Pharmacological performance of novel poly-(ionic liquid)-grafted chitosan-N-salicylidene Schiff bases and their complexes

被引:67
作者
Elshaarawy, Reda F. M. [1 ,2 ]
Refaee, Ayaat A. [3 ]
El-Sawi, Emtithal A. [3 ]
机构
[1] Suez Univ, Dept Chem, Fac Sci, Suez, Egypt
[2] Univ Dusseldorf, Inst Anorgan Chem & Strukturchem, D-40204 Dusseldorf, Germany
[3] Ain Shams Univ, Fac Women Arts Sci & Educ, Cairo, Egypt
关键词
Chitosan Schiff bases; Ionic liquids; Complexes; Antimicrobial; Antitumor; QUATERNARY AMMONIUM-SALTS; BIOLOGICAL-ACTIVITY; DERIVATIVES; WATER; CHITIN; DEACETYLATION; METALATION; SOLUBILITY; SALDACH; PD(II);
D O I
10.1016/j.carbpol.2016.03.017
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
In our endeavor to develop a new class of pharmacological candidates with antimicrobial and anticancer efficacy, a series of biopolymeric chitosan Schiff bases bearing salicylidene ionic liquid (IL-Sal) brushes (ILCSB1-3, poly-(G1cNHAc-G1cNH2-(G1cN-Sal-IL)) was successfully synthesized by adopting efficient synthetic routes. Unfortunately, metalation trials of these biopolymeric Schiff bases afford the corresponding Ag(I)/M(II) complexes (where M= Co, Pd). These designed architectures were structurally characterized and pharmacologically evaluated for their in vitro antimicrobial, against common bacterial and fungal pathogens, and anticancer activities against human colon carcinoma (HCT-116) cell line. In conclusion functionalization of chitosan with IL-Sal brushes coupled with metalation of formed ILCSBs were synergistically enhanced its antimicrobial and antitumor properties to a great extent. Noteworthy, Ag-ILCSB2 (IC50 =9.13 mu g/mL) was ca. 5-fold more cytotoxic against HCT-116 cell line than ILCSB2 (IC50 =43.30 mu g/mL). (C) 2016 Published by Elsevier Ltd.
引用
收藏
页码:376 / 387
页数:12
相关论文
共 51 条
[1]   Imidazolium ionic liquids containing selenium: synthesis and antimicrobial activity [J].
Alberto, Eduardo E. ;
Rossato, Luana L. ;
Alves, Sydney Hartz ;
Alves, Diego ;
Braga, Antonio L. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (04) :1001-1003
[2]   High-resolution atomic force microscopy studies of the Escherichia coli outer membrane:: Structural basis for permeability [J].
Amro, NA ;
Kotra, LP ;
Wadu-Mesthrige, K ;
Bulychev, A ;
Mobashery, S ;
Liu, GY .
LANGMUIR, 2000, 16 (06) :2789-2796
[3]  
[Anonymous], 2013, INT J ADV RES TECHNO
[4]  
[Anonymous], 1993, INDIAN J CHEM
[5]  
[Anonymous], CARBOHYDRATE POLYM
[6]   Switching the properties of polyelectrolyte brushes via "Hydrophobic collapse" [J].
Azzaroni, O ;
Moya, S ;
Farhan, T ;
Brown, AA ;
Huck, WTS .
MACROMOLECULES, 2005, 38 (24) :10192-10199
[7]   Influence of concentration and structure of quaternary ammonium salts on their antifouling efficiency tested against a community of marine bacteria [J].
Baudrion, F ;
Périchaud, A ;
Vacelet, E .
BIOFOULING, 2000, 14 (04) :317-331
[8]   Grafting: a versatile means to modify polymers - Techniques, factors and applications [J].
Bhattacharya, A ;
Misra, BN .
PROGRESS IN POLYMER SCIENCE, 2004, 29 (08) :767-814
[9]   Studies on N-methylene phosphonic chitosan/poly(vinyl alcohol) composite proton-exchange membrane [J].
Binsu, V. V. ;
Nagarale, R. K. ;
Shahi, Vinod K. ;
Ghosh, P. K. .
REACTIVE & FUNCTIONAL POLYMERS, 2006, 66 (12) :1619-1629
[10]   DNA Molecular Solvation in Neat Ionic Liquids [J].
Cardoso, Lena ;
Micaelo, Nuno M. .
CHEMPHYSCHEM, 2011, 12 (02) :275-277