Synthesis of molecularly imprinted polymers of vanillic acid and extraction of vanillic acid from spiked blood serum

Vanillic acid (4-hydroxy-3-methoxybenzoic acid) is a phenolic acid found in many plant extracts. It is used as aflavoring and scent agent and produces a pleasant, creamy odor. It is widely used in many applications for therapeuticpurposes to flavoring agent. Molecularly imprinted polymers of vanillic acid were synthesized by precipitationpolymerization with a noncovalent approach for the extraction from blood serum. Three different imprinted polymershave been synthesized with varying molar ratio of monomer. The synthesized polymer particles were characterizedusing Fourier-transform infrared spectroscopy and scanning electron microscopy. The extraction efficiency of highlyselected imprinted polymer of vanillic acid from spiked blood serum was about 80%.

Determination of related substances in (E)-4-[2-(4-chlorophenoxy)-2-methylpanoyloxy]-3-methoxyphenyl acrylic acid by HPLC / 中国药科大学学报

@#HPLC method was used for the determination of related substances in (E)-4-[2-(4-chlorophenoxy)-2-methylpanoyloxy]-3-methoxyphenyl acrylic acid. The separation was achieved by Ultimate XB-C18 column (4.6 mm×150 mm,5 μm) with mobile phase composed of methanol-1% acetic acid water (70∶30) at a wavelength of 275 nm. The results showed that (E)-4-[2-(4-chlorophenoxy)-2-methylpanoyloxy]-3-methoxyphenyl acrylic acid with various intermediates and compulsory destruction of degradation products were well separated. The impurity limit in three batches of API was less than 0.1% and the main impurity C was isolated and identified. Within the range from 0.20 to 59.96 μg/mL, the mass concentration of impurity C has good linear relationship with the peak area (r=0.999 9). The control method of related substances for (E)-4-[2-(4-chlorophenoxy)-2-methylpanoyloxy]-3-methoxyphenyl acrylic acid was established by impurity reference method and self-high and low concentration comparison. Methodological validation can be used for the detection of related substances of (E)-4-[2-(4-chlorophenoxy)-2-methylpanoyloxy]-3-methoxyphenyl acrylic acid.

Biomimetic remineralization of dentin / 口腔疾病防治

@#In recent years, due to precise control of the amorphous mineral precursor in the demineralization of dentine collagen fibers in orderly deposition, forming apatite crystals similar to the natural mineralized dentin, the bottom-up remineralization approach which does not depend on the existence of seed crystallites, dentin biomimetic mineralization techniques gradually become a hotspot in the research field of restoration of demineralized dentin caused by dental caries. This paper reviews the changing concepts and practices of the remineralization of demineralized dentin, emphasizing biomimetic remineralization studies. The results of the literature review show that the traditional dentin remineralization method is usually a disordered mixture of demineralized dentin and minerals, so mineralized dentin is not comparable to natural mineralized dentin in terms of the morphological characteristics and mechanical properties. With its gradual increase in recent years, dentine biomimetic mineralization technology perfectly resembles the minerals in the dentin overlapping sequence arranged with the dentine collagen fiber structure characteristics, leading to greatly improved microstructural, physical and chemical properties. As a result, dentine biomimetic mineralization technology is expected to achieve new breakthroughs in the fields of resin-dentin bonding mixing layers and the decay of dentin. At present, the technical obstacles that need to be overcome in the clinical application of the biomimetic remineralization of dentin are how to continuously supplement all the active ingredients needed for mineralization in the process of remineralization and how to keep the mechanical properties of the parent material unchanged while slowly releasing all ingredients. Researchers have successively proposed three-step transportation of the biomimetic remineralization of raw materials, as well as the preparation of mineralization precursors stabilized by polymers in advance and the reuse of mesoporous silicon nanomaterials for the transportation of the mineralized ingredient system. The concept described above provides the preliminary in vitro experimental basis for the transformation of the biomimetic remineralization strategy of dentin in clinical applications.

Preparation of the surface patterned polyacrylamide-acrylic hydrogel / 中国组织工程研究

BACKGROUND: Polyacrylamide hydrogels have good biocompatibility, but their mechanical properties are poor, which affect their application in the field of biomaterials. OBJECTIVE: To prepare the polyacrylamide-acrylic hydrogels with a particular size by micromolding graphical imprinting. METHODS: Polyacrylamide-acrylic hydrogel was prepared by sequentially mixing different volumes of polyacrylamide solution, acrylic acid and ammonium persulfate solution into an orifice plate containing a micromolded patterned seal. Group A: Polyacrylamide solution 1.4 mL, acrylic acid 0.1 mL; group B: Polyacrylamide solution 1.3 mL, acrylic acid 0.2 mL; group C: Polyacrylamide solution 1.2 mL, acrylic acid 0.3 mL; group D: Polyacrylamide solution 1.1 mL, acrylic acid 0.4 mL; group E: Polyacrylamide solution 1.0 mL, acrylic acid 0.5 mL; group F: Polyacrylamide solution 0.9 mL, acrylic acid 0.6 mL. Six groups of ammonium persulfate solution were all 50 µL. The patterned structure of the hydrogel was observed under a light microscope. The mechanical properties of the hydrogel were examined by an electronic universal testing machine. RESULTS AND CONCLUSION: Light microscope showed that the stripes on the surface of each group of hydrogels were clearly visible. The addition of acrylic acid effectively improved the mechanical properties of hydrogels. As the proportion of acrylic acid increased, the mechanical properties of hydrogels gradually increased. These results suggest that polyacrylic acid/acrylamide hydrogel has good mechanical properties and is expected to have good application prospects in the field of tissue engineering damage repair.

Simultaneous determination of six bioactive constituents in Reduning Injection by UPLC-QqQ-MS/MS / 中草药

Objective: An ultra high performance liquid chromatography coupled to triple quadrupole mass spectrometry (UPLC- QqQ-MS/MS) method has been established to simultaneously determine the contents of six bioactive constituents [japonicaside A (JA), L-phenylalanion secologanin B (PSB), luteolin, scopolamine, (1S,6R,7R,10R)-6-carboxy-10-methyl-α-methylene-1-(1- oxobutyl)-cyclohexane acrylic acid (CMCA), and 3α,5α-tetrahydrodeoxycordifoline lactam (TL)] from Reduning Injection. Methods: This chromatographic separation was performed on an Agilent Zorbax SB-Aq C18 (150 mm × 2.1 mm, 3.5 μm) column with the mobile phase consisting of 0.1% formic acid water (A) and methanol (B) in a gradient elution (0.01-2.00 min, 5% B; 2.00-4.00 min, 5%-40% B; 4.00-11.00 min, 40%-95% B; 11.00-13.00 min, 95% B; 13.00-13.10 min, 95%-5% B; 13.10-14.00 min, 5% B) at a flow rate of 0.5 mL/min and the colunm temperature was set at 20℃. The analytes were detected using electrospray ionization (ESI) source by positive and negative ion monitoring mode. A triple quadrupole mass spectrometer was operated by ESI source in positive and negative ionization mode with multiple reaction monitoring for the detection of the six compounds. In the positive ion monitoring mode, the flow rate of Collision Gas (CAD) was 8 mL/min, the flow rate of Curtain Gas (CUR) was 20 mL/min, the temperature (TEM) was 500℃ and the Ion Spray Voltage (IS) was 4 500 V. In the negative ion monitoring mode, the flow rate of Collision Gas (CAD) was 8 mL/min, the flow rate of Curtain Gas (CUR) was 20 mL/min, the temperature (TEM) was 500℃ and the Ion Spray Voltage (IS) was -4 500 V. Results: All calibration curves of the six components showed excellent linear regressions (r ≥ 0.999 0) within the test range. The average recoveries were 78.93%, 114.65%, 101.99%, 90.98%, 98.08%, and 115.58%, and the average contents of six bioactive constituents in 16 batches of Reduning Injection were 2.00, 26.63, 52.63, 5.29, 34.64, and 9.69 μg/mL, respectively. Conclusion: The established method is rapid, accurate, and has high repeatability, which could provide scientific evidences for the quality control of Reduning Injection.

Application of polyhydroxy acrylic acid and Van-clear in the detection of EGFRgene mutations in non small-cell lung cancer by qRT-PCR method / 西安交通大学学报(医学版)

Objective To compare two different methods to detect the differences of gene mutation rate, sensitivity, specificity and coincidence rate of epidermal growth factor receptor (EGFR) in non-small-cell lung cancer (NSCLC) so as to assess the clinical value of qRT-PCR method and its environmental-friendly technologyplatforms.One uses environmental fixative poly hydroxyl acrylic acid and green transparent liquid dewaxing Van-clear alone or in combination to replace the traditional fixative 4％ (volume fraction) neutral buffered formalin and the traditional transparent dewaxing liquid xylene in application of quantitative real-time polymerase chain reaction (qRT-PCR).The other uses traditional reagents in direct sequencing.Methods We selected 91 cases of primary NSCLC specimens resected between May 2013 and March 2016 in Zhongshan Bo`ai Hospital and Zhongshan Hospital of Traditional Chinese Medicine.Five samples were taken from the same tumor lesion.We used a random number table to randomly divide these samples into Groups A, B , C, D, and E.Group A received direct sequencing method in detection of EGFR gene mutations.Besides, during the experiment, 4％ neutral buffered formalin was used for fixing, and xylene transparent dewaxing was used to make slices for DNA extraction dewaxing.Group B received qRT-PCR method to detect EGFR gene mutations.Meanwhile, during the experiment, 4％ neutral buffered formalin was used for fixing, and xylene transparent dewaxing was used to make slices for DNA extraction dewaxing.Group C received qRT-PCR method in detection of EGFR gene mutations.At the same time, during the experiment, polyhydroxy acrylic acid was used for fixing, and xylene transparent dewaxing was used to make slices for DNA extraction dewaxing.Group D received qRT-PCR method to detect EGFR gene mutations.In the meantime, 4％ neutral buffered formalin was used for fixing, Van-clear transparent dewaxing was used to make slices for DNA extraction dewaxing.Group E received qRT-PCR method in detection of EGFR gene mutations.In addition, during the experiment, polyhydroxy acrylic acid was used for fixing, and Van-clear transparent dewaxing was used to make slices for DNA extraction dewaxing.In addition, during the experiment, polyhydroxy acrylic acid was used for fixing, and Van-clear transparent dewaxing was used to make slices for DNA extraction dewaxing.The mutations of Exons 18, 19, 20, and 21 in EGFR genes were respectively determined in the five groups of NSCLC.Results ① Groups B, C, D, E and A did not significantly differ in the percentage of people with mutations or target site mutation rates of EGFR genes in NSCLC (P> 0.05).② The detection results of EGFR target site mutation in Groups B, C, D, E and A had good sensitivity, strong specificity, and high compliance rate.Conclusion The green transparent liquid dewaxing Van-clear alone or in combination to replace the traditional fixative 4％ neutral buffered formalin and the traditional transparent dewaxing liquid xylene in the application of qRT-PCR so as to detect EGFR gene mutations in NSCLC has good consistent results compared with the method that uses traditional reagents in direct sequencing.It has the significance and value in clinical application.

Comparison of the role that poly hydroxy acrylic acid plays in the detection ofHER-2 gene in breast cancer by hematoxylin and eosin staining and fluorescencein situ hybridization with that of 4% neutral buffered formaldehyde / 中国癌症杂志

Background and purpose: Adequate tissue ifxation, transparent dewaxing is an important step of hematoxylin eosin (HE) staining and lfuorescence in situ hybridization (FISH) in detection of breast cancerHER-2 gene. The purpose of this study was to make a comparison between poly hydroxyl acrylic acid which is an environmen-tally friendly ifxation liquid and 4% neutral buffered formaldehyde in tissue ifxation for HE staining and FISH to detect theHER-2 gene in the breast cancer tissue sections. The study aimed to evaluate the feasibility of replacing 4% buffered formaldehyde, a traditional ifxation liquid, with the poly hydroxyl acrylic acid, an environmentally friendly ifxation lfuid.Methods:This project was performed on tissue samples collected from 69 cases of breast cancer, 41 cases of breast ifbroadenoma, 40 cases of uterine leiomyoma, 25 cases of cervical tissue, 25 cases of placenta obtained from the outpatient and inpatient departments of Zhongshan Boai Hospital from Mar. 2011 to Jan. 2015, from each of which two samples were drawn and two blocks of each specimen were divided into two groups randomly. Then one group was ifxed with 4% neutral buffered formaldehyde and made into 200 sections by HE while the other group was ifxed with poly hydroxyl acrylic acid and made into another 200 sections. The slice level of the two groups was determined by the staining condition of the sections, and SPSS 19.0 was employed to compare the excellent and good rate of HE staining. Additional 69 sections were produced with two groups of breast invasive ductal carcinoma tissues, and SPSS 19.0 was used to detect the ampliifcation ofHER-2 gene by FISH.Results:First, the number of best-quality slices stained with HE ifxed separately by poly hydroxyl acrylic acid and 4% neutral buffered formaldehyde was 155 and 166, respectively. The number of excellent pieces was 41 and 33, respectively, while the number of mediocre pieces was 3 and 1 with bad pieces being 1 and 0, respectively. The excellent and good rates of HE staining were 98% and 99.5%, respectively. There was no significant difference between the two groups (χ2=1.33,P>0.05).Second, the positive rates of the tis-sue slices by FISH ifxed separately by poly hydroxyl acrylic acid and 4% neutral buffered were 26.09% and 23.19%, respectively. There was no signiifcant difference between the two groups (χ2=0.50,P>0.05).Conclusion:The results obtained with HE staining and FISH using poly hydroxyl acrylic acid as a ifxation liquid are not signiifcantly different from those using 10% neutral buffered formaldehyde. Therefore, poly hydroxyl acrylic acid meets the requirements of environmental protection, and thus has the potential to be promoted and widely used.

Preparation of molecular imprinted polymers for solid-phase extraction of L-tetrahydropalmatine / 中草药

Objective: To prepare the molecularly imprinted polymer (MIPs) of L-tetrahydropalmatine (L-THP) by the molecular imprinting technique and study on solid-phase extraction. Methods: Using L-THP as template, methyl acrylic acid (MAA) as functional monmer, and ehtylene glycol dimethacrylate (EDMA) as a cross-linking agent to prepare the L-THP-MIPs. A test was conducted to investigate the selectivity and the specificity of solid-phase extraction. Results: The experiment showed that the MIPs had the specific adsorption to L-THP, but did not have the specific adsorption to corydaline the structural analogue with L-THP. Conclusion: The L-THP-MIPs have a good selectivity and the specificity of L-THP.

The load and sustained release performance of chloramphenicol in the poly(DMAM-co-AA) hydrogels / 中国药学杂志

OBJECTIVE: To study the load capacity and slow releasing kinetics of chloramphenicol in poly(DMAM-co-AA) hydrogel based on N,N-dimethyl acrylamide (DMAM) and acrylic acid (AA). METHODS: The dry hydrogel was soaked in chloramphenicol solution, fully saturated and swelled. The load capacity of chloramphenicol in the swelled hydrogel was investigated. The dry gel loaded chloramphenicol was put into the different solution and constantly stirred. At the same time, the release rate of chloramphenicol was studied. RESULTS: When themole ratio of reaction monomers (DMAM/AA) and concentration of chloramphenicol solution were increased, the load capacityof chloramphenicol was increased. The release rate of chloramphenicol was increased with temperature rising. The release rate of chloramphenicolin acidic or alkaline medium was larger than that in neutral medium. CONCLUSION: The load capacity of chloramphenicol in poly(DMAM-co-AA) hydrogel is increased with the solution concentration of chloramphenicol increasing. The release of chloramphenicolin various hydrogels is completed in the range of 8 to 12 h, and the total release rate of chloramphenicol could reach about 90%.

Evaluation of the effects of two novel irrigants on intraradicular dentine erosion, debris and smear layer removal

OBJECTIVES: To evaluate the effects of copolymer of acrylic acid and maleic acid (Poly[AA-co-MA]) and calcium hypochlorite (Ca(OCl)2) on root canal dentin using scanning electron microscope (SEM). MATERIALS AND METHODS: Twenty-four single-rooted teeth were instrumented and the apical and coronal thirds of each root were removed, leaving the 5 mm middle thirds, which were then separated into two pieces longitudinally. The specimens were randomly divided into six groups and subjected to each irrigant for 5 min as follows: G1, Ca(OCl)2; G2, Poly(AA-co-MA); G3, Ca(OCl)2 + Poly(AA-co-MA); G4, sodium hypochlorite (NaOCl); G5, ethylenediaminetetraacetic acid (EDTA); G6, NaOCl+EDTA. The specimens were prepared for SEM evaluation. Smear layer, debris and erosion scores were recorded by two blinded examiners. One image from G3 was analyzed with energy dispersive spectroscopy (EDS) on suspicion of precipitate formation. Data were analyzed using the Kruskal-Wallis and Dunn tests. RESULTS: G1 and G4 showed the presence of debris and smear layer and they were statistically different from G2, G3, G5 and G6 where debris and smear layer were totally removed (p < 0.05). In G1 and G4, erosion evaluation could not be done because of debris and smear layer. G2, G3 and G5 showed no erosion, and there was no significant difference between them. G6 showed severe erosion and was statistically different from G2, G3 and G5 (p < 0.05). EDS microanalysis showed the presence of Na, P, and Ca elements on the surface. CONCLUSIONS: Poly(AA-co-MA) is effective in removing the smear layer and debris without causing erosion either alone or with Ca(OCl)2.

Determination of Related Substances in Methylacrylic Acid-Ethyl Acrylate Copolymer by HPLC / 中国药房

OBJECTIVE:To establish a method for the determination of related substances in methylacrylic acid- ethyl acrylate copolymer. METHODS:HPLC was performed on the column of Agilent C18 with mobile phase of methanol-phosphate buffer(70∶30,V/V) at the flow rate of 1.0 ml/min,the detection wavelength was 202 nm,column temperature was 20 ℃,and the sample size was 20 μl. RESULTS:The linear range was 0.001%-0.015% for both methylacrylic acid(r=0.999 4)and ethyl acrylate(r=0.999 1);RSDs of precision,stability and reproducibility tests were lower than 2%;the average recoveries of methylacrylic acid and ethyl acrylate were respectively 86.59%(RSD=2.3%,n=9)and 91.24%(RSD=3.5%,n=9). CONCLUSIONS:The method is simple,accurate and reproducible,and can be used for the contents determination of related substances in methyl acrylic acid-eth-yl acrylate copolymer.

Intervention Effects of(E)-4-[2-(4-Chlorophenoxy)-2-Methylpropanoyloxy]-3-Methoxyphenyl Acrylic Acid on Fat Accumulation in Human Hepatoma HepG2 Cells / 中国药房

OBJECTIVE:To investigate the intervention effects of (E)-4-[2-(4-chlorophenoxy)-2-methylpropanoyloxy]-3-me-thoxyphenyl acrylic acid (AZ) on fat accumulation in human hepatoma HepG2 cells. METHODS:Oleic acid was used to induce fat accumulation in HepG2 cells in logarithmic phase for establishing models of fat accumulation,which were divided into a model group,a positive control group(100 μg/ml simvastatin),and the groups of 15.63,31.25,62.5,125,250,500 and 1 000 μg/ml AZ,and a normal control group was set up. MTT method was used to detect the survival rates of all groups of cells,kit was per-formed to determine the contents of triglyceride (TG) in all groups of cells and calculate the clearance rates,and oil red O stain was conducted to observe the lipid droplet morphology of all groups of cells. RESULTS:Compared to the normal control group, the model group and the groups of 15.63-125 μg/ml AZ demonstrated no obviously different survival rate of cells,and the groups of 250-1 000 μg/ml AZ had lower survival rate of cells. There was statistically significance (P<0.05). The contents of TG in the cells of the model group were higher than those in the cells of the normal control group. The positive control group and the groups of 62.5 and 125 μg/ml AZ had lower contents of TG in the cells compared to the model group,showing a TG clearance rate of (28.58 ± 0.15)%,(14.51 ± 0.09)% and (29.72 ± 0.16)% respectively. There was statistically significance (P<0.01 or P<0.05). There were much more lipid droplets in the cells of the model group than in those of the normal control group. The lipid droplets in AZ groups gradually became less in quantity and smaller with the increasing in drug concentration. CONCLUSIONS:AZ has inter-vention effect on fat accumulation in HepG2 cells.

Application of computational simulation and spectral analysis in preparation of Tanshinone IIA imprinted polymer / 中草药

To prepare Tanshinone IIA (TSIIA) molecularly imprinted polymers (MIPs) with affinity and high selectivity to TSIIA and study its mechanism. Taking TSIIA as the template molecular, synthesizing the MIPs at the surface of silica nanoparticles by grafting copolymerization in the toluene solution. A molecular modeling approach was used to elucidate template-monomer interaction. The interaction between template molecule and functional monomer was studied by UV spectrometry. The theoretical molar ratio of template-monomer was 1∶3 and methyl acrylic acid (MAA) was a better functional monomer than acrylamide (AAM) for MIPs synthesis. The MIPs can be used for the extraction and separation of TSIIA.

A Novel High-strength GIC System Composed of Poly (Acrylic Acid) With Different Molecular Architectures.

Aims: The objective of this study was to synthesize and characterize the poly (acrylic acid) or PAA with different molecular architectures, use these polymers to formulate the cements with glass fillers, and evaluate the mechanical strengths of the formed cements. Materials and Methods: The novel poly (acrylic acid)s with different molecular architectures were synthesized via ATRP technique. The reaction kinetics was studied. The formed cements were evaluated using compression, diametral compression, and 3- point bending, fracture toughness, knoop hardness, and wear resistance tests. The experimental cement was also evaluated for its in vitro biocompatibility. Results: The results showed that either hyperbranched or star-hyperbranched polymer synthesis proceeds more slowly at the early stage but accelerates more quickly at the later stage than the star-shaped polymer synthesis. The higher the arm number and initiator concentration, the faster the ATRP reaction. It was also found that the higher the arm number and branching that the polymer had, the lower the viscosity of the polymer aqueous solution and the lower the mechanical strengths of the formed cement exhibited. The mechanical strengths of all three experimental glass-ionomer cements were very similar to each other but much higher than those of Fuji II LC. The aging study showed that all the experimental cements increased their CS continuously during 30 days, unlike Fuji II LC. This novel cement system was proven to be in vitro biocompatible because it showed no any noticeable cytotoxicity to human dental pulp cells and mouse 3T3 mouse fibroblasts.

Chemical constituents from pericarp of longan fruits / 中草药

Objective: To investigate the chemical constituents of pericarp of longan (Dimocarpus longan) fruits. Methods: The chemical constituents were isolated by silica gel, polyamide, as well as Sephadex LH-20 column chromatography and their structures were identified on the basis of physical and chemical properties and spectral analysis. Results: Thirteen compounds were isolated and identified as: friedelin (1), friedelanol (2), (24R)-stigmast-4-en-3-one (3), β-sitosterol (4), β-(2-furyl) acrylic acid (5), 6-hydroxy-7- methoxycoumarin (6), β-daucosterol (7), gallic acid (8), corilagin (9), heptyl p-hydroxybenzoate (10), methyl gallate (11), 4-O-α-L- rhamnopyranosyl-ellagic acid (12), and ellagic acid (13). Conclusion: Compounds 3-7, 10, and 12 are reported from the pericarp of longan fruits for the first time, and this is the first report for compound 5 as a natural product.

Antibacterial activity of chitosan and the interpolyelectrolyte complexes of poly(acrylic acid)-chitosan

The antimicrobial activity of chitosan and water soluble interpolyelectrolyte complexes of poly(acrylic acid)-chitosan was studied. Chitosans of two different molecular weights were tested at different concentration for 0.5 to 5 g·L-1 as antimicrobial agents against P. aeruginosa and P. oleovorans. In both cases, the best microbial inhibition was obtained with the concentration of 5 g·L-1. However, the interpolyelectrolyte complexes of poly(acrylic acid)-chitosan with composition φ =2 produced higher antibacterial activity than the two chitosans at the concentration of 0.5 g·L-1. The NPEC2 complex was more effective than chitosans. This could be attributed to the number of moles of the amino groups of chitosan and the carboxylic acid groups of the interpolyelectrolyte complexes poly(acrylic acid).

A atividade antimicrobiana de quitosana e complexos interpolieletrolíticos hidrossoluvéis de poli(ácido acrílico)-quitosana foi estudada. Quitosanas de dois diferentes pesos moleculares foram testados em diferentes concentrações, 0,5 a 5 g • L-1, como agentes antimicrobianos nas P. aeruginosa e P. oleovorans. Em ambos os casos, obteu-se a melhor inibição microbiana com a concentração de 5 g • L-1, no entanto os complexos interpolieletrolíticos de poli (ácido acrílico)-quitosana com composição φ = 2 apresentaram maior atividade antibacteriana do que os dois quitosans na concentração de 0,5 g • L-1. O complexo NPEC2 foi mais eficaz do que as quitosanas, sendo que o resultado pode ser atribuído ao número de moles dos grupos aminos da quitosana e aos grupos carboxílicos dos complexos de poli(ácido acrílico).