Using chiral magnetic surface molecularly imprinted polymers for chiral separation of gossypol

Volume 4, Issue 4, August 2019     |     PP. 113-123      |     PDF (416 K)    |     Pub. Date: September 6, 2019
DOI:    219 Downloads     6713 Views  

Author(s)

Chen ZHAO, School of Electronic and Information Engineering of Xi'an Technological University, Xi’an City, Shanxi Province, 710021, Peoples Republic of China
Xiang-yan MENG, School of Electronic and Information Engineering of Xi'an Technological University, Xi’an City, Shanxi Province, 710021, Peoples Republic of China
Haixian PAN, School of Electronic and Information Engineering of Xi'an Technological University, Xi’an City, Shanxi Province, 710021, Peoples Republic of China
Guang-feng JIA, School of Electronic and Information Engineering of Xi'an Technological University, Xi’an City, Shanxi Province, 710021, Peoples Republic of China
Wenzong Lu, School of Electronic and Information Engineering of Xi'an Technological University, Xi’an City, Shanxi Province, 710021, Peoples Republic of China

Abstract
The aim of this study was to prepare a method for quick resolution of gossypol. The chiral magnetic surface molecular imprinting polymers (chiral MMIP) were utilized. A chiral reagent (N-octyl-D-glucosamine) acted as a monomer, and magnetic nanoparticles were used as carriers to obtain chiral MMIPs. The chiral MMIPs could combine with (+)-gossypol molecules, and enable the separation of (–)-gossypol from racemic gossypol.The characterization of chiral MMIPs were detected by Infrared spectroscopic analysis and transmission electron microscopic (TEM). The results showed that the presence of monomeric methacrylate in the chiral MMIPs and the particle size of chiral MMIP was about 150 nm. The binding capacity of gossypol chiral MMIP indicated that the chiral MMIPs prepared in the laboratory were capable of binding well to gossypol. The polymer was then used as the stationary phase for column chromatography, and (-)-gossypol solution was thus isolated through chromatography. The product was tested by ultraviolet spectrum and optical rotation tests and was confirmed to be (-)-gossypol. Thus, we established a simple, rapid, and cost-effective method for separating chiral compounds.

Keywords
gossypol; magnetic surface molecularly imprinted polymer; chiral reagent; ultraviolet spectrum

Cite this paper
Chen ZHAO, Xiang-yan MENG, Haixian PAN, Guang-feng JIA, Wenzong Lu, Using chiral magnetic surface molecularly imprinted polymers for chiral separation of gossypol , SCIREA Journal of Chemistry. Volume 4, Issue 4, August 2019 | PP. 113-123.

References

[ 1 ] AA Conceição,  CN Soares, et al.（2018）Development of an RP-UHPLC-PDA method for quantification of free gossypol in cottonseed cake and fungal-treated cottonseed cake. Plos one http://doi.org/10.1371/journal.pone.0196164.
[ 2 ] B Zhang,  Y Liu, Z Wang et al. (2017)  Antiviral activity and mechanism of gossypols: effects of the O2˙− production rate and the chirality. Rsc Advances7 :10266-10277 
[ 3 ] Chen CW, Hu S, Tsui KH, et al.(2018) Anti-inflammatory Effects of Gossypol on Human Lymphocytic Jurkat Cells via Regulation of MAPK Signaling and Cell Cycle. Inflammation http://doi.org/10.1007/s10753-018-0868-6
[ 4 ] Chen Z, Dao-cheng W. (2013) Rapid detection assay for the molecular imprinting of gossypol using a two-layer PMAA/SiO2 bulk structure with a piezoelectric imprinting sensor. Sen. Act: B. Chemical. 181:104-113
[ 5 ] Chen Z， Yu-miao R， Wen-zong L, Meng-jie Z.(2016) Detection of Piezoelectric Magnetic Surface Molecularly Imprinted Sensor to Chloramphenicol. Sci. Tech. Eng. 16:149-53
[ 6 ] Chen Z， Guang-feng J， Wen-zong L，Yu-miao R, Qiang G. (2016) Detection of SudanⅠ in food using magnetic molecularly imprinted polymer microspheres. Mod. Food Sci. Tech. 32:302-307.
[ 7 ] H Chen, Wu Yong. (2017) Research progress of anti-tumor mechanism of gossypol and its derivatives. Medi. Recapitulate 19:3769-3773
[ 8 ] L Zeng, Y Deng, L Weng, et al. (2017) Synthesis and anti-tumor activities of fluoride-containing gossypol derivatives compounds. Natural Sci.9:312-318
[ 9 ] S Shen, Y Wu, K Li, et al. (2017) Versatile hyaluronic acid modified AQ4N-Cu(II)-gossypol infinite coordination polymer nanoparticles: Multiple tumor targeting, highly efficient synergistic chemotherapy, and real-time self-monitoring. Biomaterials  154 :197-212
[ 10 ] Wen N, Dong Y, Song R, et al. (2018) Zero-Order Release of Gossypol Improves Its Antifertility Effect and Reduces Its side effects simultaneously. Biomacromolecules http://doi.org/10.1021/acs.biomac.7b
[ 11 ] Zeng Y, Ma J, Xu L, Wu D. (2017) Natural product gossypol and its derivatives in precision cancer medicine. Curr Med Chem. http://doi.org/ 10.2174/0929867324666170523123655
[ 12 ] Zhao C, Jia GF, Lu WZ, et al（2017）A piezoelectric magnetic molecularly imprinted surface sensor for the detection of Sudan I. J Chromatogr A 1216:3710-3719