Chemical modification of alginate with cysteine and its application for the removal of Pb(II) from aqueous solutions

Huamani-Palomino, Ronny G.; Jacinto, Christian; Alarcón, Hugo; Mejía, Ily Marilú Maza; López, Rosario; Silva, Denise de Oliveira; Cavalheiro, Éder Tadeu Gomes; Venâncio, Tiago; Dávalos, Juan Z.; Valderrama, Ana

doi:10.1016/j.ijbiomac.2018.09.096

Cited by 41 publications

(17 citation statements)

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“…Oliver et al demonstrated that the conjugation of the antioxidant catechin to alg-aldehyde under acidic conditions led to up to 22% functionalization with catechin, involving both nucleophilic addition to the carbonyl group and post-esterification of the carboxylate functionality ( Figure 10) [92]. NaBH 4 Heavy metal removal from water [89] 3-11%…”

Section: Chemical Modification Of Oxidized Alginatesmentioning

confidence: 99%

“…Imine-functionalized alg-derived self-assembled nanoparticles were obtained by the conjugation of oxidized alg to doxorubicin and an additional encapsulation of curcumin for the co-delivery of both drugs to tumor cells, which was triggered by the pH variation in the tumoral environment [87]. Further applications of alg derivatives obtained by reductive amination with thiosemicarbazide [88] and cysteine [89] include the production of sorption materials for heavy metal removal from aqueous solutions. While the coordination with metal ions was shown to mainly involve the carboxylic groups of the functionalized polymers, the chemical modification with thiol-containing units was the key to the sorption properties, which was probably due to their role as cross-linkers between the polymeric chains [88].…”

Section: Chemical Modification Of Oxidized Alginatesmentioning

confidence: 99%

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Strategies to Functionalize the Anionic Biopolymer Na-Alginate without Restricting Its Polyelectrolyte Properties

2020

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The natural anionic polyelectrolyte alginate and its derivatives are of particular interest for pharmaceutical and biomedical applications. Most interesting for such applications are alginate hydrogels, which can be processed into various shapes, self-standing or at surfaces. Increasing efforts are underway to functionalize the alginate macromolecules prior to hydrogel formation in order to overcome the shortcomings of purely ionically cross-linked alginate hydrogels that are hindering the progress of several sophisticated biomedical applications. Particularly promising are derivatives of alginate, which allow simultaneous ionic and covalent cross-linking to improve the physical properties and add biological activity to the hydrogel. This review will report recent progress in alginate modification and functionalization with special focus on synthesis procedures, which completely conserve the ionic functionality of the carboxyl groups along the backbone. Recent advances in analytical techniques and instrumentation supported the goal-directed modification and functionalization.Polymers 2020, 12, 919 2 of 23 Physicochemical and Polyelectrolyte Characteristics of AlginateThe composition, internal structure, and molar mass of the alg backbone govern the functional properties [9]. The solubility of alg in water depends on the pH value and the type of the counterions of the carboxyl groups. At pH < 3, both the M-and G-structures will precipitate as alginic acid. However, alternating M-and G-structures precipitate at lower pH values compared to the alg containing Polymers 2020, 12, 919 3 of 23 more homogeneous block structures. Neutralization of the alginic acid occurs at pH > 4, where it is converted into its corresponding salt [10]. Na-alg is an example of a water-soluble alg.Na-alg behaves in aqueous solution as a typical linear homogeneously charged polyelectrolyte. The chain conformation and consequently the solution viscosity strongly depend on the ionic strength, i.e., on both the alg concentration and the simultaneous presence of low molar mass salt. The intramolecular electrostatic repulsion between the neighboring negatively charged carboxyl groups of each monomer unit forces alg molecules into an extended random coil conformation in aqueous solution [11]. This results in highly viscous solutions even at relatively low alg concentration. The dynamic viscosity increases exponentially with the molar mass, while the intrinsic flexibility of the alg chains in solution increases in the order GG < MM < MG [12]. On the other hand, the selectivity for cation-binding and gel-forming properties strongly depends on the composition and sequence. Divalent cations preferably bind to the G-blocks. The ability to form ionotropic gels is based on this selective binding of cations. Mixing solutions of Na-alg with solutions of cationic polyelectrolytes yields precipitates of polyelectrolyte complexes.The rheological behavior of Na-alg solutions is important for a number of technologies and depends on both the concentration and th...

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Section: Chemical Modification Of Oxidized Alginatesmentioning

confidence: 99%

Section: Chemical Modification Of Oxidized Alginatesmentioning

confidence: 99%

Strategies to Functionalize the Anionic Biopolymer Na-Alginate without Restricting Its Polyelectrolyte Properties

2020

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“…Por otro lado, las etapas para llevar a cabo la extracción del alginato influyen en el tipo de alginato obtenido, teniendo un efecto en el tamaño molecular, variación en el contenido de los ácidos urónicos, contenido de iones metálicos, y la presencia de polifenoles 6 . En consecuencia, estas propiedades podrían definir el uso versátil de este polisacárido en distintos campos, así como sus derivados, presentando actividad biológica, biodegradabilidad y biocompatibilidad en sistemas vivos, en su actividad como agente anti-incrustante, intercambiador iónico (para un M/G<1), entre otros, fines de aplicación industrial 4,7 .…”

Section: Introductionunclassified

“…Es de este modo que, a lo largo de los últimos años, se han propuesto distintas metodologías para la extracción y purificación del alginato, mediante la obtención de ácido algínico 8 , a partir de la formación de geles mediante CaCl2 9 , implementación de un pre-tratamiento 5 , entre otros, las cuales en su mayoría se enfocan en optimizar el rendimiento de la extracción. En consecuencia, estas propiedades podrían definir el uso versátil de este polisacárido en distintos campos, así como sus derivados, presentando actividad biológica, biodegradabilidad y biocompatibilidad en sistemas vivos, en su actividad como agente anti-incrustante, intercambiador iónico (para un M/G<1), entre otros, fines de aplicación industrial 4,7 .…”

Section: Introductionunclassified

EXTRACCIÓN Y CARACTERIZACIÓN DEL ALGINATO DE SODIO DE LA MACROALGA Macrocystis pyrifera

B.¹,

L²,

Negrón³

2020

rsqp

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En el presente trabajo se propuso un proceso de extracción de alginato de sodio, el cual fue obtenido a partir de la macroalga parda Macrocystis pyrifera recolectada en La Punta- Callao. El proceso de extracción presentó un rendimiento del 12 % y el alginato obtenido fue caracterizado mediante las técnicas de IR-TF y RMN 13C en estado sólido, el cual fue comparado con un alginato comercial. Se ha llevado a cabo la evaluación de la presencia de bloques manurónicos y gulurónicos IR-TF, mediante el uso de la 2da derivada obteniendo señales características a 894 cm-1 para C1-H α–L–gulurónico del alginato extraído de la macroalga Macrocystis pyrifera (AlgM) y a 885 cm-1 para la región anomérica C1-H del β–D– manurónico para el alginato comercial de Sigma Aldrich (AlgC). Asimismo, se asignaron señales características para el espectro del alga a 902 cm-1 y a 812 cm-1 correspondiente a vibraciones de los bloques α–L–gulurónico. Mediante 13C RMN en estado sólido se obtuvo un pico característico a 102,4 ppm para AlgM asociado al carbono anomérico C1-H α–L– gulurónico, mientras que en AlgC se visualizaron dos picos a 101,8 ppm y a 99,8 ppm asignados a C1-H α–L–gulurónico y C1-H β–D–manurónico, respectivamente, indicando así la presencia tanto de bloques G y bloques M en el alginato comercial.

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“…The carboxylic acid-containing polymer is well-known for forming stable chelates with metal ions in aqueous solution. Immobilization of the carboxylic acid group on various supporting polymers is attracting widespread attention since chelating agents improve metal ion sorption [15][16][17][18][19] . Therefore, we attempted to prepare new chelating polymer materials containing carboxylic acid ligands, with high sorption capacity, high rate of sorption and low cost of sorbent with better analytical parameters in comparison with the similar samples 20,21 , which can be used in wastewater treatment.…”

Section: Introductionmentioning

confidence: 99%

Sorption of Lead Ion From Aqueous Solution by Carboxylic Acid Groups Containing Adsorbent Polymer

Hosseinzadeh

2019

J. Chil. Chem. Soc.

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Novel method to synthesize of p-(2,2,3,3-tetracarboxylic acid cyclopropyl)phenyl acrylate(P-TCP) was disclosed. In this study,3-(4hydroxyphenyl)cyclopropane-1,1,2,2-tetracarboxylicacid was synthesized by the new method and reacted with acryloyl chloride to preparation of P-TCP monomer. Then the resulting monomer was polymerized by free-radical polymerization initiated with benzoyl peroxide in ethyl acetate a solvent to obtain a poly-(2,2,3,3-tetra carboxylic acid cyclopropyl)phenyl acrylate (PTCP)with multicarboxylic acid cyclopropane functionalities in the pendant group as a new polymer and applied to remove Pb(II) from aqueous solution. The sorption experiments under different experimental conditions such as, contact time, temperature and pH were investigated. The functionalized polymer showed strong adsorption ability to the Pb(II), with the maximum adsorption capacities of 553 mgg -1 at pH of 5.The high adsorption rate (<50 min) was seen. The removal of Pb(II) by polymer followed the pseudo-second-order rate better than the pseudo-first-order. The removal mechanisms was described as a metal-binding organic ligand (-COOH) and the electrostatic attractions between Pb(II) and oxygenic functional groups. The synthesized monomer, polymer and its metal chelates were characterized by FT-IR, 1 H-NMR spectroscopy, scanning electronic microscopy (SEM) and atomic absorption techniques (AAS).

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Chemical modification of alginate with cysteine and its application for the removal of Pb(II) from aqueous solutions

Cited by 41 publications

References 64 publications

Strategies to Functionalize the Anionic Biopolymer Na-Alginate without Restricting Its Polyelectrolyte Properties

Strategies to Functionalize the Anionic Biopolymer Na-Alginate without Restricting Its Polyelectrolyte Properties

EXTRACCIÓN Y CARACTERIZACIÓN DEL ALGINATO DE SODIO DE LA MACROALGA Macrocystis pyrifera

Sorption of Lead Ion From Aqueous Solution by Carboxylic Acid Groups Containing Adsorbent Polymer

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