Synthesis, binding ability, and cell cytotoxicity of fluorescent probes for <scp>l</scp>‐arginine detection based on naphthalene derivatives: Experiment and theory

Li, Jie; Zhang, Yang; Chen, Yanmei; Shang, Xuefang; Ti, Tongyu; Chen, Hongli; Wang, Tianyun; Zhang, Jinlian; Xu, Xiufang

doi:10.1002/jmr.2657

Cited by 8 publications

(2 citation statements)

References 37 publications

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“…The limit of detection obtained with LOD = kS b / a , where LOD is the limit of detection; k = 3 as recommended in spectral analysis, and S b is the standard deviation of the blank signal, and a is the sensitivity of the sensor . The limit of detection of 15 nM is lower than or the same as that of other fluorescence methods. − …”

Section: Resultsmentioning

confidence: 97%

Rotation Restricted Emission and Antenna Effect in Single Metal–Organic Frameworks

2019

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Aggregation induced-emission (AIE) and antenna effects are important luminescence behaviors. Thus, investigating their emission mechanisms and revealing their behaviors have become critical but challenging. Here we design and prepare metal–organic frameworks (MOFs) with an AIE ligand (i.e., tetrakis(4-carboxyphenyl)pyrazine (L1)) and Ln3+ ions (including Eu3+, Tb3+, and Gd3+). The emission from L1 is gradually enhanced during the formation of the MOFs because coordination restricts the intramolecular rotation. Thus, the emission is called as coordination-induced emission (CIE) with the same restriction of intramolecular rotation mechanism as AIE. Meanwhile, benzene rings twist to adapt to the MOFs’ rigid structure, so the emission blueshifts gradually, as an additional evidence of CIE. Both AIE and CIE are “rotation-restricted emission (RRE)”. Eu3+ ions exhibit the strongest emission with gradually enhanced intensity during the formation of L1-Eu MOF. Combined with emission properties from Tb3+ and Gd3+ ions, the antenna effect is verified. We also validate the conditions for the efficient sensitization of Ln3+ ions experimentally and refresh the threshold value of the energy gap between triplet state of a ligand and excited state of Ln3+ ions to 3000 cm–1. Thus, RRE and antenna effects are revealed and validated simultaneously. Because CIE of L1 and antenna effect emission from Eu3+ ions are enhanced simultaneously as strong dual emissions, ratiometric fluorescence detection is realized with the detection of arginine as a model. Our results incorporate AIE and CIE into RRE, which provides explicit information for the construction and application of emission systems with AIE ligands as building blocks. MOFs are also extended to explore the emission mechanism and the energy transfer between ligands and metal ions.

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Section: Resultsmentioning

confidence: 97%

Rotation Restricted Emission and Antenna Effect in Single Metal–Organic Frameworks

2019

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“…[19] Copper(II) complexes with L-arg present strikingly good biological activity [20] because of structural similarities between L-arginine and two natural antibiotics: netropsin and distamycin. [21][22][23][24][25][26][27][28][29][30][31] Both antibiotics bind to the minor groove of double-stranded DNA reaching adenine-thymine base pairs, thus regulating the process of replication and transcription. This implies their antimicrobial and anticancer activity.…”

Section: Introductionmentioning

confidence: 99%

L‐argininato copper(II) complexes in solution exert significant selective anticancer and antimicrobial activities

Wojciechowska

Szuster‐Ciesielska

Sztandera

et al. 2020

Applied Organom Chemis

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A search for new drugs that overcome the multidrug resistance of microorganisms or are effective against cancer cells prompted us to investigate the binary and ternary Cu(II) complexes containing L-arginine, [CuCl(L-Arg)(phen)] Cl•2H 2 O (phen = 1,10-phenanthroline) (1) and [Cu(L-Arg) 2 (H 2 O)]C 2 O 4 •6H 2 O (2), for which crystal and molecular structures were characterized previously. In order to discuss the biological function, the complexes have been screened for their antitumor activity against A549 (human lung cancer cells), HepG2 (human liver hepatocellular carcinoma cells) and antimicrobial activity. To identify the complexes forms existing in the solutions of 1 and 2 crystals, the results obtained from EPR, NIR-Vis-UV and MS (mass spectrometry) measurements were correlated with those from analysis of potentiometric titration of Cu(II)-L-Arg and Cu(II)-L-Arg-phen systems. This comprehensive study indicated that the [Cu(L-Arg)(phen)] 2+ and [Cu(L-Arg) 2 ] 2+ species are dominant in the solution. Complexes 1 and 2 were found to present specific liganddependent cytotoxic and antiproliferative potential against cancer cells. They also show antibacterial activity against Gram-positive and Gram-negative bacteria as well as display antifungal properties.

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Synthesis of Substituted Naphthalenes by 1,4‐Palladium Migration Involved Annulation with Internal Alkynes

Wei

Feng

et al. 2018

Chin. J. Chem.

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Synthesis, binding ability, and cell cytotoxicity of fluorescent probes for l‐arginine detection based on naphthalene derivatives: Experiment and theory

Cited by 8 publications

References 37 publications

Rotation Restricted Emission and Antenna Effect in Single Metal–Organic Frameworks

Rotation Restricted Emission and Antenna Effect in Single Metal–Organic Frameworks

L‐argininato copper(II) complexes in solution exert significant selective anticancer and antimicrobial activities

Synthesis of Substituted Naphthalenes by 1,4‐Palladium Migration Involved Annulation with Internal Alkynes

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