Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2021 Apr 18;24(1):98-105.
doi: 10.1080/15685551.2021.1914398.

Reduction-sensitive N, N'-Bis(acryloyl) cystinamide-polymerized Nanohydrogel as a Potential Nanocarrier for Paclitaxel Delivery

Linna Yu  1   2   3 , Lingping Kong  1   2   3 , Junpeng Xie  1   2   3 , Wei Wang  4 , Chen Chang  1   2   3 , Hongli Che  1   2   3 , Mingzhe Liu  1   2   3
Affiliations

Reduction-sensitive N, N'-Bis(acryloyl) cystinamide-polymerized Nanohydrogel as a Potential Nanocarrier for Paclitaxel Delivery

Linna Yu et al. Des Monomers Polym. .

Abstract

Novel monomer, N, N'-bis(acryloyl) cystinamide (NBACA), was designed and synthesized with L-cystine as row material. By using this NBACA both as the monomer and crosslinker, reduction-sensitive nanohydrogel was prepared in ethanol via distillation-precipitation polymerization. The obtained nanohydrogel can provide a relatively hydrophobic environment and hydrogen-bonding sites inside the gel; therefore, it is suitable for loading hydrophobic drug. When paclitaxel that possess poor water-solubility was used as a model drug, the nanohydrogel represented a high drug-loading capacity, and dispersed well in aqueous solutions. Furthermore, the disulfide-group-containing nanohydrogel exhibited good reduction-sensitive drug-release behavior. The nanohydrogel biodegraded rapidly in a reducing environment, and released approximately 80% of the PTX within 24 h. Cytotoxicity assays showed that the PTX-loaded nanohydrogel exhibited high cytotoxicity against MCF-7 breast cancer cells, while blank nanohydrogels displayed a negligible cytotoxicity.

Keywords: Paclitaxel; biomaterials; drug delivery; nanohydrogel; redox stimuli.

PubMed Disclaimer

Conflict of interest statement

No potential conflict of interest was reported by the author(s).

Figures

Scheme 1.
Scheme 1.
Synthesis of N, N’- bis(acryloyl) cystinamide monomer
Figure 1.
Figure 1.
FTIR spectra of NBACA monomer (black), blank nanohydrogel (red) and PTX-loaded nanohydrogel (blue)
Figure 2.
Figure 2.
1H NMR spectrum of N, N’-bis(acryloyl) cystinamide in DMSO-d6
Figure 3.
Figure 3.
13C NMR spectrum of N, N’-bis(acryloyl) cystinamide in DMSO-d6.
Figure 4.
Figure 4.
(a) Optical image of NBACA nanohydrogels suspension in ultrapure water. (b) SEM image and (c) particle size distribution of NBACA nanohydrogels
Figure 5.
Figure 5.
Reduction-sensitive degradation of nanohydrogels in PBS buffer (pH = 7.4) at 37°C under different reducing conditions (10 mM DTT: black line, 10 mM GSH: red line and no reductant: blue line)
Figure 6.
Figure 6.
Cumulative release of PTX from nanohydrogels in PBS buffer (pH = 7.4) at 37°C under different reducing conditions (10 mM DTT: black line, 10 mM GSH: red line and no reductant: blue line)
Figure 7.
Figure 7.
MTT assays for MCF-7 cells treated with blank nanohydrogel, PTX-loaded nanohydrogel, and free PTX, respectively, for 72 h. The same PTX-loaded nanohydrogel (DLC: 22%) was used to compare with blank nanohydrogel (a) and free PTX (b) respectively
See this image and copyright information in PMC

References

    1. Hoffman AS. Hydrogels for biomedical applications. Adv Drug Del Rev. 2012;64:18–23. - PubMed
    1. Buwalda SJ, Boere KW, Dijkstra PJ, et al. Hydrogels in a historical perspective: from simple networks to smart materials. J Control Release. 2014;190:254–273. - PubMed
    1. Duan JJ, Zhang LN.. Robust and smart hydrogels based on natural polymers. Chin J Polym Sci. 2017;35:1165–1180.
    1. Tahara Y, Akiyoshi K. Current advances in self-assembled nanogel delivery systems for immunotherapy. Adv Drug Del Rev. 2015;95:65–76. - PubMed
    1. Peppas NA, Hilt JZ, Khademhosseini A, et al. Hydrogels in biology and medicine: from molecular principles to bionanotechnology. Adv Mater. 2006;18:1345–1360.

LinkOut - more resources