Chitosan As a Protective Matrix for the Squaraine Dye

Overview

Journal Materials (Basel)

Publisher MDPI

Date 2021 Apr 3

PMID 33801523

Citations 3

Authors

Halina Kaczmarek

Patryk Rybczynski

Piotr Macczak

Aleksander Smolarkiewicz-Wyczachowski

Marta Ziegler-Borowska

Affiliations

Soon will be listed here.

Abstract

Chitosan was used as a protective matrix for the photosensitive dye-squaraine (2,4-bis[4-(dimethylamino)phenyl]cyclobutane-1,3-diol). The physicochemical properties of the obtained systems, both in solution and in a solid-state, were investigated. However, it was found that diluted chitosan solutions with a few percent additions of dye show an intense fluorescence, which is suppressed in the solid-state. This is related to the morphology of the heterogeneous modified chitosan films. The important advantage of using a biopolymer matrix is the prevention of dye degradation under the influence of high energy ultraviolet (UV) radiation while the dye presence improves the chitosan heat resistance. It is caused by mutual interactions between macromolecules and dye. Owing to the protective action of chitosan, the dye release in liquid medium is limited. Chitosan solutions with a few percent additions of squaraine can be used in biomedical imaging thanks to the ability to emit light, while chitosan films can be protective coatings resistant to high temperatures and UV radiation.

Citing Articles

Chitosan Composites Containing Boron-Dipyrromethene Derivatives for Biomedical Applications.

Smolarkiewicz-Wyczachowski A, Kaczmarek H, Piskorz J, Nowak P, Ziegler-Borowska M Int J Mol Sci. 2023; 24(2).

PMID: 36675294 PMC: 9860782. DOI: 10.3390/ijms24021770.

Fluorescent Chitosan Modified with Heterocyclic Aromatic Dyes.

Kaczmarek H, Tafelska-Kaczmarek A, Roszek K, Czarnecka J, Jedrzejewska B, Zblewska K Materials (Basel). 2021; 14(21).

PMID: 34771955 PMC: 8585458. DOI: 10.3390/ma14216429.

Towards a Bioactive Food Packaging: Poly(Lactic Acid) Surface Functionalized by Chitosan Coating Embedding Clove and Argan Oils.

Stoleru E, Vasile C, Irimia A, Brebu M Molecules. 2021; 26(15).

PMID: 34361651 PMC: 8348099. DOI: 10.3390/molecules26154500.

References

Zu Y, Bi J, Yan H, Wang H, Song Y, Zhu B . Nanostructures Derived from Starch and Chitosan for Fluorescence Bio-Imaging. Nanomaterials (Basel). 2017; 6(7). PMC: 5224609. DOI: 10.3390/nano6070130. View

Wei S, Ching Y, Chuah C . Synthesis of chitosan aerogels as promising carriers for drug delivery: A review. Carbohydr Polym. 2020; 231:115744. DOI: 10.1016/j.carbpol.2019.115744. View

Zajac A, Hanuza J, Wandas M, Dyminska L . Determination of N-acetylation degree in chitosan using Raman spectroscopy. Spectrochim Acta A Mol Biomol Spectrosc. 2014; 134:114-20. DOI: 10.1016/j.saa.2014.06.071. View

Bruck S, Krause C, Turrisi R, Beverina L, Wilken S, Saak W . Structure-property relationship of anilino-squaraines in organic solar cells. Phys Chem Chem Phys. 2013; 16(3):1067-77. DOI: 10.1039/c3cp54163k. View

Ahmed F, Soliman F, Adly M, Soliman H, El-Matbouli M, Saleh M . Recent progress in biomedical applications of chitosan and its nanocomposites in aquaculture: A review. Res Vet Sci. 2019; 126:68-82. DOI: 10.1016/j.rvsc.2019.08.005. View

Ilina K, MacCuaig W, Laramie M, Jeouty J, McNally L, Henary M . Squaraine Dyes: Molecular Design for Different Applications and Remaining Challenges. Bioconjug Chem. 2019; 31(2):194-213. PMC: 7845514. DOI: 10.1021/acs.bioconjchem.9b00482. View

Yi R, Das P, Lin F, Shen B, Yang Z, Zhao Y . Fluorescence enhancement of small squaraine dye and its two-photon excited fluorescence in long-term near-infrared I&II bioimaging. Opt Express. 2019; 27(9):12360-12372. DOI: 10.1364/OE.27.012360. View

Wei Y, Hu X, Shen L, Jin B, Liu X, Tan W . Dicyanomethylene Substituted Benzothiazole Squaraines: The Efficiency of Photodynamic Therapy In Vitro and In Vivo. EBioMedicine. 2017; 23:25-33. PMC: 5605326. DOI: 10.1016/j.ebiom.2017.08.010. View

Huang H, Liu F, Chen S, Zhao Q, Liao B, Long Y . Enhanced fluorescence of chitosan based on size change of micelles and application to directly selective detecting Fe³⁺ in human serum. Biosens Bioelectron. 2012; 42:539-44. DOI: 10.1016/j.bios.2012.10.098. View

10.

Cao Y, Tan Y, Wong Y, Jie Liew M, Venkatraman S . Recent Advances in Chitosan-Based Carriers for Gene Delivery. Mar Drugs. 2019; 17(6). PMC: 6627531. DOI: 10.3390/md17060381. View

11.

Cunha-Reis C, El Haj A, Yang X, Yang Y . Fluorescent labeling of chitosan for use in non-invasive monitoring of degradation in tissue engineering. J Tissue Eng Regen Med. 2011; 7(1):39-50. DOI: 10.1002/term.494. View

12.

Calixto G, de Annunzio S, Victorelli F, Frade M, Ferreira P, Chorilli M . Chitosan-Based Drug Delivery Systems for Optimization of Photodynamic Therapy: a Review. AAPS PharmSciTech. 2019; 20(7):253. DOI: 10.1208/s12249-019-1407-y. View

13.

Mandim F, Graca V, Calhelha R, Machado I, Ferreira L, Ferreira I . Synthesis, Photochemical and In Vitro Cytotoxic Evaluation of New Iodinated Aminosquaraines as Potential Sensitizers for Photodynamic Therapy. Molecules. 2019; 24(5). PMC: 6429055. DOI: 10.3390/molecules24050863. View

14.

Ahmed K, Khan M, Siddiqui H, Jahan A . Chitosan and its oligosaccharides, a promising option for sustainable crop production- a review. Carbohydr Polym. 2019; 227:115331. DOI: 10.1016/j.carbpol.2019.115331. View

15.

Ramaiah D, Eckert I, Arun K, Weidenfeller L, Epe B . Squaraine dyes for photodynamic therapy: mechanism of cytotoxicity and DNA damage induced by halogenated squaraine dyes plus light (>600 nm). Photochem Photobiol. 2004; 79(1):99-104. View

16.

Hai T, Sugimoto R . Fluorescence control of chitin and chitosan fabricated surface functionalization using direct oxidative polymerization. RSC Adv. 2022; 8(13):7005-7013. PMC: 9078334. DOI: 10.1039/c8ra00287h. View

17.

Lee H, Kim M, Yoon Y, Park W . Fluorescent Property of Chitosan Oligomer and Its Application as a Metal Ion Sensor. Mar Drugs. 2017; 15(4). PMC: 5408251. DOI: 10.3390/md15040105. View

18.

Cicciu M, Fiorillo L, Cervino G . Chitosan Use in Dentistry: A Systematic Review of Recent Clinical Studies. Mar Drugs. 2019; 17(7). PMC: 6669505. DOI: 10.3390/md17070417. View

19.

Diab M, El-Sonbati A, Bader D . Thermal stability and degradation of chitosan modified by benzophenone. Spectrochim Acta A Mol Biomol Spectrosc. 2011; 79(5):1057-62. DOI: 10.1016/j.saa.2011.04.019. View