摘要
树状大分子是近年来蓬勃发展的一类新型高分子材料,其表面存在大量的官能团,分子内部存在空腔且分子尺寸可控,因此,树状大分子已被广泛应用于众多的领域.肽类树状大分子是指在树状大分子结构中含有肽键的一类大分子,因其具有类似蛋白质一样的球状结构,且具有优异的水溶性、生物相容性、生物降解性和细胞低毒性等特点,所以,肽类树状大分子可以作为药物传输的载体.此外,肽类树状大分子的疏水空腔可以装载疏水性药物,对其起到增溶和缓释作用.综述了肽类树状大分子的合成方法,并对其与药物分子的结合机制及其在药物传输系统中的应用进行了总结与展望.
Dendrimers are a novel polymer material, which have received more and more attention due to the functional groups on their surface, hydrophobic cavity and adjustable sizes. Thus, dendrimers have been widely used in many fields. Peptide dendrimer is a sort of dendritic polymer, which contains peptide bonds in the structure. Owing to the globular structure similar to the protein, excellent water solubility, biocompatibility, biodegradability and low toxicity, peptide dendrimer could be used as drug delivery carrier. In addition, hydrophobic cavity can be used to solubilize hydrophobic drugs, in which the drugs can be released slowly. The present review highlights the current status of synthesis of peptide dendrimers, and it also summarizes and forecasts the interaction mechanism between drug molecules and peptide dendrimers, and the application of peptide dendrimers in drug delivery system.
引文
[1]Tomalia,D.;Baker,H.;Dewald,J.;Hall,M.;Kallos,G.;Martin,S.;Roeck,J.;Ryder,J.;Smith,P.Polym.J.1985,17,117.
[2]Newkome,G.R.;Yao,Z.;Baker,G.R.;Gupta,V.K.J.Org.Chem.1985,50,2003.
[3]Tian,W.;Ma,Y.Chem.Soc.Rev.2013,42,707.
[4]Nanjwade,B.K.;Bechra,H.M.;Derkar,G.K.;Manvi,F.V.;Nanj-wade,V.K.Eur.J.Pharm.Sci.2009,38,189.
[5]Surendra,T.;Malay,K.D.J.Appl.Pharm.Sci.2013,3,143.
[6]Klajnert,B.;Bryszewskar,M.Acta Biochim.Pol.2001,48,203.
[7]Prashant,K.;Keerti,J.;Narendra,K.J.Prog.Polym.Sci.2014,39,276.
[8]Li,J.;Zeng,Y.;Zhang,X.;Yu,T.;Chen,J.;Li,Y.Acta Chim.Sinica2014,72,1158.(李婧,曾毅,张小辉,于天君,陈金平,李嫕,化学学报,2014,72,1158.)
[9]Li,J.;Zeng,Y.;Zhang,X.;Yu,T.;Chen,J.;Li,Y.Acta Chim.Sinica2015,73,827.(李婧,曾毅,张小辉,于天君,陈金平,李嫕,化学学报,2015,73,827.)
[10]Elizabeth,R.;Gillies,J.;Fréchet,M.J.Drug Discov.Today 2005,10,38.
[11]Marie,V.;Walter;Michael,M.Chem.Soc.Rev.2012,41,4593.
[12]Elham,A.;Sedigheh,F.A.;Abolfazl,A.;Morteza,M.;Hamid,T.N.;Sang,W.J.;Younes,H.;Kazem,N.-K.;Roghiyeh,P.-A.Nanoscale Res.Lett.2014,9,248.
[13]Laia,C.;Glòria,S.;Miquel,P.;Ernest,G.;Miriam,R.;Fernando,A.Chem.Rev.2005,105,1670.
[14]She,W.C.;Xu,X.H.;Wang,G.;Luo,K.;Gu,Z.W.Mater.China2012,31,21.(佘汶川,徐翔晖,王刚,罗奎,顾忠伟,中国材料进展,2012,31,21.)
[15]Gu,Z.W.;Luo,K.;She,W.C.;Wu,Y.;He,B.Scientia Sinica Chimica 2010,40,210.(顾忠伟,罗奎,佘汶川,吴尧,何斌,中国科学:化学,2010,40,210.)
[16]Xu,X.;Yuan,H.;Chang,J.;He,B.;Gu,Z.Angew.Chem.Int.Ed.2012,124,3185.
[17]Wang,F.;Xu,L.;Chu,G.;Shi,J.;Guo,Q.Chin.J.Org.Chem.2016,36,218.(王风亮,许玲,储国超,石景,郭庆祥,有机化学,2016,36,218.)
[18]Merrifield,R.B.J.Am.Chem.Soc.1964,3,1385.
[19]Daniel,K.S.;Sahar,M.;Ulrik,B.Tetrahedron Lett.2014,55,3942.
[20]Laia,C.;Glòria,S.;Beatriz,M.;Ricardo,P.T.;Miriam,R.;Miquel,P.;Fernando,A.;Ernest,G.J.Am.Chem.Soc.2002,124,8878.
[21]Kitamatsu,M.;Kitabatake,M.;Noutoshi,Y.;Ohtsuki,T.Biopolymers 2013,100,65.
[22]Lin,X.F.;Wang,Y.G.J.Org.Chem.2005,25,1157.(林旭锋,王彦广,有机化学,2005,25,1157.)
[23]Denkewalter,R.G.;Kole,J.;Lukasavage,W.J.US 4289872,1981[Chem.Abstr.1981,102,79324].
[24]Feng,Y.;He,Y.M.;Zhao,L.W.;Huang,Y.Y.;Fan,Q.H.Org.Lett.2007,9,2261.
[25]Joon,S.C.;Dong,K.J.;Chang,H.K.;Kwan,K.;Jong,S.P.J.Am.Chem.Soc.2000,122,475.
[26]Hu,J.;He,J.;Zhang,M.;Ni,P.Acta Polymerica Sinica 2013,(3),300.(胡健,何金林,张明祖,倪沛红,高分子学报,2013,(3),300.)
[27]John,E.M.;Adam,D.M.Chem.Soc.Rev.2007,36,1250.
[28]Mehmet,A.T.;Baris,K.;Yusuf,Y.Prog.Polym.Sci.2016,52,19.
[29]Dirk,T.S.R.;Wilma,E.G.;Remco,M.;Arwin,J.B.;Hans,J.F.J.;Roland,J.P.;Rob,M.J.L.Chem.Commun.2005,36,4582.
[30]Yim,C.B.;Boerman,O.C.;Visser,M.;Jong,M.;Dechesne,A.C.;Rijkers,D.T.S.;Liskamp,R.M.J.Bioconjugate Chem.2009,20,1323.
[31]Pu,Y.J.;Yuan,H.;Yang,M.;He,B.;Gu,Z.W.Chin.Chem.Lett.2013,24,917.
[32]Li,N.;Li,N.;Yi,Q.;Luo,K.;Guo,C.;Pan,D.;Gu,Z.Biomaterials2014,35,9533.
[33]Pan,D.;She,W.;Guo,C.;Luo,K.;Yi,Q.;Gu,Z.Biomaterials2014,35,10081.
[34]Zhang,C.;Pan,D.;Luo,K.;Li,N.;Guo,C.;Zheng,X.;Gu,Z.2014,5,5228.
[35]Reddy,N.;Reddy,R.;Jiang,Q.Trends Biotechnol.2015,33,362.
[36]Domeradzka,N.;Werten,M.;Wolf,F.;Vries,R.Curr.Opin.Biotechnol.2016,39,61.
[37]Li,C.Y.;Wang,H.J.;Cao,J.M.;Zhang,J.;Yu,X.Q.Eur.J.Med.Chem.2014,87,414.
[38]Buhleier,E.;Wehner,W.;V?gtle,F.Synthesis 1978,2,155.
[39]Lin,Y.;Weng,L.;Qi,Q.The Scientific World J.2015,2015,5.
[40]Hawker,C.J.;Frechet,J.M.J.Am.Chem.Soc.1990,112,7638.
[41]Scott,M.G.;Jean,M.J.F.Chem.Rev.2001,101,3819.
[42]Zhu,R.;Jiang,W.;Pu,Y.;Luo,K.;Wu,Y.;He,B.;Gu,Z.J.Mater.Chem.2011,21,5466.
[43]Pierre,M.;Gilles,Q.;Ling,P.Tetrahedron Lett.2015,56,4043.
[44]Olga,F.;Alexander,G.;Vladimir,R.J.Am.Chem.Soc.2003,125,4885.
[45]Dykes,M.G.;Brierley,J.L.;Smith,K.D.;Mc Grail,P.T.;Seeley,G.J.Chem.Eur.J,2001,7,4731.
[46]Al-Jamal,K.T.;Al-Jamal,W.;Wang,J.T.;Rubio,N.;Buddle,J.;Gathercole,D.;Zloh,M.;Kostarelos,K.ACS Nano 2013,7,1905.
[47]Li,Y.;Han,S.;Toshiyuki,U.Sen-i Gakkaishi 2015,71,13.
[48]Yuan,H.;Luo,K.;Lai,Y.;Pu,Y.;He,B.;Wang,G.;Wu,Y.;Gu,Z.Mol.Pharm.2010,7,957.
[49]Pu,Y.;Chang,S.;Yuan,H.;Wang,G.;He,B.;Gu,Z.Biomaterials2013,34,3659.
[50]Glòria,S.;Laia,C.;Ernest,G.M.R.;Fernando,A.Pept.Sci.2004,76,284.
[51]Torres,á.;Albericio,F.;Royo,M.Eur.J.Org.Chem.2013,36,8280.
[52]Emanuele,A.;Attwood,D.Adv.Drug Delivery Rev.2005,57,2147.
[53]He,X.;Alves,S.C.;Oliveira,N.;Rodrigues,J.;Zhu,J.;Bányai,I.;Tomás,H.;Shi,X.Colloids Surf.B:Biointerfaces 2015,125,83.
[54]Gillies,E.;Fréchet,J.Drug Discov.Today 2005,10,35.
[55]Boas,U.;Karlsson,A.;Waal,B.F.M.;Meijer,E.W.J.Org.Chem.2001,66,2136.
[56]Aulenta,F.;Hayes,W.S.Eur.Polym.J.2003,39,1741.
[57]Tyssen,D.;Henderson,S.A.;Johnson,A.PLo S One 2010,5,5.
[58]Fox,M.E.;Guillaudeu,S.;Fréchet,J.M.J.;Jerger,K.;Macaraeg,N.;Szoka,F.C.Mol.Pharm.2009,6,1563.
[59]Craik,D.J.;Fairlie,D.;Liras,P.S.;Price,D.Chem.Biol.Drug Des.2013,81,136.
[60]Zhang,X.;Zhang,Z.;Xu,X.;Li,Y.;Li,Y.;Jian,Y.;Gu,Z.Angew.Chem.Int.Ed.2015,54,4289.
[61]Zhang,C.;Pan,D.;Luo,K.;She,W.;Guo,C.;Yang,Y.;Gu,Z.Adv.Healthcare Mater.2014,3,1299.
[62]Kaminskas,L.M.;Kelly,B.D.;Mc Leod,V.M.;Sberna,G.;Owen,D.J.;Boyd,B.J.;Porter,C.J.H.J.Control.Release 2011,152,338.
[63]Kaminskas,L.M.;Kelly,B.D.;Mc Leod,V.M.;Boyd,B.J.;Krippne,G.Y.;Williams,E.D.;Porter,C.J.H.Mol.Pharmaceutics2009,6,1190.
[64]Kaminskas,L.M.;Kelly,B.D.;Mc Leod,V.M.;Sberna,G.;Boyd,B.J.;Owen,D.J.;Porter,C.J.H.Mol.Pharmaceutics 2011,8,338.
[65]Jain,K.;Gupta,U.;Jain,N.K.Eur.J.Pharm.Biopharm.2014,87,503.
[66]Bhadra,D.;Bhadra,S.;Jain,N.K.Pharm.Res.2006,23,628.
[67]Agrawal,P.;Gupta,U.;Jain,N.K.Biomaterials 2007,28,3349.