基于β-环糊精的有机小分子凝胶

doi:10.7536/PC180611

• •

基于β-环糊精的有机小分子凝胶

马明放¹^,^**(), 栾天翔², 邢鹏遥², 李兆楼¹, 初晓晓², 郝爱友²^,^**()

1. 济宁医学院新型抗肿瘤药物分子设计与合成实验室&济宁医学院基础医学院济宁 272067
2. 胶体与界面化学教育部重点实验室山东大学化学与化工学院济南 250100

收稿日期:2018-06-11 出版日期:2019-02-15 发布日期:2018-12-20
通讯作者: 马明放, 郝爱友
基金资助:
国家自然科学基金项目(21872087); 济宁医学院博士启动基金项目(2017JYQD03); 济宁医学院大学生创新训练计划项目(cx2018022)

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Low Molecular Weight Organic Compound Gel Based on β-cyclodextrin

Mingfang Ma¹^,^**(), Tianxiang Luan², Pengyao Xing², Zhaolou Li¹, Xiaoxiao Chu², Aiyou Hao²^,^**()

1. Laboratory of New Antitumor Drug Molecular Design and Synthesis of Jining Medical University & College of Basic Medicine, Jining Medical University, Jining 272067, China
2. Key Laboratory of Colloid and Interface Chemistry of Ministry of Education, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, China

Received:2018-06-11 Online:2019-02-15 Published:2018-12-20
Contact: Mingfang Ma, Aiyou Hao
About author:
** E-mail: mamingfang2012@163.com(Mingfang Ma);
haoay@sdu.edu.cn(Aiyou Hao)
Supported by:
National Natural Science Foundation of China(21872087); PhD Start-up Scientific Research Foundation of Jining Medical University(2017JYQD03); Undergraduate Training Programs for Innovation of Jining Medical University(cx2018022)

β-环糊精是直链淀粉在环糊精葡萄糖基转移酶作用下生成的含有7个D-吡喃葡萄糖单元的环状低聚糖,具有斜截锥形空间立体结构,腔内疏水,腔外亲水。β-环糊精以其低廉的价格、良好的水溶性和生物相容性,在超分子化学领域得到广泛的应用。β-环糊精可用于凝胶的构筑,通常的方法是将β-环糊精接枝到高分子链上,再以得到的高分子链为凝胶因子构筑高分子凝胶。虽然基于β-环糊精的高分子凝胶得到了广泛的关注和研究,但是,直接以β-环糊精为凝胶因子构筑的有机小分子凝胶却鲜有报道。2010年,本课题组首次报道了一种基于β-环糊精和二苯胺的热致有机凝胶。此后,本课题组在β-环糊精有机小分子凝胶领域做了大量的研究工作。本文在实验室研究工作的基础上,首先介绍了β-环糊精有机小分子凝胶的分类和不同因素对凝胶形成的影响,然后深入探讨了β-环糊精有机小分子凝胶的形成机理,系统介绍了β-环糊精有机小分子凝胶的刺激响应性以及在药物载运领域的应用,最后,对β-环糊精有机小分子凝胶的发展前景进行了展望。

关键词： β-环糊精, 有机小分子, 凝胶, 刺激响应, 药物载运

β-cyclodextrin is a cyclic oligosaccharide containing seven glucopyranose units, and can be produced by amylose under the action of cyclodextrin glucosyltransferase. β-cyclodextrin has cone shaped three-dimensional structure, with its cavity hydrophobic, while its outside hydrophilic. β-cyclodextrin has already been used widely in supramolecular chemistry due to its low price, good solubility and biocompatibility. β-cyclodextrin can be used to construct gel. But the usual way is grafting β-cyclodextrin onto polymer chain, and the obtained polymer chain containing β-cyclodextrin can act as gelator to construct polymer gel. Although polymer gels based on β-cyclodextrin have been studied extensively, there are few reports about low molecular weight organogel based on β-cyclodextrin. In 2010, our lab reported heat-set low molecular weight organogel based on β-cyclodextrin and diphenylamine for the first time. After that, a lot of research work about low molecular weight β-cyclodextrin organogel has been done in our group. Based on the research foundation of our lab, in this review, classification of different low molecular weight β-cyclodextrin organogel and different factors affecting the formation of low molecular weight β-cyclodextrin organogel are introduced at first. Then, the formation mechanism of low molecular weight β-cyclodextrin organogel is discussed deeply, and stimuli responsiveness of low molecular weight β-cyclodextrin organogel and application of low molecular weight β-cyclodextrin organogel on drug delivery are introduced systematically. Finally, development foreground of low molecular weight β-cyclodextrin organogel is prospected.

Key words: β-cyclodextrin, low molecular weight organic compound, gel, stimuli responsiveness, drug delivery

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图1 β-环糊精的分子结构

Fig. 1 Molecular structure of β-cyclodextrin

图2 凝胶到溶液转变机理[27]

Fig. 2 Schematic illustration of sol-gel transition[27]

图3 不同凝胶因子形成的水凝胶[28]

Fig. 3 Illustration of various hydrogels formed by different gelators.[28]

图4 β-环糊精凝胶在光学显微镜和扫描电子显微镜下的照片:(A)光学显微镜,标尺为1 μm;(B)扫描电子显微镜,标尺为2μm[29]

Fig. 4 Optical microscope images of the organogel(A, scale bar=1 μm); SEM images of xerogel of the organogel(B, scale bar=2 μm)[29]

图5 室温下β-环糊精凝胶的制备过程[38]

Fig. 5 Images of the gel preparation process at room temperature[38]

图6 凝胶溶液之间相互转变的图片:(a)冷却溶液可以得到凝胶A;(b)加热凝胶A得到的澄清溶液;(c)加热澄清溶液得到的凝胶B[41]

Fig. 6 Photographs of the gel-sol-gel transition process:(a) gel A formed after cooling the solution;(b) homogeneous solution obtained after heating gel A;(c) gel B formed after heating the solution[41]

表1 不同种类的环糊精在DMF和水的混合溶剂中的状态

Table 1 States of different types of β-cyclodextrin in the DMF/water system

Entry	CDs	State
1	α-CD	S^a
2	β-CD	G^b
3	γ-CD	S^a
4	Heptakis(6-deo-I)-β-CD	P^c
5	Heptakis(2-O-hydroxypropyl)-β-CD	S^a
6	Heptakis(2-O-sulfobutyl)-β-CD	S^a
7	Heptakis(2-deo-amino)-β-CD	S^a
8	Heptakis(2,6-di-O-methyl)-β-CD	S^a
9	Heptakis(2-O-diethylenetriamino)-β-CD	S^a
10	Heptakis(6-deo-I)-α-CD	P^c
11	Poly-β-CD	S^a

表1 不同种类的环糊精在DMF和水的混合溶剂中的状态

Table 1 States of different types of β-cyclodextrin in the DMF/water system

Entry	CDs	State
1	α-CD	S^a
2	β-CD	G^b
3	γ-CD	S^a
4	Heptakis(6-deo-I)-β-CD	P^c
5	Heptakis(2-O-hydroxypropyl)-β-CD	S^a
6	Heptakis(2-O-sulfobutyl)-β-CD	S^a
7	Heptakis(2-deo-amino)-β-CD	S^a
8	Heptakis(2,6-di-O-methyl)-β-CD	S^a
9	Heptakis(2-O-diethylenetriamino)-β-CD	S^a
10	Heptakis(6-deo-I)-α-CD	P^c
11	Poly-β-CD	S^a

图7 β-环糊精/氯化锂/DMF体系的相转变过程:(Ⅰ)120~130 ℃下为澄清溶液;(Ⅱ)加入促凝胶因子后得到凝胶;(Ⅲ)冷却至室温得到的溶液[46]

Fig. 7 The phase transition process of the β-cyclodextrin/LiCl/DMF system: a clear solution at 120~130 ℃(Ⅰ), a white gel(Ⅱ) after injecting cogelator, and a clear solution(Ⅲ) at room temperature[46]

表2 不同种类的醇对β-环糊精常温凝胶形成的影响

Table 2 The effect of alcohols on the formation of the room-temperature organogel

Solution	β-CD/DMAc/LiCl
Solution	1	2	3	4	5
Methanol	G	G	G	G	G
Ethanol	G	G	G	G	G
n-Propylalcohol	G	G	G	G	G
i-Propanol	G	G	G	G	G
n-Butyl alcohol	G	G	G	G	G
i-Butanol	G	G	G	G	G
t-Butanol	G	G	G	G	G
n-Amyl alcohol	G	G	G	G	G
n-Hexyl alcohol	G	G	G	G	G
n-Heptyl alcohol	G	G	G	G	G
n-Octanol	G	G	G	G	G
Phenylcarbinol	G	G	G	G	G
Ethanediol	S	S	S	S	S
Propanediol	S	S	S	S	S
Propanetriol	S	S	S	S	S

表2 不同种类的醇对β-环糊精常温凝胶形成的影响

Table 2 The effect of alcohols on the formation of the room-temperature organogel

Solution	β-CD/DMAc/LiCl
Solution	1	2	3	4	5
Methanol	G	G	G	G	G
Ethanol	G	G	G	G	G
n-Propylalcohol	G	G	G	G	G
i-Propanol	G	G	G	G	G
n-Butyl alcohol	G	G	G	G	G
i-Butanol	G	G	G	G	G
t-Butanol	G	G	G	G	G
n-Amyl alcohol	G	G	G	G	G
n-Hexyl alcohol	G	G	G	G	G
n-Heptyl alcohol	G	G	G	G	G
n-Octanol	G	G	G	G	G
Phenylcarbinol	G	G	G	G	G
Ethanediol	S	S	S	S	S
Propanediol	S	S	S	S	S
Propanetriol	S	S	S	S	S

表3 加入不同浓度的金属离子后体系的状态

Table 3 States of the gel after adding different salts at different concentrations

C_salt(mM)	LiCl	LiOH	Li₂CO₃	NaCl	NaOH	Na₂CO₃
50	G	CP	-	G	G	G
100	G	CP	-	G	G	G
150	G	CP	-	G	G	G
200	CP	CP	-	G	G	G
300	CP	CP	-	G	CP	G
500	CP	CP	-	G	CP	G

表3 加入不同浓度的金属离子后体系的状态

Table 3 States of the gel after adding different salts at different concentrations

C_salt(mM)	LiCl	LiOH	Li₂CO₃	NaCl	NaOH	Na₂CO₃
50	G	CP	-	G	G	G
100	G	CP	-	G	G	G
150	G	CP	-	G	G	G
200	CP	CP	-	G	G	G
300	CP	CP	-	G	CP	G
500	CP	CP	-	G	CP	G

图8 (a)小角X射线散射和(b)广角X射线散射谱图[38]

Fig. 8 Small-angle X-ray scattering(SAXS) patterns(a);and wide-angle X-ray scattering(WAXS) patterns(b)[38]

图9 β-环糊精的分子尺寸以及β-环糊精分子管状堆积模型图

Fig. 9 Idealized drawings(top image) of the shape of the β-cyclodextrin torus, with cut along the Cn axis, and the cross profile of channel-type packing(bottom image)

图10 不同凝胶的扫描电子显微镜图片:(a)DMAc凝胶;(b)DMF凝胶(Cβ-环糊精=0.167 mol/L;C百里酚酞=0.084 mol/L)[50]

Fig. 10 SEM images of xerogels prepared from various organogels:(a) DMAc gel;(b) DMF gel(Cβ-cyclodextrin=0.167 mol/L; CTP=0.084 mol/L)[50]

图11 凝胶纤维形成的可能机理(红球代表甲酸钠;黑球代表百里酚酞;等腰梯形代表β-环糊精)

Fig. 11 Schematic illustration of the formation of 3D networks of nanofibers(red balls: HCOONa; dark cylinders: thymolphthalein)

图12 β-环糊精热致凝胶的温度响应性[53]

Fig. 12 Temperature responsiveness images of the system of β-cyclodextrin/DMF/LiCl[53]

图13 外界化学刺激对β-环糊精凝胶的影响:(Ⅰ)OH-;(Ⅱ)HCl;(Ⅲ)CH3COOH;(Ⅳ)Cu2+[54]

Fig. 13 Photographs of external chemical stimuli influence on the gel for 5 h, OH-(Ⅰ), HCl(Ⅱ), CH3COOH(Ⅲ), Cu2+(Ⅳ)[54]

图14 凝胶转变图片:(a)β-环糊精/甘油胶体溶液;(b)β-环糊精/甘油凝胶;(c)载有甲氨蝶呤的β-环糊精/甘油凝胶;(d)载有5-氟尿嘧啶的β-环糊精/甘油凝胶[55]

Fig. 14 Photographs of phase transition from(a) the colloidal solution of β-cyclodextrin/glycerol to(b) β-cyclodextrin/glycerol gel, to(c) β-cyclodextrin/glycerol gel loaded with methotrexate, and to(d) β-cyclodextrin/glycerol gel loaded with 5-fluorouracil[55]

图15 不同浓度的5-氟尿嘧啶和负载5-氟尿嘧啶的β-环糊精/甘油凝胶(25 nM、50 nM和100 nM)对HepG2细胞的抑制能力比较

Fig. 15 Comparison of the inhibition rate of HepG2 cells induced by 5-Fu and 5-Fu-Gel. HepG2 cells were treated with increased concentrations of 5-Fu-Gel or 5-Fu(25 nM, 50 nM, and 100 nM) for 24 h

图16 双重载药β-环糊精有机小分子凝胶载药机理图

Fig. 16 Illustration of formation of low molecular weight β-cyclodextrin organogel loading with two kinds of drugs

图17 浸泡半小时后,吞噬凝胶释放出来的阿霉素的HeLa细胞的荧光显微镜照片:(A)吞噬阿霉素后HeLa细胞的荧光照片;(B)吞噬荧光染料DAPI后HeLa细胞的荧光照片;(C)图A和图B的重合图片[56]

Fig. 17 Fluorescence microscopy of cellular uptake of DOX released from gel observed after incubation for 0.5 h(A) DOX channel,(B) DAPI channel and(C) overlays of two images[56]

图18 载运阿霉素的β-环糊精凝胶、载运5-氟尿嘧啶的β-环糊精凝胶以及同时载运阿霉素和5-氟尿嘧啶的β-环糊精凝胶在不同的浸泡时间下对HeLa细胞的抑制率[56]

Fig. 18 The cytotoxicities of gel containing DOX, 5-FU or DOX and 5-FU against HeLa cells with different incubation time[56]

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基于β-环糊精的有机小分子凝胶

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基于β-环糊精的有机小分子凝胶

Low Molecular Weight Organic Compound Gel Based on β-cyclodextrin

C_salt(mM)	LiCl	LiOH	Li₂CO₃	NaCl	NaOH	Na₂CO₃
50	G	CP	-	G	G	G
100	G	CP	-	G	G	G
150	G	CP	-	G	G	G
200	CP	CP	-	G	G	G
300	CP	CP	-	G	CP	G
500	CP	CP	-	G	CP	G

C_salt(mM)	LiCl	LiOH	Li₂CO₃	NaCl	NaOH	Na₂CO₃
50	G	CP	-	G	G	G
100	G	CP	-	G	G	G
150	G	CP	-	G	G	G
200	CP	CP	-	G	G	G
300	CP	CP	-	G	CP	G
500	CP	CP	-	G	CP	G

C_salt(mM)	LiCl	LiOH	Li₂CO₃	NaCl	NaOH	Na₂CO₃
50	G	CP	-	G	G	G
100	G	CP	-	G	G	G
150	G	CP	-	G	G	G
200	CP	CP	-	G	G	G
300	CP	CP	-	G	CP	G
500	CP	CP	-	G	CP	G

C_salt(mM)	LiCl	LiOH	Li₂CO₃	NaCl	NaOH	Na₂CO₃
50	G	CP	-	G	G	G
100	G	CP	-	G	G	G
150	G	CP	-	G	G	G
200	CP	CP	-	G	G	G
300	CP	CP	-	G	CP	G
500	CP	CP	-	G	CP	G

C_salt(mM)	LiCl	LiOH	Li₂CO₃	NaCl	NaOH	Na₂CO₃
50	G	CP	-	G	G	G
100	G	CP	-	G	G	G
150	G	CP	-	G	G	G
200	CP	CP	-	G	G	G
300	CP	CP	-	G	CP	G
500	CP	CP	-	G	CP	G

C_salt(mM)	LiCl	LiOH	Li₂CO₃	NaCl	NaOH	Na₂CO₃
50	G	CP	-	G	G	G
100	G	CP	-	G	G	G
150	G	CP	-	G	G	G
200	CP	CP	-	G	G	G
300	CP	CP	-	G	CP	G
500	CP	CP	-	G	CP	G