Cyclodextrin-Based Polymer-Supported Bacterium for the Adsorption and in-situ Biodegradation of Phenolic Compounds

Dual function polymer materials with immobilized Sphingobium Chorophenolicum (SpC) bacterium cells are reported herein that undergo tandem adsorption and biodegradation of phenolic compounds. The cross-linked polymer materials contain β-cyclodextrin (β-CD) with incremental hexamethylene diisocyanate (HDI) cross-linker at variable mole ratios (X = 1, 3, or 6), denoted as HDI-X systems. The adsorptive uptake properties of the insoluble HDI-X polymers (X = 3 and 6) with various phenolic compounds [pentachlorophenol (PCP), 2,4,6-trichlorophenol (TCP), and 2,4,6-trimethylphenol (TMP)] were studied using batch adsorption isotherms. The molecular selective phenol removal (S_R) capacity of the HDI-3 and HDI-6 materials was evaluated by electrospray ionization mass spectrometry (ESI-MS). The results were compared against granular activated carbon (GAC) and native β-CD, where 1D/2D ¹H NMR spectral characterization of the complexes formed between phenolic guests and a soluble polymer (HDI-1) in aqueous solution provide insight on the intermolecular interactions and the role of cross-linking effects. Immobilization of SpC onto HDI-3 was shown to form a composite polymer/bacterium material. The composite system displays synergistic removal effects due to tandem PCP adsorption and SpC biodegradation to yield by-products such as 2,6-dichloro-1,4-hydroquinone (DCHQ). Apoptosis and cytotoxicity of DCHQ were evaluated using three breast cancer cell lines.