Characterization of Molecular Complexes of 1,4-Naphthoquinone Derivatives

Singh, W. Marjit; Baruah, Jubaraj B.

doi:10.1007/s10870-011-0024-8

Cited by 5 publications

(1 citation statement)

References 38 publications

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“…The thioglycolic-containing compounds were synthesized by treating 2 with either thioglycolic acid or thioglycolic methyl ester in methanol resulting in 23 and 24, respectively, in low overall yields (18 -21%). 39,40 In addition, compound 6 was obtained through derivatizing 2 with ammonium chloride following previously reported methods. 30 Finally, several attempts were made to synthesize 25 from 15 using methyl iodide and silver (I) oxide, however it yielded a mixture of inseparable products -25 and 4methoxynaphthalene-1,2-dione.…”

Section: Resultsmentioning

confidence: 99%

Identifying Key Properties that Drive Redox Mediator Activity in Lactiplantibacillus plantarum

Blackburn,

Alba,

Porokhin

et al. 2024

Preprint

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Lactiplantibacillus plantarum is known to utilize exogenous small molecule quinone mediators to perform extracellular electron transfer (EET), which allows it to produce a detectable current in a bioelectrochemical system. Utilization of quinone mediators by L. plantarum requires a type-II NADH dehydrogenase (Ndh2), however small structural variations in the core of 1,4-naphthoquinone EET mediators yields significantly different current outputs. Herein, we assembled a library of 30 naphthoquinone-based EET mediators in order to probe the important physicochemical properties and biochemical interactions that are responsible for Ndh2-dependent EET in L. plantarum. The library was designed with inspiration from naturally-occurring metabolites, and was assembled focused on structural modifications that diversified polarity (cLogP), reduction potential (Eo), and Ndh2 binding affinity as these properties are hypothesized to be driving EET activity. In general, Ndh2-dependent EET activity in an iron(III) oxide nanoparticle assay significantly correlates to the mediator's polarity and binding affinity. Five mediators were analyzed in BESs with L. plantarum and each generated Ndh2-dependent current with low background signal. Importantly, the amine containing mediators yielded incredibly stable current output over the course of the experiment (up to 5 days). These findings increase our understanding of structure-activity relationships for quinone-mediated EET and provide mediators for bioelectronic sensing.

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Section: Resultsmentioning

confidence: 99%

Identifying Key Properties that Drive Redox Mediator Activity in Lactiplantibacillus plantarum

Blackburn,

Alba,

Porokhin

et al. 2024

Preprint

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One-pot synthesis, characterization, and antioxidant capacity of sulfur- and oxygen-substituted 1,4-naphthoquinones and a structural study

et al. 2015

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In the present study, we reported the onepot synthesis of S,S-and S,O-substituted 1,4-naphthoquinones, their structural studies, and investigation of their antioxidant activity. The multicomponent reactions of 2,3-dichloro-1,4-naphthoquinone with sulfur-and oxygencontaining nucleophiles were investigated to obtain highly functionalized S,S-and S,O-substituted 1,4-naphthoquinone derivatives. All new compounds were characterized on the basis of 1 H, 19 F, and 13 C nuclear magnetic resonance spectroscopy, mass spectrometry, and Fourier transform infrared spectroscopy. Crystal structure of 2,3-dihydro-2-(hydroxymethyl)naphtho[2,3-b]-1,4-oxathiin-5,10-dione was determined by X-ray diffraction method. The synthesized compounds were screened for their antioxidant capacity and free radical scavenging activity using the cupric reducing antioxidant capacity method and DPPH method, respectively. 3-Chloro-2-[3-(3-chloro-1,4-dihydro-1,4-dioxonaphthalen-2-yloxy)propylsulfanyl]-1,4-naphthoquinone shows the highest antioxidant capacity with 0.63 cupric reducing antioxidant capacity-trolox equivalent antioxidant capacity coefficient. Graphical abstract

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Electronic Structure, Electronic Charge Density and Optical Properties of 3-methyl-1,4-dioxo-1, 4-dohydronaphthalen-2-yl- sulfanyl (C13H10O4S)

Sikander

Bíla

Kamarudin

2014

International Journal of Electrochemical Science

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Characterization of Molecular Complexes of 1,4-Naphthoquinone Derivatives

Cited by 5 publications

References 38 publications

Identifying Key Properties that Drive Redox Mediator Activity in Lactiplantibacillus plantarum

Identifying Key Properties that Drive Redox Mediator Activity in Lactiplantibacillus plantarum

One-pot synthesis, characterization, and antioxidant capacity of sulfur- and oxygen-substituted 1,4-naphthoquinones and a structural study

Electronic Structure, Electronic Charge Density and Optical Properties of 3-methyl-1,4-dioxo-1, 4-dohydronaphthalen-2-yl- sulfanyl (C13H10O4S)

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