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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.
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  • 收稿日期:  2017-11-23
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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
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