Cysteine-based amphiphilic peptide-polymer conjugates via thiol-mediated radical polymerization: Synthesis, self-assembly, RNA polyplexation and N-terminus fluorescent labeling for cell imaging

被引:13
作者
Dule, Madhab [1 ]
Biswas, Mrinmoy [1 ]
Biswas, Yajnaseni [1 ]
Mandal, Kuheli [2 ]
Jana, Nikhil R. [2 ]
Mandal, Tarun K. [1 ]
机构
[1] Indian Assoc Cultivat Sci, Polymer Sci Unit, Kolkata 700032, India
[2] Indian Assoc Cultivat Sci, Ctr Adv Mat, Kolkata 700032, India
关键词
Peptide-polymer conjugate; Amphiphilic; Fluorescent; Self-assembly; Micelles; Cell imaging; RNA polyplex; BLOCK-COPOLYMERS; DRUG-DELIVERY; PROTEIN; NANOPARTICLES; AGGREGATION; POLYELECTROLYTES; NANOSTRUCTURES; STRATEGIES; HYBRIDS; GLYCOL);
D O I
10.1016/j.polymer.2017.01.083
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
A water-soluble amphiphilic peptide-poly (1-vinylimidazole) [Boc-Cys (PVim)-Trp-OMe] bioconjugate is synthesized by 'grafting from' technique based on thiol-mediated radical polymerization. The attachment of fluorescein isothiocyanate (FITC) at the N-terminus of the peptide moiety of the bioconjugate results in the generation of fluorescent bioconjugate [FITC-Cys (PVim)-Trp-OMe]. MALDI-TOF-MS analysis confirms the attachment dipeptide moiety as well as FITC group. Owing to the amphiphilic nature, the [Boc-Cys (PVim)-Trp-OMe] bioconjugate undergoes spontaneous self-assembly into primary micelles and their subsequent secondary aggregation into spherical micellar aggregates (nanospheres) in water. The aqueous FITC-Cys (PVim)-Trp-OMe bioconjugate solution emits green light and exhibits a fluorescence emission with a maximum at 520 nm. The amphiphilicity of the fluorescent bioconjuagte molecules also triggers their self-assembly into micelles and micellar aggregates (nanospheres) with hydrophobic FITC-tagged dipeptide core and hydrophilic PVim cell in water. Further, the highly stable and non-toxic fluorescent bioconjugates are used for imaging of Chinese Hamster Ovary (CHO) cells. Finally, the polyplex formation between the untagged cationic Boc-Cys (PVim)-Trp-OMe bioconjugate and ribonucleic acid (RNA) at pH 5.5 is studied by fluorescence spectroscopy. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码:125 / 135
页数:11
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