海某二级医院革兰阴性菌流行特征的回顾性分析 . 药学实践与服务, 2024, 42(12): 1-5. doi: 10.12206/j.issn.2097-2024.202305005
    [16] 陈炳辰, 王思真, 郭贝贝, 杨峰.  紫杉醇棕榈酸酯的合成及其脂质体的制备与处方研究 . 药学实践与服务, 2024, 42(9): 379-384, 410. doi: 10.12206/j.issn.2097-2024.202404062
    [17] 崔亚玲, 吴琼, 马良煜, 胡北, 姚东, 许子华.  肝素钠肌醇烟酸酯乳膏中肌醇烟酸酯皮肤药动学研究 . 药学实践与服务, 2024, 42(): 1-5. doi: 10.12206/j.issn.2097-2024.202404006
    [18] 张艺昕, 关欣怡, 王博宁, 闻俊, 洪战英.  二氢吡啶类钙离子拮抗药物手性分析及其立体选择性药动学研究进展 . 药学实践与服务, 2024, 42(8): 319-324. doi: 10.12206/j.issn.2097-2024.202308062
    [19] 景凯, 杨慈荣, 张圳, 臧艺蓓, 刘霞.  黄芪甲苷衍生物治疗慢性心力衰竭小鼠的药效评价及作用机制研究 . 药学实践与服务, 2024, 42(5): 190-197. doi: 10.12206/j.issn.2097-2024.202310004
  • 加载中
计量
  • 文章访问数:  8343
  • HTML全文浏览量:  801
  • PDF下载量:  1665
  • 被引次数: 0
出版历程
  • 收稿日期:  2017-11-23
  • 修回日期:  2018-03-30

聚乙二醇衍生物及其蛋白药物修饰研究进展

doi: 10.3969/j.issn.1006-0111.2018.04.004

摘要: 聚乙二醇及其衍生物因其出色的亲水性、生物相容性、生物学惰性等特性而被广泛应用于蛋白药物修饰,其修饰可有效降低蛋白药物的免疫原性并延长体内半衰期。聚乙二醇衍生物的发展经历了第一代随机修饰,第二代特异性和功能性修饰,以及第三代分支型结构的应用。其应用也从简单的药物修饰扩展到生物传感、药物传输等方面。

English Abstract

张羽, 连治国, 徐明波, 冯芳. 聚乙二醇衍生物及其蛋白药物修饰研究进展[J]. 药学实践与服务, 2018, 36(4): 301-306,328. doi: 10.3969/j.issn.1006-0111.2018.04.004
引用本文: 张羽, 连治国, 徐明波, 冯芳. 聚乙二醇衍生物及其蛋白药物修饰研究进展[J]. 药学实践与服务, 2018, 36(4): 301-306,328. doi: 10.3969/j.issn.1006-0111.2018.04.004
ZHANG Yu, LIAN Zhiguo, XU Mingbo, FENG Fang. Advances in the development of PEG derivatives and pegylated protein drugs[J]. Journal of Pharmaceutical Practice and Service, 2018, 36(4): 301-306,328. doi: 10.3969/j.issn.1006-0111.2018.04.004
Citation: ZHANG Yu, LIAN Zhiguo, XU Mingbo, FENG Fang. Advances in the development of PEG derivatives and pegylated protein drugs[J]. Journal of Pharmaceutical Practice and Service, 2018, 36(4): 301-306,328. doi: 10.3969/j.issn.1006-0111.2018.04.004
参考文献 (41)

目录

    /

    返回文章
    返回