Citation: Bei-Bei Hu, Yue Yuan, Xiao-Ping Zhou, San-Ming Li. Synthesis and properties of a novel bolaamphiphile surfactant derived from proline[J]. Chinese Chemical Letters, ;2016, 27(03): 447-450. doi: 10.1016/j.cclet.2015.12.019 shu

Synthesis and properties of a novel bolaamphiphile surfactant derived from proline

a.
a. School of Pharmacy, Shenyang Pharmaceutical University, Shenyang 110016, China;
b.
b. School of Pharmacy, Jilin University, Changchun 130021, China

Corresponding author: Yue Yuan, San-Ming Li,
Received Date: 13 October 2015
Available Online: 8 December 2015
Fund Project: This work was supported by National Natural Science Foundation of China for Youth (No.81202481) (No.81202481) Education Department Foundation of Liaoning Province (No.L2015527) (No.L2015527)

A novel bolaamphiphile surfactant N,N'-(octane-1,8-diyl)bis(pyrrolidine-2-carboxamide) (DAOP), was designed and synthesized from proline and 1,8-diaminooctane, as the hydrophilic part and hydrophobic part, respectively. After separation and purification, the structures of the synthesized bola surfactants were verified by IR, MS and ¹H NMR. The pK_a was measured by a titration experiment, the turbidity was determined using a Shimadzu UV-1750 spectrophotometer, and the critical micelle concentration (CMC) values of the synthesized surfactants in water were obtained using the conductivity and fluorescence probe measurements. The synthesized bolaamphiphile surfactants demonstrate the ability of selfassemble to form vesicles that were confirmed with dynamic light scattering and transmission electron microscopy. The results showed that the novel bolaamphiphile surfactant derived from proline might potentially be an excellent carrier for drug delivery.
- Bolaamphiphile,
- Proline,
- Vesicles,
- Synthesis,
- Physicochemical characterization
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