Stepwise orthogonal click chemistry toward fabrication of paclitaxel/galactose functionalized fluorescent nanoparticles for HepG2 cell targeting and delivery.

@article{Lai2013StepwiseOC,
  title={Stepwise orthogonal click chemistry toward fabrication of paclitaxel/galactose functionalized fluorescent nanoparticles for HepG2 cell targeting and delivery.},
  author={Chian-Hui Lai and Tsung-Che Chang and Yung-Jen Chuang and Der-Lii M. Tzou and Chun‐Cheng Lin},
  journal={Bioconjugate chemistry},
  year={2013},
  volume={24 10},
  pages={
          1698-709
        }
}
In this report, we used stepwise orthogonal click chemistry (SOCC) involving strain-promoted azide-alkyne cycloaddition (SPAAC) and microwave-assisted Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) to assemble an anticancer drug (paclitaxel, PTX) and a targeting ligand (trivalent galactoside, TGal) on a fluorescent silicon oxide nanoparticle (NP) by using dialkyne linker 8 as a bridge. The fluorescent NH2@Cy3SiO2NP was fabricated using a competition method to incorporate Cy3 without loss of… 

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References

SHOWING 1-10 OF 60 REFERENCES
"Clickable", trifunctional magnetite nanoparticles and their chemoselective biofunctionalization.
TLDR
Multifunctional nanoparticles, developed in the course of the study, could selectively target and induce apoptosis to folate-receptor overexpressing cancer cells with enhanced efficacy as compared to the free drug.
  • 39
  • Retracted
Paclitaxel-functionalized gold nanoparticles.
TLDR
The method described here demonstrates that organic molecules with exceedingly complex structures can be covalently attached to gold nanocrystals in a controlled manner and fully characterized by traditional analytical techniques.
Galactose Encapsulated Multifunctional Nanoparticle for HepG2 Cell Internalization
TLDR
It is shown that the MNP is a good ligand carrier and that, when pre‐assembled, the multivalent ligand structure enhances the interactions between the surface ligands of the MNPs and receptors of HepG2 cells.
Functionalized single-walled carbon nanotubes as rationally designed vehicles for tumor-targeted drug delivery.
TLDR
It has unambiguously been proven that this tumor-targeting DDS works exactly as designed and shows high potency toward specific cancer cell lines, thereby forming a solid foundation for further development.
Surface functionalization using catalyst-free azide-alkyne cycloaddition.
TLDR
The utility of catalyst-free azide-alkyne [3 + 2] cycloaddition for the immobilization of a variety of molecules onto a solid surface and microbeads was demonstrated and an efficient synthesis of aza-dibenzocyclooctyne (ADIBO), thus far the most reactive cyclOOctyne in cycloadDition to azides was reported.
Targeting the delivery of glycan-based paclitaxel prodrugs to cancer cells via glucose transporters.
TLDR
These glycan-based prodrugs may be good drug candidates for cancer therapy, and the glycan conjugation approach is an alternative method to enhance the targeted delivery of other drugs to cancer cells that overexpress GLUTs.
Strategy for increasing drug solubility and efficacy through covalent attachment to polyvalent DNA-nanoparticle conjugates.
TLDR
An approach has been developed for increasing Paclitaxel solubility and effectiveness by covalent attachment to gold nanoparticles via DNA linkers, exhibiting greater than a 50-fold increase insolubility over the unconjugated drug.
Covalent linkage of nanodiamond-paclitaxel for drug delivery and cancer therapy.
TLDR
Together, these results provide a functional covalent conjugation of ND-paclitaxel, which can be delivered into lung carcinoma cells and preserves the anticancer activities on the induction of mitotic blockage, apoptosis and anti-tumorigenesis.
A comparative study of bioorthogonal reactions with azides.
TLDR
Both the Staudinger ligation and the strain-promoted [3 + 2] cycloaddition using optimized cyclooctynes were effective for tagging azides on live cells and provided a guide for biologists in choosing a suitable ligation chemistry.
...
...