Synthesis and Gelation Properties of Stigmasterol‑Based Supramolecular Gelators

doi:10.19894/j.issn.1000-0518.210582

Chinese Journal of Applied Chemistry ›› 2022, Vol. 39 ›› Issue (9): 1453-1463.DOI: 10.19894/j.issn.1000-0518.210582

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Synthesis and Gelation Properties of Stigmasterol‑Based Supramolecular Gelators

Kai WANG, Hai-Kuan YANG(), Hui-Lan LIU, Jia-Min LU, Chen ZHANG

School of Chemistry and Chemical Engineering，North University of China，Taiyuan 030051，China

Received:2021-12-29 Accepted:2022-04-21 Published:2022-09-01 Online:2022-09-08
Contact: Hai-Kuan YANG
About author:haikuanyang@nuc.edu.cn
Supported by:
the National Natural Science Foundation of China(21802127);the Applied Basic Research Program of Shanxi Province(20210302124637);the Scientific and Technologial Innovation Programs of Higher Education Institutions in Shanxi(2019L0561)

1. Synthesis and Gelation Properties of Stigmasterol-Based Supramolecular Gelators.pdf(331KB)

Abstract

Abstract:

Two novel stigmasterol derivatives as gelators are synthesized， and named as compounds 1 and 2， respectively. The structure and properties of gels are studied by scanning electron microscopy （SEM）， Fourier transform infrared spectroscopy （FT-IR） and UV-Vis spectrophotometer. The results of the gelation properties of compounds 1 and 2 show that they could gelate in DMSO and methanol. Compound 1 also forms a stable gel in DMSO/water mixed solvents at a volume ratio of 9∶1， 8∶2， and 7∶3， respectively. In addition， when compounds 1 and 2 are gelated at a mass concentration of 12 mg/mL in DMSO， the gel-sol phase transition temperatures （T_gel） of the two compounds are 51 and 46 ℃， respectively， indicating that the thermal stability of their gelation decreases significantly with the increase of steroidal structural units in the gelator. With the increase of steroid structural units in the gelators， the thermal stability of the gel formation decreases significantly. On this basis， the gel prepared by compound 1 is used as the carrier， and its encapsulation and release in rhodamine B and methylene blue， as well as the anticancer drug doxorubicin are studied by UV-Vis spectroscopy. The results show that the prepared gels could be used as a drug carrier， and the maximum release value reaches 84% in water at 240 min. Furthermore， this study may provide a useful idea for the preparation of stigmasterol derivative gels and its application as a drug carrier in drug delivery.

Key words: Supramolecular gel, Stigmasterol, Self-assembly, Carrier

CLC Number:

O648

Kai WANG, Hai-Kuan YANG, Hui-Lan LIU, Jia-Min LU, Chen ZHANG. Synthesis and Gelation Properties of Stigmasterol‑Based Supramolecular Gelators[J]. Chinese Journal of Applied Chemistry, 2022, 39(9): 1453-1463.

Figures/Tables 8

Fig.1 Synthesis routes of compounds 1-4

Fig.2 The gelation behaviors of compound 1 under different conditions

Fig.3 Curves of Tgelvs gel factor concentration （ρ）

Fig.4 SEM images of dry gel of compound 1 （A） and compound 2 （B） in DMSO solution at a mass concentration of 15 mg/mL

Fig.5 FT-IR spectra of compound 1 forming xerogels under different conditionsa. Compound 1 solid powder； b. xerogel in DMSO； c. xerogel in mixed DMSO/water solvents （V∶V=9∶1）； d. xerogel in mixed DMSO/water solvents （V∶V=8∶2）； e. xerogel in mixed DMSO/water solvents （V∶V=7∶3）

Fig.6 Images and UV-Vis spectra of encapsulation and release of RhB， MB and Dox with compound 1 as carriers（A） Images of RhB， MB and Dox encapsulated in DMSO/ water mixed solvent （V∶V=7∶3） to form color gel and corresponding release in water over time；（B） The release rate and UV-Vis spectra of RhB in water over time；（C） Release rate of MB in water over time and UV-Vis spectrum；（D） Release rate and UV-visible spectrum of Dox in water over time

Table 1 Gelation properties of compounds 1-4 in DMSO/water mixed solvents

DMSO和H₂O的体积比 V（DMSO）∶V（H₂O）	化合物1 Compound 1	化合物2 Compound 2	化合物3 Compound 3	化合物4 Compound 4
9∶1	G	I	I	I
8∶2	G	I	I	I
7∶3	G	I	I	I
6∶4	I	I	I	I

Fig.7 Schematic illustration for the formation of the supramolecular structures of compounds 1 and 2

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Synthesis and Gelation Properties of Stigmasterol‑Based Supramolecular Gelators

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