Fluorescent imino and secondary amino chitosans as potential sensing biomaterials

Jatunov, Sorel; Franconetti, Antonio; Prado‐Gotor, Rafael; Heras, Ángeles; Mengíbar, Marian; Cabrera‐Escribano, Francisca

doi:10.1016/j.carbpol.2015.01.061

Cited by 19 publications

(10 citation statements)

References 29 publications

(20 reference statements)

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“…Nevertheless benzothiazole exhibits the following resonance signals: C 2 (δ188), C 8 (δ180). Phenolimine ring exhibits a peak at 159 ppm and a prominent peak appears at 121 ppm for others aromatic carbon –…”

Section: Resultsmentioning

confidence: 99%

Sugar‐Based Self‐Assembly of Hydrogel Nanotubes Manifesting ESIPT: Theoretical Insight and Application in Live Cell Imaging

et al. 2018

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A biopolymeric hydrogel nanotubes (BTHBC) using 3-(benzo [d] thiazol-2-yl)-2-hydroxybenzaldehyde and chitosan have been synthesized which exhibits excited state intramolecular proton transfer (ESIPT) in both gel and solution phase. The optimized spatial structure of the monomer of BTHBC having lower energy (Energy: À1085688.464 kcal/mol) is found to be planar. FE-SEM analysis reveals that the spherical assemblies (20-100 nm) preceded gelation. Upon aging, gelation can be observed owing to the fusion of these spherical aggregates into nanotubes (200-500 nm). DFT study of BTHBC establishes that the migration of H atom from phenolic -OH group to the nitrogen of 2-(2' Hydroxyphenyl)benzothiazole (HBT) moiety is more feasible than the imine nitrogen of chitosan. The fluorescence lifetime of BTHBC is found to increase remarkably in gel phase compared to its aqueous solution. Both the cellular uptake and cell imaging efficiency suggest that the biocompatible nature of the hydrogel permits easy access of maximum number of molecules into the cells which causes enhancement of the fluorescence intensity of the cells.

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Section: Resultsmentioning

confidence: 99%

Sugar‐Based Self‐Assembly of Hydrogel Nanotubes Manifesting ESIPT: Theoretical Insight and Application in Live Cell Imaging

et al. 2018

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“…Once tacrine derivatives were obtained, they were linked to the biopolymer through amino group of chitosan obtaining different bridges between chitosan and tacrine, in the same way that other types of chitosan derivatives have been obtained by our research group. 6,7 Starting polymeric material was characterized to obtain the degree of deacetylation (DD = 84%) and molecular weight (Mw = 87875 g· mol -1 ). Both parameters are the essential fingerprint for polymers characterization.…”

Section: Scheme 2 Synthesis Of Tacrine Derivatives By Methodology Bmentioning

confidence: 99%

New Tacrine derivatives and Tacrine-Chitosan systems for application against degenerative diseases

Carrillo

Franconetti-García

Cabrera‐Escribano

2019

Proceedings of the 23rd International Electronic Conference on Synthetic Organic Chemistry

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Our research focuses on the synthesis of new tacrine derivatives with an expected similar or higher inhibitory activity of AChE and BuChE than commercial tacrine and hybrids tacrine-chitosan derivatives with tunable biological properties by reaction of the biopolymer with the different tacrine derivatives synthesized. All new compounds have been characterized by NMR techniques both in solution and in solid state.

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“…Chitosan is a non-toxic, biocompatible, and biodegradable linear polysaccharide of randomly distributed β(1→4) linked D-glucosamine (>60%) and N-acetyl-Dglucosamine. It is obtained from the alkaline deacetylation of chitin and has emerged as a valuable polymer with several applications (Ravi Kumar, Muzzarelli, Muzzarelli, Sashiwa, & Domb, 2004), such as solvent sensing (Jatunov et al, 2015), non-lineal optics (Franconetti, Contreras-Bernal, Prado-Gotor, & Cabrera-Escribano, 2015), chiral recognition of enantiomers (Jafari, Tashkhourian, & Absalan, 2018), including carbamates (Bai, et al, 2017) and ureidyl derivatives (Wang, Xi, Chen, Huang, & Bai, 2017), and catalysis (Dekamin, Azimoshan, & Ramezani, 2013;El Kadib, 2015;Mahé, Brière, & Dez, 2015). From a catalytic perspective, chitosan can be used following two strategies, that is, directly as a heterogeneous catalyst or as a platform supporting the corresponding organocatalyst.…”

Section: Introductionmentioning

confidence: 99%

Preparation of chitosan-supported urea materials and their application in some organocatalytic procedures

Gonzalo

Franconetti

Fernández

et al. 2018

Carbohydrate Polymers

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An efficient and mild procedure was developed for the preparation of three chitosan-supported ureas containing electron-withdrawing groups. These catalysts were characterized and employed as organocatalysts in different transformations, including the enantioselective cyanosilylation of α-ketoesters and aldehydes, the asymmetric addition of formaldehyde tert-butyl hydrazone to prochiral α-ketoesters and a Friedel-Crafts reaction. Several parameters that can affect the activity and selectivity of the reactions were analysed. The supported catalysts can be reused for more than 10 cycles with only a small loss in their properties. Finally, theoretical DFT calculations were carried out to interpret the results of the catalysed reactions.

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Fluorescent imino and secondary amino chitosans as potential sensing biomaterials

Cited by 19 publications

References 29 publications

Sugar‐Based Self‐Assembly of Hydrogel Nanotubes Manifesting ESIPT: Theoretical Insight and Application in Live Cell Imaging

Sugar‐Based Self‐Assembly of Hydrogel Nanotubes Manifesting ESIPT: Theoretical Insight and Application in Live Cell Imaging

New Tacrine derivatives and Tacrine-Chitosan systems for application against degenerative diseases

Preparation of chitosan-supported urea materials and their application in some organocatalytic procedures

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