Self-adjusting omniphilic
nanocarriers (OPNs) with a multisolvent aptitude were prepared via
a Schiff base reaction between chitosan, a natural polysaccharide,
and bioactive aldehydes. Experimental studies supported by atomistic
molecular dynamics simulations revealed these OPNs can encapsulate
insoluble molecular cargo, transport them in aqueous or lipid environments,
and deliver them through cross-phase barriers. N-imine dynamic covalent
bonds have been incorporated to endow the OPNs with pH responsiveness,
also allowing the amplification of their bioactivity, as demonstrated
in vitro with the ability to delay fungal proliferation in wheat grains.
The reported OPNs hold remarkable potential as biocompatible nanocarriers
for the effective delivery of active agents in agriculture, medicine,
and cosmetics.
“Side chain
engineering” research has yielded many
promising and beneficial results, with applications in various fields.
However, this research did not receive sufficient focus when nature-sourced
polymers are concerned. In this study, we have performed side chain
engineering on chitosan, a nature-sourced polysaccharide, by coupling
it with a number of aliphatic aldehydes of varying chain lengths.
The side chains’ length and the pursuing effect on the modified
products’ properties were studied in great detail. In terms
of coupling yields, it was found that some substituents have displayed
more favorable results than others by a factor of over 35 times. When
studying the modified polymers’ physical and mechanical properties,
some of them were found to exhibit more rigid mechanical properties
by a factor of 3.5 times than others. The effect was also expressed
through self-assembly concentrations and encapsulation capabilities
of the modified polymers. Remarkably, the combined experimental and
calculated kinetic studies showed the results do not necessarily follow
a linear progression relating to substituent chain length, but rather
a parabolic pattern with a specific extremum point. This study has
assisted in shedding light on the inspected phenomenon, explaining
that not only steric and electronic factors but also interfacial solubility
related factors govern the coupling reaction and the resulting modified
polymers’ properties. As chemical protocols in various academic,
clinical, and industrial studies around the world slowly shift their
norms toward finding safer ways for the production of novel materials
and technologies, nature-sourced polymers hold great promise as virtually
inexhaustible raw materials. The perfection of their chemical modification
is therefore relevant now more than ever, with far-reaching and diverse
applicative prospects.
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