Effect of Alkyl Chain Structure on the Encapsulation of Curcumin by Tween Surfactants
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摘要: 姜黄素在3种吐温聚集体中的稳定性和结合常数的大小顺序为：吐温-85囊泡 > 吐温-60囊泡 > 吐温-80胶束。通过紫外和荧光测定发现姜黄素以疏水作用为主要驱动力包载于吐温聚集体的烷基链疏水区域。核磁共振氢谱数据证实姜黄素的包载位置和作用力与吐温的烷基链结构有密切关系。相比粒径约为92 nm的吐温-60囊泡，烷基链中含有双键的吐温-80生成了具有疏松排列疏水区域的吐温-80胶束，使姜黄素表现出较低的稳定性、结合常数、以及紫外吸收和荧光发射强度。带有3条不饱和烷基链的吐温-85能够生成粒径约为150 nm的囊泡，其双分子层具有最高疏水性，因此对姜黄素有最好的包载效果。Abstract: The order of the stability and binding constant of curcumin encapsulated by three Tween aggregates is: Tween-85 vesicles > Tween-60 vesicles > Tween-80 micelles. By UV and fluorescence measurements, it is found that curcumin is encapsulated in the hydrophobic region of the alkyl chains of Tween aggregates with the hydrophobic interaction as the main driving force. The 1H NMR data confirm that the encapsulation position and force of curcumin are closely related to the alkyl chain structure of Tween surfactants. Compared with Tween-60 vesicles with a particle size of ~92 nm, the micelles formed by Tween-80 containing double bonds in the alkyl chain have loosely arranged hydrophobic region. Therefore, curcumin encapsulated by Tween-80 micelles exhibits lower stability, binding constant, and UV absorption and fluorescence emission intensities. Tween-85 with three unsaturated alkyl chains can generate vesicles with a particle size of ~150 nm, and its bilayer has the highest hydrophobicity which has the best encapsulation effect on curcumin.
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Key words:
- Tween surfactant /
- curcumin /
- double bond /
- vesicle /
- hydrophobic effect
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图 1 吐温-60、吐温-80和吐温-85的表面张力曲线
Figure 1. Surface tension curves of Tween-60, Tween-80 and Tween-85
图 2 吐温-60、吐温-80和吐温-85在1 mmol/L时的表观状态
Figure 2. Appearance of Tween-60, Tween-80 and Tween-85 at 1 mmol/L
图 3 吐温-60、吐温-80和吐温-85的粒径分布曲线
Figure 3. Size distribution curves of Tween-60, Tween-80 and Tween-85
图 4 游离姜黄素和吐温聚集体包载姜黄素的降解曲线
Figure 4. Degradation curves of free curcumin and curcumin encapsulated by Tween aggregates
图 5 吐温-60、吐温-80和吐温-85聚集体的1/(A-A0)对1/[curcumin]线性拟合曲线
Figure 5. 1/(A-A0) vs.1/[Curcumin] fitting curves in Tween-60, Tween-80 and Tween-85 aggregates
图 6 游离姜黄素和吐温聚集体包载姜黄素的紫外吸收光谱（a）和荧光发射光谱（b）
Figure 6. UV absorption spectra (a) and fluorescence emission spectra (b) of free curcumin and curcumin encapsulated by Tween aggregates
图 7 吐温-60、吐温-80和吐温-85的1H NMR图谱。
Figure 7. 1H NMR spectra of Tween-60, Tween-80 and Tween-85
The letters represent the protons of Tween surfactants in 1H NMR spectra
Table 1. Chemical shifts of protons of Tween surfactants
Group δ1 (Before) δ2 (After) Δδ (δ2−δ1) Tween-60 Tween-80 Tween-85 Tween-60 Tween-80 Tween-85 Tween-60 Tween-80 Tween-85 a 0.88 0.88 0.89 0.88 0.88 0.89 0 0 0 b 1.29 1.31 1.29 1.28 1.30 1.28 −0.01 −0.01 −0.01 c 1.59 2.02 2.02 1.58 2.00 2.01 −0.01 −0.02 −0.01 d 2.33 5.32 5.32 2.32 5.31 5.31 −0.01 −0.01 −0.01 e 4.21 1.59 1.58 4.20 1.57 1.58 −0.01 −0.02 0 f 3.69 2.31 2.31 3.69 2.30 2.31 0 −0.01 0 g 4.21 4.21 4.20 4.21 −0.01 0 h 3.69 3.69 3.69 3.69 0 0 
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