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具有自组装行为的新型农用化学品缀合物。

Novel agrochemical conjugates with self-assembling behaviour.

机构信息

Drug Delivery, Disposition and Dynamics, Monash Institute of Pharmaceutical Sciences, Monash University (Parkville Campus), 381 Royal Parade, Parkville, VIC 3052, Australia; ARC Centre of Excellence in Convergent Bio-Nano Science and Technology, Monash Institute of Pharmaceutical Sciences, Monash University (Parkville Campus), 381 Royal Parade, Parkville, VIC 3052, Australia.

Medicinal Chemistry, Monash Institute of Pharmaceutical Sciences, Monash University (Parkville Campus), 381 Royal Parade, Parkville, VIC 3052, Australia.

出版信息

J Colloid Interface Sci. 2018 Feb 15;512:369-378. doi: 10.1016/j.jcis.2017.10.070. Epub 2017 Oct 19.

Abstract

HYPOTHESIS

That conjugation of agrichemicals to pro-assembly hydrophobic moieties will enable enhanced compatibility and loading with host lyotropic liquid crystalline carrier matrix, and potentially self-assemble in their own right in aqueous environments.

EXPERIMENTS

A series of lipid-like agrochemical-conjugates were synthesized using specific amphiphilic entities conjugated onto the agrochemicals, picloram and 2,4-dichlorophenoxyacetic acid (2,4-D). The self-assembly behaviour and compatibility of the novel entities when incorporated into phytantriol and monoolein-based liquid crystalline systems were examined using small angle X-ray scattering, cryo-TEM and polarized optical microscopy.

FINDINGS

Compared to agrochemical-conjugates with simple alkyl ester groups, the esterification of the agrochemicals with amphiphilic groups such as phytantriol and monoolein led to greater structural compatibility and consequently a greater loading of the agrochemicals in the liquid crystalline systems without destabilizing phase structure. Picloram-monoolein and picloram-monoelaidin can self-assemble to form lamellar structures in water. However, certain agrochemical-conjugates such as picloram-monoelaidin and picloram-PEGn-oleate showed poor compatibility with liquid crystalline systems, resulting in phase separation.

摘要

假设

将农用化学品与亲组装疏水性部分缀合,将能够增强与主体溶致液晶载体基质的相容性和载药量,并有可能在水相环境中自行组装。

实验

使用特定的两亲实体将农业化学物缀合到农业化学物,即草甘膦和 2,4-二氯苯氧基乙酸(2,4-D)上,合成了一系列类脂农用化学品缀合物。使用小角 X 射线散射、冷冻 TEM 和偏振光显微镜检查了这些新实体掺入植物三醇和单油酸甘油酯基液晶系统时的自组装行为和相容性。

结果

与具有简单烷基酯基团的农用化学品缀合物相比,农用化学品与植物三醇和单油酸甘油酯等两亲基团的酯化反应导致更大的结构相容性,从而在不破坏相结构的情况下,在液晶系统中更大量地装载农用化学品。草甘膦-单油酸甘油酯和草甘膦-单油酸甘油酯可以自组装在水中形成层状结构。然而,某些农用化学品缀合物,如草甘膦-单油酸甘油酯和草甘膦-PEGn-油酸酯与液晶系统的相容性较差,导致相分离。

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