Selective sensing of cyanide in aqueous solution by quinone-indole ensembles – quantitative effect of substituents on the HBD property of the receptor moiety

Jayasudha, Palanisamy; Manivannan, Ramalingam; Ciattini, Samuele; Chelazzi, L.; Elango, Kuppanagounder P.

doi:10.1016/j.snb.2016.11.117

Cited by 24 publications

(10 citation statements)

References 44 publications

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“…This unique chemistry for indole makes it a potent and promising building block for various biological applications, notably for drug development . In this context, indole has been used to develop fluorescent conjugates and for sensing a wide range of analytes such as anions, more importantly acetate, fluoride, cyanide, and iodide …”

Section: Introductionmentioning

confidence: 99%

Recent chemo‐/biosensor and bioimaging studies based on indole‐decorated BODIPYs

2019

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BODIPY is an important fluorophores due to its enhanced photophysical and chemical properties including outstanding thermal/photochemical stability, intense absorption/emission profiles, high photoluminescence quantum yield, and small Stokes' shifts. In addition to BODIPY, indole and its derivatives have recently gained attention because of their structural properties and particularly biological importance, therefore these molecules have been widely used in sensing and biosensing applications. Here, we focus on recent studies that reported the incorporation of indole‐based BODIPY molecules as reporter molecules in sensing systems. We highlight the rationale for developing such systems and evaluate detection limits of the developed sensing platforms. Furthermore, we also review the application of indole‐based BODIPY molecules in bioimaging studies. This article includes the evaluation of indole‐based BODIPYs from synthesis to characterization and a comparison of the advantages and disadvantages of developed reporter systems, making it instructive for researchers in various disciplines for the design and development of similar systems.

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Section: Introductionmentioning

confidence: 99%

Recent chemo‐/biosensor and bioimaging studies based on indole‐decorated BODIPYs

2019

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“…18 It is worth noting that some 1,4-quinones have also found use as functional ligands for transition metals. [19][20][21][22] What's more, the Coenzyme Qn (CoQn) family, also named as the ubiquinones, has occupied a unique position in the design and synthesis of novel biologically active lead molecules that exert remarkable medicinal activity. 23 Besides of versatile properties, not surprisingly, ubiquinone participating in the cellular aerobic respiration process, 24 plastoquinone and phylloquinone serving as electron acceptors in electron transport chains in photosynthesis, and vitamin K participating coagulation process and preventing bleeding have also a 1,4-quinone motif.…”

Section: Introductionmentioning

confidence: 99%

“…18 It is worth noting that some 1,4-quinones have also found use as functional ligands for transition metals. 19–22…”

Section: Introductionmentioning

confidence: 99%

Natural-product-inspired design and synthesis of thiolated coenzyme Q analogs as promising agents against Gram-positive bacterial strains: insights into structure–activity relationship, activity profile, mode of action, and molecular docking

et al. 2022

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“…Organic functional groups sense cyanide ions both in the organic and aqueous medium. This includes the use of azine, [28] azo, [29] benzimidazole, [30] benzothiozole, [31,32] BODIFY, [33] coumarin, [34] hemicyanin, [35], imine, [36] indole, [37] malononitrile, [38] napthelene, [39,40] naphthalimides, [41] pyrene [42] and quinolone [43] based functional groups by different mechanisms with a detection range of nano to micro-molar.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Optimization of Diphenyl Ether‐Based Receptors for the Selective Detection of Cyanide Ions in Neutral Semi‐Aqueous Medium

Kumar

Chhibber

2022

ChemistrySelect

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The discharge of toxic cyanide ions in the environment and their uptake by life is inevitable due to industrialization. Therefore, its detection below the permissible limit is significant. Diphenyl ether‐based chromophores have been synthesized and optimized to highlight the proton abstraction mechanism for detecting anions. Absorption studies in the presence of different solvents (H2O, MeOH, ACN, DMSO, CHCl3 and semi‐aqueous ACN) and pH (10 to 4) confirmed the proton abstraction mechanism validated using 1H NMR titration, IR studies and DFT calculations. The effect of substituents on the diphenyl ether motifs highlighted the selectivity of anions under different solvent conditions. Finally, compound‐2 [2‐(2‐methoxyphenoxy)‐5‐nitrobenzoic acid] and compound‐2 c [3‐methoxy‐4‐(2‐nitrophenoxy) benzoic acid] in ACN medium detected F− (280 nM, 17 μM) AcO− (41 nM, 40 μM) and CN− (50 nM. 1.5 μM) ions in nM and μM range respectively. However, the semi‐aqueous medium (5 % water in ACN) gave selective detection of the CN− ion up to 100 nM for the compound‐2 in a 1 : 1 stoichiometry. The use of an aqueous medium in the case of compound‐2 c did not show detection for any of the ions.

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Selective sensing of cyanide in aqueous solution by quinone-indole ensembles – quantitative effect of substituents on the HBD property of the receptor moiety

Cited by 24 publications

References 44 publications

Recent chemo‐/biosensor and bioimaging studies based on indole‐decorated BODIPYs

Recent chemo‐/biosensor and bioimaging studies based on indole‐decorated BODIPYs

Natural-product-inspired design and synthesis of thiolated coenzyme Q analogs as promising agents against Gram-positive bacterial strains: insights into structure–activity relationship, activity profile, mode of action, and molecular docking

Synthesis and Optimization of Diphenyl Ether‐Based Receptors for the Selective Detection of Cyanide Ions in Neutral Semi‐Aqueous Medium

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