Teaching a Known Molecule New Tricks: Optical Cyanide Recognition by 2-[(9-Ethyl-9H-carbazol-3-yl)methylene]propanedinitrile in Aqueous Solution

Tang, Lijun; Zhao, Guizhe; Wang, Nannan

doi:10.5012/bkcs.2012.33.11.3696

Cited by 7 publications

(2 citation statements)

References 39 publications

(33 reference statements)

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“…This led to the development of numerous chemosensors based on the color change as well as fluorescence response produced owing to the disturbance created by the nucleophilic addition of cyanide anion on olefinic double bond of the respective conjugated systems. [33][34][35][36][37][38] In this regard, we have unitized one of the D-A system of present focus with cyanoacrylic moiety as potential cyanide binding site, viz. CAROT as a representative candidate for fluorometric sensing of cyanide ion.…”

Section: Introductionmentioning

confidence: 99%

Biological and Sensing Applications of a Few 1,3,4-Oxadiazole Based Donor-Acceptor Systems

et al. 2023

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1,3,4-Oxadiazole pharmacophore is still considered a viable biologically active scaffold for the synthesis of more effectual and broad-spectrum antimicrobial agents. Therefore, the present study is based on five 1,3,4-oxadiazole target structures, viz, CAROT, CAROP, CARON (D-A-D-A systems) and NOPON and BOPOB (D-A-D-A-D systems) bearing various bioactive heterocyclic moieties relevant to potential biological activities. Three of the compounds, CARON, NOPON and BOPOB were assessed in-vitro for their efficacy as antimicrobial agents against gram positive (Staphylococcus aureus and Bacillus cereus) and gram negative (Escherichia coli and Klebsiella pneumonia) bacteria; and two fungi, Aspergillus niger and Candida albicans; also, as an anti-tuberculosis agent against Mycobacterium tuberculosis.Most of the tested compounds displayed promising antimicrobial activity, especially CARON which was then analyzed for the minimum inhibitory concentration (MIC) studies. Similarly, NOPON portrayed the highest anti-TB activity among the studied compounds. Consequently, to justify the detected anti-TB activity of these compounds and to recognize the binding mode and important interactions between the compounds and the ligand binding site of the potential 2 target, these compounds were docked into the active binding site of cytochrome P450 CYP121 enzyme of Mycobacterium tuberculosis, 3G5H. The docking results were in good agreement with the result of in-vitro studies. In addition, all the five compounds were tested for their cell viability and have been investigated for cell labeling applications. To conclude, one of the target compounds, CAROT was used for the selective recognition of cyanide ion by 'turn-off' fluorescent sensing technique. The entire sensing activity was examined by spectrofluorometric method and MALDI spectral studies. The limit of detection obtained was 0.14 μM.

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Section: Introductionmentioning

confidence: 99%

Biological and Sensing Applications of a Few 1,3,4-Oxadiazole Based Donor-Acceptor Systems

et al. 2023

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“…This led to the development of numerous chemosensors based on the color change as well as uorescence response produced owing to the disturbance created by the nucleophilic addition of cyanide anion on ole nic double bond of the respective conjugated systems. [33][34][35][36][37][38] In this regard, we have unitized one of the D-A system of present focus with cyanoacrylic moiety as potential cyanide binding site, viz. CAROT as a representative candidate for uorometric sensing of cyanide ion.…”

Section: Introductionmentioning

confidence: 99%

A few 1,3,4-oxadiazole-phenothiazine based donor-acceptor systems as potential multifaceted bioactive compounds

Remya

Asha

Deepti

et al. 2022

Preprint

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1,3,4-Oxadiazole pharmacophore is still considered a viable biologically active scaffold for the synthesis of more effectual and broad-spectrum antimicrobial agents. Therefore, the present study is based on five 1,3,4-oxadiazole target structures, viz, CAROT, CAROP, CARON (D-A-D-A systems) and NOPON and BOPOB (D-A-D-A-D systems) bearing various bioactive heterocyclic moieties relevant to potential biological activities. Three of the compounds, CARON, NOPON and BOPOB were assessed in-vitro for their efficacy as antimicrobial agents against gram positive (Staphylococcus aureus and Bacillus cereus) and gram negative (Escherichia coli and Klebsiella pneumonia) bacteria; and two fungi, Aspergillus niger and Candida albicans; also, as an anti-tuberculosis agent against Mycobacterium tuberculosis. Most of the tested compounds displayed promising antimicrobial activity, especially CARON which was then analyzed for the minimum inhibitory concentration (MIC) studies. Similarly, NOPON portrayed the highest anti-TB activity among the studied compounds. Consequently, to justify the detected anti-TB activity of these compounds and to recognize the binding mode and important interactions between the compounds and the ligand binding site of the potential target, these compounds were docked into the active binding site of cytochrome P450 CYP121 enzyme of Mycobacterium tuberculosis, 3G5H. The docking results were in good agreement with the result of in-vitro studies. In addition, all the five compounds were tested for their cell viability and have been investigated for cell labeling applications. To conclude, one of the target compounds, CAROT was used for the selective recognition of cyanide ion by ‘turn-off’ fluorescent sensing technique. The entire sensing activity was examined by spectrofluorometric method and MALDI spectral studies. The limit of detection obtained was 0.14 µM.

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A targeted mitochondrial probe based on hemicyanine skeleton for the detection of cyanide ion and its application in seeds and test strips

et al. 2022

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Teaching a Known Molecule New Tricks: Optical Cyanide Recognition by 2-[(9-Ethyl-9H-carbazol-3-yl)methylene]propanedinitrile in Aqueous Solution

Cited by 7 publications

References 39 publications

Biological and Sensing Applications of a Few 1,3,4-Oxadiazole Based Donor-Acceptor Systems

Biological and Sensing Applications of a Few 1,3,4-Oxadiazole Based Donor-Acceptor Systems

A few 1,3,4-oxadiazole-phenothiazine based donor-acceptor systems as potential multifaceted bioactive compounds

A targeted mitochondrial probe based on hemicyanine skeleton for the detection of cyanide ion and its application in seeds and test strips

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