Journal
MACROMOLECULES
Volume 44, Issue 6, Pages 1298-1302Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ma102568p
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Funding
- CSM
- Natural Science Foundation of China [50903060]
- Specialized Research Fund for the Doctoral Program of Higher Education of China [20093201120004]
- Soochow University
- Division Of Materials Research
- Direct For Mathematical & Physical Scien [0821799] Funding Source: National Science Foundation
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We report here a green chemistry method to conjugate hydrophobic payloads (Lilial as a prototype) highly efficiently (35.8 wt %) with (1 -> 4)-2-amino-2-deoxy-beta-D-glucan (i.e., chitosan) via Schiff base bond formation in an ionic liquid, which renders chitosan easily dissolvable in common organic solvents and amenable to further functional modifications. As an example, thermoresponsive poly(N-isopropylacrylamide) was grafted to the chitosan-Lilial conjugate. The graft copolymer self-assembled in water at neutral pH into core-shell nanocarriers with a favorable size distribution (d similar to 142 +/- 60 nm) for intravenous administration. Under conditions of enhanced temperature and acidity (T = 37 degrees C, pH = 4.5) mimicking endosomal or lysosomal uptake, the nanocarriers fell apart and formed reversed micelles with greatly reduced sizes (d similar to 8 +/- 3 nm) favoring clearance by renal filtration, and 70% Lilial molecules were liberated within 30 h through hydrolytic cleavage of the exposed Schiff base conjugation. This smart stimuli-responsive drug release profile reveals a viable approach in the development of chitosan-based nanocarriers for intravenous administration of hydrophobic pharmaceuticals.
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