Fluorescent Chitosan Modified with Heterocyclic Aromatic Dyes

Chitosan is a valuable, functional, and biodegradable polysaccharide that can be modified to expand its applications. This work aimed to obtain chitosan derivatives with fluorescent properties. Three heterocyclic aromatic dyes (based on benzimidazole, benzoxazole, and benzothiazole) were synthesized...

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Autores principales: Halina Kaczmarek, Agnieszka Tafelska-Kaczmarek, Katarzyna Roszek, Joanna Czarnecka, Beata Jędrzejewska, Katarzyna Zblewska
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Publicado: MDPI AG 2021
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spelling oai:doaj.org-article:8c5496b0b96b4d088cc771f9da83f2932021-11-11T18:00:14ZFluorescent Chitosan Modified with Heterocyclic Aromatic Dyes10.3390/ma142164291996-1944https://doaj.org/article/8c5496b0b96b4d088cc771f9da83f2932021-10-01T00:00:00Zhttps://www.mdpi.com/1996-1944/14/21/6429https://doaj.org/toc/1996-1944Chitosan is a valuable, functional, and biodegradable polysaccharide that can be modified to expand its applications. This work aimed to obtain chitosan derivatives with fluorescent properties. Three heterocyclic aromatic dyes (based on benzimidazole, benzoxazole, and benzothiazole) were synthesized and used for the chemical modification of chitosan. Emission spectroscopy revealed the strong fluorescent properties of the obtained chitosan derivatives even at a low <i>N</i>-substitution degree of the dye. The effect of high-energy ultraviolet radiation (UV–C) on modified chitosan samples was studied in solution with UV–Vis spectroscopy and in the solid state with FTIR spectroscopy. Moreover, cytotoxicity towards three different cell types was evaluated to estimate the possibilities of biomedical applications of such fluorescent chitosan-based materials. It was found that the three new derivatives of chitosan were characterized by good resistance to UV–C, which suggests the possibility of using these materials in medicine and various industrial sectors.Halina KaczmarekAgnieszka Tafelska-KaczmarekKatarzyna RoszekJoanna CzarneckaBeata JędrzejewskaKatarzyna ZblewskaMDPI AGarticlechitosan modificationfluorescenceheterocyclic aromatic compoundsUV–C irradiationcytotoxicityTechnologyTElectrical engineering. Electronics. Nuclear engineeringTK1-9971Engineering (General). Civil engineering (General)TA1-2040MicroscopyQH201-278.5Descriptive and experimental mechanicsQC120-168.85ENMaterials, Vol 14, Iss 6429, p 6429 (2021)
institution DOAJ
collection DOAJ
language EN
topic chitosan modification
fluorescence
heterocyclic aromatic compounds
UV–C irradiation
cytotoxicity
Technology
T
Electrical engineering. Electronics. Nuclear engineering
TK1-9971
Engineering (General). Civil engineering (General)
TA1-2040
Microscopy
QH201-278.5
Descriptive and experimental mechanics
QC120-168.85
spellingShingle chitosan modification
fluorescence
heterocyclic aromatic compounds
UV–C irradiation
cytotoxicity
Technology
T
Electrical engineering. Electronics. Nuclear engineering
TK1-9971
Engineering (General). Civil engineering (General)
TA1-2040
Microscopy
QH201-278.5
Descriptive and experimental mechanics
QC120-168.85
Halina Kaczmarek
Agnieszka Tafelska-Kaczmarek
Katarzyna Roszek
Joanna Czarnecka
Beata Jędrzejewska
Katarzyna Zblewska
Fluorescent Chitosan Modified with Heterocyclic Aromatic Dyes
description Chitosan is a valuable, functional, and biodegradable polysaccharide that can be modified to expand its applications. This work aimed to obtain chitosan derivatives with fluorescent properties. Three heterocyclic aromatic dyes (based on benzimidazole, benzoxazole, and benzothiazole) were synthesized and used for the chemical modification of chitosan. Emission spectroscopy revealed the strong fluorescent properties of the obtained chitosan derivatives even at a low <i>N</i>-substitution degree of the dye. The effect of high-energy ultraviolet radiation (UV–C) on modified chitosan samples was studied in solution with UV–Vis spectroscopy and in the solid state with FTIR spectroscopy. Moreover, cytotoxicity towards three different cell types was evaluated to estimate the possibilities of biomedical applications of such fluorescent chitosan-based materials. It was found that the three new derivatives of chitosan were characterized by good resistance to UV–C, which suggests the possibility of using these materials in medicine and various industrial sectors.
format article
author Halina Kaczmarek
Agnieszka Tafelska-Kaczmarek
Katarzyna Roszek
Joanna Czarnecka
Beata Jędrzejewska
Katarzyna Zblewska
author_facet Halina Kaczmarek
Agnieszka Tafelska-Kaczmarek
Katarzyna Roszek
Joanna Czarnecka
Beata Jędrzejewska
Katarzyna Zblewska
author_sort Halina Kaczmarek
title Fluorescent Chitosan Modified with Heterocyclic Aromatic Dyes
title_short Fluorescent Chitosan Modified with Heterocyclic Aromatic Dyes
title_full Fluorescent Chitosan Modified with Heterocyclic Aromatic Dyes
title_fullStr Fluorescent Chitosan Modified with Heterocyclic Aromatic Dyes
title_full_unstemmed Fluorescent Chitosan Modified with Heterocyclic Aromatic Dyes
title_sort fluorescent chitosan modified with heterocyclic aromatic dyes
publisher MDPI AG
publishDate 2021
url https://doaj.org/article/8c5496b0b96b4d088cc771f9da83f293
work_keys_str_mv AT halinakaczmarek fluorescentchitosanmodifiedwithheterocyclicaromaticdyes
AT agnieszkatafelskakaczmarek fluorescentchitosanmodifiedwithheterocyclicaromaticdyes
AT katarzynaroszek fluorescentchitosanmodifiedwithheterocyclicaromaticdyes
AT joannaczarnecka fluorescentchitosanmodifiedwithheterocyclicaromaticdyes
AT beatajedrzejewska fluorescentchitosanmodifiedwithheterocyclicaromaticdyes
AT katarzynazblewska fluorescentchitosanmodifiedwithheterocyclicaromaticdyes
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