Solubility Enhancement of Atrazine by Complexation with Cyclosophoraose Isolated from Rhizobium leguminosarum biovar trifolii TA-1

Abstract

Rhizobium leguminosarum biovar trifolii TA-1, a kind of soil bacteria, produces cyclosophoraoses (Cys). Cyclosophoraoses contain various ring sizes with degrees of polymerization ranging from 17 to 23. Atrazine is a hardly-soluble herbicide that contaminates soil and drinking water, and remains in soil for a long time. To remove this insoluble contaminant from aqueous solutions, we have enhanced the solubility of atrazine by complexation with Cys. The complex formation of Cys and atrazine was confirmed using 1H nuclear magnetic resonance (NMR), Fourier transform infrared (FT-IR) spectroscopy, differential scanning calorimetry (DSC), field emission scanning electron microscopy (FE-SEM), rotating frame nuclear overhauser spectroscopy (ROESY), and molecular modeling studies. The aqueous solubility of atrazine was enhanced 3.69-fold according to the added concentrations (20 mM) of Cys, compared to the 1.78-fold enhancements by β-cyclodextrin (β-CD). Cyclosophoraoses as an excellent solubility enhancer with long glucose chains that can effectively capture insoluble materials showed a potential application of microbial polysaccharides in the removal of hazardous hardly-soluble materials from aqueous solutions in the fields of biological and environmental industry.

Enhancing the Solubility of Curcumin Using a Solid Dispersion System with Hydroxypropyl-β-Cyclodextrin Prepared by Grinding, Freeze-Drying, and Common Solvent Evaporation Methods

“…To address this, one of the basic goals of drug formulations is to improve the solubility of these two drug classes. Indeed, numerous strategies such as spray-drying [ 3 ], co-solvency [ 4 , 5 ], solid dispersion [ 6 , 7 , 8 ], complexation [ 9 , 10 ], and hydrotrophy [ 5 ] are used to increase drug absorption, resulting in higher bioavailability.…”

The Atrazine Removal with the Polyaniline Coated Rice Husk as a Cheap Adsorbent

“…As this literature information supports, there are characteristic peaks of PANI and RH in the FTIR spectrum of the Raw-PANI/RH composite given in Figure 1a, and the composite was produced successfully by polymerization of PANI. In addition, newly emerged peaks at 1671 and 733 cm -1 in the FTIR spectrum of the used-PANI/RH composite in Figure 1b are the peaks responsible for the atrazine-specific Triazine group and the C-H stretching on the aromatic ring [21], and these results support the adsorption of atrazine to the composite. [22,23].…”

Structural Characterization of Glycerophosphorylated and Succinylated Cyclic β-(1→2)-d-Glucan Produced by Sinorhizobium mliloti 1021

“…Fourier transform infrared spectroscopy was used to characterize the structure of anionic CG fraction ATR-FTIR spectra of anionic CG and neutral CG, shown in Figure 5 . The broad absorption peak at 3355 cm −1 indicates the stretching vibration of the hydroxyl group [ 11 ]. Neutral CG had an absorption peak at 1645 cm −1 that was an O–H bending vibration.…”

“…Recently, many studies have been conducted on inclusion complexes that use neutral CG. Since CG is very soluble, many studies have been conducted to improve insoluble compounds or bioactivity through an inclusion complex with various compounds such as ergosterol, fluorosine, indomethacin, paclitaxel, and atrazine [7][8][9][10][11]. CG molecules are larger and more diverse than cyclodextrin (CD), and have a flexible and twisted ring, so we can expect a completely different binding complex from CD, which has a smaller size and a hard ring [9].…”