DNA−Cyclodextrin Composite Material for Environmental Applications

Abstract

Recently, we prepared water-insoluble and nuclease-resistant DNA films by UV irradiation. The DNA films accumulated the harmful DNA-intercalating compounds, such as ethidium bromide and acridine orange. Additionally, the water-insoluble DNA films bound endocrine disruptors that had planar structures, such as dioxin derivatives, polychlorobiphenyl (PCB) derivatives, and benzo[a]pyrene. However, other harmful endocrine disruptors that lack a planar structure, such as bisphenol A and diethylstilbestrol, did not bind the water-insoluble DNA films. Therefore, we prepared the DNA-cyclodextrin composite material by mixing the DNA and the cyclodextrin-immobilized poly(allylamine) (PCD). As a result, these composite materials had properties of both the double-stranded DNA, such as intercalation, and the cyclodextrin, such as encapsulation of an organic molecule into the intramolecular cavity. Therefore, these materials could accumulate not only the harmful compounds with planar structures but also the nonplanar molecules, such as bisphenol A, diethylstilbestrol, and nonylphenol. These DNA-PCD composite materials may have the potential to be novel environmental materials that absorb harmful compounds.

Composite material of DNA and cyclodextrin-immobilized poly(ethyleneimine): Accumulation of harmful compounds from multi-component solution

“…The elasticity of the composite material decreased with the decrease in the concentration and the composite material was not formed at the low concentration (<5 mg/ml). A similar phenomenon has been reported at the various polyion complexes [14]. In contrast, when this composite material was incubated in an aqueous ethidium bromide solution, which is one of the famous intercalating reagents into double-stranded DNA [3,4], this white material was dyed red (data not shown).…”

“…This shift to a lower wavenumber is due to the electrostatic interaction between the phosphate group of DNA and the positively charged part of the PEICD polymer, and similar phenomena have been reported for various polyion complexes [7,14]. Additionally, the absorption band at 1460 cm −1 , attributed to the bending vibrations of N-H in the imino group [7,14,19,20], disappeared by the interaction with the DNA (see the dashed line in Fig. 4).…”

“…4 shows the IR spectra of (a) the pure DNA material, (b) the DNA-PEICD composite material, and (c) the pure PEICD material. The absorption band at 1240 cm −1 in the pure DNA material, related to the antisymmetric vibration of the phosphate group [7,14,18], was shifted to a lower wavenumber, ca. 15 cm −1 , by the composite with PEICD (see the dashed line in Fig.…”

“…Therefore, CD-immobilized polymers have been used for affinity chromatography, fluorescence sensor, or absorbent for bisphenol A [11][12][13]. Recently, we also synthesized the ␤-CD-immobilized linear poly(allylamine) (PCD) and prepared the composite material with the double-stranded DNA [14]. This composite material had properties of both the double-stranded DNA, such as intercalation, and the CD, such as encapsulation of an organic molecule into the intramolecular cavity.…”

Chiral Recognition by DNA-Immobilized TLC Plate

“…[29][30][31][32], was shifted to a lower wavenumber with the accumulation of L-Asp and D-Asp (see the dashed line in Figure 2). This is due to the electrostatic interaction between the amino group of Asp and the phosphate group of DNA, and a similar interaction has been reported for the DNA-peptide biomatrix [21] and DNA-poly(allylamine) composite material [33]. Additionally, the absorption band at 1533 cm −1 , related to the in-plane vibration of the cytosine (C) base and the stretching vibration of C = N of the guanine (G) base [29][30][31], was shifted to a higher wavenumber when the DNA-film accumulated the L-Asp (see the dashed line in Figure 2).…”