Biomimetic star-shaped porphyrin-cored poly(L-lactide)-b-glycopolymer block copolymers for targeted photodynamic therapy

Biomimetic star-shaped porphyrin-cored poly(L-lactide)-b-glycopolymer block copolymers for targeted photodynamic therapy
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DOI:
10.1007/s00396-014-3244-6
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发表时间:
2014-09-01
影响因子:
2.4
通讯作者:
Sun, Lin
Sun, Lin
中科院分区:
化学4区
文献类型:
--
作者:
Dai, Xiao-Hui;Wang, Zhi-Ming;Sun, Lin

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以卟啉为核,引发丙交酯开环聚合,合成了卟啉核聚丙交酯(SPPLA)。然后将SPPLA与苄硫基硫代羰基磺酰丙酸(BSPA)偶联,得到宏观可逆加成-断裂链转移(macroRAFT)聚合试剂SPPLA-BSPA。最后,在70 A ℃下,通过RAFT方法合成了以卟啉为核的聚(l-丙交酯)-b-聚(甲基丙烯酸酰胺乙酯)(SPPLA-b-PGAMA)嵌段共聚物。通过核磁共振谱(NMR)、凝胶渗透色谱(GPC)和差示扫描量热法(DSC)对该嵌段共聚物的结构进行了深入研究。在照射下,这种SPPLA-b-PGAMA共聚物表现出有效的单线态氧产生,并显示出高的荧光量子产率。值得注意的是,通过紫外-可见和动态光散射(DLS)分析,SPPLA-b-PGAMA显示出与伴刀豆球蛋白A(ConA)的非常特异的识别。MTT结果显示SPPLA-b-PGAMA对COS-7细胞的细胞毒性很低,当照射时间延长时,更多的BEL-7402癌细胞死亡,这将在本研究中进行研究。
Porphyrin-cored poly(l-lactide) (SPPLA) was successfully synthesized from ring-opening polymerization (ROP) of l-lactide initiated with porphyrin core. Then, SPPLA was coupled with benzylsulfanylthiocarbonylsufanylpropionic acid (BSPA), and a macro-reversible addition-fragmentation chain transfer (macroRAFT) polymerization agent SPPLA-BSPA was obtained. Finally, star-shaped porphyrin-cored poly(l-lactide)-b-poly(gluconamidoethyl methacrylate) (SPPLA-b-PGAMA) block copolymers were synthesized via RAFT of unprotected gluconamidoethyl methacrylate (GAMA) in 1-methyl-2-pyrrolidinone (NMP) solution at 70 A degrees C. The structure of this block copolymer was thoroughly studied by nuclear magnetic resonance spectroscopy (NMR), gel permeation chromatography (GPC), and differential scanning calorimetry (DSC). Under the irradiation, such SPPLA-b-PGAMA copolymer exhibits efficient singlet oxygen generation and indicates high fluorescence quantum yields. Notably, with UV-vis and dynamic light scattering (DLS) analysis, SPPLA-b-PGAMA showed a very specific recognition with concanavalin A (ConA). Particularly, MTT shows that the cytotoxicity of SPPLA-b-PGAMA against COS-7 cells was very low and, when given a longer irradiation time, more BEL-7402 cancer cells died, which will be investigated in this study.