Antibacterial activity of methylated chitosan and chitooligomer derivatives: Synthesis and structure activity relationships

Rúnarsson, Ögmundur Vidar; Holappa, Jukka; Nevalainen, Tapio; Hjálmarsdóttir, Martha Á.; Järvinen, Tomi; Loftsson, Þorsteinn; Einarsson, Jón M.; Jónsdóttir, Sigríður; Valdimarsdóttir, Margrét; Másson, Már

doi:10.1016/j.eurpolymj.2007.03.046

Cited by 156 publications

(92 citation statements)

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“…In another investigation [104] the antibacterial activity of a series of methylated chitosan and chitooligomer derivatives possessing various degrees of methylation against Staphylococcus aureus was examined. It was observed that N-quaternization was mainly responsible for the antibacterial effects at pH 7.2, whereas it did not contribute to the antibacterial activity under acidic conditions.…”

Section: Synthesized Methylated N-aryl Chitosan Derivatives Methylatmentioning

confidence: 99%

“…Antimicrobial DQ ↑ at pH 7.2, no effect at acidic conditions [104] Adjuvanticity DQ no effect [106] Antithrombin DS ↑ [109] Acid-blinding capacity DS ↑ up to 25% [111] Immune enhancing effect pH < 4 or pH > 10 ↑ [76] Calcium/cobalt blinding capacity pH ↑ [82] Transfection efficiency C↓ [51,89,90] Gene knockdown efficiency C ↓ [90] ↑ directly proportion to property; ↓ inversely proportional to property…”

Section: Biological Propertiesmentioning

confidence: 99%

“…For the obtained materials such parameters as the degree of quaternization and/or the degree of substitution should be determined and their influence on the investigated biological properties tested, -the biological properties of chitin/chitosan materials used directly in biomedical applications (e.g., antimicrobial effects) could be different that observed for materials obtained after preparation of nanoparticles, microspheres, hydrogels, films, fibers or tablets, -considerable research efforts should be directed towards developing safe and efficient chitin/chitosan-based formulations. As an example, such factors as particle size requirement, the thermal and chemical stability of the active agent, reproducibility of the kinetic release profiles, stability of the final product and residual toxicity associated with the final product depends upon the methods of preparing chitosan-based micro/nanoparticulate drug delivery systems, -the influence of physicochemical properties apart from M W and DA on chitosan-based formulation affecting the delivery of DNA and siRNA [51] and on antimicrobial properties of chitin/chitosan materials [68][69][70][71][72][73][74][85][86][87][88]94,95,104,105] is the best known. For other biological properties our knowledge is still not sufficient, -chitin/chitosan properties are interrelated and many times they could influence the bioactivity in a conflicting manner, e.g., would healing properties and permeation enhancement properties are inevitably linked to other such as mucoadhesion and cytotoxicity.…”

Section: Biological Propertiesmentioning

confidence: 99%

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Biomedical Activity of Chitin/Chitosan Based Materials—Influence of Physicochemical Properties Apart from Molecular Weight and Degree of N-Acetylation

et al. 2011

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Abstract:The physicochemical nature of chitin and chitosan, which influences the biomedical activity of these compounds, is strongly related to the source of chitin and the conditions of the chitin/chitosan production process. Apart from widely described key factors such as weight-averaged molecular weight (M W ) and degree of N-acetylation (DA), other physicochemical parameters like polydispersity (M W /M N ), crystallinity or the pattern of acetylation (P A ) have to be taken into consideration. From the biological point of view, these parameters affect a very important factor-the solubility of chitin and chitosan in water and organic solvents. The physicochemical properties of chitosan solutions can be controlled by manipulating solution conditions (temperature, pH, ionic strength, concentration, solvent). The degree of substitution of the hydroxyl and the amino groups or the degree of quaternization of the amino groups also influence the mechanical and biological properties of chitosan samples. Finally, a considerable research effort has been directed towards developing safe and efficient chitin/chitosan-based products because many factors, like the size of nanoparticles, can determine the biomedical characteristics of medicinal products. The influence of these factors on the biomedical activity of chitin/chitosan-based products is presented in this report in more detail. OPEN ACCESSPolymers 2011, 3 1876

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Section: Synthesized Methylated N-aryl Chitosan Derivatives Methylatmentioning

confidence: 99%

Section: Biological Propertiesmentioning

confidence: 99%

Section: Biological Propertiesmentioning

confidence: 99%

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Biomedical Activity of Chitin/Chitosan Based Materials—Influence of Physicochemical Properties Apart from Molecular Weight and Degree of N-Acetylation

et al. 2011

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“…They were made by sol-gel process with tetraethoxysilane (TEOS) as a base associated with three active components: silver nitrate, chitosan and hydrophobic silica. The properties of these components are well known: silver like various metals is a classic biocide for bacteria and plants [20]; chitosan is a relatively new biodegradable component used for its antibacterial [21,22] and algaecide properties [23]; hydrophobic silica is used in many fields such as the glass industry for its super hydrophobic behavior [24], which provides self cleaning and anti biofouling properties. Here we attempted to combine TEOS with one, two and all of the components in different concentrations to reach optimal biocide effectiveness and to identify the mechanism in the photosynthetic process.…”

Section: Introductionmentioning

confidence: 99%

Chlorophyll Fluorescence and Colorimetric Analysis for Monitoring the Algal Development on Biocide-Treated Stone

Eyssautier‐Chuine¹,

Vaillant‐Gaveau²,

Gommeaux³

et al. 2016

Open Conf. Proceed. J.

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Abstract:The present study used two non destructive technics, chlorophyll fluorescence and colorimetry to assess the Chlorella vulgaris growth on stone surface treated by experimental treatments for preventing biofouling. A protocol for laboratory tests was set up, consisting of inoculating treated slabs stone with a suspension of an algae culture (Chlorella vulgaris), that is a well known monument colonizing organism. The biofouling test was carried out under fluorescent lights for four weeks at room temperature which was 20°C and monitored by chlorophyll a fluorescence and colorimetry analysis. These techniques are rapid, non-invasive, and reliable.Treatments were introduced by mixing a tetraethoxysilane base with different ingredients: chitosan and/or silver nitrate for biocide effect and/or hydrophobic silica for water repellency.Results revealed four different patterns of algal development. The stones treated with the product containing chitosan and silver nitrate did not show any difference in their fluorescence signal as compared with the untreated stones (control). The stones treated with the product containing only silver nitrate showed biocide effect two weeks after the start of the experiment. The product containing silver nitrate, chitosan and hydrophobic silica at low concentrations completely inhibited algal development in the long term, the similar product with the same compounds at a higher concentration only delayed algal development by 1-2 weeks. This suggests that low concentrations of the products have a synergistic effect, that is lost if they occur in excess. In the present study, chlorophyll a fluorescence proved to be a valuable tool in detecting damage in the photosynthetic system of organisms and as a useful complement to other conventional measurements such as colorimetry.

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“…[44][45][46] Contudo, já há grupos de pesquisa que estão tentando aumentar a solubilidade de quitosanas em pHs neutros. 45,[51][52] Uma maneira é fazer modificações químicas na quitosana, garantindo uma carga positiva permanente, independentemente do pH do meio. 45,[52][53] Outra maneira é diminuir a massa molar do polímero, visto que oligômeros de quitosana possuem uma boa solubilidade a pH fisiológico.…”

Section: Motivaçãounclassified

Mecanismos de interação molecular de polieletrólitos antimicrobianos em membranas modelo por espectroscopia vibracional não linear

Rimoli¹

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AGRADECIMENTOSA Deus, por tudo e por cada segundo de vida.A toda minha família, pelo amor, exemplo, suporte e compreensão em todos os momentos. Em especial: Pai, obrigado por me ensinar a ser paciente e organizado; Mãe, obrigado por me ensinar a trabalhar com amor e determinação; Maninha, obrigado por nunca me deixar esquecer que é a companhia das pessoas queridas que faz a vida valer a pena. A todos os docentes dos quais fui aluno -muito obrigado pela dedicação e paciência.Aos funcionários do Serviço da Pós-Graduação do IFSC, Silvio, Ricardo e Priscila, pelo profissionalismo, paciência e atenção.Às meninas da biblioteca, Cris, Neusa e Ana, por sempre serem muito atenciosas, Enfim, a todos os que estiveram presentes nesta longa trajetória, que eu já tenha mencionado ou não: saibam que eu sou um pedacinho de cada um de vocês e eu sou muito grato pela nossa convivência e experiência de vida compartilhada. showed that both PAH and CO led to a small expansion of DPPC monolayers. However, for DPPG monolayers both polyelectrolytes led to significant expansion, with CO causing a more dramatic effect. SFG spectra in the CH stretch range showed that the lipid chain conformation remained always well ordered in all cases (slightly less ordered upon interacting with PAH), despite membrane expansion. This indicates that CO were inserted in the monolayer, forming islands of CO within the lipid film. Changes in the SFG spectral lineshape of OH stretches for the interfacial water molecules indicated that PAH adsorption on both DPPC and DPPG films was able to overcompensate the lipid negative charge and led to an overall surface charge reversal. The SFG spectra of the phosphate groups also indicated that in pure water the DPPC headgroups had a more ordered orientation than in the case of DPPG. Nevertheless, upon interaction with the cationic polyelectrolytes, the DPPG headgroups also become ordered, with a preferential orientation towards the subphase. Experiments with the antimicrobials injected in the subphase under a condensed Langmuir film indicated that CO were also capable of monolayer penetration, albeit causing a reduced film expansion. This comparison indicates that the choice of experimental methodology affects the outcome, but both may be complementary, as they may represent different phases of a biomembrane lifecycle.The detailed view provided here for the molecular interaction of these polyelectrolytes with lipid films may shed light on the mechanism of their biocidal activity and aid on a rational design of new antimicrobial polymers.

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Antibacterial activity of methylated chitosan and chitooligomer derivatives: Synthesis and structure activity relationships

Cited by 156 publications

References 49 publications

Biomedical Activity of Chitin/Chitosan Based Materials—Influence of Physicochemical Properties Apart from Molecular Weight and Degree of N-Acetylation

Biomedical Activity of Chitin/Chitosan Based Materials—Influence of Physicochemical Properties Apart from Molecular Weight and Degree of N-Acetylation

Chlorophyll Fluorescence and Colorimetric Analysis for Monitoring the Algal Development on Biocide-Treated Stone

Mecanismos de interação molecular de polieletrólitos antimicrobianos em membranas modelo por espectroscopia vibracional não linear

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