Synthesis and spectroscopic properties of 4-amino-1,8-naphthalimide derivatives involving the carboxylic group: a new molecular probe for ZnO nanoparticles with unusual fluorescence features

Bekere, Laura; Gachet, D.; Lokshin, Vladimir; Marine, W.; Khodorkovsky, Vladimir

doi:10.3762/bjoc.9.147

Cited by 23 publications

(15 citation statements)

References 18 publications

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“…Moreover, dendrimers with amino-1,8-naphthalimide molecules in their structures were proposed as tunable organic light-emitting diodes [62]. Bekere et al [63] evaluated the possibility of using 4substituted 1,8-naphthalimides as sensitive molecular probes for ZnO nanoparticles. In this case, the nature of the interaction and how the molecule was adsorbed onto the nanoparticle were not studied.…”

Section: Biological Effect Of Ann Cnps and Ann-cnp Towards Anabaena mentioning

confidence: 99%

Physicochemical and biological interactions between cerium oxide nanoparticles and a 1,8-naphthalimide derivative

Pulido-Reyes

Martín

Coronado

et al. 2017

Journal of Photochemistry and Photobiology B: Biology

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Cerium (Ce) oxide nanoparticles (CNPs) have attracted attention due to their high bioactivity and unique redox-chemistry. The oxygen vacancies at the surface of the nanoparticle explain the autocatalytic properties of CNPs in which the Ce atoms occupy the center of the oxygen vacancies surrounded by Ce atoms. Until now, CNPs have been associated with organic molecules at the synthesis stage to extend their applications or improve their stability. However, there is a lack of information regarding the post-synthesis interaction of CNPs and organic molecules that could enhance or induce new properties. Due to their unique optical properties and their many uses in different areas such as supramolecular chemistry or biomedicine, we have chosen a derivative from the family of naphthalimides (the 4-amino-1,8-naphthalimide-N-substituted; ANN) to study the interaction with different CNPs (CNP1-4) and their joint bioactivity compared to that of the same compounds alone. ANN-CNP complexes were formed as revealed by spectroscopic studies, but, the interaction was markedly different depending on the physicochemical properties of CNPs and their surface content of Ce sites. The ANN adsorption on all CNPs involved the amino group in the naphthalene moiety as shown by NMR spectroscopy, while the pyrrolidine ring was mainly involved in the specific interaction between ANN and CNP1. The biological effect of each CNP and ANN individually and forming complexes was assessed using a bioluminescent model bacterium. The results showed that ANN and CNP with the higher content of surface Ce (CNP1) when combined acted additively towards the used model organism. In the opposite, ANN-CNP2, ANN-CNP3 and ANN-CNP4 complexes were antagonistic when the nanoparticles dominated the mixture. The results of this study contribute to expand the knowledge of the interaction between nanoparticles and organic molecules which may be useful for understanding the behavior of nanoparticles in complex matrices.

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Section: Biological Effect Of Ann Cnps and Ann-cnp Towards Anabaena mentioning

confidence: 99%

Physicochemical and biological interactions between cerium oxide nanoparticles and a 1,8-naphthalimide derivative

Pulido-Reyes

Martín

Coronado

et al. 2017

Journal of Photochemistry and Photobiology B: Biology

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“…1,8‐Naphthalimide derivatives have been reported to be used in a variety of applications due to their strong electroactivity, fluorescence and photostability . They have been used in many fields such as fluorescent sensors, switchers and electroluminescent material .…”

Section: Introductionmentioning

confidence: 99%

“…[27][28][29][30] 1,8-Naphthalimide derivatives have been reported to be used in a variety of applications due to their strong electroactivity, fluorescence and photostability. 31 They have been used in many fields such as fluorescent sensors, switchers and electroluminescent material. 32 They have also been used as fluorescent markers and molecular probes in biotechnology and as sensitive electro-optic materials in solar cells and organic field-effect transistors.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and electropolymerization of a multifunctional naphthalimide clicked carbazole derivative

Coban

Ayrancı

2019

Polymer International

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In this study, a multifunctional ‘clicked’ naphthalimide carbazole derivative (CNaP) was synthesized via Huisgen 1,3‐dipolar cycloaddition reaction. Combining carbazole as an electroactive group with naphthalimide as a fluorescence group via click chemistry imparts multifunctional properties to this unique structure. CNaP was characterized via Fourier transform IR, 13C and 1H NMR spectroscopy as well as fluorescence and electrochemical measurements. The electrochemical polymerization of the CNaP monomer was carried out in acetonitrile/boron trifluoride diethyl etherate (2:1) (v/v) by the cyclic voltammetry technique. The resulting polycarbazole‐derived conductive polymer was characterized via optical and electrochemical measurements. PCNaP displayed multi‐electrochromism behaviour with good optical contrast (41% at 693 nm) and switching time (1.92 s at 693 nm). These results demonstrate that the new ‘clicked’ fluorescent, polycarbazole‐derived conductive polymer can be used in various applications such as electrochemical/optical sensors and electrochromic and fluorescence imaging devices. © 2019 Society of Chemical Industry

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“…However, it has been shown that dyes based on rhodamine have poor photostability [41,49]. Fluorescent dyes based on 1,8-Naphthalimide with strong photostability, tunable photophysical properties as well as low cytotoxicity make them as an ideal alternative fluorescent dyes in biomedical application [50][51][52][53]. Therefore, the objective of this research was to use the excellent photophysical properties of naphthalimide dyes and biocompatibility of PCU simultaneously, and design and synthesis novel fluorescent polymeric biomaterials (PCU) based on naphthalimide dye and study their physical, mechanical and blood-compatibility.…”

mentioning

confidence: 99%

Evaluation of the Mechanical Properties and Blood Compatibility of Polycarbonate Urethane and Fluorescent Self-Colored Polycarbonate Urethane as Polymeric Biomaterials

Zamani¹,

Yahyaei²

2020

Preprint

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<p>Fluorescent polymeric biomaterials have got significant attention due to their promising applications in biomedical fields such as labeling, monitoring, diagnostics, imaging and tracking. Polycarbonate urethane (PCU) and 1,8-naphthalimide based fluorescent dyes separately have been studied and shown great biocompatibility and physical properties. Therefore, in this work we have taken advantage of excellent fluorescence properties of naphthalimide dye and biocompatibility of PCU, and covalently attached the fluorescent dye to the PCU (self-colored PCU). Covalent attachment can increase the stability of the dye in the biomedical applications especially when biomaterials are in contact with blood and can inhibit the release of the dye to surrounding media. DMTA, AFM, and contact angle measurement were used to study the mechanical and morphological properties of the self-colored PCU and results showed that incorporation of the dye to the PCU did not change the mechanical and morphological properties of the PCU. In addition, MTT assay, hemolysis assay, PT and aPTT assays as well as protein adsorption assay was used to evaluate the blood compatibility of PCU and self-colored PCU and results indicated great bio and blood compatibility of these materials. These great mechanical and blood compatibility properties of the self-colored PCU as well as their excellent fluorescent properties suggested that, these materials could be an ideal candidates to be use in biomedical applications in which non-invasive and non-destructive fluorescent based techniques are required. </p>

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Synthesis and spectroscopic properties of 4-amino-1,8-naphthalimide derivatives involving the carboxylic group: a new molecular probe for ZnO nanoparticles with unusual fluorescence features

Cited by 23 publications

References 18 publications

Physicochemical and biological interactions between cerium oxide nanoparticles and a 1,8-naphthalimide derivative

Physicochemical and biological interactions between cerium oxide nanoparticles and a 1,8-naphthalimide derivative

Synthesis and electropolymerization of a multifunctional naphthalimide clicked carbazole derivative

Evaluation of the Mechanical Properties and Blood Compatibility of Polycarbonate Urethane and Fluorescent Self-Colored Polycarbonate Urethane as Polymeric Biomaterials

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