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Synthesis of 1,2-phenylenediamine capturing molecule for the detection of diacetyl.

ABSTRACT: Here we describe the design of 1,2-phenylenediamine capturing molecule and the synthesis steps necessary for its preparation. The designed 1,2-phenylenediamine derivative is able to capture diacetyl in solution, as shown by ESIMS, forming a chemical adduct, 1-4-quinoxaline. The methyl esters of diacetyl-adduct (DAA) and pentanedione-adduct (PDA) are incorporated to the lysines in BSA and the conjugate used for antibody screening and selection. In the research article is described an enzyme-linked immunosorbent assay developed to detect and quantify diacetyl in complex media.

SUBMITTER: Marri L

PROVIDER: S-EPMC5647469 | biostudies-literature | 2017 Dec

REPOSITORIES: biostudies-literature

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Synthesis of 1,2-phenylenediamine capturing molecule for the detection of diacetyl.

Marri Lucia L Jansson Anita M AM Christensen Caspar E CE Hindsgaul Ole O

Data in brief 20171006

Here we describe the design of 1,2-phenylenediamine capturing molecule and the synthesis steps necessary for its preparation. The designed 1,2-phenylenediamine derivative is able to capture diacetyl in solution, as shown by ESIMS, forming a chemical adduct, 1-4-quinoxaline. The methyl esters of diacetyl-adduct (DAA) and pentanedione-adduct (PDA) are incorporated to the lysines in BSA and the conjugate used for antibody screening and selection. In the research article is described an enzyme-linke ...[more]

PMID: 29062874

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Project description:Some secondary metabolites of fermentative bacteria are desired compounds for the food industry. Examples of these compounds are diacetyl and acetaldehyde, which are produced by species of the lactic acid bacteria (LAB) family. Diacetyl is an aromatic compound, giving the buttery flavor associated with dairy products, and acetaldehyde is the compound responsible for the yogurt flavor and aroma. The quantification of these compounds in food matrices is a laborious task that involves sample preparation and specific analytical methods. The ability of bacteria to naturally sense metabolites has successfully been exploited to develop biosensors that facilitate the identification and quantification of certain metabolites (Mahr and Frunzke, 2016). The presence of a specific metabolite is sensed by the biosensors, and it is subsequently translated into the expression of one or more reporter genes. In this study we aimed to develop fluorescence-based biosensors to detect diacetyl and acetaldehyde. Since the metabolic pathways for production and degradation of these compounds are present in Lactococcus lactis, the sensing mechanisms in this bacterium are expected. Thus, we identified diacetyl and acetaldehyde responsive promoters by performing transcriptome analyses in L. lactis. The characterization of the biosensors showed their response to the presence of these compounds, and a further analysis of the diacetyl-biosensors (its dynamics and orthogonality) was performed. Moreover, we attempted to produce natural diacetyl from producer strains, namely L. lactis subsp. lactis biovar diacetylactis, to benchmark the performance of our biosensors. The diacetyl-biosensors responded linearly to the amounts of diacetyl obtained in the bacterial supernatants, i.e., the increases in GFP expression were proportional to the amounts of diacetyl present in the supernatants of L. lactis subsp. lactis biovar diacetylactis MR3-T7 strain. The biosensors developed in this study may eventually be used to engineer strains or pathways for increased diacetyl and acetaldehyde production, and may facilitate the detection of these metabolites in complex food matrices.

Project description:Fluorinated chlorido[salophene]iron(III) complexes (salophene = N,N'-bis(salicylidene)-1,2-phenylenediamine) are promising anticancer agents. Apoptosis and necrosis induction have already been described as part of their mode of action. However, the involvement of ferroptosis in cell death induction, as confirmed for other chlorido[salophene]iron(III) complexes, has not yet been investigated. Furthermore, the mechanism of cellular uptake of these compounds is unknown. Therefore, the biological activity of the fluorescent chlorido[salophene]iron(III) complexes with a fluorine substituent at positions 3, 4, 5, or 6 at the salicylidene moieties (C1-C4) was evaluated in malignant and nonmalignant cell lines with focus on the involvement of the transferrin receptor-1 (TfR-1) in cellular uptake, the influence of the complexes on mitochondrial function, and the analysis of the molecular mechanism of cell death. All complexes significantly decreased the metabolic activity in the tested ovarian cancer (A2780, A2780cis), breast cancer (MDA-MB 231), and leukemia (HL-60) cell lines, while the nonmalignant human stroma cell line HS-5 at a concentration of 0.5 μM, which represents the IC50 of the complexes in most of the used tumorigenic cell lines, was not affected. The mitochondrial function was impaired, as evidenced by a reduced mitochondrial membrane potential ΔΨm and decreased mitochondrial activity. Besides apoptosis and necroptosis, ferroptosis was identified as part of the mode of action. It was further demonstrated for the first time that fluorinated chlorido[salophene]iron(III) complexes downregulate TfR-1 expression, comparable to ferristatin II, an iron transport inhibitor that acts via TfR-1 degradation. FerroOrange staining further indicated that the complexes strongly increased the intracellular iron(II) level as a driving force to induce ferroptosis. In conclusion, these fluorinated chlorido[salophene]iron(III) complexes are potent, tumor cell-specific chemotherapeutic agents, with the potential to treat various types of cancers.

Dataset Information

Synthesis of 1,2-phenylenediamine capturing molecule for the detection of diacetyl.

Publications

Synthesis of 1,2-phenylenediamine capturing molecule for the detection of diacetyl.

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