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  • Click conjugation of peptide to hydrogel nanoparticles for tumor-targeted drug delivery.

Click conjugation of peptide to hydrogel nanoparticles for tumor-targeted drug delivery.

Biomacromolecules (2014-08-28)
Ming Qin, Hong Zong, Raoul Kopelman
ABSTRACT

Here we introduce a modified peptide-decorated polymeric nanoparticle (NP) for cancer cell targeting, which can deliver drugs, such as doxorubicin (Dox), to several kinds of cancer cells. Specifically, we employ a nucleolin-targeting NP, with a matrix based on a copolymer of acrylamide (AAm) and 2-carboxyethyl acrylate (CEA). The negatively charged co(CEA-AAm) NP was conjugated with a nucleolin-targeting F3 peptide using a highly efficient and specific copper(I) catalyzed azide-alkyne click reaction. F3 peptide binds to angiogenic tumor vasculatures and other nucleolin overexpressing tumor cells. Attaching F3 peptide onto the NP increases the NP uptake by the nucleolin-expressing glioma cell line 9L and the breast cancer cell line MCF-7. Notably, the F3-conjugated NPs show much higher uptake by the nucleolin-overexpressing glioma cell line 9L than that by the breast cancer cell line MCF-7, the latter having a lower expression of nucleolin on its plasma membrane surface. Moreover, the F3 peptide also dramatically enhances the uptake of co(CEA-AAm) NPs by the drug-resistant cell line NCI/ADR-RES. Also, with this F3-conjugated co(CEA-AAm) NP, a high loading and slow release of doxorubicin were achieved.

MATERIALS
Product Number
Brand
Product Description

USP
Dimethyl sulfoxide, United States Pharmacopeia (USP) Reference Standard
Sigma-Aldrich
Hexane, anhydrous, 95%
Sigma-Aldrich
Acrylamide solution, 40%, suitable for electrophoresis, sterile-filtered
Sigma-Aldrich
Ammonium persulfate, BioXtra, ≥98.0%
Sigma-Aldrich
Ammonium persulfate, for molecular biology, suitable for electrophoresis, ≥98%
Supelco
Acrylamide solution, 40% in H2O, for molecular biology
Sigma-Aldrich
8-Octanoyloxypyrene-1,3,6-trisulfonic acid trisodium salt, suitable for fluorescence, ≥90% (HPCE)
Sigma-Aldrich
N,N,N′,N′-Tetramethylethylenediamine, ≥99.5%, purified by redistillation
Sigma-Aldrich
Ammonium persulfate, free-flowing, Redi-Dri, reagent grade, 98%
Sigma-Aldrich
Hexane, Laboratory Reagent, ≥95%
Supelco
Hexane, analytical standard
Sigma-Aldrich
N,N,N′,N′-Tetramethylethylenediamine, BioReagent, suitable for electrophoresis, ≥99.0%
Sigma-Aldrich
N,N,N′,N′-Tetramethylethylenediamine, ReagentPlus®, 99%
Sigma-Aldrich
Acetonitrile, suitable for DNA synthesis, ≥99.9% (GC)
Sigma-Aldrich
Hexane, ReagentPlus®, ≥99%
Sigma-Aldrich
Hexane, suitable for HPLC, ≥95%
USP
Residual Solvent Class 2 - Acetonitrile, United States Pharmacopeia (USP) Reference Standard
Sigma-Aldrich
Acetonitrile, suitable for HPLC-GC, ≥99.8% (GC)
Sigma-Aldrich
N,N,N′,N′-Tetramethylethylenediamine, BioReagent, for molecular biology, ≥99% (GC)
Sigma-Aldrich
Dimethyl sulfoxide, puriss. p.a., ACS reagent, ≥99.9% (GC)
Sigma-Aldrich
Acetonitrile, ≥99.5% (GC)
Sigma-Aldrich
Ammonium persulfate, reagent grade, 98%
Sigma-Aldrich
Ammonium persulfate, BioUltra, for molecular biology, ≥98.0% (RT)
Sigma-Aldrich
Ammonium persulfate, ACS reagent, ≥98.0%
Sigma-Aldrich
Hexane, suitable for HPLC, ≥97.0% (GC)
Sigma-Aldrich
Acetonitrile, ReagentPlus®, 99%
Sigma-Aldrich
Acetonitrile, ≥99.9% (GC)
Dimethyl sulfoxide, European Pharmacopoeia (EP) Reference Standard
Sigma-Aldrich
Hexane, HPLC Plus, for HPLC, GC, and residue analysis, ≥95%
Sigma-Aldrich
Acetonitrile, for preparative HPLC, ≥99.8% (GC)