Synthesis, Characterization, Molecular Docking and Cytotoxicity Studies of Bagasse Xylem Ferulate-Acrylamide/Methyl Methacrylate Composite

Document Type : Research Article

Authors

1 College of Chemistry and Bioengineering, Guilin University of Technology, Guilin 541006, Guangxi, P.R. CHINA

2 School of Chemistry and Eco-Environmental Engineering (School of Chinese Pharmacy), Guizhou Minzu University, Guiyang 550025, Guizhou, P.R. CHINA

Abstract

BXFL (bagasse xylem ferulate)-g-AM (acrylamide)/MAA (methyl methacrylate) was synthesized based on bagasse xylan(BX)-g-AM/MAA in 1-Butyl-3-methylimidazolium chloride ([Bmim] Cl) ion solution with Ferulic Acid (FL) as esterification agent. The various factors that were investigated influenced carboxylic acid ester substitution degree (DSC) of BXFL-g-AM/MAA. The structures of BXFL-g-AM/MAA were confirmed by IR, SEM and 1H NMR analysis. The cytotoxicity of BXFL-g-AM/MAA was investigated against twelve kinds of protein through Surflex-Dock Mode of Sybyl-X 2.0 software, and on three kinds of human cancer cells line and the human normal cells line were detected by MTT assay. It was shown that the maximum DSC was 1.09 in ion solution, which was superior to DSC of conventional method in organic solvent. The results of MTT assay were consistent with docking results. BXFL-g-AM/MAA exhibited relative high cytotoxicity against human gastric cancer cells (MGC-803) line.

Keywords

Main Subjects


[1] Mullard A., 2013 FDA Drug Approvals, Nat. Rev. Drug. Disco., 13 (2): 85-9 (2014).
[5] Vonderheide R.H., June C.H., Engineering T Cells for Cancer: Our Synthetic Future, Immunol. Rev., 257(1): 7-13 (2014).
[7] Cheng H.L., Liu H., Feng Q.H., Xie Y.M., Zhan H.Y., Preparation, Characterization and in Vitro Anticoagulant Activity of Corn Stover Xylan Sulfates, J. Biomater. Sci. Polym. Ed., 28 (3): 271-283 (2016).
[8] Qian J.X., Li H.P., Zuo K., Sun Y., Zhou Y.D., Synthesis and Anti-Cancer Activity of Methacrylic Acid/ Butyl Acrylate grafted onto Bagasse Xylan Gallate, Fine. Chemicals (China)., 34 (8): 912-918 (2017).
[10] Marina A., Kirsi S.M., Raimo A., Tenkanen M., Sixta H., Carboxymethylation of Alkali Extracted Xylan for Preparation of Bio-Based Packaging Films, Carbohydr. Polym., 100 (2): 89-96 (2014).
[11] Yiğitoğlu M., Aydın G., Işıklan N., Microwave-Assisted Synthesis of Alginate-g-polyvinylpyrrolidone Copolymer and Its Application in Controlled Drug Release, Polym. Bull., 71(2): 385-414 (2014).
[13] Ratke C., Pawar P.M., Balasubramanian V.K., Naumann M., Duncranz M.L., Derba-Maceluch M., Gorzsas A., Endo S., Ezcurra I., Mellerowicz E.J., Populus GT43 Family Members Group Into Distinct Sets Required for Primary and Secondary Wall Xylan Biosynthesis and Include Useful Promoters For Wood Modification, Plant. Biotechnol. J., 13(1): 26- (2015).
[14] Singh S., Peltier-Pain P., Tonelli M., Thorson J.S., A General NMR-Based Strategy for the in Situ Characterization of Sugar-Nucleotide-Dependent Biosynthetic Pathways, Org. Lett., 16 (12): 3220-3223 (2014).
[15] Dilek Ç.G., Dişli A., Öner Y., Açık L., Synthesis of Some Novel Amino and Thiotetrazole Purine Derivatives and Investigation ofTheir Antimicrobial Activity and DNA Interactions, Chem. Pharm. Bull (Tokyo)., 22(3): 578-582 (2013).
[16] Li H., Huang Y., Yuan J., Yang G., Synthesis and Characterization of Cross-Linked Graft Copolymer of Acrylamide/Methyl Methacrylate onto Bagasse xylan, New. Chemical. Materials (China)., 42 (10): 199-201 (2014).
[17] Fundador N.G.V., Enomoto-Rogers Y., Takemura A., Iwata T., Syntheses and Characterization of Xylan Esters, Polymer., 53 (18): 3885-3893 (2012).
[18] Li H.P., Yang G.W., Yang G.W., Yuan J.W., Influencing Factors and Conditions on the Synthesis of Double Activity Sulfate-Gallate Bagasse Xylan, Adv. Mater. Res., 842: 224-227 (2014).
[19] Zhang Y., Li H.L., Wang H.P., Gu J., Ma C.L., Wu H.Y., Effects of Ferulic Acid on Gastric Cancer Cell Line MGC-803 Proliferation, Chin. J. Inf. TCM., 23(9): 70-73 (2016).
[20] Zhang X., Chen M., Wang H., Liu C., Zhang A., Sun R., Characterization of Xylan-graft-Polycaprolactone Copolymers Prepared in Ionic Liquid, Ind. Eng. Chem. Res., 54 (24): 150604120533003 (2015).
[21] Beekman A.C., Woerdenbag H.J., Kampinga H.H., Konings A.W.T., Cytotoxicity of Artemisinin,
a Dimer of Dihydroartemisinin, Artemisitene and Eupatoriopicrin as Evaluated by the MTT and Clonogenic Assay
. Phytother. Res., 10 (2): 140-144 (2015).
[22] Morris G., “SYBYL-X 2.0”, Tripos Associates, St Louis (