吗啉-2,5-二酮衍生物及其聚合物的研究进展
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摘要
吗啉-2,5-二酮衍生物是一类制备可生物降解材料的环状单体,本文综述了吗啉-2,5-二酮衍生物及其聚合物的合成方法,以及其在生物医用领域的应用前景。首先介绍了吗啉-2,5-二酮衍生物的三种合成方法,以及采用吗啉-2,5-二酮衍生物均聚反应制备聚缩肽的方法,其次介绍了吗啉-2,5-二酮衍生物与ε-己内酯和丙交酯开环共聚制备基于氨基酸的共聚物。最后,总结了吗啉-2,5-二酮衍生物嵌段共聚物的制备,及其在药物释放和基因载体应用研究中的最新进展。
Morpholine-2,5-dione derivatives are a kind of cyclic monomers for the preparation of biodegradable materials.This paper summarized the synthesis methods of morpholine-2,5-dione derivatives and their copolymers,as well as their potential applications in medical field.Firstly,three synthesis methods of these derivatives were introduced,also the homopolymerization of morpholine-2,5-dione derivatives to prepare polydepsipeptides was summarized.Secondly,this paper introduced ring-opening copolymerization of morpholine-2,5-dione derivatives with e-caprolactone and lactide to prepare the copolymers based on amino acids.Finally,this paper summarized the synthesis of morpholine-2,5-dione derivatives block copolymers,and the recent development of their applications in drug delivery and gene carriers.
Morpholine-2,5-dione derivatives are a kind of cyclic monomers for the preparation of biodegradable materials.This paper summarized the synthesis methods of morpholine-2,5-dione derivatives and their copolymers,as well as their potential applications in medical field.Firstly,three synthesis methods of these derivatives were introduced,also the homopolymerization of morpholine-2,5-dione derivatives to prepare polydepsipeptides was summarized.Secondly,this paper introduced ring-opening copolymerization of morpholine-2,5-dione derivatives with e-caprolactone and lactide to prepare the copolymers based on amino acids.Finally,this paper summarized the synthesis of morpholine-2,5-dione derivatives block copolymers,and the recent development of their applications in drug delivery and gene carriers.
引文
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[46]Tian W W,Chen Q,Yu C H,Shen J.Eur Polym J,2003,39(9):1935~1938.
[47]Takahashi A,Umezaki M,Yoshida Y,Kuzuya A,Ohya Y.J Biomat Sci-Polym E,2014,25(5):444~454.
[48]Lv J,Zhang L,Khan M,Ren X K,Guo J T,Feng Y K.React Funct Polym,2014,82:89~97.
[49]Hegeman J,Nienhuis B,van den Bemt B,Weerdesteyn V,van Limbeek J,Duysens J.Hum Movement Sci,2011,30(2):384~395.
[50]戚晓红,陈汐敏,冯振卿,管晓虹,吴军,陈强,阚延静,童华.生物化学与生物物理进展,2009,36(8):1065~1063.
[51]Takahashi A,Umezaki M,Yoshida Y,Kuzuya A,Ohya Y.Polym Advan Technol,2014.DOI:10.1002/pat.3265.
[52]刘莉莉.吗琳-2,5-二酮衍生物及其聚合物的制备与应用研究.南京大学硕士学位论文,2011.
[53]Danhier F,Feron O,Préat V.J Control Release,2010,148(2):135~146.
[54]Zhao Y L,Li J,Yu H,Wang G J,Liu W.Int J Pharm,2012,430(1-2):282~291.
[55]Zhang L,Feng Y K,Tian H,Zhao M,Khan M,Guo J T.J Polym Sci Pol Chem,2013,51(15):3213~3226.
[56]Zhang L,Feng Y K,Tian H,Shi C C,Zhao H Y,Guo J T.React Funct Polym,2013,73(9):1281~1289.
[57]Yin S P,Li J,Li N N,Wang G J,Gu X C.J Nanopart Res,2014,16:2274.
[58]Shi C C,Yao F L,Huang J W,Han G L,Li Q,Khan M,Feng Y K,Zhang W C.J Mater Chem B,2014,2:1825~1837.
[59]Shi C C,Yao F L,Li Q,Khan M,Ren X K,Feng Y K,Huang J W,Zhang W C.Biomaterials,2014,35(25):7133~7145.
[2]Green J J,Zhou B Y,Mitalipova M M,Beard C,Langer R,Jaenisch R,Anderson D G.Nano Lett,2008,8(10):3126~3130.
[3]Oh S H,Lee J H.Biomed Mater,2013.DOI:10.1088/1748-6041/8/1/014101.
[4]Ulery B D,Nair L S,Laurencin C T.J Polym Sci Pol Phys,2011,49(12):832~864.
[5]Nair L S,Laurencin C T.Prog Polym Sci,2007,32(8-9):762~798.
[6]Xie Z G,Lu T C,Chen X S,Zheng Y H,Jing X B.J Biomed Mater Res A,2009,88A(1):238~245.
[7]Fonseca A C,Gil M H,Simes P N.Prog Polym Sci,2014,39(7):1291~1311.
[8]Fonseca A C,Serra A C,Coelho J F J,Gil M H,Simes P N.Polym Int,2013,62(5):736~743.
[9]Shakaby S W,Koelmel D F.EUR,0086613,1984.4.10.
[10]In′t Veld P J A,Shen Z R,Takens G A J,Dijkstra P J,Feijen J.J Polym Sci Pol Chem,1994,32(6):1063~1069.
[11]沈正荣,陈慧闯,孙伟东.化学试剂,1999,21(5):311~317.
[12]Feng Y K,Cheng C B,Zhang L,Tian H,Yuan W J.Trans Tianjin Univ,2012,18(5):315~319.
[13]Feng Y K,Guo J T.Int J Mol Sci,2009,10:589~615.
[14]Chadwick A F,Pacsu E.J Am Chem Soc,1943,65(3):392~402.
[15]Glowaky R C,Fung F M.EUR,322154,1989.6.28.
[16]Fung F N,Glowaky R C.USP,4916209,1990.4.10.
[17]Zhang G D,Wang D,Feng X D.Macromolecules,1998,31(18):6390~6092.
[18]Hartwig W,Schoellkopf U.Eur J Org Chem,1982,1982(11):1952~1970.
[19]Nakamura C E,Cosimo R D,Moran J R.USP,5466801,1995.11.14.
[20]Georgios K,Peter B,Christoph N,Steckhan E.Tetrahedron,1998,54(14):3479~348.
[21]In’t Veld P J A,Dijkstra P J,Feijen J.Macromol Chem Phys,1992,193(11):2713~2730.
[22]Nissen D,Gilon C,Goodman M.Macromol Chem Phys,1975,1(1):23~53.
[23]In’t Veld P J A.Biodegradable polyesteramides.Netherlands:University of Twente,1992.
[24]Helder J,Kohn F E,Sato S,van den Berg J W,Feijen J.Macromol Rapid Comm,1985,6(1):9~14.
[25]In’t Veld P J A,Dijkstra P J,van Lochem J H,Feijen J.Macromol Chem Phys,1990,191(8):1813~1825.
[26]Ouchi T,Shiratani M,Jinno M,Hirao M,Ohya Y.Macromol Rapid Comm,1993,14(12):825~831.
[27]Wang D,Feng X D.Macromolecules,1997,30(19):5688~5692.
[28]Yancheva D,Daskalova L,Cherneva E,Mikhova B,Djordjevic A,Smelcerovic Z,Smelcerovic A.J Mol Struct,2012,1016(30):147~154.
[29]Shirahama H,Tanaka A,Yasuda H.J Polym Sci Pol Chem,2002,40(3):302~316.
[30]Feng Y K,Klee D,Hcker H.Macromol Chem Phys,2001,202(16):3120~3125.
[31]罗丙红,廖凯荣,全大萍,卢泽俭,陈用烈.高分子学报,2003,6:803~808.
[32]Yao J Y,Yang Q F,Fan X D,Wang N,Guo B H.Front Chem China,2007,2(2):183~187.
[33]Ohya Y,Matori J,Ouchi T.React Funct Polym,2014,81:33~39.
[34]Pang Z B,Li H,He P,Wang Y Q,Ren H X,Wang H,Zhu X X.J Polym Sci Pol Chem,2012,50(19):4004~4009.
[35]Pagar K P,Vavia P R.Therapeutic Delivery,2013,4(5):553~565.
[36]Dhanaraju M D,Gopinath D,Ahmed M R,Jayakumar R,Vamsadhara C.J Biomed Mater Res A,2006,76(1):63~72.
[37]Zhang H W,Bei J Z,Wang S G.J Appl Polym Sci,2007,106(6):3757~3767.
[38]Hyun H,Kim M S,Jeong S C,Kim Y H,Lee S Y,Lee H B,Khang G.Polym Eng Sci,2006,46(9):1242~1249.
[39]Xie Z G,Lu C H,Chen X S,Chen L,Hu X L,Shi Q,Jing X B.Eur Polym J,2007,43(5):2080~2087.
[40]Julich-Gruner K K,Lwenberg C,Neffe A T,Behl M,Lendlein A.Macromol Chem Phys,2013,214(5):527~536.
[41]Wang D,Feng X D.Macromolecules,1998,31(12):3824~3831.
[42]Battig A,Hiebl B,Feng Y.Clin Hemorheol Micro,2011,48(1):161~172.
[43]Pan C J,Hou Y H,Zhang B B,Zhang L C.Bio-Med Mater Eng,2014,24(1):781~787.
[44]Peppas N A,Keys K B,Torres-Lugo M,Lowman AM.J Control Release,1999,62(1-2):81~87.
[45]Sahithi K,Swetha M,Prabaharali M,Moorthi A,Saranya N,Ramasamy K,Srinivasan N,Partridge N C,Selvamurugan N.J Biomed Nanotechnol,2010,6(4):333~339.
[45]Feng Y K,Lu J,Behl M,Lendlein A.Macromol Biosci,2010,10(9):1008~1021.
[46]Tian W W,Chen Q,Yu C H,Shen J.Eur Polym J,2003,39(9):1935~1938.
[47]Takahashi A,Umezaki M,Yoshida Y,Kuzuya A,Ohya Y.J Biomat Sci-Polym E,2014,25(5):444~454.
[48]Lv J,Zhang L,Khan M,Ren X K,Guo J T,Feng Y K.React Funct Polym,2014,82:89~97.
[49]Hegeman J,Nienhuis B,van den Bemt B,Weerdesteyn V,van Limbeek J,Duysens J.Hum Movement Sci,2011,30(2):384~395.
[50]戚晓红,陈汐敏,冯振卿,管晓虹,吴军,陈强,阚延静,童华.生物化学与生物物理进展,2009,36(8):1065~1063.
[51]Takahashi A,Umezaki M,Yoshida Y,Kuzuya A,Ohya Y.Polym Advan Technol,2014.DOI:10.1002/pat.3265.
[52]刘莉莉.吗琳-2,5-二酮衍生物及其聚合物的制备与应用研究.南京大学硕士学位论文,2011.
[53]Danhier F,Feron O,Préat V.J Control Release,2010,148(2):135~146.
[54]Zhao Y L,Li J,Yu H,Wang G J,Liu W.Int J Pharm,2012,430(1-2):282~291.
[55]Zhang L,Feng Y K,Tian H,Zhao M,Khan M,Guo J T.J Polym Sci Pol Chem,2013,51(15):3213~3226.
[56]Zhang L,Feng Y K,Tian H,Shi C C,Zhao H Y,Guo J T.React Funct Polym,2013,73(9):1281~1289.
[57]Yin S P,Li J,Li N N,Wang G J,Gu X C.J Nanopart Res,2014,16:2274.
[58]Shi C C,Yao F L,Huang J W,Han G L,Li Q,Khan M,Feng Y K,Zhang W C.J Mater Chem B,2014,2:1825~1837.
[59]Shi C C,Yao F L,Li Q,Khan M,Ren X K,Feng Y K,Huang J W,Zhang W C.Biomaterials,2014,35(25):7133~7145.