Adsorption of cinnabarinic acid from culture fluid with magnetic microbeads

Abstract

In this study, antimicrobial pigment cinnabarinic acid (CA) was produced from Pycnoporus cinnabarinus in laboratory-scale batch cultures. Magnetic poly(ethylene glycol dimethacrylate-N-methacryloyl-l-tryptophan methyl ester) [m-poly(EGDMA-MATrp)] beads (average diameter = 53-103 µm) were synthesized by copolymerizing of N-methacryloyl-l-tryptophan methyl ester (MATrp) with ethylene glycol dimethacrylate (EGDMA) in the presence of magnetite (Fe3O4) and used for the adsorption of CA. The m-poly(EGDMA-MATrp) beads were characterized by N2 adsorption/desorption isotherms (Brunauer Emmet Teller), X-ray photoelecron spectroscopy, scanning electron microscopy, infrared spectroscopy, thermal gravimetric analysis, electron spin resonance and swelling studies. The efficiency of m-poly(EGDMA-MATrp) beads for separation of CA from culture fluid was evaluated. The effects of pH, initial concentration, contact time and temperature on adsorption were analyzed. The maximum CA adsorption capacity of the m-poly(EGDMA-MATrp) beads was 272.9 mg g(-1) at pH 7.0, 25 °C. All the isotherm data can be fitted with the Langmuir, Freundlich and Dubinin-Radushkevich isotherm models. The adsorption process obeyed pseudo-second-order kinetic model. Thermodynamic parameters ΔH = 5.056 kJ mol(-1), ΔS = 52.44 J K(-1) mol(-1) and ΔG = -9.424 kJ mol-(1) to -11.27 kJ mol-(1) with the rise in temperature from 4 to 40 °C indicated that the adsorption process was endothermic and spontaneous.

Synthesis of cinnabarinic acid by metabolically engineered Pseudomonas chlororaphis GP72

“…CA is one of the most important phenoxazinones, which has antifungal, algicidal, and antiprotozoal/antimalarial activities (Eggert , 1995, 1997Göçenoğlu et al, 2015). P. cinnabarinus and animals typically produce CA, which is formed by the polymerization of two molecules of HAA (Eggert et al, 1995;Fazio et al, 2012).…”

“…humans (Nishizuka & Hayaishi, 1963). CA was also purified from the culture broth of Pycnoporus cinnabarinus and its antifungal, algicidal, and antiprotozoal/antimalarial activities were demonstrated (Eggert, Temp, & Eriksson, 1997;Eggert, Temp, Dean, & Eriksson, 1995;Göçenoğlu, Osman, Kara, Pazarlioglu, & Beşirli, 2015). It has recently been reported that CA may be involved in controlling autoimmune responses and reinforcing regulatory T cells activity, providing a new approach for the treatment of neuroinflammation (Fazio et al, 2012(Fazio et al, , 2014.…”

A Review on the Role and Function of Cinnabarinic Acid, a “Forgotten” Metabolite of the Kynurenine Pathway

“…There are, however, reports that CA is also produced in the orange dead leaf butterfly Kallima inachus , where its decrease triggers the larva-to-pupa transition [ 55 ]. CA has also been found deposited in the fruiting bodies of saprophytic white rod fungi from the Polyporaceae family in, among others, Pycnoporus cinnabarinus and Pycnoporus sanguineus [ 56 , 57 , 58 , 59 ] and in southern cinnabar polypore ( Trametes coccinea ) [ 60 ]. In the fungus Pycnoporus cinnabarinus , CA is created through the laccase-mediated oxidation of 3-hydroxanthranilic acid [ 57 , 59 ], and it is the presence of CA that gives these mushrooms their characteristic brick-brown color.…”

“…In the fungus Pycnoporus cinnabarinus , CA is created through the laccase-mediated oxidation of 3-hydroxanthranilic acid [ 57 , 59 ], and it is the presence of CA that gives these mushrooms their characteristic brick-brown color. CA is considered a natural pigment, and its isolation from Pycnoporus cinnabarinus culture media at the laboratory scale has been described [ 60 ].…”

Molecularly imprinted hydrazidine‐derived poly(acrylonitrile‐co‐divinylbenzene for enantio‐recognition of S‐fenoprofen

“…39 The advent of synthetic organic polymers has transformed the production of specialized sorbents, offering selective adsorption of various molecules and ions at low manufacturing costs, with extensive surface areas, and strong thermal and mechanical properties. [40][41][42][43][44] These sorbents' customizable features have led to widespread use in environmental cleanup, food safety, and biomedical fields, notably in isolating and purifying vital biological molecules like enzymes and nucleic acids for therapeutic and diagnostic purposes. [45][46][47] The versatility of functionalized organic polymers also supports the development of innovative MIPs, with modifications for targeted selection capabilities.…”