Optically Controlled Drug Carrier With 2-nitrobenzyl Esters

Optically controlled vesicles as a drug carrier wrapped drugs into the body and in the controlled release of the lesion site is a new, revolutionary treatments, can greatly improve the utilization rate of drugs to reduce the toxicity, but high-efficiency optically vesicles and the response of the optically group is a key factor restricting the development of the optical band. Compared with polymer drug carrier, small molecular self-assembled vesicles has higher biological compatibility, relatively low toxicity and higher study value.In this paper, nitro benzyl ester as optically controlled group, double long-chain secondary amine as the hydrophobic, diethylenetriaminepentaacetic as hydrophilic group, a surface active molecule is designed and synthesized which has the function of controlled release at the same time. Taking 4-methyl-3-nitro benzoic acid as raw material,4-bromomethyl-3-nitro benzoic acid is got by bromination, after acylation that reacts with di-n-octylamine to obtain 4-bromomethyl-3-nitro-N, N-dioctyl benzamide derivative. By organic alkali DBU as a highly efficient nucleophilic substitution catalyst, diethylenetriaminepentaacetic and benzyl bromide derivative react deftly to generate a biodegradable surfactant 4-(4-N, N, N', N'-tetracarboxymethyl diethylenetriamine acetoxymethyl-3-nitro-N, N-dioctyl benzamide, it is not only protect the terminal carboxyl but also improve the reaction selectivity. The target product and intermediates were characterized by MS,1H NMR and IR.Vesicles of 4-(4-N, N, N', N'-tetracarboxymethyl diethylenetriamine acetoxymethyl-3-nitro-N, N-dioctyl benzamide are prepared by thin-film ultrasonic method, the average particle size is about 180 nm, smaller PDI 0.02, and the uniform spherical vesicles are observed by TEM. The average particle size increases to about 250 nm at room temperature after 6 days. What's more, the vesicle size is found to decrease under 365 nm UV light, while PDI increases. It may be vesicles destruction caused by the bond break of o-nitro benzyl acetate.